Study on the interaction between active components from traditional Chinese medicine and plasma proteins
Tóm tắt
Traditional Chinese medicine (TCM), as a unique form of natural medicine, has been used in Chinese traditional therapeutic systems over two thousand years. Active components in Chinese herbal medicine are the material basis for the prevention and treatment of diseases. Research on drug-protein binding is one of the important contents in the study of early stage clinical pharmacokinetics of drugs. Plasma protein binding study has far-reaching influence on the pharmacokinetics and pharmacodynamics of drugs and helps to understand the basic rule of drug effects. It is important to study the binding characteristics of the active components in Chinese herbal medicine with plasma proteins for the medical science and modernization of TCM. This review summarizes the common analytical methods which are used to study the active herbal components-protein binding and gives the examples to illustrate their application. Rules and influence factors of the binding between different types of active herbal components and plasma proteins are summarized in the end. Finally, a suggestion on choosing the suitable technique for different types of active herbal components is provided, and the prospect of the drug-protein binding used in the area of TCM research is also discussed.
Tài liệu tham khảo
Wang ZG, Ren J (2002) Current status and future direction of Chinese herbal medicine. Trends Pharmacol Sci 23:347–348
Vuiginer K, Veuthey J, Carrupt P, Schappler J (2012) Characterization of drug–protein interactions by capillary electrophoresis hyphenated to mass spectrometry. Electrophoresis 33:3306–3315
Musteata FM, Pawliszyn J, Qian MG, Wu JT, Miwa GT (2006) Determination of drug plasma protein binding by solid phase microextraction. J Pharm Sci 95:1712–1722
Yang XN, Liu JY, Tang X (2008) Pharmacokinetics of salvianolic acids after intravenous injection, with and without Panax quinquefolium protopanaxadiol saponins, in rats. J Ethnopharmacol 3:408–414
Gonciarz A, Kus K, Szafarz M, Walczak M, Zakrzewska A, Szymura-Oleksiak J (2012) Capillary electrophoresis/frontal analysis versus equilibrium dialysis in dexamethasone sodium phosphate-serum albumin binding studies. Electrophoresis 33:3323–3330
Lohman JJHM, Merkus FWHM, Rahn KH (1986) Plasma protein binding of drugs. Pharm Weekblad 8:302–304
Buscher B, Laakso S, Mascher H, Pusecker K, Doig M, Dillen L, Wagner-Redeker W, Pfeifer T, Delrat P, Timmerman P (2014) Bioanalysis for plasma protein binding studies in drug discovery and drug development: views and recommendations of the European Bioanalysis Forum. Bioanalysis 6:673–682
Howard ML, Hill JJ, Galluppi GR, Mclean MA (2010) Plasma protein binding in drug discovery and development. Comb Chem High Throughput Screen 13:170–187
Jia HY, Yang GL, Li ZW, Xin PY, Zhao Y, Chen Y (2007) Micellar liquid chromatography with dodecyl dimethyl betaine as an in vitro method for prediction of protein-drug binding. J Chromatogr A 1143:88–97
Wen XD, Qi LW, Chen J, Song Y, Yi L, Yang XW, Li P (2007) Analysis of interaction property of bioactive components in Danggui Buxue Decoction with protein by microdialysis coupled with HPLC-DAD-MS. J Chromatogr B Anal Technol Biomed Life Sci 852:598–604
Jiang WY (2005) Therapeutic wisdom in traditional Chinese medicine: a perspective from modern science. Trends Pharmacol Sci 26:558–563
Bohnert T, Gan LS (2013) Plasma protein binding: from discovery to development. J Pharm Sci 102:2953–2994
Li M, Hagerman AE (2013) Interactions between plasma proteins and naturally occurring polyphenols. Curr Drug Metab 14:432–445
Schmidt S, Gonzalez D, Derendorf H (2010) Significance of protein binding in pharmacokinetics and pharmacodynamics. J Pharm Sci 99:1107–1122
Li HY, Chen ZX, Xu XJ, Sui XF, Guo T, Liu W, Zhang JW (2011) Predicting human plasma protein binding of drugs using plasma protein interaction QSAR analysis (PPI-QSAR). Biopharm Drug Dispos 32:333–342
Yang F, Zhang Y, Liang H (2014) Interactive association of drugs binding to human serum albumin. Int J Mol Sci 15:3580–3595
Trainor GL (2007) The importance of plasma protein binding in drug discovery. Expert Opin Drug Dis 2:51–64
Ascenzi P, Fanali G, Fasano M, Pallottini V, Trezza V (2014) Clinical relevance of drug binding to plasma proteins. J Mol Struct 1077:4–13
