Specific targeting highly conserved residues in the HIV-1 reverse transcriptase primer grip region. Design, synthesis, and biological evaluation of novel, potent, and broad spectrum NNRTIs with antiviral activity.
Identifieur interne : 004877 ( Main/Merge ); précédent : 004876; suivant : 004878Specific targeting highly conserved residues in the HIV-1 reverse transcriptase primer grip region. Design, synthesis, and biological evaluation of novel, potent, and broad spectrum NNRTIs with antiviral activity.
Auteurs : Caterina Fattorusso [Italie] ; Sandra Gemma ; Stefania Butini ; Paul Huleatt ; Bruno Catalanotti ; Marco Persico ; Meri De Angelis ; Isabella Fiorini ; Vito Nacci ; Anna Ramunno ; Manuela Rodriquez ; Giovanni Greco ; Ettore Novellino ; Alberto Bergamini ; Stefano Marini ; Massimo Coletta ; Giovanni Maga ; Silvio Spadari ; Giuseppe CampianiSource :
- Journal of medicinal chemistry [ 0022-2623 ] ; 2005.
Descripteurs français
- KwdFr :
- Agents antiVIH (), Agents antiVIH (pharmacologie), Agents antiVIH (synthèse chimique), Animaux, Cellules cultivées, Conception de médicament, Humains, Inhibiteurs de la transcriptase inverse (), Inhibiteurs de la transcriptase inverse (pharmacologie), Inhibiteurs de la transcriptase inverse (synthèse chimique), Macrophages (), Macrophages (virologie), Modèles moléculaires, Mutation, Oxazépines (), Oxazépines (pharmacologie), Oxazépines (synthèse chimique), Pyrroles (), Pyrroles (pharmacologie), Pyrroles (synthèse chimique), Relation structure-activité, Réplication virale (), Résistance virale aux médicaments, Sites de fixation, Souris, Stéréoisomérie, Synergie des médicaments, Séquence conservée, Séquence d'acides aminés, Transcriptase inverse du VIH (), VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (), VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (génétique), Zidovudine (pharmacologie).
- MESH :
- génétique : VIH-1 (Virus de l'Immunodéficience Humaine de type 1).
- pharmacologie : Agents antiVIH, Inhibiteurs de la transcriptase inverse, Oxazépines, Pyrroles, Zidovudine.
- synthèse chimique : Agents antiVIH, Inhibiteurs de la transcriptase inverse, Oxazépines, Pyrroles.
- virologie : Macrophages.
- Agents antiVIH, Animaux, Cellules cultivées, Conception de médicament, Humains, Inhibiteurs de la transcriptase inverse, Macrophages, Modèles moléculaires, Mutation, Oxazépines, Pyrroles, Relation structure-activité, Réplication virale, Résistance virale aux médicaments, Sites de fixation, Souris, Stéréoisomérie, Synergie des médicaments, Séquence conservée, Séquence d'acides aminés, Transcriptase inverse du VIH, VIH-1 (Virus de l'Immunodéficience Humaine de type 1).
English descriptors
- KwdEn :
- Amino Acid Sequence, Animals, Anti-HIV Agents (chemical synthesis), Anti-HIV Agents (chemistry), Anti-HIV Agents (pharmacology), Binding Sites, Cells, Cultured, Conserved Sequence, Drug Design, Drug Resistance, Viral, Drug Synergism, HIV Reverse Transcriptase (chemistry), HIV-1 (drug effects), HIV-1 (genetics), Humans, Macrophages (drug effects), Macrophages (virology), Mice, Models, Molecular, Mutation, Oxazepines (chemical synthesis), Oxazepines (chemistry), Oxazepines (pharmacology), Pyrroles (chemical synthesis), Pyrroles (chemistry), Pyrroles (pharmacology), Reverse Transcriptase Inhibitors (chemical synthesis), Reverse Transcriptase Inhibitors (chemistry), Reverse Transcriptase Inhibitors (pharmacology), Stereoisomerism, Structure-Activity Relationship, Virus Replication (drug effects), Zidovudine (pharmacology).
- MESH :
- chemical , chemical synthesis : Anti-HIV Agents, Oxazepines, Pyrroles, Reverse Transcriptase Inhibitors.
- chemical , chemistry : Anti-HIV Agents, HIV Reverse Transcriptase, Oxazepines, Pyrroles, Reverse Transcriptase Inhibitors.
- chemical , pharmacology : Anti-HIV Agents, Oxazepines, Pyrroles, Reverse Transcriptase Inhibitors, Zidovudine.
