Co(II) and Cu(II) pyrophosphate complexes have selectivity and potency against Mycobacteria including Mycobacteriumtuberculosis

European Journal of Medicinal Chemistry

Volumn 70, Issue , 2013, Pages 589-593

  Hoffman, Amanda E ^a   DeStefano, Michelle ^b   Shoen, Carolyn ^b   Gopinath, Krishnamoorthy ^c   Warner, Digby F ^c   Cynamon, Michael ^b   Doyle, Robert P ^a,b  

^a SYRACUSE UNIVERSITY   (United States)

^b SYRACUSE VA MEDICAL CENTER   (United States)

^c UNIVERSITY OF CAPE TOWN   (South Africa)

Author keywords

Bacteriocidal; Cobalt; Copper; MDR TB; Pyrophosphate; TB

Indexed keywords

AMIKACIN; ANTIMYCOBACTERIAL AGENT; COBALT COMPLEX; COPPER COMPLEX; LIGAND; PYROPHOSPHORIC ACID DERIVATIVE; VERAPAMIL;

ARTICLE; BACTERIAL STRAIN; BACTERICIDAL ACTIVITY; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG POTENCY; DRUG SELECTIVITY; DRUG SENSITIVITY; ESCHERICHIA COLI; HUMAN; HUMAN CELL; LUNG CANCER; MULTIDRUG RESISTANT TUBERCULOSIS; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; STAPHYLOCOCCUS AUREUS;

BACTERIOCIDAL; COBALT; COPPER; EXTENSIVELY DRUG-RESISTANT TB; INH; ISONIAZID; MDR-TB; MIC; MINIMUM INHIBITORY CONCENTRATION; MOTT; MULTIDRUG-RESISTANT TB; MYCOBACTERIA OTHER THAN TB; PYROPHOSPHATE; TB; TUBERCULOSIS; XDR-TB;

ANTI-BACTERIAL AGENTS; COBALT; COPPER; DIPHOSPHATES; DOSE-RESPONSE RELATIONSHIP, DRUG; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MYCOBACTERIUM; ORGANOMETALLIC COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84887031157     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.10.044     Document Type: Article

References (58)