Zhivkova ZD (2015) Studies on drug–human serum albumin binding: the current state of the matter. Curr Pharm Des 21:1817–1830
He XM, Carter DC (1992) Atomic structure and chemistry of human serum albumin. Nature 358:209–215
Huang BX, Kim HY, Dass C (2004) Probing three-dimensional structure of bovine serum albumin by chemical cross-linking and mass spectrometry. J Amn Soc Mass Spectr 15:1237–1247
Vuignier K, Schappler J, Veuthey JL, Carrupt PA, Martel S (2010) Drug–protein binding: a critical review of analytical tools. Anal Bioanal Chem 398:53–66
Wan H, Rehngren M (2006) High-throughput screening of protein binding by equilibrium dialysis combined with liquid chromatography and mass spectrometry. J Chromatogr A 1102:125–134
Di L, Umland JP, Trapa PE, Maurer TS (2012) Impact of recovery on fraction unbound using equilibrium dialysis. J Pharm Sci 101:1327–1335
Liu ZQ, Jiang ZH, Chan K, Zhou H, Wong YF, Bian ZX, Liu L (2005) Pharmacokinetic interaction of paeoniflorin and sinomenine: pharmacokinetic parameters and tissue distribution characteristics in rats and protein binding ability in vitro. J Pharm Sci 99:381–391
Liu ZQ, Chan K, Zhou H, Jiang ZH, Wong YF, Xu HX, Liu L (2005) The pharmacokinetics and tissue distribution of sinomenine in rats and its protein binding ability in vitro. Life Sci 77:3197–3209
Wang YL, Yuan JF, Shang W, Zhang J, Zhang ZQ (2011) Dialysis sampling on-line coupled with high-performance liquid chromatography for simultaneous investigation of the interactions between multi-components in herbs and the albumin. Analyst 136:823–828
Talbi A, Zhao D, Liu Q, Li J, Fan A, Yang W, Han X, Chen X (2014) Pharmacokinetics, tissue distribution, excretion and plasma protein binding studies of wogonin in rats. Molecules 19:5538–5549
Kurz H, Trunk H, Weitz B (1977) Evaluation of methods to determine protein-binding of drugs. Equilibrium dialysis, ultrafiltration, ultracentrifugation, gel filtration. Arzneimittel-Forsch 27:1373–1380
Kochansky CJ, Mcmasters DR, Lu P, Koeplinger KA, Kerr HH, Shou M, Korzekwa KR (2008) Impact of pH on plasma protein binding in equilibrium dialysis. Mol Pharm 5:438–448
Curran RE, Claxton CR, Hutchison L, Harradine PJ, Martin IJ, Littlewood P (2011) Control and measurement of plasma pH in equilibrium dialysis: influence on drug plasma protein binding. Drug Metab Dispos 39:551–557
Banker MJ, Clark TH, Williams JA (2003) Development and validation of a 96-well equilibrium dialysis apparatus for measuring plasma protein binding. J Pharm Sci 92:967–974
Van LS, Morrison D, Sysmans L, Nelis P, Mortishire-Smith R (2011) Development and validation of a higher-throughput equilibrium dialysis assay for plasma protein binding. J Assoc Lab Autom 16:56–67
Xu XS, Rose A, Demers R, Eley T, Ryan J, Stouffer B, Cojocaru L, Arnold M (2014) Quantitative determination of free/bound atazanavir via high-throughput equilibrium dialysis and LC–MS/MS, and the application in ex vivo samples. Bioanalysis 23:3169–3182
Waters NJ, Jones R, Williams G, Sohal B (2008) Validation of a rapid equilibrium dialysis approach for the measurement of plasma protein binding. J Pharm Sci 97:4586–4595
Kim SB, Lee T, Lee HS, Song CK, Cho HJ, Kim DD, Maeng HJ, Yoon IS (2016) Development and validation of a highly sensitive LC–MS/MS method for the determination of acacetin in human plasma and its application to a protein binding study. Arch Pharm Res 39:213–220
Fortuna A, Alves G, Soaresdasilva P, Falcão A (2012) Optimization of a parallel artificial membrane permeability assay for the fast and simultaneous prediction of human intestinal absorption and plasma protein binding of drug candidates: application to dibenz [b, f] azepine-5-carboxamide derivatives. J Pharm Sci 101:530–540
Chen X, Murawski A, Patel K, Crespi CL, Balimane PV (2008) A novel design of artificial membrane for improving the PAMPA model. Pharm Res 25:1511–1520
Wu YF, Liu H, Ni JM (2011) Advances in parallel artificial membrane permeability assay and its applications. Acta Pharm Sin 46:890–895
Singh SP, Wahajuddin Tewari D, Jain GK (2011) PAMPA permeability, plasma protein binding, blood partition, pharmacokinetics and metabolism of formononetin, a methoxylated isoflavone. Food Chem Toxicol 49:1056–1062
Banker MJ, Clark TH (2008) Plasma/serum protein binding determinations. Curr Drug Metab 9:854–859
