CoMFA and CoMSIA 3D-QSAR studies on S6-(4-nitrobenzyl)mercaptopurine riboside (NBMPR) analogs as inhibitors of human equilibrative nucleoside transporter 1 (hENT1)

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 2, 2009, Pages 314-318

  Gupte, Amol ^a   Buolamwini, John K ^a  

^a UNIVERSITY OF TENNESSEE HEALTH SCIENCE CENTER   (United States)

Author keywords

3D QSAR; CoMFA; CoMSIA; Cross validation; Equilibrative nucleoside transporter; hENT1; Inhibitor; NBMPR analogs

Indexed keywords

EQUILIBRATIVE NUCLEOSIDE TRANSPORTER 1; EQUILIBRATIVE NUCLEOSIDE TRANSPORTER 1 INHIBITOR; NITROBENZYLTHIOINOSINE; S6 (4 NITROBENZYL)MERCAPTOPURINE RIBOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BOOTSTRAPPING; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; DRUG PROTEIN BINDING; DRUG STRUCTURE; HYDROGEN BOND; HYDROPHOBICITY; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RELIABILITY; STEREOCHEMISTRY; SUBSTITUTION REACTION; VALIDITY;

EQUILIBRATIVE NUCLEOSIDE TRANSPORTER 1; HUMANS; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; THIOINOSINE;

EID: 57749118583     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.11.092     Document Type: Article

References (24)

1. Jacquez J.A. Biochim. Biophys. Acta 61 (1962) 265
2. Van Belle H. Cardiovasc. Res. 27 (1993) 68
3. Le Vraux V., Chen Y.L., Masson I., De Sousa M., Giroud J.P., Florentin I., and Chauvelot-Moachon L. Life Sci. 52 (1993) 1917
4. Hendrix C.W., Flexner C., Szebeni J., Kuwahara S., Pennypacker S., Weinstein J.N., and Lietman P.S. Antimicrob. Agents Chemother. 38 (1994) 1036
5. Weber G., Lui M.S., Natsumeda Y., and Faderan M.A. Adv. Enzyme Regul. 21 (1983) 53
6. Weber G., Jayaram H.N., Pillwein K., Natsumeda Y., Reardon M.A., and Zhen Y.S. Adv. Enzyme Regul. 26 (1987) 335
7. Baldwin S.A., Beal P.R., Yao S.Y., King A.E., Cass C.E., and Young J.D. Pflugers Arch. 447 (2004) 735
8. Gray J.H., Owen R.P., and Giacomini K.M. Pflugers Arch. 447 (2004) 728
9. Griffiths M., Beaumont N., Yao S.Y., Sundaram M., Boumah C.E., Davies A., Kwong F.Y., Coe I., Cass C.E., Young J.D., and Baldwin S.A. Nat. Med. 3 (1997) 89
10. Griffiths M., Yao S.Y., Abidi F., Phillips S.E., Cass C.E., Young J.D., and Baldwin S.A. Biochem. J. 328 (1997) 739
11. Baldwin S.A., Yao S.Y., Hyde R.J., Ng A.M., Foppolo S., Barnes K., Ritzel M.W., Cass C.E., and Young J.D. J. Biol. Chem. 280 (2005) 15880
12. Barnes K., Dobrzynski H., Foppolo S., Beal P.R., Ismat F., Scullion E.R., Sun L., Tellez J., Ritzel M.W., Claycomb W.C., Cass C.E., Young J.D., Billeter-Clark R., Boyett M.R., and Baldwin S.A. Circ. Res. 99 (2006) 510
13. Huang Q.Q., Yao S.Y., Ritzel M.W., Paterson A.R., Cass C.E., and Young J.D. J. Biol. Chem. 269 (1994) 17757
14. Wang J., Su S.F., Dresser M.J., Schaner M.E., Washington C.B., and Giacomini K.M. Am. J. Physiol. 273 (1997) F1058
15. Ritzel M.W., Ng A.M., Yao S.Y., Graham K., Loewen S.K., Smith K.M., Ritzel R.G., Mowles D.A., Carpenter P., Chen X.Z., Karpinski E., Hyde R.J., Baldwin S.A., Cass C.E., and Young J.D. J. Biol. Chem. 276 (2001) 2914
16. Buolamwini J.K. Curr. Med. Chem. 4 (1997) 35
17. Cass C.E. Drug Transport in Antimicrobial and Anticancer Chemotherapy;. In: Georgopapadakou N.H. (Ed) (1995), Marcel Dekker, New York 403-451
18. Zhu Z., and Buolamwini J.K. Bioorg. Med. Chem. 16 (2008) 3848
19. Gupte A., and Buolamwini J.K. Bioorg. Med. Chem. Lett. 14 (2004) 2257
20. Gupte A., Buolamwini J.K., Yadav V., Chu C.K., Naguib F.N., and el Kouni M.H. Biochem. Pharmacol. 71 (2005) 69
21. Gupte A., and Buolamwini J.K. Bioorg. Med. Chem. 15 (2007) 7726
22. Viswanadhan V.N., Ghose A.K., Revenkar G.R., and Robins R.K. J. Chem. Inf. Comput. Sci. 29 (1989) 163
23. Klebe G. J. Mol. Biol. 237 (1994) 212
24. Buolamwini J.K., Raghavan K., Fesen M.R., Pommier Y., Kohn K.W., and Weinstein J.N. Pharm. Res. 13 (1996) 1891