PL EN


Preferences help
enabled [disable] Abstract
Number of results
Journal
2009 | 7 | 1 | 59-65
Article title

Quantitative structure-property relationship study on the determination of binding constant by fluorescence quenching

Content
Title variants
Languages of publication
EN
Abstracts
EN
Models to predict binding constant (logK) to bovine serum albumin (BSA) should be very useful in the pharmaceutical industry to help speed up the design of new compounds, especially as far as pharmacokinetics is concerned. We present here an extensive list of logK binding constants for thirty-five compounds to BSA determined by florescence quenching from the literature. These data have allowed us the derivation of a quantitative structure-property relationship (QSPR) model to predict binding constants to BSA of compounds on the basis of their structure. A stepwise multiple linear regression (MLR) was performed to build the model. The statistical parameter provided by the MLR model (R = 0.9200, RMS = 0.3305) indicated satisfactory stability and predictive ability for the model. Using florescence quenching spectroscopy, we also experimentally determined the binding constants to BSA for two bioactive components in traditional Chinese medicines. Using the proposed model it was possible to predict the binding constants for each, which were in good agreement with the experimental results. This QSPR approach can contribute to a better understanding of structural factors of the compounds responsible for drug-protein interactions, and be useful in predicting the binding constants of other compounds. [...]
Publisher
Journal
Year
Volume
7
Issue
1
Pages
59-65
Physical description
Dates
published
1 - 3 - 2009
online
23 - 12 - 2008
References
  • [1] D.C. Carter, J.X. Ho, Adv. Protein Chem. 45, 152 (1994)
  • [2] H.P. Rang, M.M. Dale, J.M. Ritter, Pharmacology (Churchill Livingstone, Edinburgh, 1999)
  • [3] F. Herve, S. Urien, E. Albengres, J.C. Duche, J. Tillement, Clin. Pharmacokinet. 26, 44 (1994) http://dx.doi.org/10.2165/00003088-199426010-00004[Crossref]
  • [4] R.E. Olson, D.D. Christ, Annu. Rep. Med. Chem. 31, 327 (1996) http://dx.doi.org/10.1016/S0065-7743(08)60472-8[Crossref]
  • [5] S.M.T. Shaikh, J. Seetharamappa, P.B. Kandagal, S. Ashoka, J. Mol. Struct. 786, 46 (2006) http://dx.doi.org/10.1016/j.molstruc.2005.10.021[Crossref]
  • [6] J. Rownicka, A. Sulkowska, J. Pozycka, B. Bojko, W.W. Sulkowski, J. Mol. Struct. 792–793, 243 (2006) http://dx.doi.org/10.1016/j.molstruc.2006.02.001[Crossref]
  • [7] A. Sulkowska, M. Maciazek, J. Rownicka, B. Bojko, D. Rentak, W.W. Sulkowska, J. Mol. Struct. 834–836, 162 (2007) http://dx.doi.org/10.1016/j.molstruc.2006.10.058[Crossref]
  • [8] G. Falini, E. Foresti, I.G. Lesci, B. Lunelli, P. Sabatino, Chemistry 12, 1968 (2006) http://dx.doi.org/10.1002/chem.200500709[Crossref]
  • [9] V.M. Gunko, V.I. Zarko, E.F. Voronin, E.V. Goncharuk, L.S. Andriyko, N.V. Guzenko, L.V. Nosach, W. Janusz, J. Colloid Interface Sci. 300, 20 (2006) http://dx.doi.org/10.1016/j.jcis.2006.03.034[Crossref]
