Design, synthesis and anti-HIV evaluation of novel diarylnicotinamide derivatives (DANAs) targeting the entrance channel of the NNRTI binding pocket through structure-guided molecular hybridization.
Identifieur interne : 001667 ( Main/Exploration ); précédent : 001666; suivant : 001668Design, synthesis and anti-HIV evaluation of novel diarylnicotinamide derivatives (DANAs) targeting the entrance channel of the NNRTI binding pocket through structure-guided molecular hybridization.
Auteurs : Zhaoqiang Liu [République populaire de Chine] ; Wenmin Chen [République populaire de Chine] ; Peng Zhan [République populaire de Chine] ; Erik De Clercq [Belgique] ; Christophe Pannecouque [Belgique] ; Xinyong Liu [République populaire de Chine]Source :
- European journal of medicinal chemistry [ 1768-3254 ] ; 2014.
Descripteurs français
- KwdFr :
- Agents antiVIH (pharmacologie), Agents antiVIH (synthèse chimique), Cellules cancéreuses en culture, Conception de médicament, Conformation des protéines, Domaine catalytique, Humains, Infections à VIH (traitement médicamenteux), Infections à VIH (virologie), Inhibiteurs de la transcriptase inverse (pharmacologie), Inhibiteurs de la transcriptase inverse (synthèse chimique), Modèles moléculaires, Nicotinamide (), Relation dose-effet des médicaments, Relation structure-activité, Structure moléculaire, Transcriptase inverse du VIH (antagonistes et inhibiteurs), VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (), VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (enzymologie).
- MESH :
- antagonistes et inhibiteurs : Transcriptase inverse du VIH.
- enzymologie : VIH-1 (Virus de l'Immunodéficience Humaine de type 1).
- pharmacologie : Agents antiVIH, Inhibiteurs de la transcriptase inverse.
- synthèse chimique : Agents antiVIH, Inhibiteurs de la transcriptase inverse.
- traitement médicamenteux : Infections à VIH.
- virologie : Infections à VIH.
- Cellules cancéreuses en culture, Conception de médicament, Conformation des protéines, Domaine catalytique, Humains, Modèles moléculaires, Nicotinamide, Relation dose-effet des médicaments, Relation structure-activité, Structure moléculaire, VIH-1 (Virus de l'Immunodéficience Humaine de type 1).
English descriptors
- KwdEn :
- Anti-HIV Agents (chemical synthesis), Anti-HIV Agents (pharmacology), Catalytic Domain, Dose-Response Relationship, Drug, Drug Design, HIV Infections (drug therapy), HIV Infections (virology), HIV Reverse Transcriptase (antagonists & inhibitors), HIV-1 (drug effects), HIV-1 (enzymology), Humans, Models, Molecular, Molecular Structure, Niacinamide (chemistry), Protein Conformation, Reverse Transcriptase Inhibitors (chemical synthesis), Reverse Transcriptase Inhibitors (pharmacology), Structure-Activity Relationship, Tumor Cells, Cultured.
- MESH :
- chemical , antagonists & inhibitors : HIV Reverse Transcriptase.
- chemical , chemical synthesis : Anti-HIV Agents, Reverse Transcriptase Inhibitors.
- chemical , chemistry : Niacinamide.
- chemical , pharmacology : Anti-HIV Agents, Reverse Transcriptase Inhibitors.
- drug effects : HIV-1.
- drug therapy : HIV Infections.
- enzymology : HIV-1.
- virology : HIV Infections.
- Catalytic Domain, Dose-Response Relationship, Drug, Drug Design, Humans, Models, Molecular, Molecular Structure, Protein Conformation, Structure-Activity Relationship, Tumor Cells, Cultured.
Abstract
Through a structure-based molecular hybridization approach, a novel series of diarylnicotinamide derivatives (DANAs) targeting the entrance channel of HIV-1 NNRTIs binding pocket (NNIBP) were rationally designed, synthesized and evaluated for their anti-HIV activities in MT-4 cells together with the inhibition against the reverse transcriptase (RT) in an enzymatic assay. Encouragingly, most of the new DANAs were found to be active against wild-type HIV-1 with an EC50 in the range of 0.027-4.54 μM. Among them, compound 6b11 (EC50 = 0.027 μM, SI > 12518) and 6b5 (EC50 = 0.029 μM, SI = 2471) were identified as the most potent inhibitors, which were more potent than the reference drugs nevirapine (EC50 = 0.31 μM) and delavirdine (EC50 = 0.66 μM). Some DANAs were also active at micromolar concentrations against the K103N + Y181C resistant mutant. Compound 6b11 exhibited the highest enzymatic inhibition activity (IC50 = 20 nM), which is equal to that of efavirenz (EC50 = 20 nM) and 31 times higher than that of nevirapine (EC50 = 0.62 μM). Preliminary structure-activity relationships (SARs) and molecular modeling of these new DANAs have been discussed.
