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.
Original language | American English |
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Journal | Journal of Nucleosides, Nucleotides and Nucleic Acids |
Volume | 36 |
DOIs | |
State | Published - Jan 1 2017 |
Keywords
- Antimicrobial evaluation
- Potential non-nephrotoxic 3'-C-acethydrazide puromycin analog
- Stereochemical characterization
- Synthesis
DC Disciplines
- Chemistry