Phenylsulfonylfuroxans as modulators of multidrug-resistance-associated protein-1 and P-glycoprotein

Journal of Medicinal Chemistry

Volumn 53, Issue 15, 2010, Pages 5467-5475

  Fruttero, Roberta ^a   Crosetti, Marco ^a   Chegaev, Konstantin ^a   Guglielmo, Stefano ^a   Gasco, Alberto ^a   Berardi, Francesco ^b   Niso, Mauro ^b   Perrone, Roberto ^b   Panaro, Maria Antonietta ^b   Colabufo, Nicola Antonio ^b  

^a UNIVERSITY OF TURIN   (Italy)

^b UNIVERSITY OF BARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

4 BUTOXY 3 PHENYLSULFONYLFUROXAN; 4 HEXYLOXY 3 PHENYLSULFONYLFUROXAN; DOXORUBICIN; GLYCOPROTEIN P; MULTIDRUG RESISTANCE PROTEIN 1; OXADIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG EFFECT; DRUG PROTEIN BINDING; DRUG SYNTHESIS; NONHUMAN;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE; CELL PROLIFERATION; DOGS; DOXORUBICIN; DRUG INTERACTIONS; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, NEOPLASM; OXADIAZOLES; P-GLYCOPROTEIN; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONES;

EID: 77955374056     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100066y     Document Type: Article

References (42)