Wang C, Williams NS (2013) A mass balance approach for calculation of recovery and binding enables the use of ultrafiltration as a rapid method for measurement of plasma protein binding for even highly lipophilic compounds. J Pharm Biomed 75:112–117
Tang YH, Zhang SX, Lu Y, Zhu XW (2013) Analysis of plasma protein binding of sophoridine by ultrafiltration and high-performance liquid chromatography. Lat Am J Pharm 32:139–142
Tang YH, Zhu HY, Zhang YY, Huang CG (2006) Determination of human plasma protein binding of baicalin by ultrafiltration and high-performance liquid chromatography. Biomed Chromatogr 20:1116–1119
Zhao JY, Li L, Jiao FP, Ren FL (2014) Human plasma protein binding of water soluble flavonoids extracted from citrus peelsy. J Cent South Univ 21:2645–2651
Shen JM, Liu XY, Tang WJ, Wang J, Zhang HX (2012) Efficient isolation of catechins from green tea and characterization of interaction property of catechins with proteins by HPLC-UV/DAD combined with ultrafiltration. Med Chem Res 21:3549–3556
Chen Q, He H, Luo S, Xiong L, Li P (2012) A novel GC–MS method for determination of chrysophanol in rat plasma and tissues: application to the pharmacokinetics, tissue distribution and plasma protein binding studies. J Chromatogr B 973:76–83
Zhao G, Peng C, Du W, Wang S (2014) Simultaneous determination of imperatorin and its metabolites in vitro and in vivo by a GC–MS method: application to a bioavailability and protein binding ability study in rat plasma. Biomed Chromatogr BMC 28:947–956
Liang Y, Zhou YY, Liu YN (2013) Study on the plasma protein binding rate of Schisandra lignans based on the LC-IT-TOF/MS technique with relative quantitative analysis. Chin J Nat Med 11:442–448
Luo Y, Wu S, Li X, Li P (2010) LC-ESI-MS-MS determination of rat plasma protein binding of major flavonoids of Flos Lonicerae Japonicae by centrifugal ultrafiltration. Chromatographia 72:71–77
Li JM, Shi QW, Jiang Y, Liu Y (2015) Pretreatment of plasma samples by a novel hollow fiber centrifugal ultrafiltration technique for the determination of plasma protein binding of three coumarins using acetone as protein binding releasing agents. J Chromatogr B 1001:114–123
Zetterström T, Vernet L, Ungerstedt U, Tossman U, Jonzon B, Fredholm BB (1982) Purine levels in the intact rat brain. Studies with an implanted perfused hollow fibre. Neurosci Lett 29:111–115
Huang H, Zhang Y, Yang R, Tang X (2008) Determination of baicalin in rat cerebrospinal fluid and blood using microdialysis coupled with ultra-performance liquid chromatography-tandem mass spectrometry. J Chromatogr B 874:77–83
Wang HL, Zou HF, Feng AS, Zhang YK (1997) Binding of sulfamethoxazole to human serum albumin studied by a combined technique of microdialysis with liquid chromatography. Anal Chim Acta 342:159–165
Elmquist WF, Sawchuk RJ (2000) Use of microdialysis in drug delivery studies. Adv Drug Deliv Rev 45:123–124
Wang H, Zou H, Zhang Y (1998) Quantitative study of competitive binding of drugs to protein by microdialysis/high-performance liquid chromatography. Anal Chem 70:373–377
Yang XN, Wang YJ, Liu YS, Tang X (2008) Pharmacokinetics of salvianolic acids after intravenous injection, with and without Panax quinquefolium protopanaxadiol saponins, in rats. J Ethnopharmacol 117:408–414
Qian ZM, Wen XD, Li HJ, Liu Y, Qin SJ, Li P (2008) Analysis of interaction property of bioactive components in Flos Lonicerae Japonicae with protein by microdialysis coupled with HPLC-DAD-MS. Biol Pharm Bull 31:126–130
Guo M, Su X, Kong L, Li X, Zou H (2006) Characterization of interaction property of multicomponents in Chinese Herb with protein by microdialysis combined with HPLC. Anal Chim Acta 556:183–188
Chuang VT, Maruyama T, Otagiri M (2009) Updates on contemporary protein binding techniques. Drug Metab Pharmacokinet 24:358–364
Srikanth CH, Chaira T, Sampathi S, Sreekumar VB, Bambal RB (2013) Correlation of in vitro and in vivo plasma protein binding using ultracentrifugation and UPLC-tandem mass spectrometry. Analyst 138:6106–6116
Li QH, Cui MY, Sui XP, Li YJ (2008) Determination of protein bound fraction of serum of syringopicroside. J Harbin Univ Commer (Nat Sci Ed) 24:148–150
Hester P, Bosman IJ, Hermens JLM (2015) Sensitive determination of plasma protein binding of cationic drugs using mixed-mode solid-phase microextraction. J Pharm Biomed 115:534–542
