Design, synthesis, and biological evaluation of (S)-valine thiazole-derived cyclic and noncyclic peptidomimetic oligomers as modulators of human P-glycoprotein (ABCB1)

ChemBioChem

Volumn 15, Issue 1, 2014, Pages 157-169

  Singh, Satyakam ^a   Prasad, Nagarajan Rajendra ^b,c   Kapoor, Khyati ^b   Chufan, Eduardo E ^b   Patel, Bhargav A ^a   Ambudkar, Suresh V ^b   Talele, Tanaji T ^a  

^a ST JOHN'S UNIVERSITY   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

^c ANNAMALAI UNIVERSITY   (India)

Author keywords

ABC transporters; molecular modeling; multidrug resistance; P glycoprotein; peptide mimics

Indexed keywords

2 (1 AMINO 2 METHYLPROPYL)THIAZOLE 4 CARBOXYLIC ACID; 2 (1 AMINO 2 METHYLPROPYL)THIAZOLE 4 CARBOXYLIC ACID ETHYL ESTER; 2 (1 TERT BUTOXYCARBONYLAMINO 2 METHYLPROPYL)THIAZOLE 4 CARBOXYLIC ACID; 2 (1 TERT BUTOXYCARBONYLAMINO 2 METHYLPROPYL)THIAZOLE 4 CARBOXYLIC ACID ETHYL ESTER; 2 [(1 ((2 (1 ((2 (1 AMINO 2 METHYLPROPYL)THIAZOLE 4 CARBONYL)AMINO) 2 METHYLPROPYL)THIAZOLE 4 CARBONYL)AMINO) 2 METHYLPROPYL]THIAZOLE 4 CARBOCYLIC ACID ETHYL ESTER; 2 [1 ((2 (1 ((2 (1 ((2 (1 TERT BUTOXYCARBONYLAMINO 2 METHYL PROPYL)THIAZOLE 4 CARBONYL)AMINO) 2 METHYLPROPYL)THIAZOLE 4 CARBONYL)AMINO) 2 METHYLPROPYL)THIAZOLE 4 CARBONYL)AMINO) 2 METHYLPROPYL]THIAZOLE 4 CARBOXYLIC ACID ETHYL ESTER; 2 [1 ((2 (1 ((2 (1 TERT BUTOXYCARBONYLAMINO 2 METHYLPROPYL)THIAZOLE 4 CARBONYL)AMINO) 2 METHYLPROPYL)THIAZOLE 4 CARBONYL)AMINO) 2 METHYLPROPYL]THIAZOLE 4 CARBOXYLIC ACID; 2 [1 ((2 (1 ((2 (1 TERT BUTOXYCARBONYLAMINO 2 METHYLPROPYL)THIAZOLE 4 CARBONYL)AMINO) 2 METHYLPROPYL]THIAZOLE 4 CARBONYL)AMINO) 2 METHYLPROPYL]THIAZOLE 4 CARBOXYLIC ACID ETHYL ESTER; 2 [1 ((2 (1 AMINO 2 METHYLPROPYL)THIAZOLE 4 CARBONYL)AMINO) 2 METHYLPROPYL]THIAZOLE 4 CARBOXYLIC ACID ETHYL ESTER; 2 [1 ((2 (1 TERT BUTOXYCARBONYLAMINO 2 METHYLPROPLY)THIAZOLE 4 CARBONYL)AMINO) 2 METHYLPROPYL]THIAZOLE 4 CARBOXYLIC ACID ETHYL ESTER; 2 [1 ((2 (1 TERT BUTOXYCARBONYLAMINO 2 METHYLPROPYL)THIAZOLE 4 CARBONYL)AMINO) 2 METHYLPROPYL]THIAZOLE 4 CARBOXYLIC ACID; 2 [1 [(2 (1 AMINO 2 METHYLPROPYL)THIAZOLE 4 CARBONYL)AMINO) 2 METHYLPROPYL]THIAZOLE 4 CARBOXYLIC ACID; [1 (4 (1 (4 (1 (4 METHOXYPHENYL)ETHYLCARBAMOYL)THIAZOL 2 YL) 2 METHYLPROPYLCARBAMOYL)THIAZOL 2 YL) 2 METHYLPROPYL]CARBAMIC ACID TERT BUTYL ESTER; [1 (4 (1 (4 (2,4 DIMETHOXYBENZYLCARBAMOYL)THIAZOL 2 YL) 2 METHYLPROPYLCARBAMOYL)THIAZOL 2 YL) 2 METHYLPROPYL]CARBAMIC ACID TERT BUTYL ESTER; ADENOSINE TRIPHOSPHATASE; AMPHOLYTE; CYCLIC HEXAMER; CYCLIC TETRAMER; CYCLIC TRIS THIAZOLE AMINO ACID; CYCLOPEPTIDE; LINEAR HEXAMER; MULTIDRUG RESISTANCE PROTEIN; OLIGOMER; PEPTIDOMIMETIC AGENT; TARIQUIDAR; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; VALINE; VALINE DERIVED THIAZOLE;

