Modeling study of phenylsulfonylfuroxan derivatives as P-gp inhibitors: A combined approach of CoMFA, CoMSIA and HQSAR

Anti-Cancer Agents in Medicinal Chemistry

Volumn 14, Issue 7, 2014, Pages 1019-1030

  Gadhe, Changdev G ^a   Balupuri, Anand ^a   Balasubramanian, Pavithra K ^a   Cho, Seung Joo ^a  

^a Chosun University   (South Korea)

Author keywords

Anti cancer agent; CoMFA; CoMSIA; HQSAR; P gp; Phenylsulfonylfuroxan

Indexed keywords

FUROXANS; LIGAND; MULTIDRUG RESISTANCE PROTEIN; OXADIAZOLE DERIVATIVE; SULFONE;

ANTAGONISTS AND INHIBITORS; BIOLOGY; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG RESISTANCE; HUMAN; HYDROGEN BOND; MULTIDRUG RESISTANCE; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

COMPUTATIONAL BIOLOGY; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, NEOPLASM; HUMANS; HYDROGEN BONDING; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OXADIAZOLES; P-GLYCOPROTEIN; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SULFONES;

EID: 84905652385     PISSN: 18715206     EISSN: 18755992     Source Type: Journal    
DOI: 10.2174/18715206113136660335     Document Type: Article

References (59)