Goryński K, Goryńska P, Górska A, Harężlak T, Jaroch A, Jaroch K, Lendor S, Skobowiat C, Bojko B (2016) SPME as a promising tool in translational medicine and drug discovery: from bench to bedside. J Pharm Biomed 130:55–67
Kramer NI, Eijkeren JCHV, Hermens JLM (2007) Influence of albumin on sorption kinetics in solid-phase microextraction: consequences for chemical analyses and uptake processes. Anal Chem 79:6941–6948
Theodoridis G (2006) Application of solid-phase microextraction in the investigation of protein binding of pharmaceuticals. J Chromatogr B 830:238–244
Musteata FM, Pawliszyn J, Qian MG, Wu JT, Miwa GT (2006) Determination of drug plasma protein binding by solid phase microextraction. J Pharm Sci 95:1712–1722
Vaes WHJ, Ramos EU, Verhaar HJM, Seinen W, Hermens JLM (1996) Measurement of the free concentration using solid-phase microextraction: binding to protein. Anal Chem 86:4463–4467
Aresta A, Grumo FD, Zambonin C (2016) Determination of major isoflavones in soy drinks by solid-phase micro extraction coupled to liquid chromatography. Food Anal Method 9:1–9
Dymerski T, Namieśnik J, Leontowicz H, Leontowicz M, Vearasilp K, Martinez-Ayala AL, González-Aguilar GA, Robles-Sánchez M (2016) Chemistry and biological properties of berry volatiles by two-dimensional chromatography, fluorescence and Fourier transform infrared spectroscopy techniques. Food Res Int 83:74–86
Hu L, Chen D (2009) Application of headspace solid phase microextraction for study of noncovalent interaction of borneol with human serum albumin. Acta Pharmacol Sin 30:1573–1576
Trtić-Petrović T, Liu JF, Jönsson JÅ (2005) Equilibrium sampling through membrane based on a single hollow fibre for determination of drug-protein binding and free drug concentration in plasma. J Chromatogr B 826:169–176
Fu H, Guan J, Bao JJ (2007) A hollow fiber solvent microextraction approach to measure drug-protein binding. Anal Sci 22:1565–1569
Hatami M, Farhadi K (2012) Application of hollow fiber-supported liquid-phase microextraction coupled with HPLC for the determination of guaifenesin enantiomer-protein binding. Biomed Chromatogr 26:875–880
Hu S, Zhang YJ, Bai XH (2011) Rapid and simultaneous study on drug-protein binding of four furocoumarins by hollow fiber liquid phase microextraction. Biomed Chromatogr 74:503–506
Xi GC, Hu S, Bai XH (2011) Simple and rapid hollow fiber liquid phase microextraction followed by high performance liquid chromatography method for determination of drug-protein binding. Chem Res Chin U 27:764–768
Hage DS, Jackson A, Sobansky MR, Schiel JE, Yoo MJ, Joseph KS (2009) Characterization of drug-protein interactions in blood using high-performance affinity chromatography. J Sep Sci 32:835–853
Vuignier K, Guillarme D, Veuthey JL, Carrupt PA, Schappler J (2013) High performance affinity chromatography (HPAC) as a high-throughput screening tool in drug discovery to study drug-plasma protein interactions. J Pharm Biomed 74:205–212
Xuan H, Joseph KS, Wa C, Hage DS (2010) Biointeraction analysis of carbamazepine binding to alpha1-acid glycoprotein by high-performance affinity chromatography. J Sep Sci 33:2294–2301
Yoo MJ, Smith QR, Hage DS (2009) Studies of imipramine binding to human serum albumin by high-performance affinity chromatography. J Chromatogr B 887:1149–1154
Mallik R, Yoo MJ, Chen S, Hage DS (2008) Studies of verapamil binding to human serum albumin by high-performance affinity chromatography. J Chromatogr B 876:69–70
Kim HS, Wainer IW (2008) Rapid analysis of the interactions between drugs and human serum albumin (HSA) using high-performance affinity chromatography (HPAC). J Chromatogr B 870:22–26
Li YF, Zhang XQ, Hu WY, Li Z, Liu PX, Zhang ZQ (2013) Rapid screening of drug-protein binding using high-performance affinity chromatography with columns containing immobilized human serum albumin. J Anal Methods Chem. https://doi.org/10.1155/2013/439039
Cai X, Zhang Y, Yu L, Guo Z, Zhang X, Liang X (2011) Detection of drug-human serum albumin binding ratios of two Chinese medicinal ingredients by high performance affinity chromatography. Chin J Chromatogr 29:358–367
Lei GH, Liu LT, Dai XJ, Wei YM, Gong BL (2010) Investigation on the competition interaction of ferulic acid and paeonol with human serum albumin by high-performance affinity chromatography. Acta Chim Sin 68:55–61
Anastos N, Barnett NW, Lewis SW (2005) Capillary electrophoresis for forensic drug analysis: a review. Talanta 67:269–279
