微波辅助快速制备碳量子点及其对表没食子儿茶素-3-没食子酸酯的促氧化作用
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摘要
利用高通量微波消解/萃取工作站快速制备水溶性碳量子点,研究碳量子点的pH值依赖性和稳定性,探讨表没食子儿茶素-3-没食子酸酯(epigallocatechin-3-gallate,EGCG)在Cu~(2+)存在条件下产生的活性氧自由基对碳量子点荧光探针的猝灭作用及EGCG与Cu~(2+)的促氧化剂量-效应关系。结果表明:碳量子点具有pH值依赖性和良好的稳定性,相对量子产率为73.67%;Cu~(2+)与EGCG的浓度比达到2∶1时,碳量子点荧光探针的猝灭更严重,EGCG的促氧化效果更好。该研究可为EGCG作为功能性物质的应用提供理论依据。
Aqueous carbon quantum dots were prepared rapidly by high-throughput microwave digestion/extraction workstation, and their pH dependence and stability behavior were studied. The fluorescence quenching of carbon quantum dots by reactive oxygen species produced by epigallocatechin-3-gallate(EGCG) in the presence of Cu~(2+) and the pro-oxidative dose-effect of EGCG with Cu~(2+) were investigated. Experimental results indicated that the carbon quantum dots had pH dependence and good stability behavior. The relative quantum yield was 73.67%. When the concentration ratio between Cu~(2+) and EGCG was 2:1, the fluorescence quenching of carbon quantum dots was serious, and EGCG had strong pro-oxidative activity. This study provides a theoretical basis for the application of EGCG as a functional substance.
Aqueous carbon quantum dots were prepared rapidly by high-throughput microwave digestion/extraction workstation, and their pH dependence and stability behavior were studied. The fluorescence quenching of carbon quantum dots by reactive oxygen species produced by epigallocatechin-3-gallate(EGCG) in the presence of Cu~(2+) and the pro-oxidative dose-effect of EGCG with Cu~(2+) were investigated. Experimental results indicated that the carbon quantum dots had pH dependence and good stability behavior. The relative quantum yield was 73.67%. When the concentration ratio between Cu~(2+) and EGCG was 2:1, the fluorescence quenching of carbon quantum dots was serious, and EGCG had strong pro-oxidative activity. This study provides a theoretical basis for the application of EGCG as a functional substance.
引文
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[29]ZHENG L F,WEI Q Y,CAI Y J,et al.DNA damage induced by resveratrol and its synthetic analogues in the presence of Cu(II)ions:mechanism and structure-activity relationship[J].Free Radical Biology and Medicine,2006,41(12):1807-1816.DOI:10.1016/j.freeradbiomed.2006.09.007.
[30]BARRETO G,MADUREIRA D,CAPANI F,et al.The role of catechols and free radicals in benzene toxicity:an oxidative DNAdamage pathway[J].Environmental and Molecular Mutagenesis,2009,50(9):771-780.DOI:10.1002/em.20500.
[2]REN X L,LIU J,MENG X W,et al.Synthesis of ultra-stable fluorescent carbon dots from polyvinylpyrrolidone and their application in the detection of hydroxyl radicals[J].Chemistry-An Asian Journal,2014,9(4):1054-1059.DOI:10.1002/asia.201301419.
[3]WANG Y,ZHUANG Q,NI Y.Facile microwave-assisted solidphase synthesis of highly fluorescent nitrogen-sulfur-codoped carbon quantum dots for cellular imaging applications[J].Chemistry a European Journal,2015,21(37):13004-13011.DOI:10.1002/chem.201501723.
[4]YANG C S,WANG X,LU G,et al.Cancer prevention by tea:animal studies,molecular mechanisms and human relevance[J].Nature Reviews Cancer,2009,9(6):429-439.DOI:10.1038/nrc2641.
[5]GORDON N C,WAREHAM D W.Antimicrobial activity of the green tea polyphenol(-)-epigallocatechin-3-gallate(EGCG)against clinical isolates of Stenotrophomonas maltophilia[J].International Journal of Antimicrobial Agents,2010,36(2):129-131.DOI:10.1016/j.ijantimicag.2010.03.025.
[6]SINGH B N,SHANKAR S,SRIVASTAVA R K.Green tea catechin,epigallocatechin-3-gallate(EGCG):mechanisms,perspectives and clinical applications[J].Biochemical Pharmacology,2011,82(12):1807-1821.DOI:10.1016/j.bcp.2011.07.093.
[7]XIONG C W,LIU C H,PAN W J,et al.Non-destructive determination of total polyphenols content and classification of storage periods of iron buddha tea using multispectral imaging system[J].Food Chemistry,2015,176:130-136.DOI:10.1016/j.foodchem.2014.12.057.
[8]CHEN R,WANG J B,ZHANG X Q,et al.Green tea polyphenol epigallocatechin-3-gallate(EGCG)induced intermolecular crosslinking of membrane proteins[J].Archives of Biochemistry and Biophysics,2011,507(2):343-349.DOI:10.1016/j.abb.2010.12.033.
[9]FARHAN M,KHAN H Y,OVES M,et al.Cancer therapy by catechins involves redox cycling of copper ions and generation of reactive oxygen species[J].Toxins,2016,8(2):1-10.DOI:10.3390/toxins8020037.
[10]BANDELE O J,OSHEROFF N.(-)-Epigallocatechin gallate,a major constituent of green tea,poisons human type II topoisomerases[J].Chemical Research Toxicology,2008,21(4):936-943.DOI:10.1021/tx700434v.
