熊果酸与脂质分子二元混合系统单分子层的界面相行为的研究
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摘要
随着科学的发展和实验技术的日趋完善,对于生物膜系统的研究已经扩展到生命科学以外的医学、生物物理学和生物化学等很多学科领域,并逐渐成为各个领域热门而且前沿的课题。研究发现很多生命活动都与生物膜系统的结构和功能有着紧密的联系。生物膜的体外模拟技术是研究生物膜系统的理化特性的简单且有效的方法之一。本文以两种生物膜的脂质分子：二棕榈酸磷脂酰胆碱(1,2-dipalmitoyl-sn-glycero-3-phosphorcholine, DPPC)以及二棕榈酸磷脂酰乙醇胺(1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine, DPPE)作为人工生物膜的骨架,通过Langmuir单分子层技术研究了熊果酸与这两种脂质分子组成的二元混合系统单分子层在空气-水界面的相行为。记录和分析了混合单分子层的表面压力与平均分子面积关系曲线(π-A曲线),并以此为基础研究了二元混合单分子层的热力学特性,计算得到了单分子层的相关热力学参数(如弹性模量、平均分子面积、过量分子面积、过量吉布斯自由能等),以分子之间的溶合度为基础,在分子水平上分析了熊果酸和两种脂质分子在二元混合系统单分子层上的动力学特性。利用Langmuir-Blodgett(LB)膜技术结合原子力显微镜对混合单分子层的表面形貌进行了研究,研究结果与混合单分子层的热力学和动力学的理论分析的结果相一致。
(一)在熊果酸/二棕榈酸磷脂酰胆碱(UA/DPPC)二元混合单分子层中,π-A曲线随着熊果酸的摩尔比的增加呈现规律性的排列。当熊果酸所占的比例较少时,混合单分子层会出现凝聚现象,此时热力学上也更加稳定,两分子间的相互作用力为引力。随着表面压力的增加,熊果酸分子的排布会出现变化,这会影响混合单分子层的各种性质。在较低的表面压力下,少量的熊果酸容易进入到DPPC的区域,分子之间的吸引力使单分子层出现聚集的形貌,此时熊果酸所起作用于胆固醇的作用相似。与胆固醇的作用不同的是,在高的表面压力下,熊果酸分子发生翻转,使混合单分子层中的分子排布的有序性提高,此时分子间的距离较近,有可能出现两个或者多个分子间的聚集而形成聚集体。原子力显微镜对混合单分子层表面形貌的检测研究也证实了这一现象。
(二)熊果酸/二棕榈酸磷脂酰乙醇胺(UA/DPPE)二元混合系统在气-水界面上的Langmuir单分子层的π-A曲线也呈规律性的分布,说明分子之间在气-水界面上存在相互作用,而且两种分子具有可混合性。UA/DPPE混合单分子层上分子间的相互作用比UA/DPPC的程度弱。混合单分子层上两种分子的相互作用程度与各分子的摩尔比例和单分子层的表面压力都有关系。在熊果酸的摩尔分数较小时,单分子层会出现有缺陷的膜的形貌,随着熊果酸含量的增加,单分子层上出现更明显的聚集现象。随着表面压力的增加,熊果酸分子脂质分子的分布和排列方式都会出现变化,混合单分子层的表面形貌相应也会出现变化。
本文研究分析了熊果酸分别与两种脂质分子形成的二元混合系统单分子层在空气-水界面的相行为。发现熊果酸与这两种脂质分子之间都存在相互作用：在低表面压力时,熊果酸的作用效果与生物膜的重要组成成分-胆固醇相似；在高表面压力时,由于分子间距减小而排布更紧密,熊果酸分子结构的特性使分子间的相互作用发生变化。经过对比分析发现,熊果酸与不同的脂质分子间的作用程度不同。
With the development of science and the increasingly improved experimental techniques, the study of biomembrane system has been extended to medicine, biophysics and biochemistry, and other interdisciplinary fields beyond the life sciences, and gradually became popular and frontier topics of each fields. Study found that many life activities are closely linked with the structure and function of biomembrane systems. Biomembrane in vitro simulation technology is one of the simple and effective methods to research the physical and chemical characteristics of biomembrane system.1,2-dipalmitoyl-sn-glycero-3-phosphor-choline (DPPC) and1,2-dihexadecanoyl-sn-glycerol-3-phosphoethanolamine phosphatidyl-ethanolamine (DPPE) were chosen as the skeleton of the artificial membrane. The phase behavior of the binary mixtures system monolayer consisted of ursolic acid and the two lipid molecules at the air-water interface has been studied by π-A isotherm measurement and analysis based on the Langmuir monolayer technique. The thermodynamic properties of binary mixed monolayer (such as elastic modulus, the average and excess area per molecule, excess Gibbs free energy and interaction parameters) was investigated based on molecular fusion level. The theoretical analysis of the thermodynamics and kinetics of the mixed monolayer was indicated by the study of surface morphology of the artificial membrane using the Langmuir-Blodgett (LB) film technology combined with atomic force microscopy
(I) In the binary mixtures of ursolic acid/1,2-dipalmitoyl-sn-glycerol-3-phosphor-choline (UA/DPPC) monolayer. With the gradually increased molar faction of ursolic acid, the arrangement of the π-A isotherms of shown regularity. When the faction of ursolic acid is small, the agglutination occurs in the mixed monolayer and the thermodynamically of mixed monolayer is more stable. The interaction between the two molecules is attraction. With the increase of surface pressure, the arrangement of ursolic acid molecules changed, which would affect the properties of the mixed monolayer. At lower surface pressure, a small amount of ursolic acid can easily access into the DPPC area, the attraction between the molecular on monolayer makes the appearance of aggregation morphology. At this time, ursolic acid plays the same role as cholesterol. Differed from the cholesterol, at high surface pressure, ursolic acid molecules overturned, which could increase the arrange order of the molecules in the mixed monolayer, and the shortage of the distance between molecules. The aggregation between two molecules may induce the formation of dimers. The detection of the mixed monolayer surface morphology using atomic force microscopy indicated this phenomenon.
(II) Langmuir monolayer π-A isotherms of ursolic acid/1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine phosphatidyl-ethanolamine (UA/DPPE) binary mixtures at the air-water interface showed a regular distribution. There has interaction between molecules in the air-water interface and the two molecules can be mixed. The interaction of molecular on the UA/DPPE monolayer is weak than on the UA/DPPC. The interaction of different molecules on the mixed monolayer has relationship with the molar fraction and the surface pressure. When the mole fraction of ursolic acid is small, the morphology of monolayer appears defective film. With the increase of the fraction of ursolic acid on the monolayer, obviously aggregation can be found. As the increase of surface pressure, the distribution and arrangement of the lipid molecules and ursolic acid molecules will change. Correspondingly, the surface morphology of monolayer also changes.
