Spectroscopic and Chemometrics Analysis of the Hydrolytic Process of Folpet and Its Interaction with DNA
详细信息 查看全文
- 作者：Yepeng Zhang ; Guowen Zhang
- 关键词：Folpet ; Calf thymus DNA ; Hydrolysis ; Binding mode ; Spectroscopy ; Chemometrics
- 刊名：Journal of Solution Chemistry
- 出版年：2014
- 出版时间：August 2014
- 年：2014
- 卷：43
- 期：8
- 页码：1388-1401
- 全文大小：914 KB
- 参考文献：1. Gupta, R.C., Spencer-Beach, G.: Natural and endogenous DNA adducts as detected by 32P-postlabeling. Regul. Toxicol. Pharm. 23, 14-1 (1996) CrossRef
2. Laouedj, A., Schenk, C., Pfohl-Leszkowicz, A., Keith, G., Schontz, D., Guillermaut, P., Bether, B.: Detection of DNA adducts in declining hop plants grown on fields formerly treated with heptachlor, a persistent insecticide. Environ. Pollut. 90, 409-14 (1995) CrossRef
3. Lee, H.U., Shin, H.Y., Lee, J.Y., Song, Y.S., Park, C.H., Kim, S.W.: Quantitative detection of glyphosate by simultaneous analysis of UV spectroscopy and fluorescence using DNA-labeled gold nanoparticles. J. Agric. Food Chem. 58, 12096-2100 (2010) CrossRef
4. Ahmadi, F., Jafari, B., Rahimi-Nasrabadi, M., Ghasemi, S., Guanbari, K.: Proposed model for in vitro interaction between fenitrothion and DNA, by using competitive fluorescence 31PNMR, 1HNMR, FT-IR, CD and molecular modeling. Toxicol. In Vitro 27, 641-50 (2013) CrossRef
5. Shah, R.G., Lagueux, J., Kapur, S., Levallois, P., Ayoote, P., Tremblay, M., Zee, J., Poirier, G.G.: Determination of genotoxicity of the metabolites of the pesticides Guthion, Sencor, Lorox, Reglone, Daconil and Admire by P-32-postlabeling. Mol. Cell. Biochem. 169, 177-84 (1997) CrossRef
6. Zhang, Y.P., Zhang, G.W., Fu, P., Ma, Y.D., Zhou, J.: Study on the interaction of triadimenol with calf thymus DNA by multispectroscopic methods and molecular modeling. Spectrochim. Acta A 96, 1012-019 (2012) CrossRef
7. Zhang, G.W., Hu, X., Pan, J.H.: Spectroscopic studies of the interaction between pirimicarb and calf thymus DNA. Spectrochim. Acta A 78, 687-94 (2011) CrossRef
8. Parrilla, P., Vidal, J.L.M., Galera, M.M., Frenich, A.G.: Degradation of fenamiphos and folpet in water. Int. J. Environ. Anal. Chem. 63, 137-45 (1966) CrossRef
9. Couch, R.C., Siegel, M.R.: Interaction of captan and folpet with mammalian DNA and histones. Pestic. Biochem. Physiol. 7, 531-46 (1977) CrossRef
10. Wang, Y.Y., Xu, J.N., Hu, J.: EPA evaluated pesticides for potential carcinogenicity. Agrochemicals 484, 62-66 (2009)
11. Yamamoto, H., Hada, K., Yamaji, H., Katsuda, T., Ohno, H., Fukuda, H.: Application of regularized alternating least squares and independent component analysis to HPLC-DAD data of / Haematococcus pluvialis metabolites. Biochem. Eng. J. 32, 149-56 (2006) CrossRef
12. Ni, Y.N., Du, S., Kokot, S.: Interaction between quercetin–copper(II) complex and DNA with the use of the Neutral Red dye fluorophor probe. Anal. Chim. Acta 584, 19-7 (2007) CrossRef
13. Zhang, G.W., Fu, P., Wang, L., Hu, M.M.: Molecular Spectroscopic studies of farrerol interaction with calf thymus DNA. J. Agric. Food Chem. 59, 8944-952 (2011) CrossRef
14. Kashanian, S., Dolatabadi, J.E.N.: DNA binding studies of 2- / tert-butylhydroquinone (TBHQ) food additive. Food Chem. 116, 743-47 (2009) CrossRef
15. Kashanian, S., Khodaei, M.M., Pakravan, P.: Spectroscopic studies on the interaction of isatin with calf thymus DNA. DNA Cell Biol. 29, 639-46 (2010) CrossRef
16. Temerk, Y.M., Ibrahim, M.S., Kotb, M., Schuhmann, W.: Interaction of antitumor flavonoids with dsDNA in the absence and presence of Cu(II). Anal. Bioanal. Chem. 405, 3839-846 (2013) CrossRef