[11]NISHIKAWA H,KITANI S.Tea catechins have dual effect on mast cell degranulation induced by compound 48/80[J].International Immunopharmacology,2008,8(9):1207-1215.DOI:10.1016/j.intimp.2008.04.010.
[12]任婧,张献清,邢艳菲,等.茶多酚表没食子儿茶素-3-没食子酸酯对红细胞膜的促氧化作用[J].第四军医大学学报,2009,30(19):1947-1949.
[13]陈怡君,熊立瑰,黄建安,等.EGCG对细胞的促氧化作用研究进展[J].茶叶科学,2015,35(2):130-136.DOI:10.3969/j.issn.1000-369X.2015.02.006.
[14]EBARA M,FUKUDA H,HATANO R,et al.Relationship between copper,zinc and metallothionein in hepatocellular carcinoma and its surrounding liver parenchyma[J].Journal of Hepatology,2000,33(3):415-422.DOI:10.1016/S0168-8278(00)80277-9.
[15]BARATI A,SHAMSIPUR M,ABDOLLAHI H.Hemoglobin detection using carbon dots as a fluorescence probe[J].Biosensors and Bioelectronics,2015,71:470-475.DOI:10.1016/j.bios.2015.04.073.
[16]GEDDA G,LEE C Y,LIN Y C,et al.Green synthesis of carbon dots from prawn shells for highly selective and sensitive detection of copper ions[J].Sensors and Actuators B:Chemical,2016,224:396-403.DOI:10.1016/j.snb.2015.09.065.
[17]HOU J,LI H Y,WANG L,et al.Rapid microwave-assisted synthesis of molecularly imprinted polymers on carbon quantum dots for fluorescent sensing of tetracycline in milk[J].Talanta,2016,146:34-40.DOI:10.1016/j.talanta.2015.08.024.
[18]ZHU S,MENG Q,WANG L,et al.Highly photoluminescent carbon dots for multicolor patterning,sensors,and bioimaging[J].Angewandte Chemie-International Edition,2013,125(14):4045-4049.DOI:10.1002/anie.201300519.
[19]ZHANG Y Q,LIU X Y,FAN Y,et al.One-step microwave synthesis of N-doped hydroxyl-functionalized carbon dots with ultra-high fluorescence quantum yields[J].Nanoscale,2016,8(33):15281-15287.DOI:10.1039/c6nr03125k.
[20]PAN D Y,ZHANG J C,LI Z,et al.Hydrothermal route for cutting graphene sheets into blue-luminescent graphene quantum dots[J].Advanced Materials,2010,22(6):734-738.DOI:10.1002/adma.200902825.
[21]SHEN J H,ZHU Y H,CHEN C,et al.Facile preparation and upconversion luminescence of graphene quantum dots[J].Chemical Communcications,2011,47(9):2580-2582.DOI:10.1039/c0cc04812g.
[22]MOCHIZUKI M,YAMAZAKI S,KANO K,et al.Kinetic analysis and mechanistic aspects of autoxidation of catechins[J].Biochimica et Biophysica Acta,2002,1569(1/2/3):35-44.DOI:10.1016/S0304-4165(01)00230-6.
[23]AKAGAWA M,SHIGEMITSU T,SUYAMA K.Production of hydrogen peroxide by polyphenols and polyphenol-rich beverages under quasi-physiological conditions[J].Bioscience,Biotechnology and Biochemistry,2003,67(12):2632-2640.DOI:10.1271/bbb.67.2632.
[24]WEI J F,REN J,LIU J,et al.An eco-friendly,simple,and sensitive fluorescence biosensor for the detection of choline and acetylcholine based on C-dots and the Fenton reaction[J].Biosensors and Bioelectronics,2013,52:304-309.DOI:10.1016/j.bios.2013.09.006.
[25]SANG S,HOU Z,LAMBERT J D,et al.Redox properties of tea polyphenols and related biological activities[J].Antioxidants&Redox Signaling,2005,7(11/12):1704-1714.DOI:10.1089/ars.2005.7.1704.
[26]ZHANG L,BANDY B,DAVISON A J.Effects of metals,ligands and antioxidants on the reaction of oxygen with 1,2,4-benzenetriol[J].Free Radical Biology and Medicine,1996,20(4):495-505.DOI:10.1016/0891-5849(95)02089-6.
[27]OIKAWA S,FURUKAWA A,ASADA H,et al.Catechins induce oxidative damage to cellular and isolated DNA through the generation of reactive oxygen species[J].Free Radical Research,2003,37(8):881-890.DOI:10.1080/1071576031000150751.
[28]HAYAKAWA F,KIMURA T,MAEDA T,et al.DNA cleavage reaction and linoleic acid peroxidation induced by tea catechins in the presence of cupric ion[J].Biochimica et Biophysica Acta,1997,1336(2):123-131.DOI:10.1016/S0304-4165(97)00019-6.
[29]ZHENG L F,WEI Q Y,CAI Y J,et al.DNA damage induced by resveratrol and its synthetic analogues in the presence of Cu(II)ions:mechanism and structure-activity relationship[J].Free Radical Biology and Medicine,2006,41(12):1807-1816.DOI:10.1016/j.freeradbiomed.2006.09.007.
[30]BARRETO G,MADUREIRA D,CAPANI F,et al.The role of catechols and free radicals in benzene toxicity:an oxidative DNAdamage pathway[J].Environmental and Molecular Mutagenesis,2009,50(9):771-780.DOI:10.1002/em.20500.