Syntheses and antibacterial activity of N -acylated ciprofloxacin derivatives based on the trimethyl lock

ACS Medicinal Chemistry Letters

Volumn 6, Issue 6, 2015, Pages 707-710

  Ji, Cheng ^a   Miller, Patricia A ^a   Miller, Marvin J ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

antibacterial; Ciprofloxacin; drug release; trimethyl lock

Indexed keywords

CIPROFLOXACIN; N ACYL CIPROFLOXACIN DERIVATIVE; PRODRUG; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG RELEASE; DRUG SYNTHESIS; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM VACCAE; NONHUMAN; PRIORITY JOURNAL;

POSIBACTERIA;

EID: 84931262934     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/acsmedchemlett.5b00146     Document Type: Article

References (16)

1. Mitscher, L. A. Bacterial topolsomerase inhibitors: quinolone and pyridone antibacterial agents Chem. Rev. 2005, 105, 559-592
2. Drlica, K.; Hiasa, H.; Kerns, R.; Malik, M.; Mustaev, A.; Zhao, X. L. Quinolones: action and resistance updated Curr. Top. Med. Chem. 2009, 9, 981-998
3. Drlica, K.; Zhao, X.; Malik, M.; Salz, T.; Kerns, R. Fluoroquinolone resistance: mechanisms, restrictive dosing, and anti-mutant screening strategies for new compounds Antibiot. Discovery Dev. 2012, 485-514
4. Ji, C.; Miller, M. J. Chemical syntheses and in vitro antibacterial activity of two desferrioxamine B-ciprofloxacin conjugates with potential esterase and phosphatase triggered drug release linkers Bioorg. Med. Chem. 2012, 20, 3828-3836
5. Ji, C.; Miller, M. J. Siderophore-fluoroquinolone conjugates containing potential reduction-triggered linkers for drug release: synthesis and antibacterial activity BioMetals 2015, 28, 541-551
6. Levine, M. N.; Raines, R. T. Trimethyl lock: a trigger for molecular release in chemistry, biology, and pharmacology Chem. Sci. 2012, 3, 2412-2420
7. Wang, B. H.; Liu, S. M.; Borchardt, R. T. Development of a novel redox-sensitive protecting group for amines which utilizes a facilitated lactonization reaction J. Org. Chem. 1995, 60, 539-543
8. Carpino, L. A.; Triolo, S. A.; Berglund, R. A. Reductive lactonization of strategically methylated quinone propionic-acid esters and amides J. Org. Chem. 1989, 54, 3303-3310
9. Volpato, M.; Abou-Zeid, N.; Tanner, R. W.; Glassbrook, L. T.; Taylor, J.; Stratford, I.; Loadman, P. M.; Jaffar, M.; Phillips, R. M. Chemical synthesis and biological evaluation of a NAD(P)H: quinone oxidoreductase-1-targeted tripartite quinone drug delivery system Mol. Cancer Ther. 2007, 6, 3122-3130
10. Maskell, L.; Blanche, E. A.; Colucci, M. A.; Whatmore, J. L.; Moody, C. J. Synthesis and evaluation of prodrugs for anti-angiogenic pyrrolylmethylidenyl oxindoles Bioorg. Med. Chem. Lett. 2007, 17, 1575-1578
11. Cormier, R.; Burda, W. N.; Harrington, L.; Edlinger, J.; Kodigepalli, K. M.; Thomas, J.; Kapolka, R.; Roma, G.; Anderson, B. E.; Turos, E.; Shaw, L. N. Studies on the antimicrobial properties of N -acylated ciprofloxacins Bioorg. Med. Chem. Lett. 2012, 22, 6513-6520
12. Zheng, A. L.; Shan, D. X.; Shi, X. L.; Wang, B. H. A novel resin linker for solid-phase peptide synthesis which call be cleaved using two sequential mild reactions J. Org. Chem. 1999, 64, 7459-7466
13. Wencewicz, T. A.; Yang, B.; Rudloff, J. R.; Oliver, A. G.; Miller, M. J. N-O chemistry for antibiotics: discovery of N -alkyl- N -(pyridin-2-yl)hydroxylamine scaffolds as selective antibacterial agents using nitroso Diels-Alder and ene chemistry J. Med. Chem. 2011, 54, 6843-6858
14. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically, 8 th ed; Clinical and Laboratory Standards Institute (CLSI): Villanova, PS, 2009; approved standard document M07-A7.
15. Cramariuc, O.; Rog, T.; Javanainen, M.; Monticelli, L.; Polishchuk, A. V.; Vattulainen, I. Mechanism for translocation of fluoroquinolones across lipid membranes Biochim. Biophys. Acta, Biomembr. 2012, 1818, 2563-2571
16. Vadnere, M. K.; Maggiora, L.; Mertes, M. P. Thiol addition to quinones-model reactions for the inactivation of thymidylate synthase by 5-para-benzoquinonyl-2′-deoxyuridine 5′-phosphate J. Med. Chem. 1986, 29, 1714-1720