Synthesis and In Vitro Evaluation of Adenosine Deaminase Resistant N-6 Aminal and Thioaminal Prodrugs of Cordycepin

Author(s): Hui-Min Chang, Jesse Oakes, Anders Olsson, Luminita Panaitescu, B. Mark Britt, Christopher M. Kearney, Robert R. Kane.

Journal Name: Letters in Drug Design & Discovery

Volume 2 , Issue 2 , 2005

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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

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Article Details

VOLUME: 2
ISSUE: 2
Year: 2005
Page: [133 - 136]
Pages: 4
DOI: 10.2174/1570180053175151
Price: $58

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