Chemical synthesis, in vitro acetohydroxyacid synthase (AHAS) inhibition, herbicidal activity, and computational studies of isatin derivatives

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 18, 2011, Pages 9892-9900

  Wang, Jianguo ^a   Tan, Haizhong ^a   Li, Yonghong ^a   Ma, Yi ^a   Li, Zhengming ^a   Guddat, Luke W ^b  

^a NANKAI UNIVERSITY   (China)

^b UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

AHAS; biological activity; DFT calculation; docking; herbicide; isatin derivatives; molecular design; QSAR; rational design; synthesis

Indexed keywords

AHAS; DFT CALCULATION; ISATIN DERIVATIVES; MOLECULAR DESIGN; QSAR; RATIONAL DESIGN;

AMINO ACIDS; BINDING ENERGY; BIOACTIVITY; BIOCHEMISTRY; COMPUTATIONAL CHEMISTRY; DESIGN; DOCKING; MOLECULAR ORBITALS; SYNTHESIS (CHEMICAL); WEED CONTROL;

HERBICIDES;

ACETOLACTATE SYNTHASE; BRANCHED CHAIN AMINO ACID; DRUG DERIVATIVE; ENZYME INHIBITOR; HERBICIDE; ISATIN;

ARTICLE; BIOSYNTHESIS; CHEMISTRY; DRUG ANTAGONISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ACETOLACTATE SYNTHASE; AMINO ACIDS, BRANCHED-CHAIN; ENZYME INHIBITORS; HERBICIDES; ISATIN; STRUCTURE-ACTIVITY RELATIONSHIP;

ARABIDOPSIS THALIANA;

EID: 80053116206     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf2021607     Document Type: Article

References (45)

