Interaction of quinoline antimalarial drugs with ferriprotoporphyrin IX, a solid state spectroscopy study

Journal of Inorganic Biochemistry

Volumn 105, Issue 12, 2011, Pages 1662-1669

  Asghari Khiavi, Mehdi ^a,b   Vongsvivut, Jitraporn ^b   Perepichka, Inna ^a   Mechler, Adam ^b,c   Wood, Bayden R ^b   McNaughton, Don ^b   Bohle, D Scott ^a  

^a MCGILL UNIVERSITY   (Canada)

^b MONASH UNIVERSITY   (Australia)

^c LA TROBE UNIVERSITY   (Australia)

Author keywords

Antimalarial; Heme; Interaction; Malaria; Quinoline; Vibrational spectroscopy

Indexed keywords

ANTIMALARIAL AGENT; CHLOROQUINE; FERRIC ION; HEMATIN; HYDROGEN; MEPACRINE; NITROGEN; QUINOLINE DERIVATIVE;

BINDING SITE; CHEMICAL STRUCTURE; CONFERENCE PAPER; CRYSTAL STRUCTURE; DRUG BINDING; ELECTROMAGNETIC FIELD; HYDROGEN BOND; INFRARED RADIATION; OXIDATION; RAMAN SPECTROMETRY; SOLID STATE; STATIC ELECTRICITY; STOICHIOMETRY;

ANTIMALARIALS; BINDING SITES; HEMIN; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR CONFORMATION; QUINOLINES; SPECTRUM ANALYSIS, RAMAN;

EID: 80855132303     PISSN: 01620134     EISSN: 18733344     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2011.08.005     Document Type: Conference Paper

References (61)