Zhao X, You T, Liu J, Sun XH, Yan JL, Yang XR, Wang EK (2004) Drug-human serum albumin binding studied by capillary electrophoresis with electrochemiluminescence detection. Electrophoresis 25:3422–3426
Shibukawa A, Yoshimoto Y, Ohara T, Nakagawa T (1994) High-performance capillary electrophoresis/frontal analysis for the study of protein binding of a basic drug. J Pharm Sci 83:616–619
He XY, Ding YS, Li DZ, Lin BC (2004) Recent advances in the study of biomolecular interactions by capillary electrophoresis. Electrophoresis 25:697–711
Diniz A, Escuder-Gilabert L, Lopes NP, Villanueva-Camañas RM, Sagrado S, Medina-Hernández MJ (2008) Characterization of interactions between polyphenolic compounds and human serum proteins by capillary electrophoresis. Anal Bioanal Chem 391:625–632
Knjazeva T, Kaljurand M (2010) Capillary electrophoresis frontal analysis for the study of flavonoid interactions with human serum albumin. Anal Bioanal Chem 397:2211–2219
Zinellu A, Sotgia S, Scanu B, Pisanu E, Giordo R, Cossu A, Posadino AM, Carru C, Pintus G (2014) Evaluation of non-covalent interactions between serum albumin and green tea catechins by affinity capillary electrophoresis. J Chromatogr A 1367:167–171
Michalcová L, Glatz Z (2014) Comparison of various capillary electrophoretic approaches for the study of drug-protein interaction with emphasis on minimal consumption of protein sample and possibility of automation. J Sep Sci 38:325–331
Arnett SD, Osbourn DM, Moore KD, Vandaveer SS, Lunte CE (2005) Determination of 8-oxoguanine and 8-hydroxy-2′-deoxyguanosine in the rat cerebral cortex using microdialysis sampling and capillary electrophoresis with electrochemical detection. J Chromatogr B 817:16–25
Parrot S, Sauvinet V, Riban V, Depaulis A, Renaud B, Denoroy L (2004) High temporal resolution for in vivo monitoring of neurotransmitters in awake epileptic rats using brain microdialysis and capillary electrophoresis with laser-induced fluorescence detection. J Neurosci Methods 140:29–38
Ficheux A, Gayrard N, Szwarc I, Andress D, Soullier S, Duny Y, Goubert G, Thomas M, Bismuth-Mondolfo J, Daurès JP, Brunet P, Servel MF, Argilés A (2011) The use of SDS-PAGE scanning of spent dialysate to assess uraemic toxin removal by dialysis. Nephrol Dial Transpl 26:2281–2289
Zhang T, Gai Q, Qu F, Zhang Y (2011) Ionic liquid-assisted SDS-PAGE to improve human serum protein separation. Electrophoresis 20:2904–2910
Kanerva P, Sontagstrohm T, Lehtonen P (2005) Determination of prolamins in beers by ELISA and SDS-PAGE. J Inst Brew 111:61–64
Jeon YT, Ruzicka MR, Cho IK, Li QX, Kim SU (2011) Heating of freeze-dried protein samples with urea for SDS-PAGE in proteomics study. Appl Biol Chem 54:19–23
Kaldas MI, Walle UK, Van Der Woude H, Mcmillan JM, Walle T (2005) Covalent binding of the flavonoid quercetin to human serum albumin. J Agr Food Chem 53:4194–4197
Jian Y, Zheng HJ, Jin JJ, Guo P (2009) Fluorescence spectroscopy study on the interaction between Gossypol and bovine serum albumin. J Mol Struct 920:227–230
Seedher N, Bhatia S (2005) Mechanism of interaction of the non-steroidal antiinflammatory drugs meloxicam and nimesulide with serum albumin. J Pharm Biomed 39:257–262
Sułkowska A, Równicka J, Bojko B, Sułkowski W (2003) Interaction of anticancer drugs with human and bovine serum albumin. J Mol Struct 651–653:133–140
Surewicz WK, Mantsch HH, Chapman D (1999) Determination of protein secondary structure by Fourier transform infrared spectroscopy: a critical assessment. Biochemistry 32:389–394
Li Y, He W, Dong Y, Sheng F, Hu Z (2000) Human serum albumin interaction with formononetin studied using fluorescence anisotropy, FT-IR spectroscopy, and molecular modeling methods. Bioorgan Med Chem 14:1431–1436
Rowland A, Hallifax D, Nussio MR, Shapter JG, Mackenzie PI, Brian Houston J, Knights KM, Miners JO (2015) Characterization of the comparative drug binding to intra- (liver fatty acid binding protein) and extra- (human serum albumin) cellular proteins. Xenobiotica 45:1–11
Karlsson R, Fält A (1997) Experimental design for kinetic analysis of protein-protein interactions with surface plasmon resonance biosensors. J Immunol Methods 200:121–133
Bala C (2015) Surface plasmon resonance (SPR) biosensors in pharmaceutical analysis. Crit Rev Anal Chem 45:97–105
Patching SG (2014) Surface plasmon resonance spectroscopy for characterisation of membrane protein-ligand interactions and its potential for drug discovery. Biochim Biophys Acta 1838:43–55