This article investigated the phase behavior of binary mixed monolayer consisted of ursolic acid and two different lipid molecules in the air-water interface. Interactions exist between ursolic acid and two different lipid molecules. At low surface pressure, ursolic acid played the same role as cholesterol-an important components of the biomembrane. At high surface pressure, as the molecular arrangement more closely, the molecular spacing decreases, the interaction force changed because the characteristic structure of ursolic acid. Comparative analysis found that, the interaction of ursolic acid with two kinds of lipid molecules is different.
(一)在熊果酸/二棕榈酸磷脂酰胆碱(UA/DPPC)二元混合单分子层中,π-A曲线随着熊果酸的摩尔比的增加呈现规律性的排列。当熊果酸所占的比例较少时,混合单分子层会出现凝聚现象,此时热力学上也更加稳定,两分子间的相互作用力为引力。随着表面压力的增加,熊果酸分子的排布会出现变化,这会影响混合单分子层的各种性质。在较低的表面压力下,少量的熊果酸容易进入到DPPC的区域,分子之间的吸引力使单分子层出现聚集的形貌,此时熊果酸所起作用于胆固醇的作用相似。与胆固醇的作用不同的是,在高的表面压力下,熊果酸分子发生翻转,使混合单分子层中的分子排布的有序性提高,此时分子间的距离较近,有可能出现两个或者多个分子间的聚集而形成聚集体。原子力显微镜对混合单分子层表面形貌的检测研究也证实了这一现象。
(二)熊果酸/二棕榈酸磷脂酰乙醇胺(UA/DPPE)二元混合系统在气-水界面上的Langmuir单分子层的π-A曲线也呈规律性的分布,说明分子之间在气-水界面上存在相互作用,而且两种分子具有可混合性。UA/DPPE混合单分子层上分子间的相互作用比UA/DPPC的程度弱。混合单分子层上两种分子的相互作用程度与各分子的摩尔比例和单分子层的表面压力都有关系。在熊果酸的摩尔分数较小时,单分子层会出现有缺陷的膜的形貌,随着熊果酸含量的增加,单分子层上出现更明显的聚集现象。随着表面压力的增加,熊果酸分子脂质分子的分布和排列方式都会出现变化,混合单分子层的表面形貌相应也会出现变化。
本文研究分析了熊果酸分别与两种脂质分子形成的二元混合系统单分子层在空气-水界面的相行为。发现熊果酸与这两种脂质分子之间都存在相互作用：在低表面压力时,熊果酸的作用效果与生物膜的重要组成成分-胆固醇相似；在高表面压力时,由于分子间距减小而排布更紧密,熊果酸分子结构的特性使分子间的相互作用发生变化。经过对比分析发现,熊果酸与不同的脂质分子间的作用程度不同。
With the development of science and the increasingly improved experimental techniques, the study of biomembrane system has been extended to medicine, biophysics and biochemistry, and other interdisciplinary fields beyond the life sciences, and gradually became popular and frontier topics of each fields. Study found that many life activities are closely linked with the structure and function of biomembrane systems. Biomembrane in vitro simulation technology is one of the simple and effective methods to research the physical and chemical characteristics of biomembrane system.1,2-dipalmitoyl-sn-glycero-3-phosphor-choline (DPPC) and1,2-dihexadecanoyl-sn-glycerol-3-phosphoethanolamine phosphatidyl-ethanolamine (DPPE) were chosen as the skeleton of the artificial membrane. The phase behavior of the binary mixtures system monolayer consisted of ursolic acid and the two lipid molecules at the air-water interface has been studied by π-A isotherm measurement and analysis based on the Langmuir monolayer technique. The thermodynamic properties of binary mixed monolayer (such as elastic modulus, the average and excess area per molecule, excess Gibbs free energy and interaction parameters) was investigated based on molecular fusion level. The theoretical analysis of the thermodynamics and kinetics of the mixed monolayer was indicated by the study of surface morphology of the artificial membrane using the Langmuir-Blodgett (LB) film technology combined with atomic force microscopy
(I) In the binary mixtures of ursolic acid/1,2-dipalmitoyl-sn-glycerol-3-phosphor-choline (UA/DPPC) monolayer. With the gradually increased molar faction of ursolic acid, the arrangement of the π-A isotherms of shown regularity. When the faction of ursolic acid is small, the agglutination occurs in the mixed monolayer and the thermodynamically of mixed monolayer is more stable. The interaction between the two molecules is attraction. With the increase of surface pressure, the arrangement of ursolic acid molecules changed, which would affect the properties of the mixed monolayer. At lower surface pressure, a small amount of ursolic acid can easily access into the DPPC area, the attraction between the molecular on monolayer makes the appearance of aggregation morphology. At this time, ursolic acid plays the same role as cholesterol. Differed from the cholesterol, at high surface pressure, ursolic acid molecules overturned, which could increase the arrange order of the molecules in the mixed monolayer, and the shortage of the distance between molecules. The aggregation between two molecules may induce the formation of dimers. The detection of the mixed monolayer surface morphology using atomic force microscopy indicated this phenomenon.
(II) Langmuir monolayer π-A isotherms of ursolic acid/1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine phosphatidyl-ethanolamine (UA/DPPE) binary mixtures at the air-water interface showed a regular distribution. There has interaction between molecules in the air-water interface and the two molecules can be mixed. The interaction of molecular on the UA/DPPE monolayer is weak than on the UA/DPPC. The interaction of different molecules on the mixed monolayer has relationship with the molar fraction and the surface pressure. When the mole fraction of ursolic acid is small, the morphology of monolayer appears defective film. With the increase of the fraction of ursolic acid on the monolayer, obviously aggregation can be found. As the increase of surface pressure, the distribution and arrangement of the lipid molecules and ursolic acid molecules will change. Correspondingly, the surface morphology of monolayer also changes.
This article investigated the phase behavior of binary mixed monolayer consisted of ursolic acid and two different lipid molecules in the air-water interface. Interactions exist between ursolic acid and two different lipid molecules. At low surface pressure, ursolic acid played the same role as cholesterol-an important components of the biomembrane. At high surface pressure, as the molecular arrangement more closely, the molecular spacing decreases, the interaction force changed because the characteristic structure of ursolic acid. Comparative analysis found that, the interaction of ursolic acid with two kinds of lipid molecules is different.
引文
[1]姚庆生.天然药物化学[M].第3版.北京：人民卫生出版社,2002,257-268.
[2]Simon A,Najid A, Chulia AJ, et al. Inhibition of lipoxygenase acitivity and HL60 leukemic cell p roliferation by ursolic acid isolate from heather flowers ( Calluna vulgaris) [J]. Biochem Biophys Acta,1992,1125 (1) : 68.
[3]Subbaramaiah K, Telang N., Ramonetti J.T, Araki R., DeVito B, Weksler B.B. Dannenberg A J. Transcription of cyclooxygenase-2 is enhanced in transformed mammary epithelial cells [J]. Cancer Res.,1996.56:4424-4429.