1. I.W. Sherman Molecular Approaches to Malaria 2005 ASM Press Washington DC
2. D.S. Bohle, B.J. Conklin, D. Cox, S.K. Madsen, S. Paulson, P.W. Stephens, and G.T. Yee Am. Chem. Soc. Symp. Ser. 572 1994 497 515
3. A.F.G. Slater, and A. Cerami Nature 355 1992 167 169
4. L. Tilley, P. Loria, and M. Foley P.J. Rosenthal, Antimalarial Chemotherapy 2001 Humana Press Totowa, NJ 87 122
5. A.C. Chou, R. Chevli, and C.D. Fitch Biochemistry 19 1980 1543 1549
6. A. Dorn, S.R. Vippagunta, H. Matile, C. Jaquet, J.L. Vennerstrom, and R.G. Ridley Biochem. Pharmacol. 55 1998 727 736
7. S. Moreau, B. Perly, and J. Biguet Biochimie 64 1982 1015 1025
8. R.G. Ridley Exp. Parasitol. 87 1997 293 304
9. D.J. Sullivan, I.Y. Gluzman, D.G. Russell, and D.E. Goldberg Proc. Natl. Acad. Sci. U. S. A. 93 1996 1870 11865 11870
10. R. Buller, M.L. Peterson, O. Almarsson, and L. Leiserowitz Cryst. Growth Des. 2 2002 553 562
11. L.B. Casabianca, D. An, J.K. Natarajan, J.N. Alumasa, P.D. Roepe, C. Wolf, and A.C. de Dios Inorg. Chem. 47 2008 6077 6081
12. T.G. Spiro, and X.Y. Li T.G. Spiro, Biological Applications of Raman Spectroscopy 1988 Wiley New York 1 38
13. T. Kitagawa, and Y. Ozaki Structure and Bonding 1987 Springer Berlin-Heidelberg 71 114
14. J.R. Kincaid K.M. Kadish, K.M. Smith, R. Guillard, The Porphyrin Handbook 1999 Academic Press New York 225 291
15. F. Sieber, and P. Hildebrandt Vibrational Spectroscopy in Life Science 2007 Wiley Weinheim
16. T.J. Egan, E. Hempelmann, and W.W. Mavuso J. Inorg. Biochem. 73 1999 101 107
17. I. Solomonov, M. Osipova, Y. Feldman, C. Baehtz, K. Kjaer, I.K. Robinson, G.T. Webster, D. McNaughton, B.R. Wood, I. Weissbuch, and L. Leiserowitz J. Am. Chem. Soc. 129 2007 5779-5779
18. T. Frosch, B. Kustner, S. Schlucker, A. Szeghalmi, M. Schmitt, W. Kiefer, and J. Popp J. Raman Spectrosc. 35 2004 819 821
19. K.A. de Villiers, C.H. Kaschula, T.J. Egan, and H.M. Marques J. Biol. Inorg. Chem. 12 2007 101 117
20. S.E. Bell, and N.M. Sirimuthu Chem. Soc. Rev. 37 2008 1012 1024
21. S. Nie, and S.R. Emory Science 275 1997 1102 1106
22. P.C. Lee, and D. Meisel J. Phys. Chem. 86 1982 3391 3395
23. D.H. O'Keeffe, C.H. Barlow, G.A. Smythe, W.H. Fuchsman, T.H. Moss, H.R. Lilienthal, and W.S. Caughey Bioinorg. Chem. 5 1975 125 147
24. J.A. Hofmann, and D.F. Bocian J. Phys. Chem. 88 1984 1472 1479
25. E.B. Fleischer, and T.S. Srivastava J. Am. Chem. Soc. 91 1969 2403 2405
26. A.D. Becke Phys. Rev. A 38 1988 3098 3100
27. C.T. Lee, W.T. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
28. A. Schafer, C. Huber, and R. Ahlrichs J. Chem. Phys. 100 1994 5829 5835
29. D.F. Koenig Acta Crystallogr. 18 1965 663 673
30. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.J.A. Montgomery, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, 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, C. Gonzalez, and J.A. Pople Gaussian 03 Revision E.01 2004 Gaussian Inc. Wallingford CT
31. S.Z. Hu, K.M. Smith, and T.G. Spiro J. Am. Chem. Soc. 118 1996 12638 12646
32. J.M. Karle, and I.L. Karle Acta Crystallogr. C 44 Pt 9 1988 1605 1608
33. J.A. Creighton Surf. Sci. 124 1983 209 219
34. M. Moskovits, and J.S. Suh J. Phys. Chem. 88 1984 5526 5530
35. L.A. Sanchez, and T.G. Spiro J. Phys. Chem. 89 1985 763 768
36. T.M. Cotton, K.D. Parks, and R.P. Vanduyne J. Am. Chem. Soc. 102 1980 6399 6407
37. C. Asher, K.A. de Villiers, and T.J. Egan Inorg. Chem. 48 2009 7994 8003
38. A. Leed, K. DuBay, L.M.B. Ursos, D. Sears, A.C. de Dios, and P.D. Roepe Biochemistry 41 2002 10245 10255
39. M.P. Crespo, L. Tilley, and N. Klonis J. Biol. Inorg. Chem. 15 2010 1009 1022
40. T.J. Egan, R. Hunter, C.H. Kaschula, H.M. Marques, A. Misplon, and J. Walden J. Med. Chem. 43 2000 283 291
41. T.J. Egan, and K.K. Ncokazi J. Inorg. Biochem. 98 2004 144 152
42. M.J. Dascombe, M.G. Drew, H. Morris, P. Wilairat, S. Auparakkitanon, W.A. Moule, S. Alizadeh-Shekalgourabi, P.G. Evans, M. Lloyd, A.M. Dyas, P. Carr, and F.M. Ismail J. Med. Chem. 48 2005 5423 5436
43. G.T. Webster, D. McNaughton, and B.R. Wood J. Phys. Chem. B 113 2009 6910 6916
44. D.V. Behere, and H.M. Goff J. Am. Chem. Soc. 106 1984 4945 4950
45. A.C. de Dios, R. Tycko, L.M.B. Ursos, and P.D. Roepe J. Phys. Chem. A 107 2003 5821 5825
46. I. Constantinidis, and J.D. Satterlee J. Am. Chem. Soc. 110 1988 4391 4395
47. T.J. Egan J. Inorg. Biochem. 100 2006 916 926
48. T. Frosch, S. Konearevic, L. Zedler, M. Schmitt, K. Schenzel, K. Becker, and J. Popp J. Phys. Chem. B 111 2007 11047 11056
49. J.M. Burke, J.R. Kincaid, and T.G. Spiro J. Am. Chem. Soc. 100 1978 6077 6083
50. G. Chottard, P. Battioni, J.P. Battioni, M. Lange, and D. Mansuy Inorg. Chem. 20 1981 1718 1722
51. J.E. Plowman, T.M. Loehr, C.K. Schauer, and O.P. Anderson Inorg. Chem. 23 1984 3553 3559
52. T.G. Spiro A.B.P. Lever, H.B. Gray, Iron Porphyrins, Part II 1983 Addison-Wesley Reading, MA 89 139
53. S. Pagola, P.W. Stephens, D.S. Bohle, A.D. Kosar, and S.K. Madsen Nature 404 2000 307 310
54. J.M. Karle Antimicrob. Agents Chemother. 41 1997 791 794
55. J.M. Karle, and I.L. Karle Antimicrob. Agents Chemother. 46 2002 1529 1534
56. V.L. DeVito, and S.A. Asher J. Am. Chem. Soc. 111 1989 9143 9152
57. P.M. O'Neill, D.J. Willock, S.R. Hawley, P.G. Bray, R.C. Storr, S.A. Ward, and B.K. Park J. Med. Chem. 40 1997 437 448
58. C. Portela, C.M. Afonso, M.M. Pinto, and M.J. Ramos FEBS Lett. 547 2003 217 222
59. K.A. de Villiers, H.M. Marques, and T.J. Egan J. Inorg. Biochem. 102 2008 1660 1667
60. B.R. Wood, S.J. Langford, B.M. Cooke, J. Lim, F.K. Glenister, M. Duriska, J.K. Unthank, and D. McNaughton J. Am. Chem. Soc. 126 2004 9233 9239
61. H.M. Marques, K. Voster, and T.J. Egan J. Inorg. Biochem. 64 1996 7 23