Liu X, Song DQ, Zhang QL, Tian Y, Liu ZY, Zhang HQ (2006) Characterization of drug-binding levels to serum albumin using a wavelength modulation surface plasmon resonance sensor. Sens Actuators B Chem 117:188–195
Fabini E, Fiori GM, Tedesco D, Lopes NP, Bertucci C (2016) Surface plasmon resonance and circular dichroism characterization of cucurbitacins binding to serum albumins for early pharmacokinetic profiling. J Pharm Biomed 122:166–172
Vachali PP, Li B, Bartschi A, Bernstein PS (2015) Surface plasmon resonance (SPR)-based biosensor technology for the quantitative characterization of protein–carotenoid interactions. Arch Biochem Biophys 572:66–72
Vuignier K, Veuthey JL, Carrupt PA, Schappler J (2013) Global analytical strategy to measure drug-plasma protein interactions: from high-throughput to in-depth analysis. Drug Discov Today 18:1030–1034
Zhang Y, Shi S, Guo J, You Q, Feng D (2013) On-line surface plasmon resonance-high performance liquid chromatography–tandem mass spectrometry for analysis of human serum albumin binders from Radix Astragali. J Chromatogr A 1293:92–99
Lakowicz JR (1999) Principles of fluorescence spectroscopy, 2nd edn. Kluwer Academic Publishers/Plenum Press, New York
Zuo H, Tang L, Li S, Huang J (2015) Combined multispectroscopic and molecular docking investigation on the interaction between delphinidin-3-O-glucoside and bovine serum albumin. Luminescence 30:110–117
Bozoğlan BK, Tunç S, Duman O (2014) Investigation of neohesperidin dihydrochalcone binding to human serum albumin by spectroscopic methods. J Lumin 155:198–204
Li S, Huang K, Zhong M, Guo J, Wang WZ, Zhu R (2010) Comparative studies on the interaction of caffeic acid, chlorogenic acid and ferulic acid with bovine serum albumin. Spectrochim Acta A 77:680–686
Yang X, Ye Z, Yuan Y, Zheng Z, Shi J, Ying Y, Huang P (2013) Insights into the binding of paclitaxel to human serum albumin: multispectroscopic studies. Luminescence 28:427–434
Cheng Z, Liu R, Jiang X (2013) Spectroscopic studies on the interaction between tetrandrine and two serum albumins by chemometrics methods. Spectrochim Acta A 115:92–105
Gao W, Li N, Chen Y, Xu Y, Lin Y, Yin Y, Hu Z (2010) Study of interaction between syringin and human serum albumin by multi-spectroscopic method and atomic force microscopy. J Mol Struct 83:133–140
Maiti TK, Ghosh KS, Dasgupta S (2006) Interaction of (−)-epigallocatechin-3-gallate with human serum albumin: fluorescence, fourier transform infrared, circular dichroism, and docking studies. Proteins 64:355–362
Hegde AH, Sandhya B, Seetharamappa J (2011) Evaluation of binding and thermodynamic characteristics of interactions between a citrus flavonoid hesperitin with protein and effects of metal ions on binding. Mol Biol Rep 38:4921–4929
Matei I, Hillebrand M (2010) Interaction of kaempferol with human serum albumin: a fluorescence and circular dichroism study. J Pharm Biomed 51:768–773
Bhattacharyya J, Bhattacharyya M, Chakrabarty AS, Chaudhuri U, Poddar RK (1994) Interaction of chlorpromazine with myoglobin and hemoglobin. A comparative study. Biochem Pharmacol 47:2049–2053
Subramanyam R, Gollapudi A, Bonigala P, Chinnaboina M, Amooru DG (2009) Betulinic acid binding to human serum albumin: a study of protein conformation and binding affinity. J Photochem Photobiol B Biol 94:8–12
Zhang Y, Zhang GZ, Wang YM (2000) Studies of interaction of mitomycin C and serum albumin by spectrum method. J Anal Sci 16:445–449
Neelam S, GokaraM Sudhamalla B, Amooru DG, Subramanyam R (2010) Interaction studies of coumaroyltyramine with human serum albumin and its biological importance. J Phys Chem B 114:3005–3012
Subramanyam R, Goud M, Sudhamalla B, Reddeem E, Gollapudi A, Nellaepalli S, Yadavalli V, Chinnaboina M, Amooru DG (2009) Novel binding studies of human serum albumin with trans-feruloyl maslinic acid. J Photochem Photobiol B Biol 95:81–88
Xiao J, Cao H, Wang Y, Zhao J, Wei X (2009) Glycosylation of Dietary Flavonoids Decreases the Affinities for Plasma Protein. J Agr Food Chem 57:6642–6648
Leckband D (2000) Measuring the forces that control protein interactions. Annu Rev Biophys Biomol Struct 29:1–26
Ross PD, Subramanian S (1981) Thermodynamics of protein association reactions: forces contributing to stability. Biochemistry 20:3096–3102
