Synthesis and antimicrobial activity of chloramphenicol–polyamine conjugates

Magoulas, George E.; Kostopoulou, Ourania N.; Garnelis, Thomas; Athanassopoulos, Constantinos M.; Kournoutou, Georgia G.; Leotsinidis, Michalis; Dinos, George P.; Papaioannou, Dionissios; Kalpaxis, Dimitrios L.

doi:10.1016/j.bmc.2015.04.069

Cited by 17 publications

(14 citation statements)

References 52 publications

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“…Bulky substitutions at positions 1 and 3 lead to an opposite effect. For instance, we recently prepared a CAM-polyamine conjugate by introducing a spermine molecule into position 3 of the 1,3-propanediol backbone of CAM, following oxidation of the primary hydroxyl group (compound 16 ) [ 73 , 84 ]. We anticipated that the conjugated polyamine portion could enhance the binding of CAM to the ribosome, by mimicking the function of an analogous cationic center found by crystallography to coordinate the interaction between the OH group at position 3 of CAM and nucleotide U2506 in D. radiodurans [ 18 ].…”

Section: Modifications Of Cam To Obtain Antibacterials With Improvmentioning

confidence: 99%

“…However, the role of PAs not merely serves as means of a “Trojan Horse”; PAs could provide the constructs with additional binding sites through their amino functions or other incorporated groups. The above information combined with the observation that PAs are implicated in the binding of CAM to bacterial ribosome [ 17 ], motivated us to design and synthesize recently a series of CAM-PA conjugates [ 73 , 84 ]. The most potent members of this series are shown in Figure 9 (compounds 34 and 35 ).…”

Section: Modifications Of Cam To Obtain Antibacterials With Improvmentioning

confidence: 99%

“…Uptaken by E. coli cells through the SPD-preferential transport system, both compounds decreased the protein and PA content of the cells [ 84 ]. The antibacterial activity of compounds 34 and 35 was comparable or superior to that of CAM, particularly against CAM-resistance strains.…”

Section: Modifications Of Cam To Obtain Antibacterials With Improvmentioning

confidence: 99%

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

et al. 2016

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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.

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Section: Modifications Of Cam To Obtain Antibacterials With Improvmentioning

confidence: 99%

Section: Modifications Of Cam To Obtain Antibacterials With Improvmentioning

confidence: 99%

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

et al. 2016

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“…Ghaffar et al conjugated the broad spectrum antibiotic levofloxacin with the highly hydrophobic antimicrobial peptide indolicidin [ 65 , 91 ]. Coupling between both components was achieved via amide bond formation or a labile ester linkage to investigate whether a prodrug-type linkage would have any impact on activity.…”

Section: Modified Amps and Amp Conjugatesmentioning

confidence: 99%

Design and Application of Antimicrobial Peptide Conjugates

Reinhardt

Neundorf

2016

IJMS

119

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Antimicrobial peptides (AMPs) are an interesting class of antibiotics characterized by their unique antibiotic activity and lower propensity for developing resistance compared to common antibiotics. They belong to the class of membrane-active peptides and usually act selectively against bacteria, fungi and protozoans. AMPs, but also peptide conjugates containing AMPs, have come more and more into the focus of research during the last few years. Within this article, recent work on AMP conjugates is reviewed. Different aspects will be highlighted as a combination of AMPs with antibiotics or organometallic compounds aiming to increase antibacterial activity or target selectivity, conjugation with photosensitizers for improving photodynamic therapy (PDT) or the attachment to particles, to name only a few. Owing to the enormous resonance of antimicrobial conjugates in the literature so far, this research topic seems to be very attractive to different scientific fields, like medicine, biology, biochemistry or chemistry.

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“…5B). The slow and sustained release of chloramphenicol and clotrimazole protects the wound from infections, 41,42,46,47 which helps with faster wound healing in the BSc sutured animals. The presence of growth factors helped rapid tissue regeneration in the wounded area, whereas the inherent healing properties of the coating material further enhanced the tissue repairing process.…”

Section: Wound Healing Efficacy Analysismentioning

confidence: 99%