  • [10] H. Chakraborty, P.K. Chakraborty, S. Raha, P.C. Mandal, M. Sarkar, Biochim. Biophys. Acta Biomembr. 1768, 1138 (2007) http://dx.doi.org/10.1016/j.bbamem.2007.01.004[Crossref]
  • [11] E.A. Yates, C.J. Terry, C. Rees, T.R. Rudd, L. Duchesne, M.A. Skidmore, Biochem. Soc. Trans. 34, 427 (2006) http://dx.doi.org/10.1042/BST0340427[Crossref]
  • [12] C. Hansch, A. Kurup, R. Garg, H. Gao, Chem. Rev. 101, 619 (2001) http://dx.doi.org/10.1021/cr0000067[Crossref]
  • [13] A.R. Katritzky, K. Chen, U. Maran, D.A. Carlson, Anal. Chem. 72, 101 (2000) http://dx.doi.org/10.1021/ac990800w[Crossref]
  • [14] W.L. Fitch, M. Gregor, A.R. Katritzky, A. Lomaka, R. Petrukhin, M. Karelson, J. Chem. Inf. Comput. Sci. 428, 830 (2002)
  • [15] R. Bosque J. Sales, J. Chem. Inf. Comput. Sci. 41, 225 (2001) 225 [Crossref]
  • [16] J.A. Morrill, R.E. Jensen, P.H. Madison, C.F. Chabalowski, J. Chem. Inf. Comput. Sci. 44, 912 (2004) [Crossref]
  • [17] J. Shi, F. Luan, H.X. Zhang, M.C. Liu, Q.X. Guo, Z.D. Hu, B.T. Fan, QSAR Comb. Sci. 25, 147 (2006) http://dx.doi.org/10.1002/qsar.200510142[Crossref]
  • [18] R.D. Saiakhov, L.R. Stefan, G. Klopman, Perspectives in Drug Discovery and Design 19, 133 (2000) http://dx.doi.org/10.1023/A:1008723723679[Crossref]
  • [19] G. Colmenarejo, Med. Res. Rev. 23, 275 (2003) http://dx.doi.org/10.1002/med.10039[Crossref]
  • [20] N.A. Kratochwil, W. Huber, F. Muller, M. Kansy, P.R. Gerber, Biochem. Pharmacol. 64, 1355 (2002) http://dx.doi.org/10.1016/S0006-2952(02)01074-2[Crossref]
  • [21] D.J. Gao, Y. Tian, F.H. Liang, D.H. Jin, Y.H. Chen, H.Q. Zhang, A.M. Yu, J. Lumin. 127, 515 (2007) http://dx.doi.org/10.1016/j.jlumin.2007.02.062[Crossref]
  • [22] C.Q. Jiang, M.X. Gao, J.X. He, Anal. Chim. Acta 452, 185 (2002) http://dx.doi.org/10.1016/S0003-2670(01)01453-2[Crossref]
  • [23] F.L. Cui, J. Fan, J.P. Li, Z.D. Hu, Bioorg. Med. Chem. 12, 151 (2004) http://dx.doi.org/10.1016/j.bmc.2003.10.018[Crossref]
  • [24] W. Bian, Y.L. Wei, Y.P. Wang, C. Dong, Chin. J. Spectrosc. Spectral Anal. 26, 505 (2006)
  • [25] G.Z. Li, Y.M. Liu, X.Y. Guo, J.J. Wang, Chin. J. Anal. Chem. 34, 91 (2006)
  • [26] L.H. Liu, G.R. Fang, G.W. Song, J. Hebei Univers. (Nat. Sci. Ed.) 26, 131 (2004)
  • [27] N. Zhou, Y.Z. Liang, Q. Cheng, X.B. Gong, Y.C. Wang, Chin. J. Chem. 5, 376 (2007)
  • [28] G.X. Li, J.Q. Li, Y.X. Wei, D. Chuan, Chin. J. Spectrosc. Spectral Anal. 25, 1277 (2005)
  • [29] P.G. Yi, Q.S. Yu, Z.C. Shang, H. X. Zong, Chin. J. Acta Pharm. Sin. 35, 774 (2000)
  • [30] H.X. Zhang, C.N. Yan, J.Q. Tong, P. Mei, K.H. Li, Chin. J. Chem. Bioengineering 4, 26 (2005)
  • [31] L.X. Zhao, B.X. Li, Z.J. Zhang, J. Shanxi Normal Univers. (Nat. Sci. Ed.) 30, 73 (2002)
  • [32] M. Guo, P.G. Yi, W.N. Zhao, Z.C. Shang, Q.S. Yu, J. Zhejiang Univers. (Sci. Ed.) 30, 4334 (2003)
  • [33] Y.P. Feng, S.L. Cao, W.J. Xie, Y.M. Li, Y.F. Zhao, Chin. J. Instrumental Anal. 26, 323 (2007)
  • [34] A. Mallick, N. Chattopadhyay, J. Photochem. Photobiol. A 81, 419 (2005) http://dx.doi.org/10.1562/2004-07-12-RA-230.1[Crossref]
  • [35] J.Q. Lu, F. Jin, T.Q. Sun, X.W. Zhou, Int. J. Biol. Macromol. 40, 299 (2007) http://dx.doi.org/10.1016/j.ijbiomac.2006.08.010[Crossref]
