Development of a red-shifted fluorescence-based assay for SARS-coronavirus 3CL protease: identification of a novel class of anti-SARS agents from the tropical marine sponge Axinella corrugata.
Identifieur interne : 002132 ( PubMed/Corpus ); précédent : 002131; suivant : 002133Development of a red-shifted fluorescence-based assay for SARS-coronavirus 3CL protease: identification of a novel class of anti-SARS agents from the tropical marine sponge Axinella corrugata.
Auteurs : Pamela Hamill ; Derek Hudson ; Richard Y. Kao ; Polly Chow ; Meera Raj ; Hongyan Xu ; Martin J. Richer ; François JeanSource :
- Biological chemistry [ 1431-6730 ] ; 2006.
English descriptors
- KwdEn :
- Animals, Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Cell Proliferation (drug effects), Chlorocebus aethiops, Cysteine Endopeptidases (chemistry), Cysteine Endopeptidases (isolation & purification), Drug Evaluation, Preclinical, Kinetics, Molecular Structure, Porifera (chemistry), Porifera (classification), Protease Inhibitors (chemistry), Protease Inhibitors (classification), Protease Inhibitors (pharmacology), SARS Virus (drug effects), SARS Virus (enzymology), Sensitivity and Specificity, Spectrometry, Fluorescence (methods), Structure-Activity Relationship, Time Factors, Umbelliferones (chemistry), Umbelliferones (pharmacology), Vero Cells, Viral Proteins (antagonists & inhibitors), Viral Proteins (chemistry), Viral Proteins (isolation & purification), Virus Replication (drug effects), Virus Replication (physiology).
- MESH :
- chemical , antagonists & inhibitors : Viral Proteins.
- chemical , chemistry : Antiviral Agents, Cysteine Endopeptidases, Protease Inhibitors, Umbelliferones, Viral Proteins.
- chemical , classification : Protease Inhibitors.
- chemical , isolation & purification : Cysteine Endopeptidases, Viral Proteins.
- chemical , pharmacology : Antiviral Agents, Protease Inhibitors, Umbelliferones.
- chemistry : Porifera.
- classification : Porifera.
- drug effects : Cell Proliferation, SARS Virus, Virus Replication.
- enzymology : SARS Virus.
- methods : Spectrometry, Fluorescence.
- physiology : Virus Replication.
- Animals, Chlorocebus aethiops, Drug Evaluation, Preclinical, Kinetics, Molecular Structure, Sensitivity and Specificity, Structure-Activity Relationship, Time Factors, Vero Cells.
Abstract
SARS-coronavirus (SARS-CoV) encodes a main protease, 3CLpro, which plays an essential role in the viral life cycle and is currently the prime target for discovering new anti-coronavirus agents. In this article, we report our success in developing a novel red-shifted (RS) fluorescence-based assay for 3CLpro and its application for identifying small-molecule anti-SARS agents from marine organisms. We have synthesised and characterised the first generation of a red-shifted internally quenched fluorogenic substrate (RS-IQFS) for 3CLpro based on resonance energy transfer between the donor and acceptor pair CAL Fluor Red 610 and Black Hole Quencher-1 (Km and kcat values of 14 microM and 0.65 min-1). The RS-IQFS primary sequence was selected based on the results of our screening analysis of 3CLpro performed using a series of blue-shifted (BS)-IQFSs corresponding to the 3CLpro-mediated cleavage junctions of the SARS-CoV polyproteins. In contrast to BS-IQFSs, the RS-IQFS was not susceptible to fluorescence interference from coloured samples and allowed for successful screening of marine natural products and identification of a coumarin derivative, esculetin-4-carboxylic acid ethyl ester, a novel 3CLpro inhibitor (IC50=46 microM) and anti-SARS agent (EC50=112 microM; median toxic concentration>800 microM) from the tropical marine sponge Axinella corrugata.
DOI: 10.1515/BC.2006.131
PubMed: 16895476
Links to Exploration step
pubmed:16895476Le document en format XML
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<author><name sortKey="Hamill, Pamela" sort="Hamill, Pamela" uniqKey="Hamill P" first="Pamela" last="Hamill">Pamela Hamill</name>
<affiliation><nlm:affiliation>Department of Microbiology and Immunology, Life Sciences Centre, University of British Columbia, 3559-2350 Health Sciences Mall, Vancouver, BC V6T 1Z3, Canada.</nlm:affiliation>
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<author><name sortKey="Hudson, Derek" sort="Hudson, Derek" uniqKey="Hudson D" first="Derek" last="Hudson">Derek Hudson</name>
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<author><name sortKey="Kao, Richard Y" sort="Kao, Richard Y" uniqKey="Kao R" first="Richard Y" last="Kao">Richard Y. Kao</name>
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<author><name sortKey="Chow, Polly" sort="Chow, Polly" uniqKey="Chow P" first="Polly" last="Chow">Polly Chow</name>
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<author><name sortKey="Raj, Meera" sort="Raj, Meera" uniqKey="Raj M" first="Meera" last="Raj">Meera Raj</name>
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<author><name sortKey="Xu, Hongyan" sort="Xu, Hongyan" uniqKey="Xu H" first="Hongyan" last="Xu">Hongyan Xu</name>
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<author><name sortKey="Richer, Martin J" sort="Richer, Martin J" uniqKey="Richer M" first="Martin J" last="Richer">Martin J. Richer</name>
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<author><name sortKey="Jean, Francois" sort="Jean, Francois" uniqKey="Jean F" first="François" last="Jean">François Jean</name>
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<author><name sortKey="Hudson, Derek" sort="Hudson, Derek" uniqKey="Hudson D" first="Derek" last="Hudson">Derek Hudson</name>
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<author><name sortKey="Chow, Polly" sort="Chow, Polly" uniqKey="Chow P" first="Polly" last="Chow">Polly Chow</name>
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<author><name sortKey="Raj, Meera" sort="Raj, Meera" uniqKey="Raj M" first="Meera" last="Raj">Meera Raj</name>