ARTICLE; CELL MEMBRANE; COMPUTER MODEL; CRYSTAL STRUCTURE; CYCLIZATION; DRUG BINDING SITE; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; ENZYME ACTIVITY; FLOW CYTOMETRY; HELA CELL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYDROPHOBICITY; LIPOPHILICITY; MOLECULAR DOCKING; MOLECULAR SIZE; PHOTOAFFINITY LABELING; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ABC TRANSPORTERS; MOLECULAR MODELING; MULTIDRUG RESISTANCE; P-GLYCOPROTEIN; PEPTIDE MIMICS;

ANIMALS; BINDING SITES; BIOLOGICAL TRANSPORT; BORON COMPOUNDS; DRUG DESIGN; HELA CELLS; HUMANS; MICE; MOLECULAR DOCKING SIMULATION; OLIGOPEPTIDES; P-GLYCOPROTEIN; PEPTIDES, CYCLIC; PEPTIDOMIMETICS; PHOTOBLEACHING; PROTEIN BINDING; PROTEIN STRUCTURE, TERTIARY; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES; VALINE;

EID: 84890788001     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201300565     Document Type: Article

References (45)

1. S. V. Ambudkar, S. Dey, C. A. Hrycyna, M. Ramachandra, I. Pastan, M. M. Gottesman, Annu. Rev. Pharmacol. Toxicol. 1999, 39, 361-398.
2. A. H. Schinkel, J. W. Jonker, Adv. Drug Delivery Rev. 2003, 55, 3-29.
3. S. Shukla, C. Schwartz, K. Kapoor, A. Kouanda, S. V. Ambudkar, Drug Metab. Dispos. 2012, 40, 304-312.
4. S. V. Ambudkar, I. Kim, Z. E. Sauna, Eur. J. Pharm. Sci. 2006, 27, 392-400.
5. S. G. Aller, J. Yu, A. Ward, Y. Weng, S. Chittaboina, R. Zhuo, P. M. Harrell, Y. T. Trinh, Q. Zhang, I. L. Urbatsch, G. Chang, Science 2009, 323, 1718-1722.
6. S. Dey, M. Ramachandra, I. Pastan, M. M. Gottesman, S. V. Ambudkar, Proc. Natl. Acad. Sci. USA 1997, 94, 10594-10599.
7. T. W. Loo, M. C. Bartlett, D. M. Clarke, J. Biol. Chem. 2003, 278, 39706-39710.
8. M. R. Lugo, F. J. Sharom, Biochemistry 2005, 44, 14020-14029.
9. S. Orlowski, L. M. Mir, J. Belehradek Jr, M. Garrigos, Biochem. J. 1996, 317, 515-522.
10. C. F. Higgins, Nature 2007, 446, 749-757.
11. K. Kapoor, H. Sim, S. V. Ambudkar, in Resistance to Targeted Anti-Cancer Therapeutics, Vol. 1 (Ed.:, B. Bonavida,), Springer, New York, 2013, pp. 1-34.
12. I. Sekine, C. Shimizu, K. Nishio, N. Saijo, T. Tamura, Int. J. Clin. Oncol. 2009, 14, 112-119.
13. Z. Shi, A. K. Tiwari, S. Shukla, R. W. Robey, S. Singh, I. W. Kim, S. E. Bates, X. Peng, I. Abraham, S. V. Ambudkar, T. T. Talele, L. W. Fu, Z. S. Chen, Cancer Res. 2011, 71, 3029-3041.
14. S. Shukla, C. P. Wu, S. V. Ambudkar, Expert Opin. Drug Metab. Toxicol. 2008, 4, 205-223.
15. H. Tao, Y. Weng, R. Zhuo, G. Chang, I. L. Urbatsch, Q. Zhang, ChemBioChem 2011, 12, 868-873.
16. D. Boesch, C. Gavériaux, B. Jachez, A. Pourtier-Manzanedo, P. Bollinger, F. Loor, Cancer Res. 1991, 51, 4226-4233.
