Design, synthesis and biological evaluation of novel piperazine derivatives as CCR5 antagonists.
Identifieur interne : 001200 ( PubMed/Checkpoint ); précédent : 001199; suivant : 001201Design, synthesis and biological evaluation of novel piperazine derivatives as CCR5 antagonists.
Auteurs : Tao Liu [République populaire de Chine] ; Zhiyong Weng ; Xiaowu Dong ; Linjie Chen ; Ling Ma ; Shan Cen ; Naiming Zhou ; Yongzhou HuSource :
- PloS one [ 1932-6203 ] ; 2013.
Descripteurs français
- KwdFr :
- Agents antiVIH (pharmacologie), Agents antiVIH (synthèse chimique), Antagonistes des récepteurs CCR5, Cellules HEK293, Concentration inhibitrice 50, Conception de médicament, Dosage biologique, Expression des gènes, Fusion cellulaire, Gènes rapporteurs, Humains, Luciferases, Pipérazines (pharmacologie), Pipérazines (synthèse chimique), Protéine d'enveloppe gp120 du VIH (génétique), Protéine d'enveloppe gp120 du VIH (métabolisme), Relation structure-activité, Récepteurs CCR5 (métabolisme), Survie cellulaire (), VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (), VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (croissance et développement).
- MESH :
- croissance et développement : VIH-1 (Virus de l'Immunodéficience Humaine de type 1).
- génétique : Protéine d'enveloppe gp120 du VIH.
- métabolisme : Protéine d'enveloppe gp120 du VIH, Récepteurs CCR5.
- pharmacologie : Agents antiVIH, Pipérazines.
- synthèse chimique : Agents antiVIH, Pipérazines.
- Antagonistes des récepteurs CCR5, Cellules HEK293, Concentration inhibitrice 50, Conception de médicament, Dosage biologique, Expression des gènes, Fusion cellulaire, Gènes rapporteurs, Humains, Luciferases, Relation structure-activité, Survie cellulaire, VIH-1 (Virus de l'Immunodéficience Humaine de type 1).
English descriptors
- KwdEn :
- Anti-HIV Agents (chemical synthesis), Anti-HIV Agents (pharmacology), Biological Assay, CCR5 Receptor Antagonists, CD4 Antigens (genetics), CD4 Antigens (metabolism), Cell Fusion, Cell Survival (drug effects), Drug Design, Gene Expression, Genes, Reporter, HEK293 Cells, HIV Envelope Protein gp120 (genetics), HIV Envelope Protein gp120 (metabolism), HIV-1 (drug effects), HIV-1 (growth & development), Humans, Inhibitory Concentration 50, Luciferases, Piperazines (chemical synthesis), Piperazines (pharmacology), Receptors, CCR5 (metabolism), Structure-Activity Relationship.
- MESH :
- chemical , chemical synthesis : Anti-HIV Agents, Piperazines.
- chemical , genetics : CD4 Antigens, HIV Envelope Protein gp120.
- chemical , metabolism : CD4 Antigens, HIV Envelope Protein gp120, Receptors, CCR5.
- chemical , pharmacology : Anti-HIV Agents, Piperazines.
- drug effects : Cell Survival, HIV-1.
- growth & development : HIV-1.
- Biological Assay, CCR5 Receptor Antagonists, Cell Fusion, Drug Design, Gene Expression, Genes, Reporter, HEK293 Cells, Humans, Inhibitory Concentration 50, Luciferases, Structure-Activity Relationship.
Abstract
By using a fragment-assembly strategy and bioisosteric-replacement principle, a series of novel piperazine derivatives were designed, synthesized, and evaluated for their cellular target-effector fusion activities and in vitro antiviral activities against HIV-1. Preliminary structure-activity relationships (SARs) of target compounds were concluded in this study, and five compounds were found to exhibited medium to potent CCR5 fusion activities with IC(50) values in low micromolar level. Among evaluated compounds, 23 h was found to be a CCR5 antagonist with an IC(50) value of 6.29 µM and an anti-HIV-1 inhibitor with an IC(50) value of 0.44 µM.