[4]Y.S. Lee, D.Q. Jin, S.M. Beak, E.S. Lee, J.A. Kim, Inhibition of UVA modulated signaling pathways by asiatic acid and ursolic acid in HaCaT human kerotinocytes[J]. Eur. J. Pharmacol.2003,476:173-178
[5]L. Jie. Oleanolic acid and ursolic acid:research perspectives [J]. J. Ethnophma col. 2005,100:92-94.
[6]Yunlong Li, Da Xing, Qun Chen, Wei R. Chen. Enhancement of chemotherapeutic agent-induced apoptosis by inhibition of NF-κB using ursolic acid. Int. J. Cancer 2010,127(2):462-473.
[7]Yu-xi Zhang, Chui-ze Kong, Lin-hui Wang, Jin-yi Li, Xian-kui Liu, Bin Xu, Chuan-liang Xu, Ying-hao Sun. Ursolic acid overcomes Bcl-2-mediated resistance to apoptosis in prostate cancer cells involving activation of JNK-induced Bcl-2 phosphorylation and degradation [J]. Journal of Cellular Biochemistry.2010,109 (4),764-773.
[8]Yang L., Liu X., Lu Z., Yuet-Wa C. J., Zhou L., Fung K. P., Wu, P., Wu S. Ursolic acid induces doxorubicin-resistant HepG2 cell death via the release of apoptosis-inducing factor [J]. Cancer Lett..2010,298,128-138.
[9]Yan-xia Yu, Zhen-lun Gu, Jiang-lin Yin, Wen-hsien Chou, Chi-yi KWOK, Zheng-hong Qin, Zhong-qin Liang. Ursolic acid induces human hepatoma cell line SMMC-7721 apoptosis via p53-dependent pathway Chinese Medical Journal 2010,123 (14):1915-1923.
[10]Limami Y., Pinon A., Leger D. Y., Mousseau Y., Cook-Moreau J., Beneytout J. L., Delage C., Liagre B., Simon A. HT-29 colorectal cancer cells undergoing apoptosis overexpress COX-2 to delay ursolic acid-induced cell death. Biochimie.2011,93,749-757.
[11]Kim DK, Baek JH, Kang CM, Sung JW, Lee BE, Chung HY, Kim ND, Lee SH, Kim KW, Apoptotic Activity of UA May Correlate with the Inhibition of Initiation of DNA Replication [J]. Int. J. Cancer 2000,87(5):629-636.
[12]于丽波,王晶,马宝章,孙文洲.熊果酸对卵巢癌细胞HO-8910PM侵袭转移的影响[J]四川大学学报：医学版2010,41(6)：986-988.
[13]Kassi, E., Papoutsi, Z., Pratsinis, H., Aligiannis, N., Manoussakis, M., Moutsatsou, P., Ursolic acid, a naturally occurring triterpenoid, demonstrates anticancer activity on human prostate cancer cells [J]. Journal of Cancer Research and Clinical Oncology 2007,133:493-500.
[14]Chadalapaka,G., Jutooru, I., McAlees, A., Stefanac, T., Safe, S., Structuredependent inhibition of bladder and pancreatic cancer cell growth by 2-substituted glycyrrhetinic and ursolic acid derivatives [J]. Bioorganic and Medicinal Chemistry Letters 2008.18:2633-2639.
[15]Xavier, C.P., Lima, C.F., Preto, A., Seruca, R., Fernandes-Ferreira, M., Pereira-Wilson, C. Luteolin, quercetin and ursolic acid are potent inhibitors of proliferation and inducers of apoptosis inboth KRAS and BRAF mutated human colorectal cancer cells [J].Cancer Letters,2009,281:162-170.
[16]Sheng-lei Yan, Chun-yin Huang, Shwu-tzy Wua, Mei-chin Yin, Oleanolic acid and ursolic acid induce apoptosis in four human liver cancer cell lines [J]. Toxicology in Vitro 24 (2010):842-848.
[17]Gao X., Deeb, D., Jiang, H., Liu, Y., Dulchavsky, S.A., Gautam, S.C., Synthetic triterpenoids inhibit growth and induce apoptosis in human glioblastoma and neuroblastoma cells through inhibition of prosurvival Akt, NF-kappaB and Notchl signaling [J]. Journal of Neuro-oncology 2007.84,147-157.
[18]P.O. Harmand, R. Duval, C. Delage, A. Simon, Ursolic acid induces apoptosis through mitochondrial intrinsic pathway and caspase-3 activation in M4Beu melanoma cells [J]. Int. J. Cancer 2005,114 (1):1-11.
[19]Y.H. Shih, Y.C. Chein, J.-Y. Wang,Y.-S. Fu, Ursolic acid protects hippocampal neurons against kainate-induced excitotoxicity in rats [J]. Neurosci. Lett.2004 362:136-140.
[20]L.O. Somova, A. Nadar, P. Rammanan, F.O. Shode, Cardiovascular, antihyperlipidemic and antioxidant effect of oleanolic acid and ursolic acid in experimental hypertension [J]. Phytomedicine 2003,10:115-121.
[21]J. Liu, Pharmacology oleanolic acid and ursolic acid review [J]. J. Ethanopharmacol.1995,49:57-68.
[22]R. Saravanan, P. Viswanathan, K.V. Pugalendi, Protective effect of ursolic acid on ethanol mediated experimental liver damages in rats [J]. Life Sci.2006,78: 713-718.
[23]J. Lu, Y-L. Zheng, D-M. Wu, L. Luo, D-X. Sun, Q. Shan, Ursolic acid ameliorates cognition deficits and attenuates oxidativedamage in the brain of senescent mice induced by D-galactose [J]. Biochem. Pharmacol.2007,74: 1078-1090.
[24]杨福愉.生物膜[M].北京,科学出版社,2005：2.
[25]赵南明,周海梦.生物物理学[M].北京,高等教育出版社；海德堡,施普林格出版社,2000.7：103.
[26]欧阳钟灿.从液晶生物膜理论展望软凝聚态物理创新[J],中国科学院院刊,1998,6：416-418.
[27]孙润广.生物膜分子与化学药物及磁场相互作用的研究[D].西安,西安交通大学,1999.
[28]Karp G. Cell and Moleeular Biology:Concepts and Experiments [M]. Wiley&Son, 2005, ChaPter4.
[29]翟中和,王喜忠,丁明孝.细胞生物学[M].北京,高等教育出版社,2000：73.
[30]王镜岩,朱圣庚,徐长法.生物化学(上册)[M].北京,高等教育出版社,2000(第三版)：599.
[31]闫红霞.胆固醇、磷脂复合LB膜的微结构[D].开封,河南大学,2007.
[32]刘艳辉.原子力显微镜(AFM)与生物膜相互作用实验理论分析[D].贵州,贵州大学,2006.
[33]隋森芳.膜分子生物学[M].北京,高等教育出版社,2003：5.
[34]Singer,S.J., Nicolson,G.L.. The fluid mosaic model of the structure of cell membrane [J]. Science,1972,175:720-731.