1. Borst, P. Genetic mechanisms of drug resistance: A review. Acta Oncol., 1991, 30(1), 87-105.
2. Bellamy, W.T.; Dalton, W.S. Multidrug resistance in the laboratory and clinic. Adv. Clin. Chem., 1994, 31, 1-61.
3. Loe, D.W.; Deeley, R.; Cole, S.P. Biology of the multidrug resistance- associated protein, MRP. Eur. J. Cancer, 1996, 32(6), 945-957.
4. Cole, S.P.; Deeley, R.G. Multidrug resistance mediated by the ATP-binding cassette transporter protein MRP. Bioessays, 1998, 20(11), 931-940.
5. Ambudkar, S.V.; Dey, S.; Hrycyna, C.A.; Ramachandra, M.; Pastan, I.; Gottesman, M.M. Biochemical, cellular, and pharmacological aspects of the multidrug transporter 1. Annu. Rev. Pharmacol. Toxicol., 1999, 39(1), 361-398.
6. Hipfner, D.R.; Deeley, R.G.; Cole, S.P.C. Structural, mechanistic and clinical aspects of MRP1. Biochim. Biophys. Acta, 1999, 1461(2), 359-376.
7. Borst, P.; Evers, R.; Kool, M.; Wijnholds, J. The multi drug resistance protein family. Biochim. Biophys. Acta, 1999, 1461(2), 347-357.
8. Gottesman, M.M.; Fojo, T.; Bates, S.E. Multidrug resistance in cancer: Role of ATP-dependent transporters. Nat. Rev. Cancer, 2002, 2(1), 48-58.
9. Gottesman, M.M.; Pastan, I. Biochemistry of multidrug resistance mediated by the multidrug transporter. Annu. Rev. Biochem., 1993, 62(1), 385-427.
10. Juliano, R.; Ling, V.; Graves, J. Drug resistant mutants of Chinese hamster ovary cells possess an altered cell surface carbohydrate component. J. Supramol. Struct., 1976, 4(4), 521-526.
11. Hrycyna, C.A. Molecular genetic analysis and biochemical characterization of mammalian P-glycoproteins involved in multidrug resistance. Semin. Cell Dev. Biol., 2001, 12(3), 247-256.
12. Ford, R.C.; Kamis, A.B.; Kerr, I.D.; Callaghan, R. In: Transporters as Drug Carriers: Structure, Function, Substrates, G. F. Ecker and P. Chiba; Ed.; Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 2010; Vol. 44, pp. 1-48.
13. Tirino, V.; Desiderio, V.; Paino, F.; De Rosa, A.; Papaccio, F.; Fazioli, F.; Pirozzi, G.; Papaccio, G. Human primary bone sarcomas contain CD133+ cancer stem cells displaying high tumorigenicity in vivo. FASEB J., 2011, 25(6), 2022-2030.
14. Tirino, V.; Desiderio, V.; Paino, F.; De Rosa, A.; Papaccio, F.; La Noce, M.; Laino, L.; De Francesco, F.; Papaccio, G. Cancer stem cells in solid tumors: An overview and new approaches for their isolation and characterization. FASEB J., 2013, 27(1), 13-24.
15. Hong-Bo, Q.; Yuan-Ming, F.; Ming-Li, H.; Hao-Jun, L.; Jia, X.; Hong, L.; Hao, L.; Cheng-Yi, W.; Wei-Xue, T. Expression of breast cancer resistance protein and P-glycoprotein in residual breast cancer tissue after chemotherapy and its correlation with cancer stem cells. Zhongguo Yi Xue Ke Xue Yuan Xue Bao., 2013, 35(2), 171-176.
16. Moitra, K.; Lou, H.; Dean, M. Multidrug efflux pumps and cancer stem cells: Insights into multidrug resistance and therapeutic development. Clin. Pharmacol. Ther., 2011, 89(4), 491-502.
17. Higgins, C.F. ABC transporters: From microorganisms to man. Annu. Rev. Cell Biol., 1992, 8(1), 67-113.
18. Klein, I.; Sarkadi, B.; Váradi, A. An inventory of the human ABC proteins. BBA-Biomembr., 1999, 1461(2), 237-262.
19. Kuwano, M.; Toh, S.; Uchiumi, T.; Takano, H.; Kohno, K.; Wada, M. Multidrug resistance-associated protein subfamily transporters and drug resistance. Anti-Cancer Drug Des., 1999, 14(2), 123-131.
20. Linton, K.J.; Higgins, C.F. Structure and function of ABC transporters: The ATP switch provides flexible control. Pflug. Arch. Eur. J. Phy., 2007, 453(5), 555-567.
21. Schneider, G. Virtual screening: An endless staircase? Nat. Rev. Drug Discov., 2010, 9(4), 273-276.
22. Klepsch, F.; Stockner, T.; Erker, T.; Muller, M.; Chiba, P.; F Ecker, G. Using structural and mechanistic information to design novel inhibitors/substrates of P-glycoprotein. Curr. Top. Med. Chem., 2010, 10(17), 1769-1774.
