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Literature DB >> 25240255

Synthesis and characterization of valyloxy methoxy luciferin for the detection of valacyclovirase and peptide transporter.

Zachary F Walls¹, Sheeba Varghese Gupta¹, Gordon L Amidon¹, Kyung-Dall Lee¹.

Abstract

An amino acid ester derivative of luciferin (valoluc) was synthesized to mimic the transport and activation of valacyclovir. This molecule was characterized in vitro for specificity and enzymatic constants, and then assayed in two different, physiologically-relevant conditions. It was demonstrated that valoluc activation is sensitive to the same cellular factors as valacyclovir and thus has the potential to elucidate the dynamics of amino acid ester prodrug therapies in a functional, high-throughput manner.

Entities: CellLine Chemical Disease Gene Species

Keywords: Luciferin; PEPT1; Prodrug; VACVase

Mesh：

Substances：

Year: 2014 PMID： 25240255 PMCID： PMC4192071 DOI： 10.1016/j.bmcl.2014.09.011

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

11 in total

Review 1. Bioluminescent assays for ADMET.

Authors: James J Cali; Andrew Niles; Michael P Valley; Martha A O'Brien; Terry L Riss; John Shultz
Journal: Expert Opin Drug Metab Toxicol Date: 2008-01 Impact factor: 4.481

2. A novel nucleoside prodrug-activating enzyme: substrate specificity of biphenyl hydrolase-like protein.

Authors: Insook Kim; Xueqin Song; Balvinder S Vig; Sachin Mittal; Ho-Chul Shin; Philip J Lorenzi; Gordon L Amidon
Journal: Mol Pharm Date: 2004 Mar-Apr Impact factor: 4.939

3. Sensitive luciferin derived probes for selective carboxypeptidase activity.

Authors: Yu-Cheng Chang; Pei-Wen Chao; Ching-Hsuan Tung
Journal: Bioorg Med Chem Lett Date: 2011-05-14 Impact factor: 2.823

4. Synthesis and conformational analysis of a coumarinic acid-based cyclic prodrug of an opioid peptide with modified sensitivity to esterase-catalyzed bioconversion.

Authors: H Ouyang; D G Vander Velde; R T Borchardt; T J Siahaan
Journal: J Pept Res Date: 2002-04

5. Identification of a human valacyclovirase: biphenyl hydrolase-like protein as valacyclovir hydrolase.

Authors: Insook Kim; Xiao-Yan Chu; Seonyoung Kim; Chester J Provoda; Kyung-Dall Lee; Gordon L Amidon
Journal: J Biol Chem Date: 2003-05-05 Impact factor: 5.157

6. 5'-Amino acid esters of antiviral nucleosides, acyclovir, and AZT are absorbed by the intestinal PEPT1 peptide transporter.

Authors: H Han; R L de Vrueh; J K Rhie; K M Covitz; P L Smith; C P Lee; D M Oh; W Sadée; G L Amidon
Journal: Pharm Res Date: 1998-08 Impact factor: 4.200

Synthesis and characterization of valyloxy methoxy luciferin for the detection of valacyclovirase and peptide transporter.

Review 1. Bioluminescent assays for ADMET.

2. A novel nucleoside prodrug-activating enzyme: substrate specificity of biphenyl hydrolase-like protein.

3. Sensitive luciferin derived probes for selective carboxypeptidase activity.

4. Synthesis and conformational analysis of a coumarinic acid-based cyclic prodrug of an opioid peptide with modified sensitivity to esterase-catalyzed bioconversion.

5. Identification of a human valacyclovirase: biphenyl hydrolase-like protein as valacyclovir hydrolase.

6. 5'-Amino acid esters of antiviral nucleosides, acyclovir, and AZT are absorbed by the intestinal PEPT1 peptide transporter.

7. Ether, carbonate and urethane deoxynucleoside derivatives as prodrugs.

8. Specificity of a prodrug-activating enzyme hVACVase: the leaving group effect.

Review 9. Prodrugs of nucleoside analogues for improved oral absorption and tissue targeting.

10. Molecular basis of prodrug activation by human valacyclovirase, an alpha-amino acid ester hydrolase.

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