New peptides with metal binding abilities and their use as drug carriers

Bioconjugate Chemistry

Volumn 25, Issue 10, 2014, Pages 1811-1819

  Allam, Anas ^a   Maigre, Laure ^b   Alimi, Mickael ^a   Alves De Sousa, Rodolphe ^a   Hessani, Assia ^a   Galardon, Erwan ^a   Pagès, Jean Marie ^b   Artaud, Isabelle ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHELATION; COBALT COMPOUNDS; COPPER COMPOUNDS; ESCHERICHIA COLI; LIGANDS; METALS; ORGANIC ACIDS; SCAFFOLDS; SCAFFOLDS (BIOLOGY); ZINC COMPOUNDS;

BINDING ABILITIES; CHELATING PEPTIDES; DRUG CARRIER; E. COLI; EFFLUX PUMPS; HYDROXAMIC ACIDS; IN-VITRO; METAL BINDING; METALLO-PROTEASE; MUELLER;

PEPTIDES;

CHAPERONE; CHELATING AGENT; CUPRIC ION; DRUG CARRIER; HYDROXAMIC ACID; INDOLE DERIVATIVE; LIGAND; METAL COMPLEX; METALLOPROTEINASE; PEPTIDE DEFORMYLASE INHIBITOR; PEPTIDE DERIVATIVE; POLYPEPTIDE ANTIBIOTIC AGENT; TETRAPEPTIDE; AMIDASE; ANTIINFECTIVE AGENT; COORDINATION COMPOUND; PEPTIDE; PEPTIDE DEFORMYLASE; PYRIDINE DERIVATIVE; TRIS(2-PYRIDYLMETHYL)AMINE;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL GROWTH; ESCHERICHIA COLI; GRAM NEGATIVE BACTERIUM; IN VITRO STUDY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METAL BINDING; MINIMUM INHIBITORY CONCENTRATION; PROTON NUCLEAR MAGNETIC RESONANCE; WILD TYPE; ANTAGONISTS AND INHIBITORS; CHEMISTRY; DRUG EFFECTS; ENZYMOLOGY; ESCHERICHIA COLI INFECTIONS; HUMAN; METABOLISM; MICROBIAL SENSITIVITY TEST;

AMIDOHYDROLASES; ANTI-BACTERIAL AGENTS; COORDINATION COMPLEXES; DRUG CARRIERS; ESCHERICHIA COLI; ESCHERICHIA COLI INFECTIONS; HUMANS; MICROBIAL SENSITIVITY TESTS; PEPTIDES; PYRIDINES;

EID: 84908043546     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc500317u     Document Type: Article

References (38)