23. Raub, T.J. P-glycoprotein recognition of substrates and circumvention through rational drug design. Mol. Pharm., 2006, 3(1), 3-25.
24. Pleban, K.; Ecker, G.F. Inhibitors of p-glycoprotein-lead identification and optimisation. Mini Rev. Med. Chem., 2005, 5(2), 153-163.
25. Gadhe, C.G.; Madhavan, T.; Kothandan, G.; Cho, S.J. In silico quantitative structure-activity relationship studies on P-gp modulators of tetrahydroisoquinoline-ethyl-phenylamine series. BMC Struct. Biol., 2011, 11(1), 5.
26. Kothandan, G.; Gadhe, C.G.; Madhavan, T.; Choi, C.H.; Cho, S.J. Docking and 3D-QSAR (quantitative structure activity relationship) studies of flavones, the potent inhibitors of p-glycoprotein targeting the nucleotide binding domain. Eur. J. Med. Chem., 2011, 46(9), 4078-4088.
27. Gadhe, C.G.; Kothandan, G.; Cho, S.J. Large variation in electrostatic contours upon addition of steric parameters and the effect of charge calculation schemes in CoMFA on mutagenicity of MX analogues. Mol. Simulat., 2012, 38(11), 861-871.
28. Gadhe, C.G.; Madhavan, T.; Kothandan, G.; Lee, T.B.; Lee, K.; Cho, S.J. Various partial charge schemes on 3D-QSAR models for P-gp inhibiting adamantyl derivatives. Bull. Korean Chem. Soc., 2011, 32(5), 1605-1612.
29. Kothandan, G.; Gadhe, C.G.; Cho, S.J. Structural insights from binding poses of CCR2 and CCR5 with clinically important antagonists: A combined in silico study. PLoS One, 2012, 7(3), e32864.
30. Kothandan, G.; Gadhe, C.G.; Madhavan, T.; Cho, S.J. Binding site analysis of CCR2 through in silico methodologies: Docking, CoMFA, and CoMSIA. Chem. Biol. Drug Des., 2011, 78(1), 161-174.
31. Pasha, F.A.; Neaz, M.M.; Cho, S.J.; Ansari, M.; Mishra, S.K.; Tiwari, S. In silico quantitative structure-toxicity relationship study of aromatic nitro compounds. Chem. Biol. Drug Des., 2009, 73(5), 537-544.
32. Gadhe, C.G.; Kothandan, G.; Cho, S.J. Computational modeling of human coreceptor CCR5 antagonist as a HIV-1 entry inhibitor: Using an integrated homology modeling, docking, and membrane molecular dynamics simulation analysis approach. J. Biomol. Struct. Dyn., 2013, 31(11),1251-1276.
33. Vyas, V.; Ghate, M. CoMFA and CoMSIA studies on aryl carboxylic acid amide derivatives as dihydroorotate dehydrogenase (DHODH) inhibitors. Curr. Comput.Aided Drug Des., 2012, 8(4), 271-282.
34. Ferreira, L.; Andricopulo, A. Structure-and ligand-based structure- activity relationships for a series of inhibitors of aldolase. Curr. Comput. Aided Drug Des., 2012, 8(4), 309-316.
35. Madhavan, T.; Chung, J.Y.; Kothandan, G.; Gadhe, C.G.; Cho, S.J. 3D-QSAR studies of JNK1 inhibitors utilizing various alignment methods. Chem. Biol. Drug Des., 2012, 79(1), 53-67.
36. Aller, S.G.; Yu, J.; Ward, A.; Weng, Y.; Chittaboina, S.; Zhuo, R.; Harrell, P.M.; Trinh, Y.T.; Zhang, Q.; Urbatsch, I.L.; Chang, G. Structure of P-glycoprotein reveals a molecular basis for poly- specific drug binding. Science, 2009, 323(5922), 1718-1722.
37. Fruttero, R.; Crosetti, M.; Chegaev, K.; Guglielmo, S.; Gasco, A.; Berardi, F.; Niso, M.; Perrone, R.; Panaro, M.A.; Colabufo, N.A. Phenylsulfonylfuroxans as modulators of multidrug-resistance- associated protein-1 and P-glycoprotein. J. Med. Chem., 2010, 53(15), 5467-5475.
38. Gasco, A.; Fruttero, R.; Sorba, G.; Di Stilo, A.; Calvino, R. NO donors: Focus on furoxan derivatives. Pure Appl. Chem., 2004, 76(5), 973-982.
39. Di Stilo, A.; Visentin, S.; Cena, C.; Gasco, A.M.; Ermondi, G.; Gasco, A. New 1, 4-dihydropyridines conjugated to furoxanyl moieties, endowed with both nitric oxide-like and calcium channel antagonist vasodilator activities. J. Med. Chem., 1998, 41(27), 5393-5401.
