Synthesis and antibacterial evaluation of amino acid–antibiotic conjugates

Ibrahim, Mohamed A.; Panda, Siva S.; Birs, Antoinette; Serrano, Juan Carlos; González, Claudio F.; Alamry, Khalid A.; Katritzky, Alan R.

doi:10.1016/j.bmcl.2014.01.065

Cited by 44 publications

(36 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We have also observed duplication of peaks in 13 C NMR of 8a ′ and 8b ′ , whereas in the case of 8a and 8b, extra peaks were not observed.…”

Section: Resultsmentioning

confidence: 74%

“…We previously used benzotriazole methodology to prepare diverse peptide conjugates (13)(14)(15)(16)(17).…”

Section: Resultsmentioning

confidence: 99%

“…Melting points were determined on a capillary point apparatus equipped with a digital thermometer. NMR spectra were recorded in DMSO-d 6 on Mercury or Gemini NMR spectrometers operating at 300 MHz for 1 H (with TMS as an internal standard) and 75 MHz for 13 C. Elemental analyses were performed on a Carlo Erba-EA1108 instrument. All microwaveassisted reactions were carried out with a single-mode cavity Discover Microwave Synthesizer.…”

Section: Experimental Designmentioning

confidence: 99%

See 2 more Smart Citations

Green and catalyst-free synthesis of olsalazine analogs

Ibrahim

Elagawany

Ibrahim

2016

Green Chemistry Letters and Reviews

Self Cite

View full text Add to dashboard Cite

A greener protocol for the synthesis of olsalazine analogs is reported. Olsalazine analogs are prepared in high yields by a one-pot reaction of two molecules of mesalazine with benzotriazole-activated aspartic acid and glutamic acid in water under microwave irradiation. GRAPHICAL ABSTRACTA greener protocol for the synthesis of olsalazine analogs is reported. Olsalazine analogs are prepared in high yields by a one-pot reaction of two molecules of mesalazine and aspartic/ glutamic benzotriazoles in water under microwave irradiation. ARTICLE HISTORY

show abstract

“…We have also observed duplication of peaks in 13 C NMR of 8a ′ and 8b ′ , whereas in the case of 8a and 8b, extra peaks were not observed.…”

Section: Resultsmentioning

confidence: 74%

“…We previously used benzotriazole methodology to prepare diverse peptide conjugates (13)(14)(15)(16)(17).…”

Section: Resultsmentioning

confidence: 99%

Section: Experimental Designmentioning

confidence: 99%

See 1 more Smart Citation

Green and catalyst-free synthesis of olsalazine analogs

Ibrahim

Elagawany

Ibrahim

2016

Green Chemistry Letters and Reviews

Self Cite

View full text Add to dashboard Cite

show abstract

“…12 Cell-permeating antimicrobial agents potentially play an important role in eliminating infections by intracellular pathogens and amino acids have been used as carriers for drugs because of their ability to insert into mammalian tissue. Prodrugs formed from quinolone acids and amino acid esters are more lipophilic than the parent drugs [13][14][15] so, can show enhanced in vivo antibacterial properties [16][17][18] with pronounced therapeutic effects against Pseudomonas aeruginosa, 10,11 Escherichia coli, 12 Staphylococcus aureus 19 and Salmonella typhi. 18 Despite global resistance quinolones continue to be the most recommended antibacterial agents for chemical modification.…”

Section: Introductionmentioning

confidence: 99%

Novel antibacterial active quinolone–fluoroquinolone conjugates and 2D-QSAR studies

Panda

Liaqat

Girgis

et al. 2015

Bioorganic & Medicinal Chemistry Letters

Self Cite

View full text Add to dashboard Cite

“…Furthermore, several different analogs of clarithromycin and β-lactam antibiotics have been synthesized that are less susceptible towards developing resistance to certain bacterial strains [8,9]. Amino acid sequences have also been utilized to chemically modify antibiotics in order to increase the drug’s hydrophobicity and concentration at the target delivery site [10]. …”

Section: Introductionmentioning

confidence: 99%

Erythromycin Modification That Improves Its Acidic Stability while Optimizing It for Local Drug Delivery

et al. 2017

View full text Add to dashboard Cite

The antibiotic erythromycin has limited efficacy and bioavailability due to its instability and conversion under acidic conditions via an intramolecular dehydration reaction. To improve the stability of erythromycin, several analogs have been developed—such as azithromycin and clarithromycin—which decrease the rate of intramolecular dehydration. We set out to build upon this prior work by developing a conjugate of erythromycin with improved pH stability, bioavailability, and preferential release from a drug delivery system directly at the low pH of an infection site. To develop this new drug conjugate, adamantane-1-carbohydrazide was covalently attached to erythromycin via a pH-degradable hydrazone bond. Since Staphylococcus aureus infection sites are slightly acidic, the hydrazone bond will undergo hydrolysis liberating erythromycin directly at the infection site. The adamantane group provides interaction with the drug delivery system. This local delivery strategy has the potential of reducing off-target and systemic side-effects. This work demonstrates the synthesis of a pH-cleavable, erythromycin conjugate that retains the inherent antimicrobial activity of erythromycin, has an increased hydrophobicity, and improved stability in acidic conditions; thereby enhancing erythromycin’s bioavailability while simultaneously reducing its toxicity.

show abstract

Synthesis and antibacterial evaluation of amino acid–antibiotic conjugates

Cited by 44 publications

References 17 publications

Green and catalyst-free synthesis of olsalazine analogs

Green and catalyst-free synthesis of olsalazine analogs

Novel antibacterial active quinolone–fluoroquinolone conjugates and 2D-QSAR studies

Erythromycin Modification That Improves Its Acidic Stability while Optimizing It for Local Drug Delivery

Contact Info

Product

Resources

About