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Antibiotics 2016, 5(2), 20; doi:10.3390/antibiotics5020020

Chloramphenicol Derivatives as Antibacterial and Anticancer Agents: Historic Problems and Current Solutions

1
Department of Biochemistry, School of Medicine, University of Patras, GR-26504 Patras, Greece
2
Laboratory of Synthetic Organic Chemistry, Department of Chemistry, University of Patras, GR-26504 Patras, Greece
3
Department of Biochemistry and Biotechnology, University of Thessaly, Ploutonos 26, GR-41221 Larissa, Greece
*
Authors to whom correspondence should be addressed.
Academic Editor: Claudio O. Gualerzi
Received: 24 February 2016 / Revised: 17 May 2016 / Accepted: 24 May 2016 / Published: 3 June 2016
(This article belongs to the Special Issue Inhibitors of the Translational Apparatus)
View Full-Text   |   Download PDF [4326 KB, uploaded 3 June 2016]   |  

Abstract

Chloramphenicol (CAM) is the D-threo isomer of a small molecule, consisting of a p-nitrobenzene ring connected to a dichloroacetyl tail through a 2-amino-1,3-propanediol moiety. CAM displays a broad-spectrum bacteriostatic activity by specifically inhibiting the bacterial protein synthesis. In certain but important cases, it also exhibits bactericidal activity, namely against the three most common causes of meningitis, Haemophilus influenzae, Streptococcus pneumoniae and Neisseria meningitidis. Resistance to CAM has been frequently reported and ascribed to a variety of mechanisms. However, the most important concerns that limit its clinical utility relate to side effects such as neurotoxicity and hematologic disorders. In this review, we present previous and current efforts to synthesize CAM derivatives with improved pharmacological properties. In addition, we highlight potentially broader roles of these derivatives in investigating the plasticity of the ribosomal catalytic center, the main target of CAM. View Full-Text
Keywords: chloramphenicol; antibiotics; antibiotic resistance; side effects; anticancer agents; chemical synthesis; translation; ribosome; peptidyl transferase; puromycin reaction chloramphenicol; antibiotics; antibiotic resistance; side effects; anticancer agents; chemical synthesis; translation; ribosome; peptidyl transferase; puromycin reaction
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Dinos, G.P.; Athanassopoulos, C.M.; Missiri, D.A.; Giannopoulou, P.C.; Vlachogiannis, I.A.; Papadopoulos, G.E.; Papaioannou, D.; Kalpaxis, D.L. Chloramphenicol Derivatives as Antibacterial and Anticancer Agents: Historic Problems and Current Solutions. Antibiotics 2016, 5, 20.

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