17. F. Loor, Expert Opin. Invest. Drugs 1999, 8, 807-835.
18. M. C. Bagley, J. W. Dale, E. A. Merritt, X. Xiong, Chem. Rev. 2005, 105, 685-714.
19. A. Bertram, J. S. Hannam, K. A. Jolliffe, F. González-Lõpez de Turiso, G. Pattenden, Synlett 1999, 1723-1726.
20. A. Bertram, A. J. Blake, F. González-Lõpez de Turiso, J. S. Hannam, K. A. Jolliffe, G. Pattenden, M. Skae, Tetrahedron 2003, 59, 6979-6990.
21. E. A. Merritt, M. C. Bagley, Synthesis 2007, 3535-3541.
22. M. W. Bredenkamp, C. W. Holzapfel, W. J. van Zyl, Synth. Commun. 1990, 20, 2235-2249.
23. E. Aguilar, A. I. Meyers, Tetrahedron Lett. 1994, 35, 2473-2476.
24. C. D. J. Boden, G. Pattenden, T. Ye, Synlett 1995, 417-419.
25. C. Moody, M. Bagley, J. Chem. Soc. Perkin Trans. 1 1998, 601-608.
26. P. S. Ramamoorthy, J. Gervay, J. Org. Chem. 1997, 62, 7801-7805.
27. D. Hudson, J. Org. Chem. 1988, 53, 617-624.
28. A. J. Blake, J. S. Hannam, K. A. Jolliffe, G. Pattenden, Synlett 2000, 1515-1518.
29. C. Martin, G. Berridge, P. Mistry, C. Higgins, P. Charlton, R. Callaghan, Br. J. Pharmacol. 1999, 128, 403-411.
30. P. Mistry, A. J. Stewart, W. Dangerfield, S. Okiji, C. Liddle, D. Bootle, J. A. Plumb, D. Templeton, P. Charlton, Cancer Res. 2001, 61, 749-758.
31. E. Fox, S. E. Bates, Expert Rev. Anticancer Ther. 2007, 7, 447-459.
32. W. Priebe, N. T. Van, T. G. Burke, R. Perez-Soler, Anticancer Drugs 1993, 4, 37-48.
33. B. Sarkadi, E. M. Price, R. C. Boucher, U. A. Germann, G. A. Scarborough, J. Biol. Chem. 1992, 267, 4854-4858.
34. S. V. Ambudkar, I. H. Lelong, J. Zhang, C. O. Cardarelli, M. M. Gottesman, I. Pastan, Proc. Natl. Acad. Sci. USA 1992, 89, 8472-8476.
35. H. Omote, M. K. Al-Shawi, J. Biol. Chem. 2002, 277, 45688-45694.
36. A. K. Tiwari, K. Sodani, C. L. Dai, A. H. Abuznait, S. Singh, Z. J. Xiao, A. Patel, T. T. Talele, L. Fu, A. Kaddoumi, J. M. Gallo, Z. S. Chen, Cancer Lett. 2013, 328, 307-317.
37. G. Klopman, L. M. Shi, A. Ramu, Mol. Pharmacol. 1997, 52, 323-334.
38. P. Crivori, B. Reinach, D. Pezzetta, I. Poggesi, Mol. Pharm. 2006, 3, 33-44.
39. I. K. Pajeva, C. Globisch, M. Wiese, ChemMedChem 2009, 4, 1883-1896.
40. T. W. Loo, D. M. Clarke, J. Biol. Chem. 2001, 276, 14972-14979.
41. F. Tiberghien, F. Loor, Anticancer Drugs 1996, 7, 568-578.
42. R. W. Robey, K. Steadman, O. Polgar, K. Morisaki, M. Blayney, P. Mistry, S. E. Bates, Cancer Res. 2004, 64, 1242-1246.
43. S. Shukla, R. W. Robey, S. E. Bates, S. V. Ambudkar, Drug Metab. Dispos. 2009, 37, 359-365.
44. S. V. Ambudkar, Methods Enzymol. 1998, 292, 504-514.
45. Z. E. Sauna, S. V. Ambudkar, Proc. Natl. Acad. Sci. USA 2000, 97, 2515-2520.