Abstract
Cordycepin (3;-deoxyadenosine) is a potent anti-leukemic, anti-fungal, and anti-parasitic nucleoside antibiotic. Unfortunately, the biological activity of cordycepin is attenuated by its rapid conversion to 3;-deoxyinosine by adenosine deaminase (ADA). We have synthesized a series of ADA-resistant N-aminal and N-thioaminal cordycepin derivatives, which are protected from inactivation by deamination and yet retain biological activity. These compounds are hydrolyzed at various rates to efficiently release the parent drug cordycepin, and likely serve as simple hydrolytically activated prodrugs.
Keywords: cordycepin, adenosine deaminase, leukemia, prodrug
Letters in Drug Design & Discovery
Title: Synthesis and In Vitro Evaluation of Adenosine Deaminase Resistant N-6 Aminal and Thioaminal Prodrugs of Cordycepin
Volume: 2 Issue: 2
Author(s): Hui-Min Chang, Jesse Oakes, Anders Olsson, Luminita Panaitescu, B. Mark Britt, Christopher M. Kearney and Robert R. Kane
Affiliation:
Keywords: cordycepin, adenosine deaminase, leukemia, prodrug
Abstract: Cordycepin (3;-deoxyadenosine) is a potent anti-leukemic, anti-fungal, and anti-parasitic nucleoside antibiotic. Unfortunately, the biological activity of cordycepin is attenuated by its rapid conversion to 3;-deoxyinosine by adenosine deaminase (ADA). We have synthesized a series of ADA-resistant N-aminal and N-thioaminal cordycepin derivatives, which are protected from inactivation by deamination and yet retain biological activity. These compounds are hydrolyzed at various rates to efficiently release the parent drug cordycepin, and likely serve as simple hydrolytically activated prodrugs.
Export Options
About this article
Cite this article as:
Chang Hui-Min, Oakes Jesse, Olsson Anders, Panaitescu Luminita, Britt Mark B., Kearney M. Christopher and Kane R. Robert, Synthesis and In Vitro Evaluation of Adenosine Deaminase Resistant N-6 Aminal and Thioaminal Prodrugs of Cordycepin, Letters in Drug Design & Discovery 2005; 2 (2) . https://dx.doi.org/10.2174/1570180053175151
DOI https://dx.doi.org/10.2174/1570180053175151 |
Print ISSN 1570-1808 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-628X |
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers