Chemistry: Faculty Publications (1990-2023)
Synthesis, Stereochemical Characterization, and Antimicrobial Evaluation of a Potential Non-Nephrotoxic 3'-c-acethydrazide Puromycin Analog
Document Type
Article
Publication Date
1-1-2017
Publication Title
Journal of Nucleosides, Nucleotides and Nucleic Acids
DOI
10.1080/15257770.2016.1264590
ISSN
1532-2335
Abstract
Puromycin is a peptidyl nucleoside endowed with significant antibiotic and anticancer properties, but also with an unfortunate nephrotoxic character that has hampered its use as a chemotherapeutic agent. Since hydrolysis of puromycin's amide to puromycin aminonucleoside is the first metabolic step leading to nephrotoxicity, we designed a 3′-C-hydrazide analog where the nitrogen and carbon functionality around the amide carbonyl of puromycin are inverted. The title compound, synthesized in 11 steps from D-xylose, cannot be metabolized to the nephrotoxic aminonucleoside. Evaluation of the title compound on Staphylococcus epidermidis and multi-drug resistance Staphylococcus aureus did not show significant antimicrobial activity up to a 400 μM concentration.
Recommended Citation
Carter, Josh, Blair A. Weaver, Maria A. Chiacchio, Amy R. Messersmith, Will E. Lynch, Brent D. Feske, Giuseppe Gumina.
2017.
"Synthesis, Stereochemical Characterization, and Antimicrobial Evaluation of a Potential Non-Nephrotoxic 3'-c-acethydrazide Puromycin Analog."
Journal of Nucleosides, Nucleotides and Nucleic Acids, 36 (3): 224-241.
doi: 10.1080/15257770.2016.1264590
https://digitalcommons.georgiasouthern.edu/chem-facpubs/121
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