1. S. Hurtley, C. Ash, and L. Roberts Tuberculosis & malaria. Landscapes of infection. Introduction Science 328 2010 841
2. J. Poehlsgaard, and S. Douthwaite The bacterial ribosome as a target for antibiotics, nature reviews Microbiology 3 2005 870 881 (Pubitemid 41693182)
3. B.R. Bloom, and C.J. Murray Tuberculosis: commentary on a reemergent killer Science 257 1992 1055 1064
4. Y.L. Janin Antituberculosis drugs: ten years of research Bioorg. Med. Chem. 15 2007 2479 2513 (Pubitemid 46367698)
5. G.B. Migliori, K. Dheda, R. Centis, P. Mwaba, M. Bates, J. O'Grady, M. Hoelscher, and A. Zumla Review of multidrug-resistant and extensively drug-resistant TB: global perspectives with a focus on sub-Saharan Africa Trop. Med. Int. Health 15 2010 1052 1066
6. D.G. Datiko, M.A. Yassin, L.T. Chekol, L.E. Kabeto, and B. Lindtjorn The rate of TB-HIV co-infection depends on the prevalence of HIV infection in a community BMC Public Health 8 2008 266
7. S.H. Kappe, A.M. Vaughan, J.A. Boddey, and A.F. Cowman That was then but this is now: malaria research in the time of an eradication agenda Science 328 2010 862 866
8. M.J. Miller, A.J. Walz, H. Zhu, C. Wu, G. Moraski, U. Mollmann, E.M. Tristani, A.L. Crumbliss, M.T. Ferdig, L. Checkley, R.L. Edwards, and H.I. Boshoff Design, synthesis, and study of a mycobactin-artemisinin conjugate that has selective and potent activity against tuberculosis and malaria J. Am. Chem. Soc. 133 2011 2076 2079
9. P. Nunn, B. Williams, K. Floyd, C. Dye, G. Elzinga, and M. Raviglione Tuberculosis control in the era of HIV, nature reviews Immunology 5 2005 819 826 (Pubitemid 41400855)
10. M.A. Aziz, A. Wright, A. Laszlo, A. De Muynck, F. Portaels, A. Van Deun, C. Wells, P. Nunn, L. Blanc, M. Raviglione W.H.I.U.A. Tuberculosis, S. Lung disease global project on anti-tuberculosis drug resistance Epidemiology of antituberculosis drug resistance (the Global Project on Anti-Tuberculosis Drug Resistance Surveillance): an updated analysis Lancet 368 2006 2142 2154 (Pubitemid 44914009)
11. G. Riccardi, M.R. Pasca, and S. Buroni Mycobacterium tuberculosis: drug resistance and future perspectives Future Microbiol. 4 2009 597 614
12. H. Cox, S. Hargreaves, and G. Ismailov Effect of multidrug resistance on global tuberculosis control Lancet 362 2003 1858 1859 (Pubitemid 37494771)
13. T.H. Holtz, and J.P. Cegielski Origin of the term XDR-TB Eur. Respir. J. 30 2007 396
14. G.B. Migliori, M. D'Arcy Richardson, G. Sotgiu, and C. Lange Multidrug-resistant and extensively drug-resistant tuberculosis in the West. Europe and United States: epidemiology, surveillance, and control Clin. Chest Med. 30 2009 637 665 vii
15. A. Pablos-Mendez, M.C. Raviglione, A. Laszlo, N. Binkin, H.L. Rieder, F. Bustreo, D.L. Cohn, C.S. Lambregts-van Weezenbeek, S.J. Kim, P. Chaulet, and P. Nunn Global surveillance for antituberculosis-drug resistance, 1994-1997. World Health Organization-International Union against tuberculosis and lung disease working group on anti-tuberculosis drug resistance surveillance New Engl. J. Med. 338 1998 1641 1649
16. A. Wright, M. Zignol, A. Van Deun, D. Falzon, S.R. Gerdes, K. Feldman, S. Hoffner, F. Drobniewski, L. Barrera, D. van Soolingen, F. Boulabhal, C.N. Paramasivan, K.M. Kam, S. Mitarai, P. Nunn, and M. Raviglione Global project on anti-tuberculosis drug resistance, epidemiology of antituberculosis drug resistance 2002-07: an updated analysis of the global project on anti-tuberculosis drug resistance surveillance Lancet 373 2009 1861 1873
17. C.E. Barry Lessons from seven decades of antituberculosis drug discovery Curr. Top. Med. Chem. 11 2011 1216 1225
18. J.A. Caminero Likelihood of generating MDR-TB and XDR-TB under adequate national tuberculosis control programme implementation Int. J. Tuberculosis Lung Dis. 12 2008 869 877
19. N.S. Shah, A. Wright, G.H. Bai, L. Barrera, F. Boulahbal, N. Martin-Casabona, F. Drobniewski, C. Gilpin, M. Havelkova, R. Lepe, R. Lumb, B. Metchock, F. Portaels, M.F. Rodrigues, S. Rusch-Gerdes, A. Van Deun, V. Vincent, K. Laserson, C. Wells, and J.P. Cegielski Worldwide emergence of extensively drug-resistant tuberculosis Emerging Infect. Dis. 13 2007 380 387 (Pubitemid 46348124)
20. K. Duncan, and C.E. Barry 3rd Prospects for new antitubercular drugs Curr. Opin. Microbiol. 7 2004 460 465 (Pubitemid 39297125)
