荧光探针法检测活性羰基化合物甲醛的研究进展
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摘要
活性羰基化合物广泛存在于生物体内,参与维持人体内稳态平衡,当其水平发生变化,会导致机体发生病理变化产生疾病。甲醛(FA)作为结构最简单的活性醛基化合物,含有反应活性极高的羰基,化学性质活泼,被认为是人类的自然毒物和致癌物。设计合成用于检测生物体内甲醛的探针,对探究甲醛的生理、病理的研究以及疾病诊断和控制等方面具有重大意义。荧光探针具有实时性、灵敏度高、选择性好、生理学毒性低等优点,使得其在甲醛的检测上有很大优势。因此,发展利用荧光探针对甲醛进行检测得到了广泛的重视。文中对识别甲醛的小分子荧光探针作了概述,将探针分子识别甲醛的机理进行了归纳总结(Aza-cope重排、NHNH2和NH2与甲醛的反应及其他反应类型),对探针的设计思路、识别机理以及生物应用等方面进行了论述,并展望了测定甲醛荧光探针的设计思路和应用前景。
The active carbonyl compound,existing widely in the organism,is involved in maintaining the homeostasis of the human body. When its level changes,it would lead to pathological changes and produce diseases. Formaldehyde( FA),as one of the simplest active aldehydes with active chemical properties,is considered as a natural poison and carcinogen of human being due to its highly reactive carbonyl groups. Therefore,designing and synthesizing some probe for detecting formaldehyde in biological bodies has great importance to explore the physiological and pathological studies of formaldehyde and diagnosis and control of related diseases. Fluorescence probe has great advantages in formaldehyde detection owing to its real-time feature,high sensitivity,good selectivity and low physiological toxicity. Thus,the development and application of fluorescence detection of formaldehyde are extensively concerned and studied. In this review,the fluorescence probes for the recognition of formaldehyde are summarized. The mechanism of formaldehyde recognition is summarized into four categories: Aza-cope rearrangement,reaction of NHNH2 and NH2 with formaldehyde and other types of reaction. The design idea,recognition mechanism and biological application of these probes are reviewed,and the design idea and application prospect of formaldehyde fluorescent probe are also prospected.
The active carbonyl compound,existing widely in the organism,is involved in maintaining the homeostasis of the human body. When its level changes,it would lead to pathological changes and produce diseases. Formaldehyde( FA),as one of the simplest active aldehydes with active chemical properties,is considered as a natural poison and carcinogen of human being due to its highly reactive carbonyl groups. Therefore,designing and synthesizing some probe for detecting formaldehyde in biological bodies has great importance to explore the physiological and pathological studies of formaldehyde and diagnosis and control of related diseases. Fluorescence probe has great advantages in formaldehyde detection owing to its real-time feature,high sensitivity,good selectivity and low physiological toxicity. Thus,the development and application of fluorescence detection of formaldehyde are extensively concerned and studied. In this review,the fluorescence probes for the recognition of formaldehyde are summarized. The mechanism of formaldehyde recognition is summarized into four categories: Aza-cope rearrangement,reaction of NHNH2 and NH2 with formaldehyde and other types of reaction. The design idea,recognition mechanism and biological application of these probes are reviewed,and the design idea and application prospect of formaldehyde fluorescent probe are also prospected.
引文
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[12] NIKI E. Lipid peroxidation:Physiological levels and dual biological effects[J]. Free Radical Biology and Medicine,2009,47:469-484.
[13] METZ T O,ALDERSON N L,THORPE S R,et al.Pyridoxamine,an inhibitor of advanced glycation and lipoxidation reactions:A novel therapy for treatment of diabetic complications[J]. Archives of Biochemistry and Biophysics,2003,419:41-49.
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[15] TURK Z. Glycotoxines,carbonyl stress andrelevance todiabetes and its complications[J]. Physiological Research,2010,59:147-156.
[16] ONYANGO A N. Small reactive carbonyl compounds as tissue lipid oxidation products,and the mechanisms of their formation thereby[J]. Chemistry and Physics of Lipids,2012,165:777-786.
