Abstract
Effects of 4-(1,3-diphenyl-1H-pyrazol-5-yl)phenol(APP), 4-(1,5-diphenyl-1H-pyrazol-3-yl)phenol(BPP) and 4-(3,5-diphenyl-1H-pyrazol-1-yl)phenol(CPP) on 2,2′-azobis-(2-amidinopropane hydrochloride)(AAPH)-induced oxidation of DNA were measured in the presence of various concentrations of Triton X-100, cetyltrimethylammonium bromide(CTAB), or sodium dodecyl sulfate(SDS) in order to clarify the influence of neutral, cationic and anionic microenvironments on antioxidant capacities of APP, BPP and CPP. Although these surfactants can protect DNA against AAPH-induced oxidation, the pyrazoles in the presence of these surfactants functioned as prooxidants when the concentrations of Triton X-100 and CTAB increased. However, CPP exhibited antioxidant property with the increase of the concentration of CTAB. On the contrary, APP, BPP and CPP were antioxidants in the presence of various concentrations of SDS. The added surfactants resulted in the complication of the microenvironments around DNA, pyrazoles and peroxyl radical(ROO·) derived from AAPH. The anionic charge of SDS was beneficial to enhancing the antioxidant effectiveness of these pyrazoles. It can be concluded that the charge property of surfactants markedly influenced the behavior of an antioxidant in AAPH-induced oxidation of DNA.
Similar content being viewed by others
References
van Horssen J., Witte M. E., Schreibelt G., de Vries H. E., Biochim. Biophys. Acta, 2011, 1812, 141
de Cavanagh E. M. V., Inserra F., Ferder L., Cardiovasc. Res., 2011, 89, 31
Benigni R., Bossa C., Chem. Rev., 2011, 111, 2507
Kong Q., Lin C. G., Cell. Mol. Life Sci., 2010, 67, 1817
Jomova K., Jenisova Z., Feszterova M., Baros S., Liska J., Hudecova D., Rhodes C. J., Valko M., J. Appl. Toxicol., 2011, 31, 95
Hosseinimehr S. J., Drug Discovery Today, 2010, 15, 907
Astruc D., Boisselier E., Ornelas C., Chem. Rev., 2010, 110, 1857
Lee C. Y., Sharma A., Cheong J. E., Nelson J. L., Bioorg. Med. Chem. Lett., 2009, 19, 6326
Lee C. Y., Sharma A., Uzarski R. L., Cheong J. E., Xu H., Held R. A., Upadhaya S. K., Nelson J. L., Free Radical Biol. Med., 2011, 50, 918
Bandgar B. P., Gawande S. S., Bodade R. G., Gawande N. M., Khobragade C. N., Bioorg. Med. Chem., 2009, 17, 8168
Riyadh S. M., Farghaly T. A., Abdallah M. A., Abdalla M. M., Abd El-Aziz M. R., Eur. J. Med. Chem., 2010, 45, 1042
Dedon P. C., Chem. Res. Toxicol., 2008, 21, 206
Shao J., Geacintov N. E., Shafirovich V., Chem. Res. Toxicol., 2010, 23, 933
Møller P., Loft S., Environ. Health Perspect., 2010, 118, 1126
Zhou B., Miao Q., Yang L., Liu Z. L., Chem. Eur. J., 2005, 11, 680
Shang Y. J., Jin X. L., Shang X. L., Tang J. J., Liu G. Y., Dai F., Qian Y. P., Fan G. J., Liu Q., Zhou B., Food Chem., 2010, 119, 1435
Rudiuk S., Franceschi-Messant S., Chouini-Lalanne N., Perez E., Rico-Lattes I., Langmuir, 2008, 24, 8452
Zhang P., Omaye S. T., Food Chem. Toxicol., 2001, 39, 239
Shao J., Geacintov N. E., Shafirovich V., J. Phys. Chem. B, 2010, 114, 6685
Shang H., Chang W. S., Kan S., Majetich S. A., Lee G. U., Langmuir, 2006, 22, 2516
Li Y. F., Liu Z. Q., Free Radical Biol. Med., 2012, 52, 103
Author information
Authors and Affiliations
Corresponding author
Additional information
Support by the Project of the Jilin Provincial Science and Technology Department, China(No.20130206075GX).
Rights and permissions
About this article
Cite this article
Li, Yf., Liu, Zq. Effects of micelle on pyrazoles as antioxidants in radical-induced oxidation of DNA. Chem. Res. Chin. Univ. 29, 671–677 (2013). https://doi.org/10.1007/s40242-013-3059-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s40242-013-3059-x