DOI: 10.1371/journal.pone.0053636
PubMed: 23308267
Affiliations:
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Fusion</term><term>Drug Design</term><term>Gene Expression</term><term>Genes, Reporter</term><term>HEK293 Cells</term><term>Humans</term><term>Inhibitory Concentration 50</term><term>Luciferases</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Antagonistes des récepteurs CCR5</term><term>Cellules HEK293</term><term>Concentration inhibitrice 50</term><term>Conception de médicament</term><term>Dosage biologique</term><term>Expression des gènes</term><term>Fusion cellulaire</term><term>Gènes rapporteurs</term><term>Humains</term><term>Luciferases</term><term>Relation structure-activité</term><term>Survie cellulaire</term><term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">By using a fragment-assembly strategy and bioisosteric-replacement principle, a series of novel piperazine derivatives were designed, synthesized, and evaluated for their cellular target-effector fusion activities and in vitro antiviral activities against HIV-1. Preliminary structure-activity relationships (SARs) of target compounds were concluded in this study, and five compounds were found to exhibited medium to potent CCR5 fusion activities with IC(50) values in low micromolar level. Among evaluated compounds, 23 h was found to be a CCR5 antagonist with an IC(50) value of 6.29 µM and an anti-HIV-1 inhibitor with an IC(50) value of 0.44 µM.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">23308267</PMID><DateCompleted><Year>2013</Year><Month>07</Month><Day>02</Day></DateCompleted><DateRevised><Year>2018</Year><Month>11</Month><Day>13</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1932-6203</ISSN><JournalIssue CitedMedium="Internet"><Volume>8</Volume><Issue>1</Issue><PubDate><Year>2013</Year></PubDate></JournalIssue><Title>PloS one</Title><ISOAbbreviation>PLoS ONE</ISOAbbreviation></Journal><ArticleTitle>Design, synthesis and biological evaluation of novel piperazine derivatives as CCR5 antagonists.</ArticleTitle><Pagination><MedlinePgn>e53636</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1371/journal.pone.0053636</ELocationID><Abstract><AbstractText>By using a fragment-assembly strategy and bioisosteric-replacement principle, a series of novel piperazine derivatives were designed, synthesized, and evaluated for their cellular target-effector fusion activities and in vitro antiviral activities against HIV-1. Preliminary structure-activity relationships (SARs) of target compounds were concluded in this study, and five compounds were found to exhibited medium to potent CCR5 fusion activities with IC(50) values in low micromolar level. Among evaluated compounds, 23 h was found to be a CCR5 antagonist with an IC(50) value of 6.29 µM and an anti-HIV-1 inhibitor with an IC(50) value of 0.44 µM.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Liu</LastName><ForeName>Tao</ForeName><Initials>T</Initials><AffiliationInfo><Affiliation>Zhejiang University-École Normale Supérieure Joint Laboratory of Medicinal Chemistry, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China. 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Antagonists</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D015704" MajorTopicYN="N">CD4 Antigens</DescriptorName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D002459" MajorTopicYN="N">Cell Fusion</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D002470" MajorTopicYN="N">Cell Survival</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015195" MajorTopicYN="N">Drug Design</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D015870" MajorTopicYN="N">Gene Expression</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D017930" MajorTopicYN="N">Genes, Reporter</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D057809" MajorTopicYN="N">HEK293 Cells</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D015699" MajorTopicYN="N">HIV Envelope Protein gp120</DescriptorName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015497" MajorTopicYN="N">HIV-1</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName><QualifierName UI="Q000254" MajorTopicYN="N">growth & development</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D020128" MajorTopicYN="N">Inhibitory Concentration 50</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008156" MajorTopicYN="N">Luciferases</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010879" MajorTopicYN="N">Piperazines</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical 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first="Yongzhou" last="Hu">Yongzhou Hu</name><name sortKey="Ma, Ling" sort="Ma, Ling" uniqKey="Ma L" first="Ling" last="Ma">Ling Ma</name><name sortKey="Weng, Zhiyong" sort="Weng, Zhiyong" uniqKey="Weng Z" first="Zhiyong" last="Weng">Zhiyong Weng</name><name sortKey="Zhou, Naiming" sort="Zhou, Naiming" uniqKey="Zhou N" first="Naiming" last="Zhou">Naiming Zhou</name></noCountry><country name="République populaire de Chine"><region name="Zhejiang"><name sortKey="Liu, Tao" sort="Liu, Tao" uniqKey="Liu T" first="Tao" last="Liu">Tao Liu</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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