[35]Remi Lasserre, Xiao-Jun Guo, Fabien Conchonaud. Raft nanodomains contribute to Akt/PKB plasma membrane recruitment and activation [J]. Nature Chemical Biology,2008,4:538-547.
[36]常怡光.两性霉素B与脂质分子混合单层膜热力学特性研究与原子力显微镜观测[D].西安,陕西师范大学,2010.
[37]杨福愉.生物膜[M].北京,科学出版社,2005：345.
[38]徐德选,杨根元,何亚楠,徐芬红.冠心病患者红细胞膜脂蛋白及胆固醇变化的研究[J],心肺血管学报,1991,4：301-302.
[39]程时.生物膜与疾病[J],生理科学,1988,8(5)：27-277.
[40]野沢義则,香川靖雄,杨畔农译.生物膜与疾病[M].北京,人民卫生出版社1985：200-225.
[41]Katharine B.Blodgett, Irving Langmuir.Built up Films of Stearate and Their Opticalproperties [J]. Phys Rev.1937,51:964-982.
[42]De la Fuente Feria. J, Rodriguez Patino. J M, The effect of the subphase composition on monostearin-distearin mixed monolayers [J].Colloids Surf.1995, 104:29-40.
[43]Perillo M A, Maestri D M, Surface behavior of jojoba oil alone or in mixtures with soybean oil [J]. Colloids Surf. A:Physicochem. Eng. Asp,2005,256: 199-205.
[44]王玉国.一种新型材料LB膜的制备技术及其应用[J].化学新型材料,1993,7：15-19.
[45]王一兵,吴卫红,陆菲,王海水,席时权.TMB·TCNQ和硬脂酸混合LB膜制备与表征[J].光谱学与光谱分析,2008,28(5)：1400-1444.
[46]张军,薛群基.Langnuir-B lodgett膜及其摩擦行为[J].摩擦学学报,1992,12(2)：97-104.
[47]谢丹.NO2气敏LB膜及其微结构传感器研究[D],成都,电子科技大学,2001.
[48]王海龙.脂筏微区分子的分离与重组研究[D],西安,陕西师范大学,2008.
[49]中国表面活性剂网,应用技术详细内容LB膜的类型[EB/OL].http://www.surfactant.com.cn/yingyongj ishu/yingyongj sview.aspx?id=1794
[50]郝长春.脂筏结构拆离与重建的原子力显微镜研究[D].西安,陕西师范大学,2007.
[51]M.Florsheimer, H. Mohwald, Superimposed ordering transitions in phospholipid monolayers [J].Colloids and Surfaces,1991,55:173-189.
[52]Stanislaw J. Pogorzelski, Structural and thermodynamic characteristics of natural marine films derived from force-area studies [J], Colloids and Surfaces A: Physicochemical and Engineering Aspects,2001,189(1-3):163-176.
[53]桑文斌,刘引烽.甲壳胺膜中MS(M=Cd,Zn)半导体纳米微粒形成机理的探讨[J].原子与分子物理学报,1999,16：358-363.
[54]赵南明,周海梦.生物物理学[M].北京,高等教育出版社,2000：415.
[55]熊丹.基于AFM与干涉光谱的薄膜厚度测量系统[D].杭州,浙江大学,2007.
[56]赵南明,周海梦.生物物理学[M].北京,高等教育出版社,2000：104-105.
[57]王夫雨,孙润广,陈莹莹,王小梅,柴政.乌苏酸/DPPC混合单层膜相互作用的研究[J],化学学报,2012,70(5)：667-673
[58]赵翠翠,钱正子,王华庆,宋拯,孟祥睿,赵静,阎昭,郝希山.熊果酸纳米脂质体I期临床单次耐受性试验研究[J],中国新药杂志,2011,20(2)：147-151
[59]Yunlan Su, Qingzhong Li, Lin Chen, Zhiwu Yu. Condensation effect of cholesterol, stigmasterol, and sitosterol on dipalmitoylphosphatidylcholine in molecular monolayers. Colloids and Surfaces A:Physicochem. Eng. Aspects 2007, 293:123-129
[60]Magne Kna, Katerina Bilkova, Egil Gulbrandse, Per Carlsen, Johan Sjoblom. Langmuir-Blodgett film of dococyltricthylammonium bromidc and octadecanol on iron.Deposition and eorrosion inllibitor performance in CO2 eontaining brine [J] .Corrosion Seienee,2006,48(9):2592-2613.
[61]陈莹莹.桦木酸与不同分子二元系统单分子层的界面相行为研究[D].西安,陕西师范大学,2011.
[62]郝长春,孙润广Langmuir-Blodgett膜超分子SM/DOPC/Chol三元脂系的原子力显微镜观察[J].化学学报,2007,65(20)：2325～2330.
[63]Dynarowicz, A. P, Kita, K. Molecular interaction in mixed monolayers at the air/water interface. Adv Colloid Interf Sci,1999,79:1-17.
[64]常怡光,孙润广,郝长春,薛慧君,韩涛,王小梅.胆固醇/两性霉素B混合单层膜相互作用的研究[J]化学学报,2010,68,2181-2185.
[65]Changchun H, Runguang S, Jing Z, Yiguang C, Chunling N. Behavior of sulfatide/cholesterol mixed monolayers at the air/water interface [J]. Colloids and Surfaces B:Biointerfaces,2009,69:201-206.
[66]郝长春,孙润广,张静DOPC, DOPE和神经酰胺对鞘磷脂/胆固醇双层膜结构的影响[J]高等学校化学学报,2009,30：913-918.
[67]Solomon Y, Jennifer C S, Alexandre S, Ting L, Nangou Liu C, Jeffrey B, William C, Large-conductance cholesterolamphotericin B channels in reconstituted lipid bilayers [J]. Biosensors and Bioelectronics,2007,22:1359-1367.
[68]Katarzyna H W, Pawel W. The study on the interaction between phytosterols and phospholipids in model membranes [J]. Chem. Phys. Lipids,2007, 150:22-34
[69]Lee Y. L., Lin J. Y., Chang C H, Thermodynamic characteristics and Langmuir-Blodgett deposition behavior of mixed DPPA/DPPC monolayers at air/liquid interfaces[J].Colloid Interface Sci,2006,296:647-654.
[70]Yunlan Su, Qingzhong Li, Lin Chen, Zhiwu Yu. Condensation effect of cholesterol, stigmasterol, and sitosterol on dipalmitoylphosphatidylcholine in molecular monolayers [J]. Colloids and Surfaces A:Physicochem.2007,293: 123-129
[71]郝长春,孙润广,张静,常怡光,牛春玲.鞘氨醇/胆固醇单层分子膜的热力学特性及表面形态的AFM观测[J].中国科学B辑：化学2008,38(11)1018-1024
[72]Hac-Wydro K, Dynarowicz-Latka P, Grzybowska J, Borowski E. How does the N-acylation and esterification of amphotericin B molecule affect its interactions with cellular membrane components--the Langmuir monolayer study[J] Colloids and Surfaces B:Biointerfaces,2005,46:7-19.