1. Chopra, I., Schofield, C., Everett, M., ONeill, A., Miller, K., Wilcox, M., Frère, J.-M., Dawson, M., Czaplewski, L., Urleb, U., and Courvalin, P. (2008) Treatment of health-care-associated infections caused by Gram-negative bacteria: a consensus statement Lancet Inf. Dis. 8, 133-139
2. Gandhi, T. N., DePestel, D. D., Collins, C. D., Nagel, J., and Washer, L. L. (2010) Managing antimicrobial resistance in intensive care units Crit. Care Med. 38, S315-23
3. Pages, J.-M., James, C. E., and Winterhalter, M. (2008) The porin and the permeating antibiotic: a selective diffusion barrier in Gram-negative bacteria Nat. Rev. Microbiol. 6, 893-903
4. Nikaido, H. and Pages, J.-M. (2011) Broad-specificity efflux pumps and their role in multidrug resistance of Gram-negative bacteria FEMS Microbiol. Rev. 36, 340-363
5. Sharma, A., Khuller, G. K., and Sharma, S. (2009) Peptide deformylase - a promising therapeutic target for tuberculosis and antibacterial drug discovery Expert Opin. Ther. Targets 13, 753-765
6. Xu, Z.-Q., Flavin, M. T., and Flavin, J. (2014) Combating multidrug-resistant Gram-negative bacterial infections Expert Opin. Invest. Drugs 23, 163-182
7. Boularot, A., Giglione, C., Petit, S., Duroc, Y., Alves de Sousa, R., Larue, V., Cresteil, T., Dardel, F., Artaud, I., and Meinnel, T. (2007) Discovery and refinement of a new structural class of potent peptide deformylase inhibitors J. Med. Chem. 50, 10-20
8. Petit, S., Duroc, Y., Larue, V., Giglione, C., Léon, C., Soulama, C., Denis, A., Dardel, F., Meinnel, T., and Artaud, I. (2009) Structure-activity relationship analysis of the peptide deformylase inhibitor 5-bromo-1 H -indole-3-acetohydroxamic acid ChemMedChem 4, 261-275
9. Goemaere, E., Melet, A., Larue, V., Lieutaud, A., Alves de Sousa, R., Chevalier, J., Yimga-Djapa, L., Giglione, C., Huguet, F., Alimi, M., Meinnel, T., Dardel, F., Artaud, I., and Pages, J. M. (2012) New peptide deformylase inhibitors and cooperative interaction: a combination to improve antibacterial activity J. Antimicrob. Chemother. 67, 1392-1400
10. Mamelli, L., Petit, S., Chevalier, J., Giglione, C., Lieutaud, A., Meinnel, T., Artaud, I., and Pages, J.-M. (2009) New antibiotic molecules: bypassing the membrane barrier of gram negative bacteria increases the activity of peptide deformylase inhibitors PLoS One 4, e6443
11. Sava, G., Bergamo, A., and Dyson, P. J. (2011) Metal-based antitumour drugs in the post-genomic era: what comes next? Dalton Trans. 40, 9069
12. Graf, N. and Lippard, S. J. (2012) Redox activation of metal-based prodrugs as a strategy for drug delivery Adv. Drug Delivery Rev. 64, 993-1004
13. Barry, N. P. E. and Sadler, P. J. (2013) Exploration of the medical periodic table: towards new targets Chem. Commun. 49, 5106-5131
14. Mjos, K. D. and Orvig, C. (2014) Metallodrugs in medicinal inorganic chemistry Chem. Rev. 114, 4540-4563
15. Hambley, T. W. (2007) Chemistry. Metal-based therapeutics Science 318, 1392-1393
16. Bonnitcha, P. D., Kim, B. J., Hocking, R. K., Clegg, J. K., Turner, P., Neville, S. M., and Hambley, T. W. (2012) Cobalt complexes with tripodal ligands: implications for the design of drug chaperones Dalton Trans. 41, 11293-11304
17. Failes, T. W., Cullinane, C., Diakos, C. I., Yamamoto, N., Lyons, J. G., and Hambley, T. W. (2007) Studies of a cobalt(III) complex of the MMP inhibitor marimastat: a potential hypoxia-activated prodrug Chem.-Eur. J. 13, 2974-2982
18. Chang, E. L., Simmers, C., and Knight, D. A. (2010) Cobalt complexes as antiviral and antibacterial agents Pharmaceuticals 3, 1711-1728
19. Strøm, M. B., Haug, B. E., Skar, M. L., Stensen, W., Stiberg, T., and Svendsen, J. S. (2003) The pharmacophore of short cationic antibacterial peptides J. Med. Chem. 46, 1567-1570
20. Zasloff, M. (2002) Antimicrobial peptides of multicellular organisms Nature 415, 389-395