40. Boschi, D.; Tron, G.C.; Di Stilo, A.; Fruttero, R.; Gasco, A.; Poggesi, E.; Motta, G.; Leonardi, A. New potential uroselective NO-donor α1-antagonists. J. Med. Chem., 2003, 46(17), 3762-3765.
41. Turnbull, C.M.; Cena, C.; Fruttero, R.; Gasco, A.; Rossi, A.G.; Megson, I.L. Mechanism of action of novel NO-releasing furoxan derivatives of aspirin in human platelets. Br. J. Pharmacol., 2009, 148(4), 517-526.
42. Ferioli, R.; Folco, G.; Ferretti, C.; Gasco, A.; Medana, C.; Fruttero, R.; Civelli, M.; Gasco, A. A new class of furoxan derivatives as NO donors: Mechanism of action and biological activity. Br. J. Pharmacol., 2012, 114(4), 816-820.
43. Riganti, C.; Miraglia, E.; Viarisio, D.; Costamagna, C.; Pescarmona, G.; Ghigo, D.; Bosia, A. Nitric oxide reverts the resistance to doxorubicin in human colon cancer cells by inhibiting the drug efflux. Cancer Res., 2005, 65(2), 516-525.
44. Colabufo, N.A.; Contino, M.; Berardi, F.; Perrone, R.; Panaro, M.A.; Cianciulli, A.; Mitolo, V.; Azzariti, A.; Quatrale, A.; Paradiso, A. A new generation of MDR modulating agents with dual activity: P-gp inhibitor and iNOS inducer agents. Toxicol. In Vitro, 2011, 25(1), 222-230.
45. SYBYL 8.1 Tripos International, 1699 South Hanley Rd., St. Louis, Missouri, 63144, U.S.A., 2008.
46. Gasteiger, J.; Marsili, M. Iterative partial equalization of orbital electronegativity-a rapid access to atomic charges. Tetrahedron, 1980, 36(22), 3219-3228.
47. Cramer, R.D.; Patterson, D.E.; Bunce, J.D. Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J. Am. Chem. Soc., 1988, 110(18), 5959-5967.
48. Klebe, G.; Abraham, U.; Mietzner, T. Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J. Med. Chem., 1994, 37(24), 4130-4146.
49. Dunn, W.; Wold, S.; Edlund, U.; Hellberg, S.; Gasteiger, J. Multivariate structure-activity relationships between data from a battery of biological tests and an ensemble of structure descriptors: The PLS method. Quant. Struct.Act. Relat., 1984, 3(4), 131-137.
50. Clark, R.D.; Sprous, D.G. In: Rational Approaches to Drug Design: Proceedings of the 13th European Symposium on Quantitative Structure-Activity Relationships, Barcelona, August 27 - September, 1, 2000; H. D. Holtje and W. Sippl; Eds. Prous Science: Barcelona, Spain, 2001, pp. 475-485.
51. Clark, R.D.; Fox, P.C. Statistical variation in progressive scrambling. J. Comput.Aided Mol. Des., 2004, 18(7), 563-576.
52. Hurst, T.; Heritage, T. HQSAR-A highly predictive QSAR technique based on molecular holograms. 213th ACS Natl. Meeting, San Francisco, CA, 1997.
53. Ash, S.; Cline, M.A.; Homer, R.W.; Hurst, T.; Smith, G.B. SYBYL line notation (SLN): A versatile language for chemical structure representation. J. Chem. Inf. Comput. Sci., 1997, 37(1), 71-79.
54. Gupta, P.; Roy, N.; Garg, P. Docking-based 3D-QSAR study of HIV-1 integrase inhibitors. Eur. J. Med. Chem., 2009, 44(11), 4276-4287.
55. Willett, P.; Winterman, V. A comparison of some measures for the determination of inter-molecular structural similarity measures of inter-molecular structural similarity. Quant. Struct. Act. Relat., 1986, 5(1), 18-25.
56. Golbraikh, A.; Tropsha, A. Beware of q2! J. Mol. Graph. Model., 2002, 20(4), 269-276.
57. Feelisch, M.; Schönafingeri, K.; Noack, H. Thiol-mediated generation of nitric oxide accounts for the vasodilator action of furoxans. Biochem. Pharmacol., 1992, 44(6), 1149-1157.
58. Sorba, G.; Medana, C.; Fruttero, R.; Cena, C.; Di Stilo, A.; Galli, U.; Gasco, A. Water soluble furoxan derivatives as NO prodrugs. J. Med. Chem., 1997, 40(4), 463-469.
59. Medana, C.; Ermondi, G.; Fruttero, R.; Di Stilo, A.; Ferretti, C.; Gasco, A. Furoxans as nitric oxide donors. 4-Phenyl-3- furoxancarbonitrile: Thiol-mediated nitric oxide release and biological evaluation. J. Med. Chem., 1994, 37(25), 4412-4416.