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Synthesis of New N-isobutyryl-L-cysteine/MEA Conjugates: Evaluation of Their Free Radical-Scavenging Activities and anti-HIV Properties in Human Macrophages

Michael Smietana, Pascal Clayette, Patricia Mialocq, Jean-Jacques Vasseur, Joël Oiry

Bioorg Chem. 2008 Jun;36(3):133-40.

PMID: 18367231

Abstract:

Four novel N-isobutyryl-L-cysteine/2-mercaptoethylamine (MEA, cysteamine) conjugates have been designed and synthesized. The antioxidant activities of these new series were evaluated by three different free radical scavenging methods (DPPH test, ABTS test, and deoxyribose assay) and their metal binding capacity was evaluated by the ethidium bromide fluorescence binding assay. These results were compared with those obtained with their pro-GSH acetyl analogues recently developed in our laboratory. We observed that most of these compounds exhibit free radical-scavenging activities similar to those of Trolox, but always superior than NAC. While none of these new derivatives had pro-GSH activities, they displayed anti-HIV properties in human monocyte-derived macrophages infected in vitro. The present study demonstrates that these new N-isobutyryl derivatives, which are expected to have a greater bioavailability than their acetyl analogues, may have useful applications in HIV infection in respect to their antioxidant and anti-HIV activities.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP124529028 N-Isobutyryl-L-cysteine N-Isobutyryl-L-cysteine 124529-02-8 Price
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