In vitro study of DNA interaction with clodinafop-propargyl herbicide

DNA and Cell Biology

Volumn 27, Issue 10, 2008, Pages 581-586

  Kashanian, Soheila ^a   Askari, Soyebeh ^a   Ahmadi, Farhad ^b   Omidfar, Kobra ^c   Ghobadi, Sirous ^a   Tarighat, Fereshteh Abasi ^a  

^a RAZI UNIVERSITY   (Iran)

^b KERMANSHAH UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

4 (2 HYDROXYETHYL) 1 PIPERAZINEETHANESULFONIC ACID; CLODINAFOP PROPARGYL; DNA; HERBICIDE; METHYLENE BLUE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; BASE PAIRING; BINDING COMPETITION; CALF (BOVINE); CIRCULAR DICHROISM; CONTROLLED STUDY; DNA DENATURATION; INTERCALATION COMPLEX; MELTING POINT; MOLECULAR INTERACTION; NONHUMAN; PH MEASUREMENT; PRIORITY JOURNAL; SPECTROFLUOROMETRY; SPECTROPHOTOMETRY; THERMODYNAMICS; THYMUS; ULTRAVIOLET SPECTROSCOPY; VISCOMETRY;

ACETYL-COA CARBOXYLASE; ANIMALS; CATTLE; CIRCULAR DICHROISM; DNA; FLUORESCENCE; HERBICIDES; INTERCALATING AGENTS; NUCLEIC ACID DENATURATION; PROPIONATES; PYRIDINES; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; TEMPERATURE; THERMODYNAMICS; VISCOSITY;

EID: 52749083204     PISSN: 10445498     EISSN: None     Source Type: Journal    
DOI: 10.1089/dna.2008.0740     Document Type: Article

References (60)