- drug effects : HIV-1, Macrophages, Virus Replication.
- genetics : HIV-1.
- virology : Macrophages.
- Amino Acid Sequence, Animals, Binding Sites, Cells, Cultured, Conserved Sequence, Drug Design, Drug Resistance, Viral, Drug Synergism, Humans, Mice, Models, Molecular, Mutation, Stereoisomerism, Structure-Activity Relationship.
Abstract
Pyrrolobenzoxazepinones (PBOs) represent a new class of human immunodeficiency virus type 1 (HIV-1) nonnucleoside reverse transcriptase (RT) inhibitors (NNRTIs) whose prototype is 5. Molecular modeling studies based on the X-ray structures of HIV-1 RT prompted the synthesis of novel analogues which were tested as anti-HIV agents. The PBO derivatives specifically designed to target the highly conserved amino acid residues within the beta12-beta13 hairpin, namely primer grip, proved to be very potent against the most common mutant enzymes, including the highly resistant K103N mutant strain. Structure-activity relationships (SARs) are discussed in terms of a possible interaction with the RT binding site, depending on the nature of the substituents at C-6. Among the pyrrolobenzoxazepines investigated, 15c appeared to be the most promising NNRTI of the series characterized by potent antiviral activity, broad spectrum, and low cytotoxicity. 15c showed synergistic antiviral activity with AZT.
DOI: 10.1021/jm050257d
PubMed: 16279773
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pubmed:16279773Le document en format XML
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<author><name sortKey="Fattorusso, Caterina" sort="Fattorusso, Caterina" uniqKey="Fattorusso C" first="Caterina" last="Fattorusso">Caterina Fattorusso</name>
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<author><name sortKey="Greco, Giovanni" sort="Greco, Giovanni" uniqKey="Greco G" first="Giovanni" last="Greco">Giovanni Greco</name>
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<author><name sortKey="Marini, Stefano" sort="Marini, Stefano" uniqKey="Marini S" first="Stefano" last="Marini">Stefano Marini</name>
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<series><title level="j">Journal of medicinal chemistry</title>
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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Amino Acid Sequence</term>
<term>Animals</term>
<term>Anti-HIV Agents (chemical synthesis)</term>
<term>Anti-HIV Agents (chemistry)</term>
<term>Anti-HIV Agents (pharmacology)</term>
<term>Binding Sites</term>
<term>Cells, Cultured</term>
<term>Conserved Sequence</term>
<term>Drug Design</term>
<term>Drug Resistance, Viral</term>
<term>Drug Synergism</term>
<term>HIV Reverse Transcriptase (chemistry)</term>
<term>HIV-1 (drug effects)</term>
<term>HIV-1 (genetics)</term>
<term>Humans</term>
<term>Macrophages (drug effects)</term>
<term>Macrophages (virology)</term>
<term>Mice</term>
<term>Models, Molecular</term>
<term>Mutation</term>
<term>Oxazepines (chemical synthesis)</term>
<term>Oxazepines (chemistry)</term>
<term>Oxazepines (pharmacology)</term>
<term>Pyrroles (chemical synthesis)</term>
<term>Pyrroles (chemistry)</term>
<term>Pyrroles (pharmacology)</term>
<term>Reverse Transcriptase Inhibitors (chemical synthesis)</term>
<term>Reverse Transcriptase Inhibitors (chemistry)</term>
<term>Reverse Transcriptase Inhibitors (pharmacology)</term>
<term>Stereoisomerism</term>
<term>Structure-Activity Relationship</term>
<term>Virus Replication (drug effects)</term>
<term>Zidovudine (pharmacology)</term>
</keywords>
<keywords scheme="KwdFr" xml:lang="fr"><term>Agents antiVIH ()</term>
<term>Agents antiVIH (pharmacologie)</term>
<term>Agents antiVIH (synthèse chimique)</term>
<term>Animaux</term>
<term>Cellules cultivées</term>
<term>Conception de médicament</term>
<term>Humains</term>
<term>Inhibiteurs de la transcriptase inverse ()</term>
<term>Inhibiteurs de la transcriptase inverse (pharmacologie)</term>
<term>Inhibiteurs de la transcriptase inverse (synthèse chimique)</term>
<term>Macrophages ()</term>
<term>Macrophages (virologie)</term>
<term>Modèles moléculaires</term>
<term>Mutation</term>
<term>Oxazépines ()</term>
<term>Oxazépines (pharmacologie)</term>
<term>Oxazépines (synthèse chimique)</term>
<term>Pyrroles ()</term>
<term>Pyrroles (pharmacologie)</term>
<term>Pyrroles (synthèse chimique)</term>
<term>Relation structure-activité</term>
<term>Réplication virale ()</term>
<term>Résistance virale aux médicaments</term>
<term>Sites de fixation</term>
