Study of structure-activity relationship of enantiomeric, protonated and deprotonated forms of warfarin via vibrational spectroscopy and DFT calculations

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

Volumn 113, Issue , 2013, Pages 439-446

  Mishra, Alok ^a   Srivastava, Sunil Kumar ^b   Swati, D ^a  

^a BANARAS HINDU UNIVERSITY   (India)

^b GURU GHASIDAS UNIVERSITY   (India)

Author keywords

DFT method; Enantiomer; Molecular electrostatic potential; Potential energy distribution; Warfarin

Indexed keywords

DENSITY FUNCTIONAL THEORY; ELECTROSTATICS; ENANTIOMERS; MOLECULAR INTERACTIONS; MOLECULAR PHYSICS; MOLECULES; POTENTIAL ENERGY; PROTONATION; STRUCTURES (BUILT OBJECTS); VIBRATIONAL SPECTROSCOPY;

ANTI-COAGULANT DRUGS; DFT METHOD; MOLECULAR ELECTROSTATIC POTENTIALS; POTENTIAL ENERGY DISTRIBUTION; RAMAN AND IR SPECTRUM; SPECTROSCOPIC SIGNATURES; STRUCTURE ACTIVITY RELATIONSHIPS; WARFARIN;

DRUG PRODUCTS;

EID: 84878704430     PISSN: 13861425     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.saa.2013.04.086     Document Type: Article

References (41)

1. K.P. Link, Circulation 19 (1959) 97-107.
2. R.A. O'Reilly, P.M. Aggeler, L.S. Leong, J. Clin. Invest. 42 (1963) 1542-1551.
3. C.P. Fitch, J. Anim. Sci. 1924 (1924) 37-41.
4. J.E. Brooks, A.M. Bowerman, J. Hyg. 71 (1973) 217-222.
5. H.O. Ammar, M. Ghorab, S.A. el-Nahhas, T.S. Makram, Pharmazie 52 (1997) 946-950.
6. P. McCulloch, W.D. George, Br. J. Cancer 59 (1989) 179-183.
7. P. McCulloch, W.D. George, Br. J. Surg. 74 (1987) 879-883.
8. D.S. Whitlon, J.A. Sadowski, J.W. Suttie, Biochemistry 17 (1978) 1371-1377.
9. A.E. Rettie, G. Tai, Mol. Intervent. 6 (2006) 223-227.
10. F. Kamali, H. Wynne, Annu. Rev. Med. 61 (2010) 63-75.
11. C.H. Davis, D. Deerfield, D.W. Stafford, L.G. Pedersen, J. Phys. Chem. A 111 (2007) 7257-7261.
12. J. Ansell, J. Hirsh, L. Poller, H. Bussey, A. Jacobson, E. Hylek, Chest 126 (2004) 204S-233S.
13. C. Members, V. Fuster, L.E. Rydén, R.W. Asinger, D.S. Cannom, H.J. Crijns, R.L. Frye, J.L. Halperin, G.N. Kay, W.W. Klein, S. Lévy, R.L. McNamara, E.N. Prystowsky, L.S. Wann, D.G. Wyse, R.J. Gibbons, E.M. Antman, J.S. Alpert, D.P. Faxon, G. Gregoratos, L.F. Hiratzka, A.K. Jacobs, R.O. Russell, S.C. Smith, E.C.f.P. Guidelines, P.C. Members, A. Alonso-Garcia, C. Blomström-Lundqvist, G. de Backer, M. Flather, J. Hradec, A. Oto, A. Parkhomenko, S. Silber, A. Torbicki, Circulation 104 (2001) 2118-2150.
14. F. Verheugt, Neth. Heart. J. 18 (2010) 314-318.
15. A. Akyol, Balkan. Med. J. 27 (2010) 001-006.
16. S. Velu, G.Y.H. Lip, J. Atheroscler. Thromb. 18 (2011) 257-273.
17. G.Y.H. Lip, D.A. Lane, Am. J. Med. 123 (2010) 785-789.
18. I. Georgieva, I. Kostova, N. Trendafilova, V.K. Rastogi, G. Bauer, W. Kiefer, J. Raman. Spectrosc. 37 (2006) 742-754.
19. N. Trendafilova, I. Kostova, V.K. Rastogi, I. Georgieva, G. Bauer, W. Kiefer, J. Raman. Spectrosc. 37 (2006) 808-815.
20. I. Kostova, N. Trendafilova, T. Mihaylov, Chem. Phys. 314 (2005) 73-84.
21. I. Kostova, N. Trendafilova, I. Georgieva, Spectrosc. Lett. 40 (2007) 65-81.
22. T. Mihaylov, N. Trendafilova, I. Kostova, I. Georgieva, G. Bauer, Chem. Phys. 327 (2006) 209-219.
23. T. Mihaylov, N. Trendafilova, I. Georgieva, I. Kostova, Chem. Phys. 374 (2010) 37-45.
24. N. Trendafilova, I. Kostova, I. Manolov, G. Bauer, T. Mihaylov, I. Georgieva, Synth. React. Inorg. Met.-Org. Chem. 34 (2004) 1635-1650.
25. I. Kostova, I. Manolov, I. Nicolova, S. Konstantinov, M. Karaivanova, Eur. J. Med. Chem. 36 (2001) 339-347.
26. I. Kostova, I. Manolov, S. Konstantinov, M. Karaivanova, Eur. J. Med. Chem. 34 (1999) 63-68.
27. I. Kostova, T. Stefanova, J. Trace. Elem. Med. Biol. 24 (2010) 7-13.
28. I. Kostova, I. Manolov, G. Momekov, T. Tzanova, S. Konstantinov, M. Karaivanova, Eur. J. Med. Chem. 40 (2005) 1246-1254.
29. I. Kostova, I. Manolov, G. Momekov, Eur. J. Med. Chem. 39 (2004) 765-775.
30. E.J. Valente, W.F. Trager, L.H. Jensen, Acta Crystallogr. Sec. B 31 (1975) 954-960.
31. S. Lal, S.R. Jada, X. Xiang, W.T. Lim, E.J. Lee, B. Chowbay, Clin. Pharmacokinet. 45 (2006) 1189-1200.
32. E.D. Tekin, F. Erkoç, I. Yildiz, S. Erkoç, Commun. Comput. Phys. 4 (2008) 161-176.
33. M. Amalanathan, J.I. Hubert, I. Kostova, J. Raman Spectrosc. 41 (2010) 1076-1084.
34. C. Öǧretir, S. Aydemir, M. Duran, M.S. Kiliçkaya, J. Chem. Eng. Data 55 (2010) 1477-1485.
35. B.C.G. Karlsson, A.M. Rosengren, P.O. Andersson, I.A. Nicholls, J. Phys. Chem. B 111 (2007) 10520-10528.
36. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammy, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvodar, J.J. Dannenberg, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 03, Revision B.05, Gaussian Inc., Pittsburgh, PA, 2003.
37. I.I.R. Dennington, T. Keith, J. Millam, K. Eppinnett, W.L. Hovell, R. Gilliland, GaussView 03, Semichem Inc., Shawnee Mission, KS (2003).
38. C. Lee, W.R. Yang, G. Parr, Phys. Rev. B 37 (1988) 785-789.
39. A.D. Becke, J. Chem. Phys. 98 (1993) 5648-5652.
40. R. Krishnan, J.S. Binkley, R. Seeger, J.A. Pople, J. Chem. Phys. 72 (1980) 650-654.
41. B. Mennucci, J. Tomasi, J. Chem. Phys. 106 (1997) 5151-5158. Technology