1. Airoldi, M., Alberti, U.D., Gut, H., and Topik, R. (1997). New postemergence graminicide for wheat. Informatore Fitopatologico 47, 57-60.
2. Bell, C.E. (1999). Field evaluation of MKH-6561 for Phalaris minor control in durum wheat. Proceedings of Brighton Crop Protection Conference. Weeds 1, 211-216.
3. Bhattacharya, S., and Banerjee, M. (2004). Spectrophotometric and thermodynamic studies of complexation of [60]fullerene with a series of anisoles: a rational approach towards charge transfer interaction. Chem Phys Lett 396, 377-383.
4. Blackshaw, R.E., Semach, G., and Entz, T. (1998). Post-emergence control of foxtail barley (Hordeum jubatum) seedlings in spring wheat (Triticum aestivum) and flax (Linum usitatissimum). Weed Technol 12, 610-616.
5. Bolognesi, C. (2003). Genotoxicity of pesticides: a review of human biomonitoring studies. Mutat Res 543, 251-272.
6. Bonjean, K., de Pauw-Gillet, M.C., and Defresne, M.P. (1998). The DNA intercalating alkaloid cryptolepine interferes with topoisomerase II and inhibits primarily DNA synthesis in B16 melanoma cells. Biochemistry 37, 5136-5146.
7. Brar, L.S., Walia, U.S., and Dhaliwal, B.K. (1999). Bio-efficacy of new herbicides for the control of resistant Phalaris minor in wheat. Pestic Res J 11, 177-180.
8. Britos, L., Goyenola, G., and Orono, S.U. (2004). Simple protocol for secondary school hands-on activity-Electrophoresis of prestained nucleic acids on agar-agar borate gels. Mol Biol Educ 32, 341-347.
9. Catena, G.C., and Bright, F.V. (1989). Thermodynamic study on the effects of beta-cyclodextrin inclusion with anilinonaphthalenesulfonates. Anal Chem 61, 905-909.
10. Chaires, J.B., Dattagupta, N., and Crothers, D.M. (1982). Ribonucleic acid equilibrium binding studies on interaction of daunomycin with deoxyribonucleic-acid. Biochemistry 21, 3933-3940.
11. Cohen, G., and Eisenberg, H. (1969). Viscosity and sedimentation study of sonicated DNA-proflavine complexes. Biopolymers 8, 45-55.
12. Dalgleish, D.G., Fey, G., and Kersten, W. (1974). Circular dichroism studies of complexes of the antibiotics daunomycin, nogalamycin, chromomycin, and mithramycin with DNA. Biopolymers 13, 1757-1766.
13. Davis, T.M., and Wilson, W.D. (2001). Surface plasmon resonance biosensor analysis of RNA-small molecule interactions. Methods Enzymol 340, 22-51.
14. Day, Y.S., Baird, C.L., Rich, R.L., and Myszka, D.G. (2002). Direct comparison of binding equilibrium, thermodynamic, and rate constants determined by surface and solution-based biophysical methods. Protein Sci 11, 1017-1025.
15. Dearfield, K.L., Stack, H.F., Quest, J.A., Whithing, R.J., and Waters, M.D. (1993). A survey of EPArOPP and open literature data on selected pesticide chemicals tested for mutagenicity: I Introduction and first ten chemicals. Mutat Res 297, 197-233.
16. Drummond, D.S., Pritchard, N.J., Simpson-Gildemeister, V.F.W., and Peacocke, A.R. (1966). Interaction of aminoacridines with deoxyribonucleic acid viscosity of the complexes. Biopolymers 4, 971-987.
17. Dunitz, J.D. (1994). The entropic cost of bound water in crystals and biomolecules. Science 264, 670.
18. Fasman, G.D. (1996). Circular Dichroism and Conformational Analysis of Biomolecules (Plenum Press, NY) pp. 433-465.
19. Fujimoto, B.S., Clendenning, J.B., Delrow, J.J., Heath, P.J., and Schurr, M. (1994). Fluorescence and photobleaching studies of methylene blue binding to DNA. J Phys Chem 98, 6633-6643.
20. Garaj-Vrhovac, V., and Zeljezic, D.R. (2000). Evaluation of DNA damage in workers occupationally exposed to pesticides using single-cell gel electrophoresis (SCGE) assay pesticide genotoxicity revealed by comet assay. Mutat Res 469, 279-285.
21. Garrett, N.E., Stack, H.F., and Waters, M.D. (1986). Evaluation of the genetic activity profiles of 65 pesticides. Mutat Res 168, 301-325.