Cheng X, Fan X, Jiang F, Liu Y, Lei K (2015) Resonance energy transfer, pH-induced folded states and the molecular interaction of human serum albumin and icariin. Luminescence 30:1026–1033
Förster T, Sinanoglu O (1966) Modern Quantum Chemistry. Academic Press, New York
Tang L, Zuo H, Shu L (2014) Comparison of the interaction between three anthocyanins and human serum albumins by spectroscopy. J Lumin 153:54–63
Zhang G, Wang L, Pan J (2012) Probing the binding of the flavonoid diosmetin to human serum albumin by multispectroscopic techniques. J Agr Food Chem 60:2721–2729
Sheng F, Wang Y, Zhao X, Tian N, Hu H, Li P (2014) Separation and identification of anthocyanin extracted from mulberry fruit and the pigment binding properties toward human serum albumin. J Agr Food Chem 62:6813–6819
Yuan JL, Lv Z, Liu ZG, Hu Z, Zou GL (2007) Study on interaction between apigenin and human serum albumin by spectroscopy and molecular modeling. J Instrum Anal 191:104–113
Kanakis CD, Tarantilis PA, Polissiou MG, Diamantoglou S, Tajmir-Riahi HA (2006) Antioxidant flavonoids bind human serum albumin. J Mol Struct 798:69–74
Tang JH. Study on interaction of several organic small molecules substances with human serum albumin. PhD thesis. Lanzhou University: College of Chemistry and Chemical Engineering. 2006
Haris PI, Severcan F (1999) FTIR spectroscopic characterization of protein structure in aqueous and non-aqueous media. J Mol Catal B Enzym 7:207–221
Tang J, Luan F, Chen X (2006) Binding analysis of glycyrrhetinic acid to human serum albumin: fluorescence spectroscopy, FTIR, and molecular modeling. Bioorgan Med Chem 14:3210–3217
Greenfield NJ, Fasman GD (1969) Computed circular dichroism spectra for the evaluation of protein conformation. Biochemistry 10:4108–4116
Liu BM, Zhang J, Hao AJ, Xu L, Wang D, Ji H, Sun SJ, Chen BQ, Liu B (2015) The increased binding affinity of curcumin with human serum albumin in the presence of rutin and baicalin: a potential for drug delivery system. Spectrochim Acta A 155:88–94
Poór M, Li Y, Kunsági-Máté S, Petrik J, Vladimir-Knežević S, Kőszegi T (2013) Molecular displacement of warfarin from human serum albumin by flavonoid aglycones. J Lumin 142:122–127
Bari LD, Ripoli S, Pradhan S, Salvadori P (2010) Interactions between quercetin and Warfarin for albumin binding: a new eye on food/drug interference. Chirality 22:593–596
Soligard HT, Bratlid D, Cao C, Liang A, Nilsen OG (2011) Displacement of Bilirubin from Albumin in Plasma from Jaundiced Newborns. An in vitro study of purified Chinese herbal constituents and sulfisoxazole. Phytother Res 25:1068–1072
Sun B, Gou Y, Xue Z, Zheng X, Ma Y, Hu F, Zhao W (2016) Protections of bovine serum albumin protein from damage on functionalized graphene-based electrodes by flavonoids. Mater Sci Eng C 62:197–205
Daneshegar P, Moosavimovahedi AA, Norouzi P, Reza GM, Mohammad F, Nader S (2012) Characterization of paracetamol binding with normal and glycated human serum albumin assayed by a new electrochemical method. J Brazil Chem Soc 23:315–321
Tang DP, Yuan R, Chai YQ (2006) Novel immunoassay for carcinoembryonic antigen based on protein A-conjugated immunosensor chip by surface plasmon resonance and cyclic voltammetry. Bioprocess Biosyst Eng 28:315–321
Gowda JI, Nandibewoor ST (2014) Binding and conformational changes of human serum albumin upon interaction with 4-aminoantipyrine studied by spectroscopic methods and cyclic voltammetry. Spectrochim Acta A 124:397–403
Um HJ, Kim M, Lee SH, Min J, Kim H, Choi YW, Kim YH (2011) Electrochemically oriented immobilization of antibody on poly-(2-cyano-ethylpyrrole)-coated gold electrode using a cyclic voltammetry. Talanta 84:330–334
Xiao CQ, Jiang FL, Zhou B, Li R, Liu Y (2011) Interaction between a cationic porphyrin and bovine serum albumin studied by surface plasmon resonance, fluorescence spectroscopy and cyclic voltammetry. Photochem Photobio Sci 10:1110–1117
Freitas PG, Barbosa AF, Saraiva LA, Camps I, Silveiraand NJFD, Veloso MP, Santors MH, Schneedorf JM (2012) Mangiferin binding to serum albumin is non-saturable and induces conformational changes at high concentrations. J Lumin 132:3027–3034
Ni Y, Zhang X, Kokot S (2009) Spectrometric and voltammetric studies of the interaction between quercetin and bovine serum albumin using warfarin as site marker with the aid of chemometrics. Spectrochim Acta A 71:1865–1872
Saboury AA (2006) A review on the ligand binding studies by isothermal titration calorimetry. J Iran Chem Soc 3:1–21
