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cPrPMEDAP

Catalog No. T39269   CAS 182798-83-0

cPrPMEDAP, an intermediate metabolite of GS-9219, acts as a prodrug for the guanine nucleotide analog PMEG, demonstrating antiproliferative activity. It is negatively charged at physiological pH, resulting in poor skin permeability.

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cPrPMEDAP Chemical Structure
cPrPMEDAP, CAS 182798-83-0
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Biological Description
Chemical Properties
Storage & Solubility Information
Description cPrPMEDAP, an intermediate metabolite of GS-9219, acts as a prodrug for the guanine nucleotide analog PMEG, demonstrating antiproliferative activity. It is negatively charged at physiological pH, resulting in poor skin permeability.
In vitro cPrPMEDAP displays antiproliferative properties against SiHa cells (HPV-transformed cervical carcinoma cell lines) with an EC50 value of 290 nM[1]. Its counterpart, PMEG, generates an active phosphorylated metabolite, PMEG diphosphate (PMEG-DP), which effectively inhibits growth in various transformed cell lines by strongly suppressing nuclear DNA polymerases α, δ, and ?, thus hindering DNA synthesis and/or repair. Although PMEG demonstrates antiproliferative efficacy in animal models, its application as an antiproliferative agent is constrained by its limited cellular uptake and pronounced toxicity. cPrPMEDAP, on the other hand, exhibits comparable in vitro antiproliferative effectiveness and diminished toxicity in vivo. However, similar to PMEG, it faces challenges with skin permeability due to its negative charge at physiological pH[1].
Molecular Weight 328.269
Formula C11H17N6O4P
CAS No. 182798-83-0

Storage

Powder: -20°C for 3 years | In solvent: -80°C for 1 year

TargetMolReferences and Literature

1. Compton ML, et al. 9-(2-Phosphonylmethoxyethyl)-N6-cyclopropyl-2,6-diaminopurine (cpr-PMEDAP) as a prodrug of 9-(2-phosphonylmethoxyethyl)guanine (PMEG). Biochem Pharmacol. 1999;58(4):709-714. 2. Wolfgang GH, et al. GS-9191 is a novel topical prodrug of the nucleotide analog 9-(2-phosphonylmethoxyethyl)guanine with antiproliferative activity and possible utility in the treatment of human papillomavirus lesions. Antimicrob Agents Chemother. 2009;53(7):2777-2784.

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