DOI: 10.1016/j.ejmech.2014.09.054
PubMed: 25240095
Affiliations:
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Electronic address: xinyongl@sdu.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44, West Culture Road, 250012 Jinan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author></analytic><series><title level="j">European journal of medicinal chemistry</title><idno type="eISSN">1768-3254</idno><imprint><date when="2014" type="published">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Anti-HIV Agents (chemical synthesis)</term><term>Anti-HIV Agents (pharmacology)</term><term>Catalytic Domain</term><term>Dose-Response Relationship, Drug</term><term>Drug Design</term><term>HIV Infections (drug therapy)</term><term>HIV Infections (virology)</term><term>HIV Reverse Transcriptase (antagonists & inhibitors)</term><term>HIV-1 (drug effects)</term><term>HIV-1 (enzymology)</term><term>Humans</term><term>Models, Molecular</term><term>Molecular Structure</term><term>Niacinamide (chemistry)</term><term>Protein Conformation</term><term>Reverse Transcriptase Inhibitors (chemical synthesis)</term><term>Reverse Transcriptase Inhibitors (pharmacology)</term><term>Structure-Activity Relationship</term><term>Tumor Cells, Cultured</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Agents antiVIH (pharmacologie)</term><term>Agents antiVIH (synthèse chimique)</term><term>Cellules cancéreuses en culture</term><term>Conception de médicament</term><term>Conformation des protéines</term><term>Domaine catalytique</term><term>Humains</term><term>Infections à VIH (traitement médicamenteux)</term><term>Infections à VIH (virologie)</term><term>Inhibiteurs de la transcriptase inverse (pharmacologie)</term><term>Inhibiteurs de la transcriptase inverse (synthèse chimique)</term><term>Modèles moléculaires</term><term>Nicotinamide ()</term><term>Relation dose-effet des médicaments</term><term>Relation structure-activité</term><term>Structure moléculaire</term><term>Transcriptase inverse du VIH (antagonistes et inhibiteurs)</term><term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ()</term><term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (enzymologie)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>HIV Reverse Transcriptase</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Anti-HIV Agents</term><term>Reverse Transcriptase Inhibitors</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Niacinamide</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Anti-HIV Agents</term><term>Reverse Transcriptase Inhibitors</term></keywords><keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr"><term>Transcriptase inverse du VIH</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>HIV-1</term></keywords><keywords scheme="MESH" qualifier="drug therapy" xml:lang="en"><term>HIV Infections</term></keywords><keywords scheme="MESH" qualifier="enzymologie" xml:lang="fr"><term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</term></keywords><keywords scheme="MESH" qualifier="enzymology" xml:lang="en"><term>HIV-1</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Agents antiVIH</term><term>Inhibiteurs de la transcriptase inverse</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Agents antiVIH</term><term>Inhibiteurs de la transcriptase inverse</term></keywords><keywords scheme="MESH" qualifier="traitement médicamenteux" xml:lang="fr"><term>Infections à VIH</term></keywords><keywords scheme="MESH" qualifier="virologie" xml:lang="fr"><term>Infections à VIH</term></keywords><keywords scheme="MESH" qualifier="virology" xml:lang="en"><term>HIV Infections</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Catalytic Domain</term><term>Dose-Response Relationship, Drug</term><term>Drug Design</term><term>Humans</term><term>Models, Molecular</term><term>Molecular Structure</term><term>Protein Conformation</term><term>Structure-Activity Relationship</term><term>Tumor Cells, Cultured</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Cellules cancéreuses en culture</term><term>Conception de médicament</term><term>Conformation des protéines</term><term>Domaine catalytique</term><term>Humains</term><term>Modèles moléculaires</term><term>Nicotinamide</term><term>Relation dose-effet des médicaments</term><term>Relation structure-activité</term><term>Structure moléculaire</term><term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Through a structure-based molecular hybridization approach, a novel series of diarylnicotinamide derivatives (DANAs) targeting the entrance channel of HIV-1 NNRTIs binding pocket (NNIBP) were rationally designed, synthesized and evaluated for their anti-HIV activities in MT-4 cells together with the inhibition against the reverse transcriptase (RT) in an enzymatic assay. Encouragingly, most of the new DANAs were found to be active against wild-type HIV-1 with an EC50 in the range of 0.027-4.54 μM. Among them, compound 6b11 (EC50 = 0.027 μM, SI > 12518) and 6b5 (EC50 = 0.029 μM, SI = 2471) were identified as the most potent inhibitors, which were more potent than the reference drugs nevirapine (EC50 = 0.31 μM) and delavirdine (EC50 = 0.66 μM). Some DANAs were also active at micromolar concentrations against the K103N + Y181C resistant mutant. Compound 6b11 exhibited the highest enzymatic inhibition activity (IC50 = 20 nM), which is equal to that of efavirenz (EC50 = 20 nM) and 31 times higher than that of nevirapine (EC50 = 0.62 μM). Preliminary structure-activity relationships (SARs) and molecular modeling of these new DANAs have been discussed.</div></front></TEI><affiliations><list><country><li>Belgique</li><li>République populaire de Chine</li></country></list><tree><country name="République populaire de Chine"><noRegion><name sortKey="Liu, Zhaoqiang" sort="Liu, Zhaoqiang" uniqKey="Liu Z" first="Zhaoqiang" last="Liu">Zhaoqiang Liu</name></noRegion><name sortKey="Chen, Wenmin" sort="Chen, Wenmin" uniqKey="Chen W" first="Wenmin" last="Chen">Wenmin Chen</name><name sortKey="Liu, Xinyong" sort="Liu, Xinyong" uniqKey="Liu X" first="Xinyong" last="Liu">Xinyong Liu</name><name sortKey="Zhan, Peng" sort="Zhan, Peng" uniqKey="Zhan P" first="Peng" last="Zhan">Peng Zhan</name></country><country name="Belgique"><noRegion><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name></noRegion><name sortKey="Pannecouque, Christophe" sort="Pannecouque, Christophe" uniqKey="Pannecouque C" first="Christophe" last="Pannecouque">Christophe Pannecouque</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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