<term>Souris</term>
<term>Stéréoisomérie</term>
<term>Synergie des médicaments</term>
<term>Séquence conservée</term>
<term>Séquence d'acides aminés</term>
<term>Transcriptase inverse du VIH ()</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ()</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (génétique)</term>
<term>Zidovudine (pharmacologie)</term>
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<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Anti-HIV Agents</term>
<term>Oxazepines</term>
<term>Pyrroles</term>
<term>Reverse Transcriptase Inhibitors</term>
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<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Anti-HIV Agents</term>
<term>HIV Reverse Transcriptase</term>
<term>Oxazepines</term>
<term>Pyrroles</term>
<term>Reverse Transcriptase Inhibitors</term>
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<keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Anti-HIV Agents</term>
<term>Oxazepines</term>
<term>Pyrroles</term>
<term>Reverse Transcriptase Inhibitors</term>
<term>Zidovudine</term>
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<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>HIV-1</term>
<term>Macrophages</term>
<term>Virus Replication</term>
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<keywords scheme="MESH" qualifier="genetics" xml:lang="en"><term>HIV-1</term>
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<keywords scheme="MESH" qualifier="génétique" xml:lang="fr"><term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</term>
</keywords>
<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Agents antiVIH</term>
<term>Inhibiteurs de la transcriptase inverse</term>
<term>Oxazépines</term>
<term>Pyrroles</term>
<term>Zidovudine</term>
</keywords>
<keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Agents antiVIH</term>
<term>Inhibiteurs de la transcriptase inverse</term>
<term>Oxazépines</term>
<term>Pyrroles</term>
</keywords>
<keywords scheme="MESH" qualifier="virologie" xml:lang="fr"><term>Macrophages</term>
</keywords>
<keywords scheme="MESH" qualifier="virology" xml:lang="en"><term>Macrophages</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Amino Acid Sequence</term>
<term>Animals</term>
<term>Binding Sites</term>
<term>Cells, Cultured</term>
<term>Conserved Sequence</term>
<term>Drug Design</term>
<term>Drug Resistance, Viral</term>
<term>Drug Synergism</term>
<term>Humans</term>
<term>Mice</term>
<term>Models, Molecular</term>
<term>Mutation</term>
<term>Stereoisomerism</term>
<term>Structure-Activity Relationship</term>
</keywords>
<keywords scheme="MESH" xml:lang="fr"><term>Agents antiVIH</term>
<term>Animaux</term>
<term>Cellules cultivées</term>
<term>Conception de médicament</term>
<term>Humains</term>
<term>Inhibiteurs de la transcriptase inverse</term>
<term>Macrophages</term>
<term>Modèles moléculaires</term>
<term>Mutation</term>
<term>Oxazépines</term>
<term>Pyrroles</term>
<term>Relation structure-activité</term>
<term>Réplication virale</term>
<term>Résistance virale aux médicaments</term>
<term>Sites de fixation</term>
<term>Souris</term>
<term>Stéréoisomérie</term>
<term>Synergie des médicaments</term>
<term>Séquence conservée</term>
<term>Séquence d'acides aminés</term>
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<front><div type="abstract" xml:lang="en">Pyrrolobenzoxazepinones (PBOs) represent a new class of human immunodeficiency virus type 1 (HIV-1) nonnucleoside reverse transcriptase (RT) inhibitors (NNRTIs) whose prototype is 5. Molecular modeling studies based on the X-ray structures of HIV-1 RT prompted the synthesis of novel analogues which were tested as anti-HIV agents. The PBO derivatives specifically designed to target the highly conserved amino acid residues within the beta12-beta13 hairpin, namely primer grip, proved to be very potent against the most common mutant enzymes, including the highly resistant K103N mutant strain. Structure-activity relationships (SARs) are discussed in terms of a possible interaction with the RT binding site, depending on the nature of the substituents at C-6. Among the pyrrolobenzoxazepines investigated, 15c appeared to be the most promising NNRTI of the series characterized by potent antiviral activity, broad spectrum, and low cytotoxicity. 15c showed synergistic antiviral activity with AZT.</div>
</front>
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