21. A.M. Ginsberg, M.W. Laurenzi, D.J. Rouse, K.D. Whitney, and M.K. Spigelman Safety, tolerability, and pharmacokinetics of PA-824 in healthy subjects Antimicrob. Agents Chemother. 53 2009 3720 3725
22. C. Harper Tuberculosis, a neglected opportunity? Nat. Med. 13 2007 309 312 (Pubitemid 46376676)
23. A. Koul, E. Arnoult, N. Lounis, J. Guillemont, and K. Andries The challenge of new drug discovery for tuberculosis Nature 469 2011 483 490
24. V. Makarov, G. Manina, K. Mikusova, U. Mollmann, O. Ryabova, B. Saint-Joanis, N. Dhar, M.R. Pasca, S. Buroni, A.P. Lucarelli, A. Milano, E. De Rossi, M. Belanova, A. Bobovska, P. Dianiskova, J. Kordulakova, C. Sala, E. Fullam, P. Schneider, J.D. McKinney, P. Brodin, T. Christophe, S. Waddell, P. Butcher, J. Albrethsen, I. Rosenkrands, R. Brosch, V. Nandi, S. Bharath, S. Gaonkar, R.K. Shandil, V. Balasubramanian, T. Balganesh, S. Tyagi, J. Grosset, G. Riccardi, and S.T. Cole Benzothiazinones kill Mycobacterium tuberculosis by blocking arabinan synthesis Science 324 2009 801 804
25. C.K. Stover, P. Warrener, D.R. VanDevanter, D.R. Sherman, T.M. Arain, M.H. Langhorne, S.W. Anderson, J.A. Towell, Y. Yuan, D.N. McMurray, B.N. Kreiswirth, C.E. Barry, and W.R. Baker A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis Nature 405 2000 962 966 (Pubitemid 30435054)
26. Z.J. Guo, and P.J. Sadler Metals in medicine Angew. Chem. Int. Ed. 38 1999 1513 1531 (Pubitemid 29288755)
27. L. Ronconi, and P.J. Sadler Using coordination chemistry to design new medicines Coord. Chem. Rev. 251 2007 1633 1648
28. S.H. van Rijt, and P.J. Sadler Current applications and future potential for bioinorganic chemistry in the development of anticancer drugs Drug Discov. Today 14 2009 1089 1097
29. N. Graf, and S.J. Lippard Redox activation of metal-based prodrugs as a strategy for drug delivery Adv. Drug Delivery Rev. 64 2012 993 1004
30. A. Jamadar, A.K. Duhme-Klair, K. Vemuri, M. Sritharan, P. Dandawate, and S. Padhye Synthesis, characterisation and antitubercular activities of a series of pyruvate-containing aroylhydrazones and their Cu-complexes Dalton Trans. 41 2012 9192 9201
31. G.J. Kharadi Antitubercular and fluorescence studies of copper(II) complexes with quinolone family member, ciprofloxacin Spectrochim. Acta. Part A 79 2011 898 903
32. O.F. Ikotun, E.M. Higbee, W. Ouellette, and R.P. Doyle Pyrophosphate-bridged complexes with picomolar toxicity J. Inorg. Biochem. 103 2009 1254 1264
33. O.F. Ikotun, W. Ouellette, F. Lloret, P.E. Kruger, M. Julve, and R.P. Doyle Synthesis, structural, thermal and magnetic characterization of a pyrophosphato-bridged cobalt(II) complex Eur. J. Inorg. Chem. 2008 2691 2697
34. N. Marino, A.R. Vortherms, A.E. Hoffman, and R.P. Doyle Expanding monomeric pyrophosphate complexes beyond platinum Inorg. Chem. 49 2010 6790 6792
35. B. Gold, H. Deng, R. Bryk, D. Vargas, D. Eliezer, J. Roberts, X. Jiang, and C. Nathan Identification of a copper-binding metallothionein in pathogenic mycobacteria Nat. Chem. Biol. 4 2008 609 616
36. C. Manca, L. Tsenova, A. Bergtold, S. Freeman, M. Tovey, J.M. Musser, C.E. Barry 3rd, V.H. Freedman, and G. Kaplan Virulence of a Mycobacterium tuberculosis clinical isolate in mice is determined by failure to induce Th1 type immunity and is associated with induction of IFN-alpha/beta Proc. Natl. Acad. Sci. U. S. A. 98 2001 5752 5757 (Pubitemid 32435714)
37. S.P. Klemens, M.S. DeStefano, and M.H. Cynamon Therapy of multidrug-resistant tuberculosis: lessons from studies with mice Antimicrob. Agents Chemother. 37 1993 2344 2347 (Pubitemid 23324455)
38. J.M. Rubin-Preminger, L. Kozlov, and I. Goldberg Hydrogen-bonding and pi-pi stacking interactions in apuachloridobis(1,10-phenanthroline)cobalt(II) chloride dichloridobis(1,10-phenanthroline)cobalt(II) hexahydrate Acta Crystallogr. C 64 2008 M83 M86
39. L.P. Lu, S.D. Qin, P. Yang, and M.L. Zhu Chlorobis(1,10-phenanthroline) copper(II) chloride methanol solvate 4.5-hydrate Acta Crystallogr. E 60 2004 M574 M576
40. M. Malik, T. Lu, X.L. Zhao, A. Singh, C.M. Hattan, J. Domagala, R. Kerns, and K. Drlica Lethality of quinolones against Mycobacterium smegmatis in the presence or absence of chloramphenicol Antimicrob. Agents Chemother. 49 2005 2008 2014 (Pubitemid 40631619)
