Enantioselective toxicity of metolachlor to Scenedesmus obliquus in the presence of cyclodextrins

Chirality

Volumn 24, Issue 2, 2012, Pages 181-187

  Liu, Hui Jun ^a   Cai, Wei D ^a   Huang, Ruo N ^a   Xia, Hui L ^a   Wen, Yue Z ^b  

^a ZHEJIANG GONGSHANG UNIVERSITY   (China)

^b ZHEJIANG UNIVERSITY   (China)

Author keywords

Complexation; Cyclodextrin; Enantioselective toxicity; Metolachlor; Scenedesmus obliquus

Indexed keywords

ALPHA CYCLODEXTRIN; BETA CYCLODEXTRIN; CYCLODEXTRIN DERIVATIVE; METOLACHLOR;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; CONTROLLED STUDY; ECOSYSTEM RESTORATION; ECOTOXICITY; ENANTIOMER; ENANTIOSELECTIVITY; ENTHALPY; EQUILIBRIUM CONSTANT; MOLECULAR RECOGNITION; NONHUMAN; PRIORITY JOURNAL; SCENEDESMUS; SCENEDESMUS OBLIQUUS; THERMODYNAMICS; TOXICITY TESTING;

ACETAMIDES; ALPHA-CYCLODEXTRINS; BETA-CYCLODEXTRINS; CYCLODEXTRINS; FRESH WATER; HERBICIDES; SCENEDESMUS; STEREOISOMERISM; THERMODYNAMICS; TOXICITY TESTS, ACUTE;

EID: 84855508389     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.21981     Document Type: Article

References (36)