[73]Davies J. T, Rideal E. K, Interfacial Phenomena[M], Academic Press, New York,1963,265.
[74]Barbara G M, Maria P, Studies of lipid interaction in mixed Langmuir monolayers [J]. Thin Solid Film,2008,516:8865-8872.
[75]Ronzon, F., Desbat, B., Chauvet, J. P., Roux, B. Behavior of a GPI-anchored protein in phospholipid monolayers at the air-water interface. Biochim Biophys Acta.2002,18,1560(1-2):1-13.
[76]Li, X. M., Momsen, M. M., Smaby, J. M., Brockman, H. L.;Brown, R. E.Cholesterol decreases the interfacial elasticity and detergent solubility of sphingomyelins.
[77]Kodama, M.; Shibata, O.; Nakamura, S.; Lee, S.; Sugihara, G. A monolayer study on three binary mixed systems of dipalmitoylphosphatidylcholine with cholesterol, cholestanol and stigmasterol Colloids and Surfaces B:Biointerfaces.2004,33, (3-4):211-226
[78]孙润广,郝长春,常怡光,张静,牛春玲.鞘氨醇与DPPC,DPPE单层膜的热力学特性及形态观察[J].化学学报,2009,67：1808-1814.
[79]Joos P. Theory on the collapse pressure of mixed insoluble monolayers with miscible components [J]. Bulletin des Societes Chimiques Belges 1969,78:3-4.
[80]Nagadome S, Suzuki NS, Mine Y, Yamaguchi T, Nakahara H, Shibata O, Chang CH, Sugihara G. Monolayers (Langmuir films) behavior of multi-component systems composed of a bile acid with different sterols and with their 1:1 mixtures. Colloids and Surfaces B:Biointerfaces,2007,58(2):121-136
[81]L.M. Ilhareo, A. R. Gareia, A. M. Fidalgo, R. Barros, A. F. Vale, J. Lopes da Silva, A. M. Goncalves da Silva. A Transmission FTIR Spectroscoic Study on Mixed Langmuir-Blodgett Films of Cadmium Heptadecanoate-Chloro/ Bromohexadec ane [J]. Langmuir,1995,11:2745-2750.
[82]A. M. Goncalves da Silva, J. C. Guerreiro, N. G. Rodrigues, T. O. Rodrigues. Mixed Monolayers of Heptadecanoic Acid with Chlorohexadecane and Bromohexadecane:Effeets of Temperature and of Metal Ionsin the Subphase [J]. Langmuir,1996,12(18):4442-4448
[83]Aneliya N. Zdravkova, J. P. J. M. van der Eerden. Phase behavior in binary mixed Langmuir Blodgett monolayers of triglyeerides [J]. Journal of Crystal Growth, 2007,307(1):192-202.
[84]隋森芳.膜分子生物学[M].北京,高等教育出版社,2003,420.
[85]常怡光,孙润广,郝长春.磷酯酰乙醇胺与硬脂酸、十八醇二元混合系统单层膜的热力学特性和AFM观测[J].高等学校化学学报,2010,31(3)：559-565.
[86]AnaC. T. Teixeira, Anabela C. Femandes, AnaR. Gareia, Laura M. Ilhareo, Pedr Brogueira, Amelia M. P. S., Goncalves da Silva. Microdomains in mixed monolayers of oleanolic and stearic acids:thermodynamic study and BAM observation at the air-water interface and AFM and FTIR analysis of LB monolayers [J]. Chemistry and Physics of Lipids,2007,149(1-2):1-13.
[87]G. Brezesinski, D. Vollhardt, K. Iimura, H. Colfen. Struetural Features of Mixed Monolayers of Oleanolic Acid and Stearic Aeid[J]. The Journal of Physical Chemistry C,2008,112(40):15777-15783.
[88]Gerald Brezesinski, Dieter Vollhardt. Model Studies of the Interfacial Ordering of Oleanolic Acid in the Cuticula [J]. Chem. Phys. Chem.,2008,9 (12):1670-167.
[89]JonHoly, Oksana Kolomitsyna, Dmytro Krasutsky, Paulo J. Oliveira, Edward Perkins, Pavel A. Krasutsky. Dimethylaminopyridine derivatives of lupane triterpenoids are potent disruptors of mitochondrial structure and fuction [J]. Bioorganic & Medicinal Chemistry,2010,18(16):6080-6088
[90]Slim Azouzi, Karim El Kirat, Sandrine Moranda. The Potent Antimalarial Drug Cyelosporin A Preferentially Destabilizes Sphingomyelin-Rich Membranes [J]. Langmuir,2010,26(3):1960-1965.
[91]M.l.Sandez Maeho, A. Gil Gonzalez, A.Suarez Varela. Mixed Monolayers of Cyclosporin-A and Phospholipids at the Air-Water interface [J]. Journal of Colloid and Interface Seienee,2001,235(2):241-246
[92]Katarzyna Hac-Wydro, Patrycja Dynarowicz-Latka. Interaction between nystatin and natural membrane lipids in Langmuir monolayers. The role of a phospholipid in the mechanism of Polyenes mode of action [J]. Biophysical Chemistry,2006, 123(2-3):154-161.
[93]Seoane R, Minones J, Conde O, Iribarnegray E, Casas M. Interactions between Amphotericin B and Sterols in Monolayers. Mixed Films of Amphotericin B-Cholesterol [J]. Langmuir 1999,15:5567-5573
[94]P. Dynarowicz-Latka, R. Seoane, J. Minones Jr., M. Velo, J. Minones. Study of Penetration of amphoteriein B into cholesterol or ergosterol containing dipalmitoyl phosphatidylcholine Langmuir monolayers [J].Colloids and Surfaees B:Biointerfaees,2003,27(2-3):249-263.
[95]J. Minones, Jr, J. Minones, O. Conde, J. M. Rodriguez Patino, P. Dynarowiez-Latka. Mixed Monolayers of Amphoteriein B-Dipalmitoyl Phosphatidyl Choline: Study of Complex Formation [J]. Langmuir,2002,18(7):2817-2827.
[96]Ling-yun Zhao, Si-Shen Feng. Effeets of lipid chain length on molecular interactions between paclitaxel and phospholipid within model biomembranes [J]. Journal of Colloid and Interfaee Seienee,2004,274(1):55-68.
[97]Tzung-Han Chou, I-Ming Chu, Chien-Hsiang Chang. Interaction of paclitaxel with DSPC in monolayers at the air/water interface at different temperatures [J]. Colloids and Surfaces B:Biointerfaees,2002,25(2):147-155.
[2]Simon A,Najid A, Chulia AJ, et al. Inhibition of lipoxygenase acitivity and HL60 leukemic cell p roliferation by ursolic acid isolate from heather flowers ( Calluna vulgaris) [J]. Biochem Biophys Acta,1992,1125 (1) : 68.