1. Duggleby, R. G.; Pang, S. S. Acetohydroxyacid synthase J. Biochem. Mol. Biol. 2000, 33 (1) 1-36
2. Chaleff, R. S.; Mauvais, C. J. Acetolactate synthase is the site of action of two sulfonylurea herbicides in higher plants Science 1984, 224, 1443-1445
3. LaRossa, R. A.; Schloss, J. V. The sulfonylurea herbicide sulfometuron methyl is an extremely potent and selective inhibitor of acetolactate synthase in Salmonella typhimurium J. Biol. Chem. 1984, 259, 8753-8757 (Pubitemid 14097938)
4. Ray, T. B. Site of action of chlorsulfuron: inhibition of valine and isoleucine biosynthesis of plants Plant Physiol. 1984, 75, 827-831
5. Whitcomb, C. E. An introduction to ALS-inhibiting herbicides Toxicol. Ind. Health 1999, 15 (1-2) 231-239
6. McCourt, J. A.; Duggleby, R. G. Acetohydroxyacid synthase and its role in the biosynthetic pathway for branched-chain amino acids Amino Acids 2006, 31, 173-210 (Pubitemid 44222578)
7. Tan, S.; Evans, R. R.; Dahmer, M. L.; Singh, B. K.; Shaner, D. L. Imidazolinone-tolerant crops: history, current status and future Pest. Manag. Sci. 2005, 61 (3) 246-257 (Pubitemid 40326226)
8. Moss, S. R. Herbicide-resistant weeds in Europe: the wider implications Commun. Agric. Appl. Biol. Sci. 2004, 69 (3) 3-11
9. Gressel, J. Crops with target-site herbicide resistance for Orobanche and Striga control Pest. Manag. Sci. 2009, 65 (5) 560-565
10. Green, J. M.; Hazel, C. B.; Forney, D. R.; Pugh, L. M. New multiple-herbicide crop resistance and formulation technology to augment the utility of glyphosate Pest. Manag. Sci. 2008, 64 (4) 332-339 (Pubitemid 351449453)
11. Corbett, C. A.; Tardif, F. J. Detection of resistance to acetolactate synthase inhibitors in weeds with emphasis on DNA-based techniques: a review Pest. Manag. Sci. 2006, 62 (7) 584-597 (Pubitemid 44031309)
12. Pang, S. S.; Duggleby, R. G.; Guddat, L. W. Crystal structure of yeast acetohydroxyacid synthase: a target for herbicidal inhibitors J. Mol. Biol. 2002, 317, 249-262 (Pubitemid 34722192)
13. Pang, S. S.; Guddat, L. W.; Duggleby, R. G. Molecular basis of sulfonylurea herbicide inhibition of acetohydroxyacid synthase J. Biol. Chem. 2003, 278, 7639-7644 (Pubitemid 36800773)
14. McCourt, J. A.; Pang, S. S.; Guddat, L. W.; Duggleby, R. G. Elucidating the specificity of sulfonylurea herbicide binding to acetohydroxyacid synthase Biochemistry 2005, 44, 2330-2338 (Pubitemid 40279537)
15. McCourt, J. A.; Pang, S. S.; King-Scott, J.; Guddat, L. W.; Duggleby, R. G. Herbicide binding sites revealed in the structure of plant acetohydroxyacid synthase Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 569-573 (Pubitemid 43153066)
16. Wang, J. G.; Lee, P.; Dong, Y. H.; Pang, S. S.; Duggleby, R. G.; Li, Z. M.; Guddat, L. W. Crystal structures of two novel sulfonylurea herbicides in complex with Arabidopsis thaliana acetohydroxyacid synthase FEBS. J. 2009, 276, 1282-1290
17. Wang, J. G.; Xiao, Y. J.; Li, Y. H.; Ma, Y.; Li, Z. M. Identification of some novel AHAS inhibitors via molecular docking and virtual screening approach Bioorg. Med. Chem. 2007, 15 (1) 374-380 (Pubitemid 44738568)
18. Gil-Turnes, M. S.; Hay, M. E.; Fenical, W. Symbiotic marine bacteria chemically defend crustacean embryos from a pathogenic fungus Science 1989, 246, 116-118 (Pubitemid 20422356)
19. Binda, C.; Li, M.; Hubalek, F.; Restelli, N.; Edmondson, D. E.; Mattevi, A. Insights into the mode of inhibition of human mitochondrial monoamine oxidase B from high-resolution crystal structures Proc. Natl. Acad. Sci. U.S.A. 2003, 100 (17) 9750-9755 (Pubitemid 37087013)
20. Igosheva, N.; Lorz, C.; O'Conner, E.; Glover, V.; Mehmet, H. Isatin, an endogenous monoamine oxidase inhibitor, triggers a dose- and time-dependent switch from apoptosis to necrosis in human neuroblastoma cells Neurochem. Int. 2005, 47, 216-224 (Pubitemid 40848684)
21. Surendra, N. P.; Sivakumar, S.; Mayank, J.; Seshaiah, K. S. Biological activities of isatin and its derivatives Acta Pharm. 2005, 55, 27-46
22. Tan, H. Z.; Wang, W. M.; Shang, J. L.; Song, H. B.; Li, Z. M.; Wang, J. G. Syntheses, crystal structures and bioactivities of two isatin derivatives Chinese J. Struct. Chem. 2011, 30 (4) 502-507
23. Haga, T.; Nagano, H.; Enomoto, M.; Morita, K.; Sato, M. Preparation of isatin derivatives as herbicides. Jpn. Patent 63313770, 1988.