22. González, M., Soloneski, S., Reigosa, M.A., and Larramendy, M.L. (2003). Effect of dithiocarbamate pesticide zineb and its commercial formulation, azzurro IV. DNA damage and repair kinetics assessed by single cell gel electrophoresis (SCGE) assay on Chinese hamster ovary (CHO) cells. Mutat Res 534, 145-154.
23. Grisolia, C.K. (2002). A comparison between mouse and fish micronucleus test using cyclophosphamide, mitomycin C and various pesticides. Mutat Res 518, 145-150.
24. Kashanian, S., Gholivand, M.B., Ahmadi, F., and Ravan, H. (2008). Interaction of Diazinon with DNA and the protective role of selenium in DNA damage. DNA Cell Biol 27, 325-332.
25. Kasparkova, J., Vrana, O., Farrell, N., and Brabec, V. (2004). Effect of the geometry of the central coordination sphere in antitumor trinuclear platinum complexes on DNA binding. J Inorg Biochem 98, 1560-1569.
26. Lerman, L.S. (1961). Structural considerations in the interaction of DNA and acridines. Mol Biol 3, 18-30.
27. Li, F.H., Zhao, G.H., Wu, H.X., Lin, H., Wu, X.X., Zhu, S.R., and Lin, H.K. (2006). Synthesis, characterization and biological activity of lanthanum (III) complexes containing 2-methylene-1,10-phenanthroline units bridged by aliphatic diamines. J Inorg Biochem 100, 36-43.
28. 2 (phen)/nucleotides aqueous and solid-state coordination chemistry and its DNA binding studies. J Inorg Biochem 64, 181-195.
29. Li, Y.Q., White, J., David, S., Gary, S., and Michael, S. (2001). Capillary electrophoresis as a method to study DNA reassociation. Biotechnol Prog 17, 348-354.
30. Long, E.C., and Barton, J.K. (1990). On demonstrating and intercalation. Acc Chem Res 23, 271-273.
31. Mahadevan, S., and Palaniandavar, M. (1998). Spectroscopic and voltammetric studies on copper complexes of 2,9-dimethyl-1,10-phenanthrolines bound to calf thymus DNA. Inorg Chem 37, 693-700.
32. Miller, J.I. (2000). Name of Chemical: Clodinafop-propargyl (United States Environmental Protection Agency Office of Prevention, Pesticides and Toxic Substances (7501C), Washington, DC) pp. 1-17.
33. Naguib El-Khatib, E., Abd El-Aziz, M., Badr, Y., and Kamal, N. (2006). In vivo genotoxicity of the synthetic pyrethroid pesticide "cypermethrin" in rat liver cells by Comet assay. Toxicol Lett 164S, S1.
34. Oliveira-Brett, A.M., and Diculescu, V.C. (2004). Electrochemical study of quercetin-DNA interactions: Part I. Analysis in incubated solutions. Bioelectrochemistry 64, 133-141.
35. Olmsted, J., and Kearns, D.R. (1977). Mechanism of ethidium bromide fluorescence enhancement on binding to nucleic acids. Biochemistry 16, 3647-3654.
36. Patra, A.K., Nethaji, M., and Chakravarty, A.R. (2007). Synthesis, crystal structure, DNA binding and photo-induced DNA cleavage activity of (S-methyl-L-cysteine) copper(II) complexes of heterocyclic bases. J Inorg Biochem 101, 233-244.
37. Plaper, A., Golob, M., Hafner, I., Oblak, M., Solmajer, T., and Jerala, R. (2003). Characterization of quercetin binding site on DNA gyrase. Biochem Biophys Res Commun 306, 530-536.
38. Poklar, N., Pilch, D.S., Lippard, S.J., Redding, E.A., Dunham, S.H., and Breslauer, K.J. (1996). Influence of cisplatin intrastrand cross-linking on the conformation, thermal stability, and energetics of a 20-mer DNA duplex. Proc Natl Acad Sci USA 93, 7606-7611.
39. Rahman, A., Shahabuddin, S., Hadi, S.M., and Parish, J.H. (1990). Complexes involving quercetin, DNA and Cu(II). Carcinogenesis 11, 2001-2003.
40. Ramakrishnan, S., and Palaniandavar, M. (2005). Mixed-ligand copper (II) complexes of dipicolylamine and 1,10-phenanthrolines: the role of diimines in the interaction of the complexes with DNA. J Chem Sci 117, 179-186.
