Study of the enantioselective interaction of diclofop and human serum albumin by spectroscopic and molecular modeling approaches in vitro

Chirality

Volumn 25, Issue 11, 2013, Pages 719-725

  Zhang, Ping ^a   Li, Zhe ^a   Wang, Xinru ^a   Shen, Zhigang ^a   Wang, Yao ^a   Yan, Jin ^a   Zhu, Wentao ^a  

^a CHINA AGRICULTURAL UNIVERSITY   (China)

Author keywords

diclofop; enantioselectivity; fluorescence; human serum albumin; molecular modeling

Indexed keywords

2 [4 (2,4 DICHLOROPHENOXY)PHENOXY]PROPANOIC ACID; HUMAN SERUM ALBUMIN; PROPIONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING SITE; ENANTIOMER; ENANTIOSELECTIVITY; FLUORESCENCE SPECTROSCOPY; HYDROGEN BOND; HYDROPHOBICITY; IN VITRO STUDY; LIGHT ABSORPTION; MOLECULAR INTERACTION; MOLECULAR MODEL; PRIORITY JOURNAL; PROTEIN SECONDARY STRUCTURE; SIMULATION; STEADY STATE; THERMODYNAMICS; ULTRAVIOLET SPECTROSCOPY;

DICLOFOP; ENANTIOSELECTIVITY; FLUORESCENCE; HUMAN SERUM ALBUMIN; MOLECULAR MODELING;

BINDING SITES; HEK293 CELLS; HUMANS; MODELS, MOLECULAR; PHENYL ETHERS; PROPIONATES; PROTEIN STRUCTURE, SECONDARY; SERUM ALBUMIN; SPECTROMETRY, FLUORESCENCE; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 84886641731     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22204     Document Type: Article

References (25)

1. Diao J, Xu P, Wang P, Lu Y, Lu D, Zhou Z,. Environmental behavior of the chiral aryloxyphenoxypropionate herbicide diclofop-methyl and diclofop: enantiomerization and enantioselective degradation in soil. Environ Sci Technol 2010; 44: 2042-2047.
2. Palut D, Kostka G, Wiadrowska B, Bankowski R,. The effect of diclofop on some drug metabolizing enzymes in the liver of Wistar rats. Rocz Panstw Zakl Hig 2002; 53: 1-9 [in Polish].
3. Diao J, Xu P, Liu D, Lu Y, Zhou Z,. Enantiomer-specific toxicity and bioaccumulation of alpha-cypermethrin to earthworm Eisenia fetida. J Hazard Mater 2011; 192: 1072-1078.
4. Diao J, Xu P, Wang P, Lu D, Lu Y, Zhou Z,. Enantioselective degradation in sediment and aquatic toxicity to Daphnia magna of the herbicide lactofen enantiomers. J Agric Food Chem 2010; 58: 2439-2445.
5. Wang Q, Qiu J, Zhu W, Jia G, Li J, Bi C, Zhou Z,. Stereoselective degradation kinetics of theta-cypermethrin in rats. Environ Sci Technol 2006; 40: 721-726.
6. Zhang P, Dang Z, Shen Z, Zhu W, Xu X, Liu D, Zhou Z,. Enantioselective degradation of hexaconazole in rat hepatic microsomes in vitro. Chirality 2012; 24: 283-288.
7. Scollon EJ, Starr JM, Godin SJ, DeVito MJ, Hughes MF,. In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms. Drug Metab Dispos 2009; 37: 221-228.
8. Zhu W, Dang Z, Qiu J, Liu Y, Lv C, Diao J, Zhou Z,. Species differences for stereoselective metabolism of ethofumesate and its enantiomers in vitro. Xenobiotica 2009; 39: 649-655.
9. Ghuman J, Zunszain PA, Petitpas I, Bhattacharya AA, Otagiri M, Curry S,. Structural basis of the drug-binding specificity of human serum albumin. J Mol Biol 2005; 353: 38-52.
10. He XM, Carter DC,. Atomic structure and chemistry of human serum albumin. Nature 1992; 358: 209-215.
11. Varshney A, Sen P, Ahmad E, Rehan M, Subbarao N, Khan RH,. Ligand binding strategies of human serum albumin: how can the cargo be utilized? Chirality 2010; 22: 77-87.
12. Ding F, Li XN, Diao JX, Sun Y, Zhang L,. Chiral recognition of metalaxyl enantiomers by human serum albumin: evidence from molecular modeling and photophysical approach. Chirality 2012; 24: 471-480.
13. Monti S, Manet I, Manoli F, Sortino S,. Binding and photochemistry of enantiomeric 2-(3-benzoylphenyl)propionic acid (ketoprofen) in the human serum albumin environment. Photochem Photobiol Sci 2007; 6: 462-470.
14. Monti S, Manet I, Marconi G,. Combination of spectroscopic and computational methods to get an understanding of supramolecular chemistry of drugs: from simple host systems to biomolecules. Phys Chem Chem Phys 2011; 13: 20893-20905.
15. Shi D, Jin YX, Tang YH, Hu HH, Xu SY, Yu LS, Jiang HD, Zeng S,. Stereoselective binding of mexiletine and ketoprofen enantiomers with human serum albumin domains. Acta Pharmacol Sin 2012; 33: 710-716.
16. Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, Goodsell DS, Olson AJ,. AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. J Comput Chem 2009; 30: 2785-2791.
17. Lakowicz JR, Weber G,. Quenching of protein fluorescence by oxygen. Detection of structural fluctuations in proteins on the nanosecond time scale. Biochemistry 1973; 12: 4171-4179.
18. Barbero N, Barni E, Barolo C, Quagliotto P, Viscardi G, Napione L, Pavan S, Bussolino F,. A study of the interaction between fluorescein sodium salt and bovine serum albumin by steady-state fluorescence. Dyes Pigments 2009; 80: 307-313.
19. Ding F, Diao JX, Sun Y,. Bioevaluation of human serum albumin-hesperidin bioconjugate: insight into protein vector function and conformation. J Agric Food Chem 2012; 60: 7218-7228.
20. Carter WG, Tarhoni M, Rathbone AJ, Ray DE,. Differential protein adduction by seven organophosphorus pesticides in both brain and thymus. Hum Exp Toxicol 2007; 26: 347-354.
21. Noort D, Hulst AG, van Zuylen A, van Rijssel E, van der Schans MJ,. Covalent binding of organophosphorothioates to albumin: a new perspective for OP-pesticide biomonitoring? Arch Toxicol 2009; 83: 1031-1036.
22. Tarhoni MH, Lister T, Ray DE, Carter WG,. Albumin binding as a potential biomarker of exposure to moderately low levels of organophosphorus pesticides. Biomarkers 2008; 13: 343-363.
23. Peeples ES, Schopfer LM, Duysen EG, Spaulding R, Voelker T, Thompson CM, Lockridge O,. Albumin, a new biomarker of organophosphorus toxicant exposure, identified by mass spectrometry. Toxicol Sci 2005; 83: 303-312.
24. Soares S, Mateus N, Freitas V,. Interaction of different polyphenols with bovine serum albumin (BSA) and human salivary alpha-amylase (HSA) by fluorescence quenching. J Agric Food Chem 2007; 55: 6726-6735.
25. Ross PD, Subramanian S,. Thermodynamics of protein association reactions: forces contributing to stability. Biochemistry 1981; 20: 3096-3102.