[3]Subbaramaiah K, Telang N., Ramonetti J.T, Araki R., DeVito B, Weksler B.B. Dannenberg A J. Transcription of cyclooxygenase-2 is enhanced in transformed mammary epithelial cells [J]. Cancer Res.,1996.56:4424-4429.
[4]Y.S. Lee, D.Q. Jin, S.M. Beak, E.S. Lee, J.A. Kim, Inhibition of UVA modulated signaling pathways by asiatic acid and ursolic acid in HaCaT human kerotinocytes[J]. Eur. J. Pharmacol.2003,476:173-178
[5]L. Jie. Oleanolic acid and ursolic acid:research perspectives [J]. J. Ethnophma col. 2005,100:92-94.
[6]Yunlong Li, Da Xing, Qun Chen, Wei R. Chen. Enhancement of chemotherapeutic agent-induced apoptosis by inhibition of NF-κB using ursolic acid. Int. J. Cancer 2010,127(2):462-473.
[7]Yu-xi Zhang, Chui-ze Kong, Lin-hui Wang, Jin-yi Li, Xian-kui Liu, Bin Xu, Chuan-liang Xu, Ying-hao Sun. Ursolic acid overcomes Bcl-2-mediated resistance to apoptosis in prostate cancer cells involving activation of JNK-induced Bcl-2 phosphorylation and degradation [J]. Journal of Cellular Biochemistry.2010,109 (4),764-773.
[8]Yang L., Liu X., Lu Z., Yuet-Wa C. J., Zhou L., Fung K. P., Wu, P., Wu S. Ursolic acid induces doxorubicin-resistant HepG2 cell death via the release of apoptosis-inducing factor [J]. Cancer Lett..2010,298,128-138.
[9]Yan-xia Yu, Zhen-lun Gu, Jiang-lin Yin, Wen-hsien Chou, Chi-yi KWOK, Zheng-hong Qin, Zhong-qin Liang. Ursolic acid induces human hepatoma cell line SMMC-7721 apoptosis via p53-dependent pathway Chinese Medical Journal 2010,123 (14):1915-1923.
[10]Limami Y., Pinon A., Leger D. Y., Mousseau Y., Cook-Moreau J., Beneytout J. L., Delage C., Liagre B., Simon A. HT-29 colorectal cancer cells undergoing apoptosis overexpress COX-2 to delay ursolic acid-induced cell death. Biochimie.2011,93,749-757.
[11]Kim DK, Baek JH, Kang CM, Sung JW, Lee BE, Chung HY, Kim ND, Lee SH, Kim KW, Apoptotic Activity of UA May Correlate with the Inhibition of Initiation of DNA Replication [J]. Int. J. Cancer 2000,87(5):629-636.
[12]于丽波,王晶,马宝章,孙文洲.熊果酸对卵巢癌细胞HO-8910PM侵袭转移的影响[J]四川大学学报：医学版2010,41(6)：986-988.
[13]Kassi, E., Papoutsi, Z., Pratsinis, H., Aligiannis, N., Manoussakis, M., Moutsatsou, P., Ursolic acid, a naturally occurring triterpenoid, demonstrates anticancer activity on human prostate cancer cells [J]. Journal of Cancer Research and Clinical Oncology 2007,133:493-500.
[14]Chadalapaka,G., Jutooru, I., McAlees, A., Stefanac, T., Safe, S., Structuredependent inhibition of bladder and pancreatic cancer cell growth by 2-substituted glycyrrhetinic and ursolic acid derivatives [J]. Bioorganic and Medicinal Chemistry Letters 2008.18:2633-2639.
[15]Xavier, C.P., Lima, C.F., Preto, A., Seruca, R., Fernandes-Ferreira, M., Pereira-Wilson, C. Luteolin, quercetin and ursolic acid are potent inhibitors of proliferation and inducers of apoptosis inboth KRAS and BRAF mutated human colorectal cancer cells [J].Cancer Letters,2009,281:162-170.
[16]Sheng-lei Yan, Chun-yin Huang, Shwu-tzy Wua, Mei-chin Yin, Oleanolic acid and ursolic acid induce apoptosis in four human liver cancer cell lines [J]. Toxicology in Vitro 24 (2010):842-848.
[17]Gao X., Deeb, D., Jiang, H., Liu, Y., Dulchavsky, S.A., Gautam, S.C., Synthetic triterpenoids inhibit growth and induce apoptosis in human glioblastoma and neuroblastoma cells through inhibition of prosurvival Akt, NF-kappaB and Notchl signaling [J]. Journal of Neuro-oncology 2007.84,147-157.
[18]P.O. Harmand, R. Duval, C. Delage, A. Simon, Ursolic acid induces apoptosis through mitochondrial intrinsic pathway and caspase-3 activation in M4Beu melanoma cells [J]. Int. J. Cancer 2005,114 (1):1-11.
[19]Y.H. Shih, Y.C. Chein, J.-Y. Wang,Y.-S. Fu, Ursolic acid protects hippocampal neurons against kainate-induced excitotoxicity in rats [J]. Neurosci. Lett.2004 362:136-140.
[20]L.O. Somova, A. Nadar, P. Rammanan, F.O. Shode, Cardiovascular, antihyperlipidemic and antioxidant effect of oleanolic acid and ursolic acid in experimental hypertension [J]. Phytomedicine 2003,10:115-121.
[21]J. Liu, Pharmacology oleanolic acid and ursolic acid review [J]. J. Ethanopharmacol.1995,49:57-68.
[22]R. Saravanan, P. Viswanathan, K.V. Pugalendi, Protective effect of ursolic acid on ethanol mediated experimental liver damages in rats [J]. Life Sci.2006,78: 713-718.
[23]J. Lu, Y-L. Zheng, D-M. Wu, L. Luo, D-X. Sun, Q. Shan, Ursolic acid ameliorates cognition deficits and attenuates oxidativedamage in the brain of senescent mice induced by D-galactose [J]. Biochem. Pharmacol.2007,74: 1078-1090.
[24]杨福愉.生物膜[M].北京,科学出版社,2005：2.
[25]赵南明,周海梦.生物物理学[M].北京,高等教育出版社；海德堡,施普林格出版社,2000.7：103.
[26]欧阳钟灿.从液晶生物膜理论展望软凝聚态物理创新[J],中国科学院院刊,1998,6：416-418.
[27]孙润广.生物膜分子与化学药物及磁场相互作用的研究[D].西安,西安交通大学,1999.
[28]Karp G. Cell and Moleeular Biology:Concepts and Experiments [M]. Wiley&Son, 2005, ChaPter4.
[29]翟中和,王喜忠,丁明孝.细胞生物学[M].北京,高等教育出版社,2000：73.
[30]王镜岩,朱圣庚,徐长法.生物化学(上册)[M].北京,高等教育出版社,2000(第三版)：599.
[31]闫红霞.胆固醇、磷脂复合LB膜的微结构[D].开封,河南大学,2007.