17. Kashanian, S., Dolatabadi, J.E.N.: In vitro study of calf thymus DNA interaction with butylated hydroxyanisole. DNA Cell Biol. 28, 535-40 (2009) CrossRef
18. Xu, M., Ma, Z.R., Huang, L., Chen, F.J., Zeng, Z.Z.: Spectroscopic studies on the interaction between Pr(III) complex of an ofloxacin derivative and bovine serum albumin or DNA. Spectrochim. Acta A 78, 503-11 (2011) CrossRef
19. Tauler, R.: Multivariate curve resolution applied to second order data. Chemom. Intell. Lab. Syst. 30, 133-46 (1995) CrossRef
20. Malinowski, E.R.: Factor analysis in chemistry. John Wiley & Sons, New York (2002)
21. Maeder, M.: Evolving factor analysis for the resolution of overlapping chromatographic peaks. Anal. Chem. 59, 527-30 (1987) CrossRef
22. Windig, W., Guilment, J.: Interactive self-modeling mixture analysis. Anal. Chem. 63, 1425-432 (1991) CrossRef
23. Ghasemi, J., Ahmadi, S., Ahmad, A.I., Ghobadi, S.: Spectroscopic characterization of thiazole orange-3 DNA interaction. Appl. Biochem. Biotechnol. 149, 9-2 (2008) CrossRef
24. Garrido, M., Rius, F.X., Larrechi, M.S.: Multivariate curve resolution–alternating least squares (MCR–ALS) applied to spectroscopic data from monitoring chemical reactions processes. Anal. Bioanal. Chem. 390, 2059-066 (2008) CrossRef
25. Tauler, R., Casassas, E., Izquierdo-Ridorsa, A.: Self-modeling curve resolution in studies of spectrometric titrations of multi-equilibria systems by factor analysis. Anal. Chim. Acta 248, 447-58 (1991) CrossRef
26. Wang, Y.X., Ni, Y.N., Kokot, S.: Voltammetric behavior of complexation of salbutamol with calf thymus DNA and its analytical application. Anal. Biochem. 419, 76-0 (2011) CrossRef
27. Berthet, A., Bouchard, M., Danuser, B.: Toxicokinetics of captan and folpet biomarkers in orally exposed volunteers. J. Appl. Toxicol. 32, 194-01 (2012) CrossRef
28. Bhakta, D., Siva, R.: Morindone, an anthraquinone, intercalates DNA sans toxicity: a spectroscopic and molecular modeling perspective. Appl. Biochem. Biotech. 167, 885-96 (2012) CrossRef
29. Xie, H.P., Chu, X., Jiang, J.H., Cui, H., Shen, G.L., Yu, R.Q.: Competitive interactions of adriamycin and ethidium bromide with DNA as studied by full rank parallel factor analysis of fluorescence three-way array data. Spectrochim. Acta A 59, 743-49 (2003) CrossRef
30. Hegde, A.H., Prashanth, S.N., Seetharamappa, J.: Interaction of antioxidant flavonoids with calf thymus DNA analyzed by spectroscopic and electrochemical methods. J. Pharm. Biomed. Anal. 63, 40-6 (2012) CrossRef
31. Ihmelsm, H., Otto, D.: Intercalation of organic dye molecules into double-stranded DNA—general principles and recent developments. Top. Curr. Chem. 258, 161-04 (2005) CrossRef
32. Bi, S.Y., Zhang, H.Q., Qiao, C.Y.: Studies of interaction of emodin and DNA in the presence of ethidium bromide by spectroscopic method. Spectrochim. Acta A 69, 123-29 (2008) CrossRef
33. Zhang, G.W., Fu, P., Pan, J.H.: Multispectroscopic studies of paeoniflorin binding to calf thymus DNA in vitro. J. Lumin. 134, 303-09 (2013) CrossRef
34. Zhao, P., Huang, J.W., Mei, W.J., He, J., Ji, L.N.: DNA binding and photocleavage specificities of a group of tricationic metalloporphyrins. Spectrochim. Acta A 75, 1108-114 (2010) CrossRef
35. Shen, H.Y., Shao, X.L., Xu, H., Li, J., Pan, S.D.: In vitro study of DNA interaction with trichlorobenzenes by spectroscopic and voltammetric techniques. Int. J. Electrochem. Sci. 6, 532-47 (2011)
36. Chen, Y.M., Liu, Y.J., Li, Q., Wang, K.Z.: pH- and DNA-induced dual molecular light switches based on a novel ruthenium(II) complex. J. Inorg. Biochem. 103, 1395-404 (2009) CrossRef