  • [36] S. Deepa, A. K. Mishra, J. Pharm. Biomed. Anal. 38, 556 (2005) http://dx.doi.org/10.1016/j.jpba.2005.01.023[Crossref]
  • [37] B.C. Yu, H.T. Wu, P.J. Zhou, S.Q. Nan, G.H. Lu, F. Song, Chin. J. Enviromental Sci. 27, 977 (2006)
  • [38] S.F. Sun, W.J. Li, L. Sun, Chin. J. Chem. Bioengineering 24, 75 (2007)
  • [39] Z.C. Shang, Y.P. Gui, Q.S. Yu, R.S. Lin, Chin. J. Acta Phys.-Chim. Sin. 17, 48 (2001)
  • [40] A. Mallick, S.C. Bera, S. Maiti, N. Biophys. Chem. 112, 9 (2004) http://dx.doi.org/10.1016/j.bpc.2004.06.009[Crossref]
  • [41] A. Barik, K.I. Priyadarsini, H. Mohan, Photochem. Photobiol. 77, 597 (2003) http://dx.doi.org/10.1562/0031-8655(2003)077<0597:PSOBOC>2.0.CO;2[Crossref]
  • [42] A. Sulkowska, J. Rownicka, B. Bojko, J. Pozycka, I. Zubik-Skupien, W. Sulkowski, J. Mol. Struct. 704, 291 (2004) http://dx.doi.org/10.1016/j.molstruc.2003.12.065[Crossref]
  • [43] A.K. Singh, P.K. Hota, J. Phys. Org. Chem. 20, 624 (2007) http://dx.doi.org/10.1002/poc.1222[Crossref]
  • [44] S.M.T. Shaikh, J. Seetharamappa, S. Ashoka, P.B. Kandagal, Dyes Pigm. 73, 211 (2007) http://dx.doi.org/10.1016/j.dyepig.2005.11.008[Crossref]
  • [45] Y. Cui, J.F. Guo, B.J. Xu, Z.Y. Chen, Pestic. Biochem. Physiol. 85, 110 (2006) http://dx.doi.org/10.1016/j.pestbp.2005.11.004[Crossref]
  • [46] Y.P. Wang, Y.I. Wei, C. Dong, J. Photochem. Photobiol. A 177, 6 (2006) http://dx.doi.org/10.1016/j.jphotochem.2005.04.040[Crossref]
  • [47] N. Zhou, Y.Z. Liang, P. Wang, J. Photochem. Photobiol. A 185, 271 (2007) http://dx.doi.org/10.1016/j.jphotochem.2006.06.019[Crossref]
  • [48] S.M.T. Shaikh, J. Seetharamappa, P.B. Kandagal, D.H. Manjunatha, Dyes Pigm. 74, 665 (2007) http://dx.doi.org/10.1016/j.dyepig.2006.04.010[Crossref]
  • [49] B. Huang, G.L. Zou, T.M. Yang, Chin. J. Acta Chim. Sin. 60, 1867 (2002)
  • [50] J.Z. You, S. Shao, Q.F. Lei, J. Zhejiang Univers. (Sci. Ed.) 34, 205 (2007)
  • [51] ISIS Draw2.3, MDL Information Systems, Inc. (1990–2000)
  • [52] HyperChem 6.01, Hypercube, Inc. (2000)
  • [53] M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, J.J.P. Stewart, J. Am. Chem. Soc. 107, 3898 (1985) http://dx.doi.org/10.1021/ja00299a023[Crossref]
  • [54] MOPAC, v.6.0 Quantum Chemistry Program Exchange, Program 455, Indiana University, Bloomington, IN (1989)
  • [55] A.R. Katritzky, V.S. Lobanov, M. Karelson, CODESSA: Reference Manual (University of Florida, Gainesville, 1994)
  • [56] M. Oblak, M. Randic, T. Solmajer, J. Chem. Inf. Comput. Sci. 40, 994 (2000) [Crossref]
  • [57] E. Deponinck, D. Coomans, Y.V. Heyden, J. Pharm. Biomed. Anal. 43, 119 (2007) http://dx.doi.org/10.1016/j.jpba.2006.06.022[Crossref]
  • [58] D.L. Massart, B.G.M. Vandeginste, L.M.C. Buydens, S.D. Jong, P.J. Lewi, J. Smeyers-Verbeke, Handbook of Chemometrics and Qualimetrics-Part A (Elsevier Science, Amsterdam, 1997)
  • [59] J.C. Li, N. Li, Q.H. Wu, Z. Wang, J.J. Ma, C. Wang, L.J. Zhang, J. Mol. Struct. 833, 184 (2007) http://dx.doi.org/10.1016/j.molstruc.2006.09.019[Crossref]
Document Type
Publication order reference
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_s11532-008-0095-3
Identifiers
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.