Biguanide is a modifiable pharmacophore for recruitment of endogenous Zn2+ to inhibit cysteinyl cathepsins: review and implications
Identifieur interne : 000A05 ( Main/Exploration ); précédent : 000A04; suivant : 000A06Biguanide is a modifiable pharmacophore for recruitment of endogenous Zn2+ to inhibit cysteinyl cathepsins: review and implications
Auteurs : Thomas D. LockwoodSource :
- Biometals [ 0966-0844 ] ; 2019.
Abstract
Excessive activities of cysteinyl cathepsins (CysCts) contribute to the progress of many diseases; however, therapeutic inhibition has been problematic. Zn2
Phenformin-Zn2+ Complex
Url:
DOI: 10.1007/s10534-019-00197-1
PubMed: 31044334
PubMed Central: 6647370
Affiliations:
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Biguanide is a modifiable pharmacophore for recruitment of endogenous Zn<sup>2+</sup> to inhibit cysteinyl cathepsins: review and implications</title><author><name sortKey="Lockwood, Thomas D" sort="Lockwood, Thomas D" uniqKey="Lockwood T" first="Thomas D." last="Lockwood">Thomas D. Lockwood</name><affiliation><nlm:aff id="Aff1"></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">31044334</idno><idno type="pmc">6647370</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6647370</idno><idno type="RBID">PMC:6647370</idno><idno type="doi">10.1007/s10534-019-00197-1</idno><date when="2019">2019</date><idno type="wicri:Area/Pmc/Corpus">000217</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000217</idno><idno type="wicri:Area/Pmc/Curation">000217</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000217</idno><idno type="wicri:Area/Pmc/Checkpoint">000941</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">000941</idno><idno type="wicri:Area/Ncbi/Merge">000582</idno><idno type="wicri:Area/Ncbi/Curation">000582</idno><idno type="wicri:Area/Ncbi/Checkpoint">000582</idno><idno type="wicri:doubleKey">0966-0844:2019:Lockwood T:biguanide:is:a</idno><idno type="wicri:Area/Main/Merge">000A05</idno><idno type="wicri:Area/Main/Curation">000A05</idno><idno type="wicri:Area/Main/Exploration">000A05</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Biguanide is a modifiable pharmacophore for recruitment of endogenous Zn<sup>2+</sup> to inhibit cysteinyl cathepsins: review and implications</title><author><name sortKey="Lockwood, Thomas D" sort="Lockwood, Thomas D" uniqKey="Lockwood T" first="Thomas D." last="Lockwood">Thomas D. Lockwood</name><affiliation><nlm:aff id="Aff1"></nlm:aff></affiliation></author></analytic><series><title level="j">Biometals</title><idno type="ISSN">0966-0844</idno><idno type="eISSN">1572-8773</idno><imprint><date when="2019">2019</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><sec><title>Abstract</title><p id="Par1">Excessive activities of cysteinyl cathepsins (CysCts) contribute to the progress of many diseases; however, therapeutic inhibition has been problematic. Zn<sup>2<bold>+</bold></sup> is a natural inhibitor of proteases with CysHis dyads or CysHis(Xaa) triads. Biguanide forms bidentate metal complexes through the two imino nitrogens. Here, it is discussed that phenformin (phenylethyl biguanide) is a model for recruitment of endogenous Zn<sup>2<bold>+</bold></sup> to inhibit CysHis/CysHis(X) peptidolysis. Phenformin is a Zn<sup>2<bold>+</bold></sup>-interactive, anti-proteolytic agent in bioassay of living tissue. Benzoyl-<sc>l</sc>-arginine amide (BAA) is a classical substrate of papain-like proteases; the amide bond is scissile. In this review, the structures of BAA and the phenformin-Zn<sup>2<bold>+</bold></sup> complex were compared in silico. Their chemistry and dimensions are discussed in light of the active sites of papain-like proteases. The phenyl moieties of both structures bind to the “S2” substrate-binding site that is typical of many proteases. When the phenyl moiety of BAA binds to S2, then the scissile amide bond is directed to the position of the thiolate-imidazolium ion pair, and is then hydrolyzed. However, when the phenyl moiety of phenformin binds to S2, then the coordinated Zn<sup>2<bold>+</bold></sup> is directed to the identical position; and catalysis is inhibited. Phenformin stabilizes a “Zn<sup>2<bold>+</bold></sup> sandwich” between the drug and protease active site. Hundreds of biguanide derivatives have been synthesized at the 1 and 5 nitrogen positions; many more are conceivable. Various substituent moieties can register with various arrays of substrate-binding sites so as to align coordinated Zn<sup>2<bold>+</bold></sup> with catalytic partners of diverse proteases. Biguanide is identified here as a modifiable pharmacophore for synthesis of therapeutic CysCt inhibitors with a wide range of potencies and specificities.</p></sec><sec><title>Graphical abstract</title><p id="Par2">Phenformin-Zn<sup>2+</sup> Complex<graphic position="anchor" xlink:href="10534_2019_197_Figa_HTML" id="MO1"></graphic></p></sec></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Abbas, Sy" uniqKey="Abbas S">SY Abbas</name></author><author><name sortKey="Basyouni, Wm" uniqKey="Basyouni W">WM Basyouni</name></author><author><name sortKey="El Bayouki, Kam" uniqKey="El Bayouki K">KAM El-Bayouki</name></author><author><name sortKey="Abdel Rahman, Rf" uniqKey="Abdel Rahman R">RF Abdel-Rahman</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Agbowuro, Aa" uniqKey="Agbowuro A">AA Agbowuro</name></author><author><name sortKey="Huston, Wm" uniqKey="Huston W">WM Huston</name></author><author><name 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Tremaroli</name></author><author><name sortKey="Khan, Mt" uniqKey="Khan M">MT Khan</name></author><author><name sortKey="Caesar, R" uniqKey="Caesar R">R Caesar</name></author><author><name sortKey="Manner S Holm, L" uniqKey="Manner S Holm L">L Mannerås-Holm</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Wurtz, A" uniqKey="Wurtz A">A Wurtz</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Xu, H" uniqKey="Xu H">H Xu</name></author><author><name sortKey="Ren, D" uniqKey="Ren D">D Ren</name></author></analytic></biblStruct></listBibl></div1></back></TEI><affiliations><list></list><tree><noCountry><name sortKey="Lockwood, Thomas D" sort="Lockwood, Thomas D" uniqKey="Lockwood T" first="Thomas D." last="Lockwood">Thomas D. 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