[17] KALAPOS M P. Where does plasma methylglyoxal originate from[J]. Diabetes Research and Clinical Practice,2013,99:260-271.
[18] SEMCHYSHYN H M. Reactive carbonyl species in vivo:Generation and dual biological effects[J]. The Scientific World Journal,2014,2014:1-10.
[19] GUGLIUCCI A. Glycation as the glucose link to diabetic complications[J]. The Journal of the American Osteopathic Association,2000,100:621-634.
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[22] PICKLO M J,MONTINE T J,AMARNATH V,et al.Carbonyl toxicology and Alzheimer's disease[J].Toxicology and Applied Pharmacology,2002,184:187-197.
[23] BOURAJJAJ M,STEHOUWER C D A,VAN HINSBERGH V W M,et al. Role of methylglyoxal adducts in the development of vascular complications in diabetes mellitus[J]. Biochemical Society Transactions,2003,31:1400-1402.
[24] CHANG T,WU L. Methylglyoxal,oxidative stress,and hypertension[J]. Canadian Journal of Physiology and Pharmacology,2006,84:1229-1238.
[25] FORMAN H J,FUKUTO J M,MILLER T,et al. The chemistry of cell signaling by reactive oxygen and nitrogen species and 4-hydroxynonenal[J]. Archives of Biochemistry and Biophysics,2008,477:183-195.
[26] LITEPLO R,BEAUCHAMP R,MEEK M,CHENIER R. Formaldehyde(Concise International Chemical Assessment Documents)[M]. Geneva:World Health Organization,2002.
[27] BAAN R,GROSSE Y,STRAIF K,et al. A review of human carcinogens-Part F:Chemical agents and related occupations[J]. Lancet Oncology,2009,10(12):1143-1144.
[28] ZHANG L,STEINMAUS C,EASTMOND D A,et al.Formaldehyde exposure and leukemia:A new meta-analysis and potential mechanisms[J]. Mutation Research/Reviews in Mutation Research, 2009,681:150-168.
[29] SALTHAMMER T,MENTESE S,MARUTZKY R.Formaldehyde in the indoor environment[J]. Chemical Reviews,2010,110:2536-2572.
[30] SONGUR A,OZEN O A,SARSILMAZ M. The toxic effects of formaldehyde on the nervous system[J].Reviews of Environmental Contamination&Toxicology,2010,203:105-118.
[31] TULPULE K,HOHNHOLT M C,DRINGEN R. Formaldehyde metabolism and formaldehyde-induced stimulation of lactate production and glutathione export in cultured neurons[J]. Journal of Neurochemistry,2013,125:260-272.
[32] UNAETA M,SOLE M,BOADA M,et al. Characterization of A7r5 cell line transfected in a stable form by h SSAO/VAP-1 gene(A7r5 h SSAO/VAP-1 cell line)[J]. Journal of Neural Transmission,2007,114:857-862.
[33] TULPULE K,DRINGEN R. Formaldehyde in brain:an overlooked player in neurodegeneration[J]. Journal of Neurochemistry,2013,127:7-21.
[34] EBELER S E,CLIFFORD A J,SHIBAMOTO T. Quantitative analysis by gas chromatography of volatile carbonyl compounds in expired air from mice and human[J]. Journal of Chromatography B:Biomedical Sciences and Applications,1997,702:211-215.
[35] SONGUR A,OZEN O A,SARSILMAZ M. The toxic effects of formaldehyde on the nervous system[J].Reviews of Environmental Contamination and Toxicology,2010,203:105-118.
[36] HAUPTMANN M,STEWART P A,LUBIN J H,et al.Mortality from lymphohematopoietic malignancies and brain cancer among embalmers exposed to formaldehyde[J]. Journal of the National Cancer Institute,2011,101:1696-708.
[37] VOULGARIDOU G P,ANESTOPOULOS I,FRANCO R,et al. DNA damage induced by endogenous aldehydes:current state of knowledge[J]. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis,2011,711:13-27.
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