1. Szejtli J. Introduction and general overview of cyclodextrin chemistry. Chem Rev 1998;98:1743-1753. (Pubitemid 128633435)
2. Folch-Cano C, Jullian C, Speisky H, Olea-Azar C. Antioxidant activity of inclusion complexes of tea catechins with β-cyclodextrins by ORAC assays. Food Res Int 2010;43:2039-2044.
3. Cal K, Centkowska K. Use of cyclodextrins in topical formulations: practical aspects. Eur J Pharm Biopharm 2008;68:467-478. (Pubitemid 351318207)
4. Zhang AP, Liu WP, Wang LM, Wen YZ. Characterization of inclusion complexation between fenoxaprop-p-ethyl and cyclodextrin. J Agric Food Chem 2005;53:7193-7197.
5. Villaverde J, Morillo E, Pérez-Martínez JI, Ginézs JM, Maqueda C. Preparation and characterization of inclusion complex of norflurazon and β-cyclodextrin to improve herbicide formulations. J Agric Food Chem 2004;52:864-869.
6. Manolikar MK, Sawant MR. Study of solubility of isoproturon by its complexation with β-cyclodextrin. Chemosphere 2003;51:811-816. (Pubitemid 36396738)
7. Cai XY, Liu WP, Chen SW. Environmental effects of inclusion complexation between methylated α-Cyclodextrin and diclofop-methyl. J Agric Food Chem 2005;53:6744-6749.
8. Kamiya M, Kameyama K, Ishiwata S. Effects of cyclodextrins on photodegradation of organophosphorus pesticides in humic water. Chemosphere 2001;42:251-255.
9. Morillo E, Pérez-Martínez JI, Ginés JM. Leaching of 2, 4-D from a soil in the presence of β-cyclodextrin: laboratory columns experiments. Chemosphere 2001;44:1065-1069. (Pubitemid 32728984)
10. Sekhon BS. Chiral pesticides. J Pestic Sci 2009;34:1-12.
11. Liu WP, Gan JY, Schlenk D, Jury WA. Enantioselectivity in environmental safety of current chiral insecticides. PNAS 2005;102:701-706. (Pubitemid 40282729)
12. Garrison AW. Probing the enantioselectivity of chiral pesticides. Environ Sci Technol 2006;40:16-23. (Pubitemid 43069882)
13. Wen YZ, Li CD, Fang ZH, Zhuang SL, Liu WP. Elucidation of the enantioselective enzymatic hydrolysis of chiral herbicide dichlorprop methyl by chemical modification. J Agric Food Chem 2011;59:1924-1930.
14. Wen YZ, Chen H, Shen CS, Zhao MR, Liu WP. Enantioselectivity tuning of chiral herbicide dichlorprop by copper: roles of reactive oxygen species. Environ Sci Technol 2011;45:4778-4784.
15. Lewis DL, Garrison AW, Wommack KE, Whittemore A, Steudler P, Mellilo J. Influence of environmental changes on degradation of chiral pollutants in soils. Nature 1999;401:898-901. (Pubitemid 29518954)
16. Wen YZ, Yuan YL, Chen H, Xu DM, Lin KD, Liu WP. Effect of chitosan on the enantioselective bioavailability of the herbicide dichlorprop to Chlorella pyrenoidosa. Environ Sci Technol 2010;44:4981-4987.
17. Szegvaari D, Zelkó R, Horvaath P, Gergely A. Tracking of enantioselective solubility of rac-norgestrel in the presence of cyclodextrin by a CD spectroscopic method. Chirality 2006;18:121-126. (Pubitemid 43172790)
18. Blaser H, Pugin B, Spindler F, Thommen M. From a chiral switch to a ligand portfolio for symmetric catalysis. Acc Chem Res 2007;40:1240-1250.
19. Liu HJ, Xiong MY. Comparative toxicity of racemic metolachlor and S-metolachlor to Chlorella pyrenoidosa. Aquat Toxicol 2009;93:100-106.
20. Xie F, Liu HJ, Cai WD. Enantioselectivity of racemic metolachlor and S-metolachlor in maize seedlings. J Environ Sci Health B 2010;45:774-782.
21. Ma Y, Liu WP, Wen YZ. Enantioselective degradation of Rac-metolachlor and S-metolachlor in soil. Pedosphere 2006;16:489-494.
22. CNEPA (Chinese National Environmental Protection Agency).Algal growth inhibiting test. Guidelines for testing of chemicals. Beijing, China: The Chinese Chemical Industry Press; 1990.
23. Zhang AP, Xu C, Liu WP. Influence of toxicity and dissipation of racemic fenoxaprop and its R-enantiomer in Scenedesmus obliquus suspension by cyclodextrins. J Environ Sci Health B 2008;43:231-236. (Pubitemid 351451053)
24. Gao YA, Zhao XY, Dong B, Zheng LQ, Li N, Zhang SH. Inclusion complexes of β-cyclodextrin with ionic liquid surfactants. J Phys Chem B 2006;110:8576-8581. (Pubitemid 43798562)
25. Liang C, Huang CF, Mohanty N, Lu CJ, Kurakalva RM. Hydroxypropyl-β- cyclodextrin-mediated iron-activated persulfate oxidation of trichloroethylene and tetrachloroethylene. Ind Eng Chem Res 2007;46:6466-6479. (Pubitemid 47598380)
26. Chen M, Diao GW, Zhang ER. Study of inclusion complex of β-cyclodextrin and nitrobenzene. Chemosphere 2006;63:522-529.
27. Cuypers C, Pancras T, Grotenhuis T, Rulkens W. The estimation of PAH bioavailability in contaminated sediments using hydroxypropyl-b-cyclodextrin and Triton X-100 extraction techniques. Chemosphere 2002;46:1235-1245. (Pubitemid 34188652)
28. Cserháti T, Forgács E. Effect of carboxymethyl-β- cyclodextrin on the hydrophobicity parameters of steroidal drugs. Carbohydr Polym 1999;38:171-177.
29. Cai BC, Gao SX, Lu GF. β-Cyclodextrin and its derivatives-enhanced solubility and biodegradation of 2-nitrobiphenyl. J Environ Sci 2006;18:1157-1160.
30. Kamiya M, Nakamura K. Cyclodextrin inclusion effects on photodegradation rates of organophosphorus pesticides. Environ Int 1995;21:299-304.
31. Martin EM, Valle D. Cyclodextrins and their uses: a review. Process Biochem 2004;39:1033-1046.
32. Araujo DR, Braga Ade F, Moraes CM, Fraceto LF, Paula E. Complexation of 50% enantiomeric excess (S75-R25) bupivacaine with cyclodextrins and spinal block anesthesia in rats. Rev Bras Anestesiol 2006;56:495-506. (Pubitemid 44540099)
33. Benesi HA, Hildebrand JH. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc 1949;71:2703-2707.
34. Inoue Y, Liu Y, Tong LH, Shen BJ, Jin DS. Calorimetric titration of inclusion complexation with modified β-cyclodextrins. Enthalpy-entropy compensation in host - guest complexation from ionophore to cyclodextrin and cyclophane. J Am Chem Soc 1993;115:10637-10644.
35. Müller BW, Albers E. Complexation of dihydropyridine derivatives with cyclodextrins and 2-hydroxypropyl-β-cyclodextrin in solution. Int J Pharm 1992;79:273-288.
36. Oh I, Lee MY, Lee YB, Shin SC, Park I. Spectroscopic characterization of ibuprofen/2-hydroxypropyl-β-cyclodextrin inclusion complex. Int J Pharm 1998;175:215-223. (Pubitemid 28517977)