41. F. Wolschendorf, D. Ackart, T.B. Shrestha, L. Hascall-Dove, S. Nolan, G. Lamichhane, Y. Wang, S.H. Bossmann, R.J. Basaraba, and M. Niederweis Copper resistance is essential for virulence of Mycobacterium tuberculosis Proc. Natl. Acad. Sci. U. S. A. 108 2011 1621 1626
42. S. Mehtar, I. Wiid, and S.D. Todorov The antimicrobial activity of copper and copper alloys against nosocomial pathogens and Mycobacterium tuberculosis isolated from healthcare facilities in the Western Cape: an in-vitro study J. Hosp. Infect. 68 2008 45 51
43. L. Rodrigues, J. Ramos, I. Couto, L. Amaral, and M. Viveiros Ethidium bromide transport across Mycobacterium smegmatis cell-wall: correlation with antibiotic resistance BMC Microbiol. 11 2011
44. E.C. Spoelstra, H.V. Westerhoff, H.M. Pinedo, H. Dekker, and J. Lankelma The multidrug-resistance-reverser verapamil interferes with cellular P-glycoprotein-mediated pumping of daunorubicin as a non-competing substrate Eur. J. Biochem. 221 1994 363 373 (Pubitemid 24120581)
45. C.L. Dupont, G. Grass, and C. Rensing Copper toxicity and the origin of bacterial resistance-new insights and applications Metallomics: Integr. Biometal Sci. 3 2011 1109 1118
46. B. Bottari, R. Maccari, F. Monforte, R. Ottana, E. Rotondo, and M.G. Vigorita Isoniazid-related copper(II) and nickel(II) complexes with antimycobacterial in vitro activity. Part 9 Bioorg. Med. Chem. Lett. 10 2000 657 660 (Pubitemid 30186672)
47. B. Bottari, R. Maccari, F. Monforte, R. Ottana, E. Rotondo, and M.G. Vigorita Antimycobacterial in vitro activity of cobalt(II) isonicotinoylhydrazone complexes. Part 10 Bioorg. Med. Chem. Lett. 11 2001 301 303 (Pubitemid 32117696)
48. R. Maccari, R. Ottana, B. Bottari, E. Rotondo, and M.G. Vigorita In vitro advanced antimycobacterial screening of cobalt(II) and copper(II) complexes of fluorinated isonicotinoylhydrazones Bioorg. Med. Chem. Lett. 14 2004 5731 5733 (Pubitemid 39421509)
49. M.A. Zoroddu, S. Zanetti, R. Pogni, and R. Basosi An electron spin resonance study and antimicrobial activity of copper(II)-phenanthroline complexes J. Inorg. Biochem. 63 1996 291 300 (Pubitemid 26275205)
50. A. Kellett, M. O'Connor, M. McCann, O. Howe, A. Casey, P. McCarron, K. Kavanagh, M. McNamara, S. Kennedy, D.D. May, P.S. Skell, D. O'Shea, and M. Devereux Water-soluble bis(1,10-phenanthroline) octanedioate Cu2+ and Mn2+ complexes with unprecedented nano and picomolar in vitro cytotoxicity: promising leads for chemotherapeutic drug development Medchemcomm 2 2011 579 584
51. A. Kellett, M. O'Connor, M. McCann, M. McNamara, P. Lynch, G. Rosair, V. McKee, B. Creaven, M. Walsh, S. McClean, A. Foltyn, D. O'Shea, O. Howe, and M. Devereux Bis-phenanthroline copper(II) phthalate complexes are potent in vitro antitumour agents with 'self-activating' metallo-nuclease and DNA binding properties Dalton Trans. 40 2011 1024 1027
52. M. O'Connor, A. Kellett, M. McCann, G. Rosair, M. McNamara, O. Howe, B.S. Creaven, S. McClean, A.F.A. Kia, D. O'Shea, and M. Devereux Copper(II) complexes of salicylic acid combining superoxide dismutase mimetic properties with DNA binding and cleaving capabilities display promising chemotherapeutic potential with fast acting in vitro cytotoxicity against cisplatin sensitive and resistant cancer cell lines J. Med. Chem. 55 2012 1957 1968
53. A. Prisecaru, M. Devereux, N. Barron, M. McCann, J. Colleran, A. Casey, V. McKeee, and A. Kellett Potent oxidative DNA cleavage by the di-copper cytotoxin: [Cu-2(mu-terephthalate)(1,10-phen)(4)](2+) Chem. Commun. 48 2012 6906 6908
54. S. Melnic, D. Prodius, H. Stoeckli-Evans, S. Shova, and C. Turta Synthesis and anti-tuberculosis activity of new hetero(Mn, Co, Ni)trinuclear iron(III) furoates Eur. J. Med. Chem. 45 2010 1465 1469
55. J.L. Rowland, and M. Niederweis Resistance mechanisms of Mycobacterium tuberculosis against phagosomal copper overload Tuberculosis 92 2012 202 210
56. J. Hu, M. Sharma, H. Qin, F.P. Gao, and T.A. Cross Ligand binding in the conserved interhelical loop of CorA, a magnesium transporter from Mycobacterium tuberculosis J. Biol. Chem. 284 2009 15619 15628
57. J.M. Arguello, M. Gonzalez-Guerrero, and D. Raimunda Bacterial transition metal P(1B)-ATPases: transport mechanism and roles in virulence Biochemistry 50 2011 9940 9949
58. D. Agranoff, and S. Krishna Metal ion transport and regulation in Mycobacterium tuberculosis Front. Biosci. J. Virtual Libr. 9 2004 2996 3006