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<author><name sortKey="Xu, Hongyan" sort="Xu, Hongyan" uniqKey="Xu H" first="Hongyan" last="Xu">Hongyan Xu</name>
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<author><name sortKey="Richer, Martin J" sort="Richer, Martin J" uniqKey="Richer M" first="Martin J" last="Richer">Martin J. Richer</name>
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<series><title level="j">Biological chemistry</title>
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<term>Antiviral Agents (chemistry)</term>
<term>Antiviral Agents (pharmacology)</term>
<term>Cell Proliferation (drug effects)</term>
<term>Chlorocebus aethiops</term>
<term>Cysteine Endopeptidases (chemistry)</term>
<term>Cysteine Endopeptidases (isolation & purification)</term>
<term>Drug Evaluation, Preclinical</term>
<term>Kinetics</term>
<term>Molecular Structure</term>
<term>Porifera (chemistry)</term>
<term>Porifera (classification)</term>
<term>Protease Inhibitors (chemistry)</term>
<term>Protease Inhibitors (classification)</term>
<term>Protease Inhibitors (pharmacology)</term>
<term>SARS Virus (drug effects)</term>
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<term>Sensitivity and Specificity</term>
<term>Spectrometry, Fluorescence (methods)</term>
<term>Structure-Activity Relationship</term>
<term>Time Factors</term>
<term>Umbelliferones (chemistry)</term>
<term>Umbelliferones (pharmacology)</term>
<term>Vero Cells</term>
<term>Viral Proteins (antagonists & inhibitors)</term>
<term>Viral Proteins (chemistry)</term>
<term>Viral Proteins (isolation & purification)</term>
<term>Virus Replication (drug effects)</term>
<term>Virus Replication (physiology)</term>
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<keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>Viral Proteins</term>
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<term>Cysteine Endopeptidases</term>
<term>Protease Inhibitors</term>
<term>Umbelliferones</term>
<term>Viral Proteins</term>
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<term>Protease Inhibitors</term>
<term>Umbelliferones</term>
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<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Cell Proliferation</term>
<term>SARS Virus</term>
<term>Virus Replication</term>
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<keywords scheme="MESH" qualifier="enzymology" xml:lang="en"><term>SARS Virus</term>
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<keywords scheme="MESH" qualifier="methods" xml:lang="en"><term>Spectrometry, Fluorescence</term>
</keywords>
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<term>Chlorocebus aethiops</term>
<term>Drug Evaluation, Preclinical</term>
<term>Kinetics</term>
<term>Molecular Structure</term>
<term>Sensitivity and Specificity</term>
<term>Structure-Activity Relationship</term>
<term>Time Factors</term>
<term>Vero Cells</term>
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<front><div type="abstract" xml:lang="en">SARS-coronavirus (SARS-CoV) encodes a main protease, 3CLpro, which plays an essential role in the viral life cycle and is currently the prime target for discovering new anti-coronavirus agents. In this article, we report our success in developing a novel red-shifted (RS) fluorescence-based assay for 3CLpro and its application for identifying small-molecule anti-SARS agents from marine organisms. We have synthesised and characterised the first generation of a red-shifted internally quenched fluorogenic substrate (RS-IQFS) for 3CLpro based on resonance energy transfer between the donor and acceptor pair CAL Fluor Red 610 and Black Hole Quencher-1 (Km and kcat values of 14 microM and 0.65 min-1). The RS-IQFS primary sequence was selected based on the results of our screening analysis of 3CLpro performed using a series of blue-shifted (BS)-IQFSs corresponding to the 3CLpro-mediated cleavage junctions of the SARS-CoV polyproteins. In contrast to BS-IQFSs, the RS-IQFS was not susceptible to fluorescence interference from coloured samples and allowed for successful screening of marine natural products and identification of a coumarin derivative, esculetin-4-carboxylic acid ethyl ester, a novel 3CLpro inhibitor (IC50=46 microM) and anti-SARS agent (EC50=112 microM; median toxic concentration>800 microM) from the tropical marine sponge Axinella corrugata.</div>
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<Title>Biological chemistry</Title>
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<Abstract><AbstractText>SARS-coronavirus (SARS-CoV) encodes a main protease, 3CLpro, which plays an essential role in the viral life cycle and is currently the prime target for discovering new anti-coronavirus agents. In this article, we report our success in developing a novel red-shifted (RS) fluorescence-based assay for 3CLpro and its application for identifying small-molecule anti-SARS agents from marine organisms. We have synthesised and characterised the first generation of a red-shifted internally quenched fluorogenic substrate (RS-IQFS) for 3CLpro based on resonance energy transfer between the donor and acceptor pair CAL Fluor Red 610 and Black Hole Quencher-1 (Km and kcat values of 14 microM and 0.65 min-1). The RS-IQFS primary sequence was selected based on the results of our screening analysis of 3CLpro performed using a series of blue-shifted (BS)-IQFSs corresponding to the 3CLpro-mediated cleavage junctions of the SARS-CoV polyproteins. In contrast to BS-IQFSs, the RS-IQFS was not susceptible to fluorescence interference from coloured samples and allowed for successful screening of marine natural products and identification of a coumarin derivative, esculetin-4-carboxylic acid ethyl ester, a novel 3CLpro inhibitor (IC50=46 microM) and anti-SARS agent (EC50=112 microM; median toxic concentration>800 microM) from the tropical marine sponge Axinella corrugata.</AbstractText>
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