Synthesis and evaluation of atorvastatin esters as prodrugs metabolically activated by human carboxylesterases

[Display omitted] We synthesized 11 kinds of prodrug with an esterified carboxylic acid moiety of atorvastatin in moderate to high yields. We discovered that they underwent metabolic activation specifically by the human carboxylesterase 1 (CES1) isozyme. The results suggested that these ester compou...

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Published inBioorganic & medicinal chemistry letters Vol. 26; no. 3; pp. 921 - 923
Main Authors Mizoi, Kenta, Takahashi, Masato, Haba, Masami, Hosokawa, Masakiyo
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.02.2016
Elsevier
Subjects
Atorvastatin
Atorvastatin Calcium - chemical synthesis
Atorvastatin Calcium - chemistry
Atorvastatin Calcium - metabolism
Carboxylesterase
Carboxylic Acids - chemistry
Carboxylic Ester Hydrolases - metabolism
CES1
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Esters - metabolism
Humans
Life Sciences & Biomedicine
Liver - metabolism
Metabolism
Microsomes - metabolism
Pharmacology & Pharmacy
Physical Sciences
Prodrug
Prodrugs - chemical synthesis
Prodrugs - chemistry
Prodrugs - metabolism
Science & Technology
THF
EDC
DMP
DMAP
Atorvastatin
Prodrug
Carboxylesterase
Metabolism
TsOH
CES1
REDUCTASE INHIBITORS
ASYMMETRIC-SYNTHESIS
CPT-11 HYDROLYSIS
SPECIFICITY
SIDE-CHAIN
IDENTIFICATION
HCE-1
HUMAN LIVER
CDNA CLONING
EXPRESSION
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Abstract [Display omitted] We synthesized 11 kinds of prodrug with an esterified carboxylic acid moiety of atorvastatin in moderate to high yields. We discovered that they underwent metabolic activation specifically by the human carboxylesterase 1 (CES1) isozyme. The results suggested that these ester compounds of atorvastatin have the potential to act as prodrugs in vivo.
AbstractList We synthesized 11 kinds of prodrug with an esterified carboxylic acid moiety of atorvastatin in moderate to high yields. We discovered that they underwent metabolic activation specifically by the human carboxylesterase 1 (CES1) isozyme. The results suggested that these ester compounds of atorvastatin have the potential to act as prodrugs in vivo. (C) 2015 Elsevier Ltd. All rights reserved.
[Display omitted] We synthesized 11 kinds of prodrug with an esterified carboxylic acid moiety of atorvastatin in moderate to high yields. We discovered that they underwent metabolic activation specifically by the human carboxylesterase 1 (CES1) isozyme. The results suggested that these ester compounds of atorvastatin have the potential to act as prodrugs in vivo.
We synthesized 11 kinds of prodrug with an esterified carboxylic acid moiety of atorvastatin in moderate to high yields. We discovered that they underwent metabolic activation specifically by the human carboxylesterase 1 (CES1) isozyme. The results suggested that these ester compounds of atorvastatin have the potential to act as prodrugs in vivo.
We synthesized 11 kinds of prodrug with an esterified carboxylic acid moiety of atorvastatin in moderate to high yields. We discovered that they underwent metabolic activation specifically by the human carboxylesterase 1 (CES1) isozyme. The results suggested that these ester compounds of atorvastatin have the potential to act as prodrugs in vivo. Abbreviations * DMP, 2,2-dimethoxypropane * TsOH, p-toluenesulfonic acid * THF, tetrahydrofuran * EDC, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide * DMAP, 4-dimethylaminopyridine
Author Takahashi, Masato
Hosokawa, Masakiyo
Mizoi, Kenta
Haba, Masami
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Issue 3
Keywords THF
EDC
DMP
DMAP
Atorvastatin
Prodrug
Carboxylesterase
Metabolism
TsOH
CES1
REDUCTASE INHIBITORS
ASYMMETRIC-SYNTHESIS
CPT-11 HYDROLYSIS
SPECIFICITY
SIDE-CHAIN
IDENTIFICATION
HCE-1
HUMAN LIVER
CDNA CLONING
EXPRESSION
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Snippet [Display omitted] We synthesized 11 kinds of prodrug with an esterified carboxylic acid moiety of atorvastatin in moderate to high yields. We discovered that...
We synthesized 11 kinds of prodrug with an esterified carboxylic acid moiety of atorvastatin in moderate to high yields. We discovered that they underwent...
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SubjectTerms Atorvastatin
Atorvastatin Calcium - chemical synthesis
Atorvastatin Calcium - chemistry
Atorvastatin Calcium - metabolism
Carboxylesterase
Carboxylic Acids - chemistry
Carboxylic Ester Hydrolases - metabolism
CES1
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Esters - metabolism
Humans
Life Sciences & Biomedicine
Liver - metabolism
Metabolism
Microsomes - metabolism
Pharmacology & Pharmacy
Physical Sciences
Prodrug
Prodrugs - chemical synthesis
Prodrugs - chemistry
Prodrugs - metabolism
Science & Technology
Title Synthesis and evaluation of atorvastatin esters as prodrugs metabolically activated by human carboxylesterases
URI https://dx.doi.org/10.1016/j.bmcl.2015.12.069
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https://www.ncbi.nlm.nih.gov/pubmed/26750256
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https://search.proquest.com/docview/1768567812
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