24. Schreiber, K.; Stephan, U.; Wegner, G. Agent for controlling the growth of clover, especially red clover. Ger. Patent DD121011, 1976.
25. Hambsch, E. Isatins as selective herbicides. Ger. Patent DE1013469, 1957.
26. Wang, J. G.; Ma, N.; Wang, B. L.; Wang, S. H.; Song, H. B.; Li, Z. M. Synthesis, crystal structure and biological activity of N -(4-methylpyrimidin-2- yl)- N ′-2-(nitrophenylsulfonyl)urea and its docking with yeast AHAS Chinese J. Org. Chem. 2006, 26 (5) 648-652 (Pubitemid 44065491)
27. Dulin, W. E.; Wright, J. B.; Dulin, W. E.; Wright, J. B. U.S. Patent 3150148, 1964
28. Cooper, M.; Receveur, J.-M.; Hoegberg, T.; Nielsen, P. A.; Linget, J.-M.; Noeregaard, P. K. Preparation of pyrazolecarboxamide compounds as CB1 receptor modulators. PCT Int. Appl. WO 2008074982, 2008
29. Platonova, O. V.; Volkova, S. B.; Malin, S. A.; Veretennikov, E. A.; Laskin, B. M.; Malin, A. S. Synthesis of new substituted thiazoles containing aminooxadiazole ring Russ. J. App. Chem. 2008, 81 (3) 513-515
30. Chang, A. K.; Duggleby, R. G. Herbicide-resistant forms of Arabidopsis thaliana acetohydroxyacid synthase: characterization of the catalytic properties and sensitivity to inhibitors of four defined mutants Biochem. J. 1998, 333, 765-777 (Pubitemid 28398547)
31. Wang, J. G.; Li, Z. M.; Ma, N.; Wang, B. L.; Jiang, L.; Pang, S. S.; Lee, Y. T.; Guddat, L. W.; Duggleby, R. G. Structure-activity relationships for a new family of sulfonylurea herbicides J. Comput.-Aided Mol. Des. 2005, 19 (11) 801-820
32. Cramer, M.; Cramer, R. D.; Jones, D. M. Comparative molecular field analysis. 1. Effect of shape on binding of steroids to carrier proteins J. Am. Chem. Soc. 1988, 110, 5959-5967
33. Zhu, Y. Q.; Wu, C.; Li, H. B.; Zou, X. M.; Si, X. K.; Hu, F. Z.; Yang, H. Z. Design, synthesis, and quantitative structure-activity relationship study of herbicidal analogues of pyrazolo[5,1- d ][1,2,3,5]tetrazin-4(3 H)ones J. Agric. Food Chem. 2007, 55 (4) 1364-1369
34. Wang, L.; Ma, Y; Liu, X. H.; Li, Y. H.; Song, H. B.; Li, Z. M. Synthesis, herbicidal activities and comparative molecular field analysis study of some novel triazolinone derivatives Chem. Biol. Drug Des. 2009, 73 (6) 674-681
35. Wang, J. G.; Fu, X. L.; Wang, Y. M.; Ma, Y.; Li, Z. M.; Zhang, Z. X. 3D-QASR sudy of quinoline-2,4-dione derivatives against wheat leaf rust Chem. J. Chinese Univ. 2003, 24 (11) 2010-2013
36. Becke, A. D. Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 1993, 98, 5648-5652
37. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B 1988, 37, 785-789
38. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; AlLaham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C01; Gaussian, Inc.: Wallingford, U.K., 2004.
39. Rarey, M.; Kramer, B.; Lengauer, T.; Klebe, G. A fast flexible docking method using an incremental construction algorithm J. Mol. Biol. 1996, 261, 470-489 (Pubitemid 26335901)
40. Sun, Y.; Lu, J.; Zhang, D.; Song, H. Synthesis and crystal structure of isatin-3-isonicotinoylhydrazone Anal. Sci. 2006, 22, 237-238
41. Sandra, S.; Konstantinović; Agneš, K.; Blaga, C.; Radovanović; Andrea, D. Synthesis, X-ray and antimicrobial activity of isatin-3-phenylhydrazone CI&CEQ 2008, 14 (1) 27-34
42. Wang, B. L.; Duggleby, R. G.; Li, Z. M.; Wang, J. G.; Li, Y. H.; Wang, S. H.; Song, H. B. Synthesis, crystal structure and herbicidal activity of mimics of intermediates of the KARI reaction Pest Manag. Sci. 2005, 61 (4) 407-412 (Pubitemid 40460486)
43. Huang, X.; Liu, T; Gu, J.; Luo, X.; Ji, R.; Cao, Y.; Xue, H.; Wong, J. T.; Wong, B. L.; Pei, G.; Jiang, H.; Chen, K. 3D-QSAR model of flavonoids binding at benzodiazepine site in GABAA receptors J. Med. Chem. 2001, 44, 1883-1891 (Pubitemid 32884513)
44. Ma, Y.; Wang, J. G.; Wang, B.; Li, Z. M. Integrating molecular docking, DFT and CoMFA/CoMSIA approaches for a series of naphthoquinone fused cyclic α-aminophosphonates that act as novel topoisomerase II inhibitors J. Mol. Model. 2011, 17 (8) 1899-1909
45. Liu, X. H.; Chen, P. Q.; Wang, B. L.; Li, Y. H.; Wang, S. H.; Li, Z. M. Synthesis, bioactivity, theoretical and molecular docking study of 1-cyano-N-substituted-cyclopropanecarboxamide as ketol-acid reductoisomerase inhibitor Bioorg. Med. Chem. Lett. 2007, 17 (13) 3784-3788