1. Gottesman, M. M. Mechanisms of cancer drug resistance Annu. Rev. Med. 2002, 53, 615-627
2. Simon, S. M.; Schindler, M. Cell biological mechanisms of multidrug resistance in tumors Proc. Nat. Acad. Sci. U.S.A. 1994, 91, 3497-3504
3. Ross, D. D.; Doyle, L. A. Mining our ABCs: pharmacogenomic approach for evaluating transporter function in cancer drug resistance Cancer Cell 2004, 6, 105-107
4. Pharm, A.-N.; Penchala, S.; Graf, R. A.; Wang, J.; Huang, Y. Pharmacogenomic Characterization of ABC Transporters Involved in Multidrug Resistance. In Multidrug Resistance: Biological and Pharmaceutical Advance in the Antitumour Treatment; Colabufo, N. A., Ed.; Research Signpost: Kerala, India, 2008; pp 19 - 62.
5. Avendaño, C.; Menéndez, J. C. Inhibitors of multidrug resistance to antitumor agents (MDR) Curr. Med. Chem. 2002, 9, 159-193
6. Colabufo, N. A.; Berardi, F.; Cantore, M.; Contino, M.; Inglese, C.; Niso, M.; Perrone, R. Perspectives of P-glycoprotein modulating agents in oncology and neurodegenerative diseases: pharmaceutical, biological and diagnostic potentials J. Med. Chem. 2010, 53, 1883-1997
7. Colabufo, N. A.; Berardi, F.; Contino, M.; Niso, M.; Perrone, R. ABC pumps and their role in active drug transport Curr. Top. Med. Chem. 2009, 9, 119-129
8. Ohtsuki, S.; Terasaki, T. Contribution of carrier-mediated transport systems to the blood?brain barrier as a supporting and protecting interface for the brain; importance for CNS drug discovery and development Pharm. Res. 2007, 24, 1745-1758
9. Pérez-Tomás, R. Multidrug resistance: retrospect and prospects in anti-cancer drug treatment Curr. Med. Chem. 2006, 13, 1859-1876
10. Teodori, E.; Dei, S.; Martelli, S.; Scapecchi, F.; Gualtieri, F. The functions and structure of ABC transporters: implications for the design of new inhibitors of Pgp and MRP1 to control multidrug resistance (MDR) Curr. Drug Targets 2006, 7, 893-909
11. Giménez-Bonafé, P.; Guillén Canovas, A.; Ambrosio, S.; Tortosa, A.; Pérez-Tomás, R. Drugs Modulating MDR. In Multidrug Resistance: Biological and Pharmaceutical Advance in the Antitumour Treatment; Colabufo, N. A., Ed.; Research Signpost: Kerala, India, 2008; pp 63 - 99.
12. Planting, A. S.; Sonneveld, P.; van der Gaast, A.; Sparreboom, A.; van der Burg, M. E.; Luyten, G. P.; de Leeuw, K.; de Boer-Dennert, M.; Wissel, P. S.; Jewell, R. C.; Paul, E. M.; Purvis, N. B., Jr.; Verweij, J. A phase I and pharmacologic study of the MDR converter GF120918 in combination with doxorubicin in patients with advanced solid tumors Cancer Chemother. Pharmacol. 2005, 55, 91-99 (Pubitemid 40064500)
13. Kuppens, I. E.; Witteveen, E. O.; Jewell, R. C.; Radema, S. A.; Paul, E. M.; Mangum, S. G.; Beijnen, J. H.; Voest, E. E.; Schellens, J. H. A phase I, randomized, open-label, parallel-cohort, dose-finding study of elacridar (GF120918) and oral topotecan in cancer patients Clin. Cancer Res. 2007, 13, 3276-3285
14. 99mTc-sestamibi accumulation in normal liver and drug-resistant tumors after the administration of the glycoprotein inhibitor, XR9576 Clin. Cancer Res. 2003, 9, 650-656
15. Fox, E.; Bates, S. E. Tariquidar (XR9576): A P-glycoprotein drug efflux pump inhibitor Expert Rev. Anticancer Ther. 2007, 7, 447-459
16. Pusztai, L.; Wagner, P.; Ibrahim, N.; Rivera, E.; Theriault, R.; Booser, D.; Symmans, F. W.; Wong, F.; Blumenschein, G.; Fleming, D. R.; Rouzier, R.; Boniface, G.; Hortobagyi, G. N. Phase II study of tariquidar, a selective P-glycoprotein inhibitor, in patients with chemotherapy-resistant, advanced breast carcinoma Cancer 2005, 104, 682-691
17. van Zuylen, L.; Sparreboom, A.; van der Gaast, A.; van der Burg, M. E.; van Beurden, V.; Bol, C. J.; Woestenborghs, R.; Palmer, P. A.; Verweij, J. The orally administered P-glycoprotein inhibitor R101933 does not alter the plasma pharmacokinetics of docetaxel Clin. Cancer Res. 2000, 6, 1365-1371
18. 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, 516-525
19. Teicher, B. A. Hypoxia and drug resistance Cancer Metastasis Rev. 1994, 13, 139-168
20. Matthews, N. E.; Adams, M. A.; Maxwell, L. R.; Gofton, T. E.; Graham, C. H. Nitric oxide-mediated regulation of chemosensitivity in cancer cells J. Natl. Cancer Inst. 2001, 93, 1879-1885