21. Hancock, R. E. W. and Sahl, H.-G. (2006) Antimicrobial and host-defense peptides as new anti-infective therapeutic strategies Nat. Biotechnol. 24, 1551-1557
22. Pages, J.-M., Sandrine, A.-F., Mahamoud, A., Bolla, J.-M., Davin-Regli, A., Chevalier, J., and Garnotel, E. (2010) Efflux pumps of gram-negative bacteria, a new target for new molecules Curr. Top. Med. Chem. 10, 1848-1857
23. Lamers, R. P., Cavallari, J. F., and Burrows, L. L. (2013) The efflux inhibitor phenylalanine-arginine beta-naphthylamide (PAβN) permeabilizes the outer membrane of gram-negative bacteria PLoS One 8, e60666
24. Pages, J.-M., Kaščáková, S., Maigre, L., Allam, A., Alimi, M., Chevalier, J., Galardon, E., Réfrégiers, M., and Artaud, I. (2013) New Peptide-based antimicrobials for tackling drug resistance in bacteria: single-cell fluorescence imaging ACS Med. Chem. Lett. 4, 556-559
25. Alimi, M., Allam, A., Selkti, M., Tomas, A., Roussel, P., Galardon, E., and Artaud, I. (2012) Characterization of cobalt(III) hydroxamic acid complexes based on a tris(2-pyridylmethyl)amine scaffold: reactivity toward cysteine methyl ester Inorg. Chem. 51, 9350-9356
26. Yamamoto, N., Danos, S., Bonnitcha, P. D., Failes, T. W., New, E. J., and Hambley, T. W. (2008) Cellular uptake and distribution of cobalt complexes of fluorescent ligands J. Biol. Inorg. Chem. 13, 861-871
27. Nikaido, H. (2003) Molecular basis of bacterial outer membrane permeability revisited Microbiol. Mol. Biol. Rev. 67, 593-656
28. Joyner, J. C., Hodnick, W. F., Cowan, A. S., Tamuly, D., Boyd, R., and Cowan, J. A. (2013) Antimicrobial metallopeptides with broad nuclease and ribonuclease activity Chem. Commun. 49, 2118-2120
29. álvarez, C. A., Guzmán, F., Cárdenas, C., Marshall, S. H., and Mercado, L. (2014) Antimicrobial activity of trout hepcidin, Fish & Shellfish Immunology [Online Early Access] DOI: 10.1016/j.fsi.2014.04.013
30. Joyner, J. C. and Cowan, J. A. (2013) Target-directed catalytic metallodrugs Braz. J. Med. Biol. Res. 46, 465-485
31. Libardo, M. D., Cervantes, J. L., Salazar, J. C., and Angeles-Boza, A. M. (2014) Improved bioactivity of antimicrobial peptides by addition of amino-terminal copper and nickel (ATCUN) binding motifs ChemMedChem 9, 1892-1901
32. Hartinger, C. G., Groessl, M., Meier, S. M., Casini, A., and Dyson, P. J. (2013) Application of mass spectrometric techniques to delineate the modes-of-action of anticancer metallodrugs Chem. Soc. Rev. 42, 6186-6199
33. Girardello, R., Bispo, P. J. M., Yamanaka, T. M., and Gales, A. C. (2012) Cation concentration variability of four distinct Mueller-Hinton agar brands influences polymyxin B susceptibility results J. Clin. Microbiol. 50, 2414-2418
34. Calvo, J., del Arco, A., and Martínez-Martínez, L. (2009) High concentrations of manganese in Mueller-Hinton agar increase MICs of tigecycline determined by Etest J. Clin. Microbiol. 47, 827-829
35. Anderegg, G., Hubmann, E., Podder, N. G., and Wenk, F. (1977) Pyridinderivate als Komplexbildner. XI. Die thermodynamik der metallkomplexbildung mit bis-, tris- und tetrakis[(2-pyridyl)methyl]-aminen Helv. Chim. Acta 60, 123-140
36. Mallea, M., Chevalier, J., Bornet, C., Eyraud, A., Davin-Regli, A., Bollet, C., and Pagès, J. M. (1998) Porin alteration and active efflux: two in vivo drug resistance strategies used by Enterobacter aerogenes Microbiology 144 (Pt 11) 3003-3009
37. Berenbaum, M. C. (1978) A method for testing for synergy with any number of agents J. Infect. Dis. 137, 122-130
38. European Committee for Antimicrobial Susceptibility Testing (EUCAST) of the European Society of Clinical Microbiology and Infectious Dieases (ESCMID). (2000, September) EUCAST Definitive Document E.Def 1.2, May 2000: Terminology relating to methods for the determination of susceptibility of bacteria to antimicrobial agents. Clin. Microbiol. Infect. 6, 503-508.