Callies O, Daranas AH (2016) Application of isothermal titration calorimetry as a tool to study natural product interactions. Nat Prod Rep 33:881–904
Liang Y (2008) Applications of isothermal titration calorimetry in protein science. Acta Biochim et Biophys Sin 40:565–576
Grolier JPE, Rio JMD (2012) Isothermal titration calorimetry: a thermodynamic interpretation of measurements. J Chem Thermodyn 55:193–202
Zhao Q, Xu XY, Sun XJ, Liu M, Sun DZ, Li LW (2009) A calorimetric study on interactions of colchicine with human serum albumin. J Mol Struct 931:31–34
Li X, Hao Y (2015) Probing the binding of (+)-catechin to bovine serum albumin by isothermal titration calorimetry and spectroscopic techniques. J Mol Struct 1091:109–117
Bruylants G, Wouters J, Michaux C (2005) Differential scanning calorimetry in life science: thermodynamics, stability, molecular recognition and application in drug design. Curr Med Chem 12:2011–2020
Celej MS, Dassie SA, González M, Bianconi ML, Fidelio GD (2006) Differential scanning calorimetry as a tool to estimate binding parameters in multiligand binding proteins. Anal Biochem 350:227–284
Burgos MI, Fernández RA, Celej MS, Rossi LI, Fidelio GD, Dassie SA (2011) Binding of the highly toxic tetracycline derivative, anhydrotetracycline, to bovine serum albumin. Biol Pharm Bull 34:1301–1306
Khan AY, Hossain M, Kumar GS (2013) Binding of plant alkaloids berberine and palmatine to serum albumins: a thermodynamic investigation. Mol Biol Rep 403:553–566
Hossain M, Khan AY, Kumar GS (2012) Study on the thermodynamics of the binding of iminium and alkanolamine forms of the anticancer agent sanguinarine to human serum albumin. J Chem Thermodyn 47:90–99
Pastukhov AV, Levchenko LA, Sadkov AP (2007) Spectroscopic study on binding of rutin to human serum albumin. J Mol Struct 842:60–66
Chen X, Qian K, Chen Q (2015) Comparison between loureirin A and cochinchinenin C on the interaction with human serum albumin. Eur J Med Chem 93:492–500
Shang Y, Li H (2010) Studies of the interaction between apigenin and bovine serum albumin by spectroscopic methods. Russ J Gen Chem 80:1710–1717
Jin J, Zhu J, Yao X, Wu L (2007) Study on the binding of farrerol to human serum albumin. J Photochem Photobiol A Chem 191:59–65
Wang J, Wang Q, Wu D, Yan J, Wu Y, Li H (2015) Comparative studies on the interactions of baicalein and Al(III)-baicalein complex with human serum albumin. Luminescence 31:54–62
Li S, Tang L, Bi H (2016) Study on the interaction between pelargonidin-3-O-glucoside and bovine serum albumin using spectroscopic, transmission electron microscopy and molecular modeling techniques. Luminescence 31:442–452
Caruso ÍP, Vilegas W, Fossey MA, Cornélio ML (2012) Exploring the binding mechanism of Guaijaverin to human serum albumin: fluorescence spectroscopy and computational approach. Spectrochim Acta A 97:449–455
Marszalek M, Konarska A, Szajdzinskapietek E, Wolszczak M (2013) Interaction of cationic protoberberine alkaloids with human serum albumin. No spectroscopic evidence on binding to Sudlow’s site 1. J Phys Chem B 117:15987–15993
Zhang HM, Fei ZH, Tang BP, Chen J, Tao WH, Wang YQ (2012) The interaction of blood proteins with brucine. Mol Biol Rep 39:4937–4947
Hu YJ, Chen CH, Zhou S, Bai AM, Yu OY (2012) The specific binding of chlorogenic acid to human serum albumin. Mol Biol Rep 39:2781–2787
Liu MH, Zou W, Fan LD, Li PB, Su WW (2012) Comparative protein binding of naringin and its aglycone naringenin in rat, dog and human plasma. Afr J Pharm Pharm 6:934–940
Cahyana Y, Gordon MH (2013) Interaction of anthocyanins with human serum albumin: influence of pH and chemical structure on binding. Food Chem 141:2278–2285
Zhu CJ, Zhang JT (2009) Stereoselective plasma protein binding and target tissue distribution of clausenamide enantiomers in rats. Chirality 21:402–406
Sun DL, Huang SD, Wu PS, Li J, Ye YJ, Jiang HD (2010) Stereoselective protein binding of tetrahydropalmatine enantiomers in human plasma, HSA, and AGP, but not in rat plasma. Chirality 22:618–623
Gu Y, Wang G, Sun J, Jia Y, Xu M, Wang W (2006) In vitro assessment of plasma protein binding of 20(R)-ginsenoside Rh2 by equilibrium dialysis and LC-MS analysis: a case of species differences. Biol Pharm Bull 29:951–956
Colclough N, Ruston L, Wood JM, Macfaul PA (2006) Species differences in drug plasma protein binding. MedChemComm 5:963–967