[32]刘艳辉.原子力显微镜(AFM)与生物膜相互作用实验理论分析[D].贵州,贵州大学,2006.
[33]隋森芳.膜分子生物学[M].北京,高等教育出版社,2003：5.
[34]Singer,S.J., Nicolson,G.L.. The fluid mosaic model of the structure of cell membrane [J]. Science,1972,175:720-731.
[35]Remi Lasserre, Xiao-Jun Guo, Fabien Conchonaud. Raft nanodomains contribute to Akt/PKB plasma membrane recruitment and activation [J]. Nature Chemical Biology,2008,4:538-547.
[36]常怡光.两性霉素B与脂质分子混合单层膜热力学特性研究与原子力显微镜观测[D].西安,陕西师范大学,2010.
[37]杨福愉.生物膜[M].北京,科学出版社,2005：345.
[38]徐德选,杨根元,何亚楠,徐芬红.冠心病患者红细胞膜脂蛋白及胆固醇变化的研究[J],心肺血管学报,1991,4：301-302.
[39]程时.生物膜与疾病[J],生理科学,1988,8(5)：27-277.
[40]野沢義则,香川靖雄,杨畔农译.生物膜与疾病[M].北京,人民卫生出版社1985：200-225.
[41]Katharine B.Blodgett, Irving Langmuir.Built up Films of Stearate and Their Opticalproperties [J]. Phys Rev.1937,51:964-982.
[42]De la Fuente Feria. J, Rodriguez Patino. J M, The effect of the subphase composition on monostearin-distearin mixed monolayers [J].Colloids Surf.1995, 104:29-40.
[43]Perillo M A, Maestri D M, Surface behavior of jojoba oil alone or in mixtures with soybean oil [J]. Colloids Surf. A:Physicochem. Eng. Asp,2005,256: 199-205.
[44]王玉国.一种新型材料LB膜的制备技术及其应用[J].化学新型材料,1993,7：15-19.
[45]王一兵,吴卫红,陆菲,王海水,席时权.TMB·TCNQ和硬脂酸混合LB膜制备与表征[J].光谱学与光谱分析,2008,28(5)：1400-1444.
[46]张军,薛群基.Langnuir-B lodgett膜及其摩擦行为[J].摩擦学学报,1992,12(2)：97-104.
[47]谢丹.NO2气敏LB膜及其微结构传感器研究[D],成都,电子科技大学,2001.
[48]王海龙.脂筏微区分子的分离与重组研究[D],西安,陕西师范大学,2008.
[49]中国表面活性剂网,应用技术详细内容LB膜的类型[EB/OL].http://www.surfactant.com.cn/yingyongj ishu/yingyongj sview.aspx?id=1794
[50]郝长春.脂筏结构拆离与重建的原子力显微镜研究[D].西安,陕西师范大学,2007.
[51]M.Florsheimer, H. Mohwald, Superimposed ordering transitions in phospholipid monolayers [J].Colloids and Surfaces,1991,55:173-189.
[52]Stanislaw J. Pogorzelski, Structural and thermodynamic characteristics of natural marine films derived from force-area studies [J], Colloids and Surfaces A: Physicochemical and Engineering Aspects,2001,189(1-3):163-176.
[53]桑文斌,刘引烽.甲壳胺膜中MS(M=Cd,Zn)半导体纳米微粒形成机理的探讨[J].原子与分子物理学报,1999,16：358-363.
[54]赵南明,周海梦.生物物理学[M].北京,高等教育出版社,2000：415.
[55]熊丹.基于AFM与干涉光谱的薄膜厚度测量系统[D].杭州,浙江大学,2007.
[56]赵南明,周海梦.生物物理学[M].北京,高等教育出版社,2000：104-105.
[57]王夫雨,孙润广,陈莹莹,王小梅,柴政.乌苏酸/DPPC混合单层膜相互作用的研究[J],化学学报,2012,70(5)：667-673
[58]赵翠翠,钱正子,王华庆,宋拯,孟祥睿,赵静,阎昭,郝希山.熊果酸纳米脂质体I期临床单次耐受性试验研究[J],中国新药杂志,2011,20(2)：147-151
[59]Yunlan Su, Qingzhong Li, Lin Chen, Zhiwu Yu. Condensation effect of cholesterol, stigmasterol, and sitosterol on dipalmitoylphosphatidylcholine in molecular monolayers. Colloids and Surfaces A:Physicochem. Eng. Aspects 2007, 293:123-129
[60]Magne Kna, Katerina Bilkova, Egil Gulbrandse, Per Carlsen, Johan Sjoblom. Langmuir-Blodgett film of dococyltricthylammonium bromidc and octadecanol on iron.Deposition and eorrosion inllibitor performance in CO2 eontaining brine [J] .Corrosion Seienee,2006,48(9):2592-2613.
[61]陈莹莹.桦木酸与不同分子二元系统单分子层的界面相行为研究[D].西安,陕西师范大学,2011.
[62]郝长春,孙润广Langmuir-Blodgett膜超分子SM/DOPC/Chol三元脂系的原子力显微镜观察[J].化学学报,2007,65(20)：2325～2330.
[63]Dynarowicz, A. P, Kita, K. Molecular interaction in mixed monolayers at the air/water interface. Adv Colloid Interf Sci,1999,79:1-17.
[64]常怡光,孙润广,郝长春,薛慧君,韩涛,王小梅.胆固醇/两性霉素B混合单层膜相互作用的研究[J]化学学报,2010,68,2181-2185.
[65]Changchun H, Runguang S, Jing Z, Yiguang C, Chunling N. Behavior of sulfatide/cholesterol mixed monolayers at the air/water interface [J]. Colloids and Surfaces B:Biointerfaces,2009,69:201-206.
[66]郝长春,孙润广,张静DOPC, DOPE和神经酰胺对鞘磷脂/胆固醇双层膜结构的影响[J]高等学校化学学报,2009,30：913-918.
[67]Solomon Y, Jennifer C S, Alexandre S, Ting L, Nangou Liu C, Jeffrey B, William C, Large-conductance cholesterolamphotericin B channels in reconstituted lipid bilayers [J]. Biosensors and Bioelectronics,2007,22:1359-1367.
[68]Katarzyna H W, Pawel W. The study on the interaction between phytosterols and phospholipids in model membranes [J]. Chem. Phys. Lipids,2007, 150:22-34
[69]Lee Y. L., Lin J. Y., Chang C H, Thermodynamic characteristics and Langmuir-Blodgett deposition behavior of mixed DPPA/DPPC monolayers at air/liquid interfaces[J].Colloid Interface Sci,2006,296:647-654.
