Amino acid ester prodrugs of the antiviral agent 2-bromo-5,6-dichloro-1-(beta-D-ribofuranosyl)benzimidazole as potential substrates of hPEPT1 transporter.

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Song X, Vig BS, Lorenzi PL, Drach JC, Townsend LB, Amidon GL

Amino acid ester prodrugs of the antiviral agent 2-bromo-5,6-dichloro-1-(beta-D-ribofuranosyl)benzimidazole as potential substrates of hPEPT1 transporter.

J Med Chem. 2005 Feb 24;48(4):1274-7.

PubMed ID
15715497 [ View in PubMed
]
Abstract

Amino acid ester prodrugs of 2-bromo-5,6-dichloro-1-(beta-d-ribofuranosyl)benzimidazole (BDCRB) were synthesized and evaluated for their affinity for hPEPT1, an intestinal oligopeptide transporter. Assays of competitive inhibition of [(3)H]glycylsarcosine (Gly-Sar) uptake in HeLa/hPEPT1 cells by the amino acid ester prodrugs of BDCRB suggested their 2- to 4-fold higher affinity for hPEPT1 compared to BDCRB. Further, promoieties with hydrophobic side chains and l-configuration were preferred by the hPEPT1 transporter.

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Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
ValaciclovirSolute carrier family 15 member 1IC 50 (nM)431000N/AN/ADetails