41. Safe, S. (1984). Polychlorinated biphenyls (PCBs) and polybrominated biphenyls (PBB): biochemistry, toxicology, and mechanisms of action. CRC Crit Rev Toxicol 13, 319-395.
42. Sambrook, J., Fritsche, E.F., and Maniatis, T. (1989). Molecular Cloning: A Laboratory Manual (Cold Spring Harbor Laboratory, Cold Spring Harbor, NY).
43. Satyanarayana, S., Dabrowiak, J.C., and Chaires, J.B. (1992). Neither delta-nor lambda-tris(phenanthroline) ruthenium(II) binds to DNA by classical intercalation. Biochemistry 31, 9319-9324.
44. Sherman, S.E., and Lippard, S.J. (1987). Structural aspects of platinum anticancer drugs interactions with DNA. Chem Rev 87, 1153-1181.
45. Shi, S., Liu, J., Li, J., Zheng, K.C., Huang, X.M., Tan, C.P., Chen, L.M., and Ji, L.N. (2006). Synthesis, characterization and DNA-binding of novel chiral complexes D- and K-[Ru(bpy)2L] 2+(L=o-mopip and p-mopip). J Inorg Biochem 100, 385-395.
46. Tuite, E., and Norden, B. (1994). Sequence-specific interactions of methylene-blue with polynucleotides and DNA - a spectroscopic study. J Am Chem Soc 116, 7548-7556.
47. Vigreux, C., Poul, J.M., Deslandes, E., Lebailly, P., Godard, T., Sichel, F., Henry-Amar, M., and Gauduchon, P. (1998). DNA damaging effects of pesticides measured by the single cell gel electrophoresis assay comet assay and the chromosomal aberration test, in CHOK1 cells. Mutat Res 419, 79-90.
48. 4. Biochim Biophys Acta 1475, 157-162.
49. Wainwright, M., and Giddens, R.M. (2003). Phenothiazinium photosensitizers: choices in synthesis and application. Dyes Pigments 57, 245-257.
50. Walia, U.S., Dhaliwal, B.K., and Brar, L.S. (1998). Response of Phalaris minor Rtez. biotypes to various herbicides. Indian J Weed Sci 30, 116-120.
51. Williams, F.M., Atherton, K.M., Jamieson, S., and Mutch, E. (2006). DNA damage by organophosphate pesticides and repair profiles in human lymphocytes, in vitro, abstract. Toxicol Lett 164S, S261.
52. Wilson, W.D., Ratmeyer, L., Zhao, M., Strekowski, L., and Beykin, D. (1993). The search for structure-specific nucleic acid-interactive drugs: effects of compound structure on RNA versus DNA interaction strength. Biochemistry 32, 4098-4104.
53. Wilson, W.D., and Sight, T. (2002). Analyzing biomolecular interactions. Science 295, 2103-2105.
54. Wilson, W.D., Tanious, F.A., Barton, H.J., Wydra, R.L., Jones, R.L., Boykin, D.W., and Strekowski, L. (1990). The interaction of unfused polyaromatic heterocycles with DNA: intercalation, groove-binding and bleomycin amplification. Anticancer Drug Des 5, 31-42.
55. Wilson, W.D., Tanious, F.A., Fernandez-Saiz, M., and Rigl, C.T. (1997). Evaluation of drug-nucleic acid interactions by thermal melting curves. Methods Mol Biol 90, 219-240.
56. Ya Nez, L.V., Borja-Aburto, H., Rojas, E., de la Fuente, H., Gonzalez-Amaro, R., Gomez, H., Jongitud, A.A., and Dyáz-Barriga, F. (2004). DDT induces DNA damage in blood cells. Studies in vitro and in women chronically exposed to this insecticide. Environ Res 94, 18-24.
57. Yong, Z.C., Li, X.X., and Pin, Y. (2007). Studies on DNA binding to metal complexes of Sal2trien. Biochemistry (Mosc) 72, 37-43.
58. Zeynep, D., Ralph, P., Jan, A.R.S., Sukunath, N., and Clemens, R. (2004). 5′-tethered stilbene derivatives as fidelity- and affinity-enhancing modulators of DNA duplex stability. J Am Chem Soc 126, 4762-4763.
59. Zhong, W., Yu, J., Liang, Y., Fan, K., and Lai, L. (2004). Chlorobenzylidine-calf thymus DNA interaction II: circular dichroism and nuclear magnetic resonance studies. Spectrochimica Acta A 60, 2985-2992.
60. Zhou, Ch.Y., Zhao, J., Wu, Y.B., Yin, C.X., and Yang, P. (2007). Synthesis, characterization and studies on DNA-binding of a new Cu(II) complex with N1,N8-bis(l-methyl-4 nitro pyrrole-2 carbonyl)triethylenetetramine. J Inorg Biochem 101, 10-18.