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Spectrophotometric and Voltammetric Studies on the Interaction of 7-Ethyl-10-hydroxycamptothecin (SN-38) as the Metabolized Compound of CPT-11 with ds-DNA
Corresponding Author(s) : Guan H. Tan
Asian Journal of Chemistry,
Vol. 25 No. 1 (2013): Vol 25 Issue 1
Abstract
The interaction of 7-ethyl-10-hydroxycamptothecin (SN-38) and double stranded DNA (ds-DNA) was studied by absorption spectroscopy and cyclic voltammetry at different temperatures. The results revealed that double stranded-DNA caused the hypochromicity of SN-38 absorption spectra at 384 nm. The binding constant Kb and the number of binding sites n, corresponding thermodynamic parameters between SN-38 and double stranded-DNA at different temperatures were calculated. In addition, the van't Hoff plot of 1/T versus ln Kb suggests that the SN-38 binds endothermically to double stranded-DNA, which is characterized by large positive enthalpy and entropy changes. The Kb at a low concentration of salt is dominated by electrostatic interaction (99.9 %) while that at a high concentration of salt is weakly controlled by non-electrostatic processes (2.23 %). The intercalation of SN-38 with DNA produces an electrochemically inactive macromolecule complex and the peak current of SN-38 was decreased upon the addition of double stranded-DNA molecules. The diffusion coefficients of SN-38 in the absence and presence of double stranded-DNA was calculated as 4.64 × 10-4 and 4.23 × 10-4 cm2 s-1, respectively.
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References
M.E. Wall, M.C. Wani, C.E. Cook, K.H. Palmer, A.T. McPhail and G.A. Sim, J. Am. Chem. Soc., 88, 3888 (1966).
T.R. Govindachari and N. Visnawathan, Phytochemistry, 11, 3529 (1972).
J.A. Gottlieb, A.M. Guarino, J.B. Call, V.T. Oliverio and J.B. Block, Cancer Chemother. Rep., 54, 461 (1970).
C.G. Moertel, A.J. Schutt, R.J. Reiterneier and R.G. Hahn, Cancer Chemother. Rep., 56, 95 (1972).
F.M. Muggia, P.J. Creaven, H.H. Hansen, M.H. Cohen and O.S. Selawry, Cancer Chemother. Rep., 56, 515 (1972).
Y.H. Hsiang, R. Hertzberg, S. Hecht and L.F. Liu, J. Biol. Chem., 260, 14873 (1985).
Y.-H. Hsiang and L.F. Liu, Cancer Res., 48, 1722 (1988).
Q.Y. Chen, D.H. Hi, Y. Zhao and J.X. Guo, Analyst, 124, 901 (1999).
R. Hajian, N. Iravani, F. Ghanbari and N. Shams, Asian J. Chem., 24, 3656 (2012).
S. Mahadevan and M. Palaniandavar, Inorg. Chem., 37, 693 (1998).
M. Purcell, J.F. Neault and T. Riahi, Biochim. Biophys. Acta, 1478, 61 (2000).
N.Y. Mudasir and H. Inoue, J. Inorg. Biochem., 77, 239 (1999).
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J.R. Quintana, K. Grzeskowiak, K. Yanagi and R.E. Dickerson, J. Mol. Biol., 379, 225 (1992).
R.C. Petter, J.S. Salek, C.T. Sikorski, G. Kumaravel and F.T. Lin, J. Am. Chem. Soc., 112, 3860 (1990).
Y.N. Ni, D.Q. Lin and S. Kokot, Talanta, 65, 1295 (2005).
C.V. Kumar, R.S. Turner and E.H. Asuncion, J. Photochem. Photobiol. A-Chem., 74, 231 (1993).
U. Chaveerach, A. Meenongwa, Y. Trongpanich, C. Soikum and P. Chaveerach, Polyhedron, 29, 731 (2010).
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D.W. Pang and H.D. Abruna, Anal. Chem., 70, 3162 (1998).
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M.T. Carter, M. Rodriguez and A.J. Bard, J. Am. Chem. Soc., 111, 8901 (1989).
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