21. Frederiksen, L. J.; Siemens, D. R.; Heaton, J. P.; Maxwell, L. R.; Adams, M. A.; Graham, C. H. Hypoxia induced resistance to doxorubicin in prostate cancer cells is inhibited by low concentrations of glyceryl trinitrate J. Urol. 2003, 170, 1003-1007
22. Gasco, A.; Boulton, A. J. Furoxans and benzofuroxans Adv. Heterocycl. Chem. 1981, 29, 251-340
23. Feelisch, M.; Schonafinger, K.; Noack, E. Thiol-mediated generation of nitric oxide accounts for the vasodilator action of furoxans Biochem. Pharmacol. 1992, 44, 1149-1157
24. 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, 4412-4416
25. 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, 463-469
26. Gasco, A.; Shönafinger, K. The NO-Releasing Heterocyclic. In Nitric Oxide Donors; Wang, P. G.; Cai, T. B.; Taniguchi, N., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2005; pp 131 - 175.
27. Cerecetto, H.; Porcal, W. Pharmacological properties of furoxans and benzofuroxans: recent developments Mini-Rev. Med. Chem. 2005, 5, 57-71 (Pubitemid 40136481)
28. 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. 2006, 148, 517-526
29. Rai, G.; Sayed, A. A.; Lea, W. A.; Luecke, H. F.; Chakrapani, H.; Prast-Nielsen, S.; Jadhav, A.; Leister, W.; Shen, M.; Inglese, J.; Austin, C. P.; Keefer, L.; Arnér, E. S. J.; Simeomov, A.; Maloney, D. J.; Williams, D. L.; Thomas, C. J. Structure mechanism insights and the role of nitric oxide donation guide the development of oxadiazole-2-oxides as therapeutic agents against schistosomiasis J. Med. Chem. 2009, 52, 6474-6483
30. 13C NMR study of a series of isomeric pairs of furoxans and the structure of the two isomeric chloro-phenyl-furoxans J. Heterocycl. Chem. 1982, 19, 427-430
31. Fruttero, R.; Ferrarotti, B.; Serafino, A.; Gasco, A. Phenylfuroxancarboxylic acids and their derivatives Liebigs Ann. Chem. 1990, 335-338
32. Sorba, G.; Ermondi, G.; Fruttero, R.; Galli, U.; Gasco, A. Reaction of benzenesulfonyl substituted furoxans with ethanol and ethanethiol in basic medium J. Heterocycl. Chem. 1996, 33, 327-334
33. Feng, B.; Mills, J. B.; Davidson, R. E.; Mireles, R. J.; Janiszewski, J. S.; Troutman, M. D.; de Morais, S. M. In vitro P-glycoprotein assays to predict the in vivo interactions of P-glycoprotein with drugs in the central nervous system Drug Metab. Dispos. 2008, 36, 268-275
34. GraphPad Prism Software, version for Windows; GraphPad Software, Inc.: San Diego, CA, 1998.
35. Colabufo, N. A.; Berardi, F.; Cantore, M.; Perrone, M. G.; Contino, M.; Inglese, C.; Niso, M.; Perrone, R. Multi drug resistance reverting agents: 2-aryloxazole and 2-arylthiazole derivatives as potent BCRP or MRP1 inhibitors ChemMedChem 2009, 4, 188-195
36. Kim, R. B. Drugs as P-glycoprotein substrates, inhibitors, and inducers Drug Metab. Rev. 2002, 34, 47-54
37. Hammann, F.; Gutmann, H.; Jecklin, U.; Maunz, A.; Helma, C.; Drewe, J. Development of decision tree models for substrates, inhibitors, and inducers of p-glycoprotein Curr. Drug Metab. 2009, 10, 339-346
38. Chegaev, K.; Rolando, B.; Guglielmo, S.; Fruttero, R.; Gasco, A. Methyl and phenylfuroxansulfonic acids and related sulfonamides J. Heterocycl. Chem. 2009, 46, 866-872
39. Kulikov, A. S.; Ovghinnikov, I. V.; Molotov, S. I.; Makhova, N. N. Synthesis of furoxan derivatives based on 4-aminofuroxan-3-carboxylic acid azide Russ. Chem. Bull. 2003, 52, 1822-1828 (English translation)
40. Sheremetev, A. B.; Makhova, N. Monocyclic furazans and furoxans Adv. Heterocycl. Chem. 2001, 78, 65-188
41. Colabufo, N. A.; Berardi, F.; Contino, M.; Niso, M.; Abate, C.; Perrone, R.; Tortorella, V. Antiproliferative and cytotoxic effects of some ?2 agonists and ?1 antagonists in tumour cell lines Naunyn-Schmiedeberg's Arch. Pharmacol. 2004, 370, 106-113
42. Azzariti, A.; Colabufo, N. A.; Berardi, F.; Porcelli, L.; Niso, M.; Simone, M. G.; Perrone, R.; Paradiso, A. Cyclohexylpiperazine derivative PB28, a ?2 agonist and ?1 antagonist receptor, inhibits cell growth, modulates P-glycoprotein, and synergizes with anthracyclines in breast cancer Mol. Cancer Ther. 2006, 5, 1807-1816