[70]Yunlan Su, Qingzhong Li, Lin Chen, Zhiwu Yu. Condensation effect of cholesterol, stigmasterol, and sitosterol on dipalmitoylphosphatidylcholine in molecular monolayers [J]. Colloids and Surfaces A:Physicochem.2007,293: 123-129
[71]郝长春,孙润广,张静,常怡光,牛春玲.鞘氨醇/胆固醇单层分子膜的热力学特性及表面形态的AFM观测[J].中国科学B辑：化学2008,38(11)1018-1024
[72]Hac-Wydro K, Dynarowicz-Latka P, Grzybowska J, Borowski E. How does the N-acylation and esterification of amphotericin B molecule affect its interactions with cellular membrane components--the Langmuir monolayer study[J] Colloids and Surfaces B:Biointerfaces,2005,46:7-19.
[73]Davies J. T, Rideal E. K, Interfacial Phenomena[M], Academic Press, New York,1963,265.
[74]Barbara G M, Maria P, Studies of lipid interaction in mixed Langmuir monolayers [J]. Thin Solid Film,2008,516:8865-8872.
[75]Ronzon, F., Desbat, B., Chauvet, J. P., Roux, B. Behavior of a GPI-anchored protein in phospholipid monolayers at the air-water interface. Biochim Biophys Acta.2002,18,1560(1-2):1-13.
[76]Li, X. M., Momsen, M. M., Smaby, J. M., Brockman, H. L.;Brown, R. E.Cholesterol decreases the interfacial elasticity and detergent solubility of sphingomyelins.
[77]Kodama, M.; Shibata, O.; Nakamura, S.; Lee, S.; Sugihara, G. A monolayer study on three binary mixed systems of dipalmitoylphosphatidylcholine with cholesterol, cholestanol and stigmasterol Colloids and Surfaces B:Biointerfaces.2004,33, (3-4):211-226
[78]孙润广,郝长春,常怡光,张静,牛春玲.鞘氨醇与DPPC,DPPE单层膜的热力学特性及形态观察[J].化学学报,2009,67：1808-1814.
[79]Joos P. Theory on the collapse pressure of mixed insoluble monolayers with miscible components [J]. Bulletin des Societes Chimiques Belges 1969,78:3-4.
[80]Nagadome S, Suzuki NS, Mine Y, Yamaguchi T, Nakahara H, Shibata O, Chang CH, Sugihara G. Monolayers (Langmuir films) behavior of multi-component systems composed of a bile acid with different sterols and with their 1:1 mixtures. Colloids and Surfaces B:Biointerfaces,2007,58(2):121-136
[81]L.M. Ilhareo, A. R. Gareia, A. M. Fidalgo, R. Barros, A. F. Vale, J. Lopes da Silva, A. M. Goncalves da Silva. A Transmission FTIR Spectroscoic Study on Mixed Langmuir-Blodgett Films of Cadmium Heptadecanoate-Chloro/ Bromohexadec ane [J]. Langmuir,1995,11:2745-2750.
[82]A. M. Goncalves da Silva, J. C. Guerreiro, N. G. Rodrigues, T. O. Rodrigues. Mixed Monolayers of Heptadecanoic Acid with Chlorohexadecane and Bromohexadecane:Effeets of Temperature and of Metal Ionsin the Subphase [J]. Langmuir,1996,12(18):4442-4448
[83]Aneliya N. Zdravkova, J. P. J. M. van der Eerden. Phase behavior in binary mixed Langmuir Blodgett monolayers of triglyeerides [J]. Journal of Crystal Growth, 2007,307(1):192-202.
[84]隋森芳.膜分子生物学[M].北京,高等教育出版社,2003,420.
[85]常怡光,孙润广,郝长春.磷酯酰乙醇胺与硬脂酸、十八醇二元混合系统单层膜的热力学特性和AFM观测[J].高等学校化学学报,2010,31(3)：559-565.
[86]AnaC. T. Teixeira, Anabela C. Femandes, AnaR. Gareia, Laura M. Ilhareo, Pedr Brogueira, Amelia M. P. S., Goncalves da Silva. Microdomains in mixed monolayers of oleanolic and stearic acids:thermodynamic study and BAM observation at the air-water interface and AFM and FTIR analysis of LB monolayers [J]. Chemistry and Physics of Lipids,2007,149(1-2):1-13.
[87]G. Brezesinski, D. Vollhardt, K. Iimura, H. Colfen. Struetural Features of Mixed Monolayers of Oleanolic Acid and Stearic Aeid[J]. The Journal of Physical Chemistry C,2008,112(40):15777-15783.
[88]Gerald Brezesinski, Dieter Vollhardt. Model Studies of the Interfacial Ordering of Oleanolic Acid in the Cuticula [J]. Chem. Phys. Chem.,2008,9 (12):1670-167.
[89]JonHoly, Oksana Kolomitsyna, Dmytro Krasutsky, Paulo J. Oliveira, Edward Perkins, Pavel A. Krasutsky. Dimethylaminopyridine derivatives of lupane triterpenoids are potent disruptors of mitochondrial structure and fuction [J]. Bioorganic & Medicinal Chemistry,2010,18(16):6080-6088
[90]Slim Azouzi, Karim El Kirat, Sandrine Moranda. The Potent Antimalarial Drug Cyelosporin A Preferentially Destabilizes Sphingomyelin-Rich Membranes [J]. Langmuir,2010,26(3):1960-1965.
[91]M.l.Sandez Maeho, A. Gil Gonzalez, A.Suarez Varela. Mixed Monolayers of Cyclosporin-A and Phospholipids at the Air-Water interface [J]. Journal of Colloid and Interface Seienee,2001,235(2):241-246
[92]Katarzyna Hac-Wydro, Patrycja Dynarowicz-Latka. Interaction between nystatin and natural membrane lipids in Langmuir monolayers. The role of a phospholipid in the mechanism of Polyenes mode of action [J]. Biophysical Chemistry,2006, 123(2-3):154-161.
[93]Seoane R, Minones J, Conde O, Iribarnegray E, Casas M. Interactions between Amphotericin B and Sterols in Monolayers. Mixed Films of Amphotericin B-Cholesterol [J]. Langmuir 1999,15:5567-5573
[94]P. Dynarowicz-Latka, R. Seoane, J. Minones Jr., M. Velo, J. Minones. Study of Penetration of amphoteriein B into cholesterol or ergosterol containing dipalmitoyl phosphatidylcholine Langmuir monolayers [J].Colloids and Surfaees B:Biointerfaees,2003,27(2-3):249-263.
[95]J. Minones, Jr, J. Minones, O. Conde, J. M. Rodriguez Patino, P. Dynarowiez-Latka. Mixed Monolayers of Amphoteriein B-Dipalmitoyl Phosphatidyl Choline: Study of Complex Formation [J]. Langmuir,2002,18(7):2817-2827.
[96]Ling-yun Zhao, Si-Shen Feng. Effeets of lipid chain length on molecular interactions between paclitaxel and phospholipid within model biomembranes [J]. Journal of Colloid and Interfaee Seienee,2004,274(1):55-68.
[97]Tzung-Han Chou, I-Ming Chu, Chien-Hsiang Chang. Interaction of paclitaxel with DSPC in monolayers at the air/water interface at different temperatures [J]. Colloids and Surfaces B:Biointerfaees,2002,25(2):147-155.