37. Rajendrakumar, C.S.V., Suryanarayanam, T., Reddy, A.R.: DNA helix destabilization by proline and betaine: possible role in the salinity tolerance process. FEBS Lett. 410, 201-05 (1997) CrossRef
38. Kashanian, S., Zeidali, S.H., Omidfar, K., Shahabadi, N.: Multi-spectroscopic DNA interaction studies of sunset yellow food additive. Mol. Biol. Rep. 39, 10045-0051 (2012) CrossRef
39. Shahabadi, N., Kashanian, S., Ahmadipour, Z.: DNA binding and gel electrophoresis studies of a new sliver(I) complex containing 2,9-dimethyl-1,10-phenanthroline ligands. DNA Cell Biol. 3, 187-94 (2011) CrossRef
40. Zhang, Y., Zhang, G.W., Zhou, X.Y., Li, Y.: Determination of acetamiprid partial-intercalative binding to DNA by use of spectroscopic, chemometrics, and molecular docking techniques. Anal. Bioanal. Chem. 405, 8871-883 (2013) CrossRef
41. Skyrianou, K.C., Psycharis, V., Raptopoulou, C.P., Kessissoglou, D.P., Psomas, G.: Nickel-quinolones interaction. Part 4—Structure and biological evaluation of nickel(II)–enrofloxacin complexes compared to zinc(II) analogues. J. Inorg. Biochem. 105, 63-4 (2011) CrossRef
42. Wang, X.L., Chao, H., Li, H., Hong, X.L., Liu, Y.J., Tan, L.F., Ji, L.N.: DNA interactions of cobalt(III) mixed-polypyridyl complexes containing asymmetric ligands. J. Inorg. Biochem. 98, 1143-150 (2004) CrossRef
43. Sahoo, B.K., Ghosh, K.S., Bera, R., Dasgupta, S.: Studies on the interaction of diacetylcurcumin with calf thymus-DNA. Chem. Phys. 351, 163-69 (2008) CrossRef
44. Paul, P., Kumar, G.S.: Toxic interaction of thionine to deoxyribonucleic acids: elucidation of the sequence specificity of binding with polynucleotides. J. Hazard. Mater. 184, 620-26 (2010) CrossRef
45. Xu, X.Y., Wang, D.D., Sun, X.J., Zeng, S.Y., Li, L.W., Sun, D.Z.: Thermodynamic and spectrographic studies on the interactions of ct-DNA with 5-fluorouracil and tegafur. Thermochim. Acta 493, 30-6 (2009) CrossRef
46. Jangir, D.K., Dey, S.K., Kundu, S., Mehrotra, R.: Assessment of amsacrine binding with DNA using UV–visible, circular dichroism and Raman spectroscopic techniques. J. Photochem. Photobiol. B 114, 38-3 (2012) CrossRef - 作者单位：Yepeng Zhang (1)
Guowen Zhang (1)
1. State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang, 330047, China - ISSN：1572-8927
文摘
Hydrolysis of the pesticide folpet [N-(trichloromethylthio) phthalimide] in aqueous solution in the absence or presence of calf thymus DNA (ctDNA) was investigated using UV–Vis absorption spectroscopy, and the interactions of folpet and its hydrolyzates with ctDNA were determined by fluorescence and circular dichroism spectroscopy, coupled with viscosity and melting temperature measurements. The absorption spectra data was further analyzed by alternate least squares, a chemometrics method, and the concentration profiles of the reacting species (folpet, unstable intermediate, phthalimide and phthalic acid) and their pure component spectra were simultaneously extracted to monitor the hydrolytic process. It was found that the hydrolytic process consists of at least two steps, generation of an unstable intermediate and production of its end hydrolyzates, phthalimide and phthalic acid. Addition of ctDNA significantly affects the hydrolysis of folpet. The results from the competitive binding with intercalator ethidium bromide, ctDNA melting and viscosity measurements, and circular dichroism studies indicate that folpet and the intermediate can intercalate into the double-helix of DNA, phthalic acid is bound to DNA by a partial intercalation, while phthalimide does not show binding to ctDNA. Moreover, the binding of folpet (or the intermediate) and phthalic acid to ctDNA induced structural changes of the DNA.