Synthesis and Biological Evaluation of Reniochalistatins A-E and a Reniochalistatin E Analogue.
Identifieur interne : 002F55 ( Ncbi/Checkpoint ); précédent : 002F54; suivant : 002F56Synthesis and Biological Evaluation of Reniochalistatins A-E and a Reniochalistatin E Analogue.
Auteurs : Rong Zhou [République populaire de Chine] ; Yueguang Sun [République populaire de Chine] ; Hangbin Li [République populaire de Chine] ; Weili Long [République populaire de Chine] ; Xiaojian Liao [République populaire de Chine] ; Pengju Feng [République populaire de Chine] ; Shihai Xu [République populaire de Chine]Source :
- ChemMedChem [ 1860-7187 ] ; 2018.
Descripteurs français
- KwdFr :
- Animaux, Anti-infectieux (), Anti-infectieux (pharmacologie), Anti-infectieux (synthèse chimique), Anti-inflammatoires (), Anti-inflammatoires (pharmacologie), Anti-inflammatoires (synthèse chimique), Antinéoplasiques (), Antinéoplasiques (pharmacologie), Antinéoplasiques (synthèse chimique), Cyclisation, Cyclooxygenase 1 (métabolisme), Cyclooxygenase 2 (métabolisme), Humains, Lignée cellulaire tumorale, Peptides cycliques (), Peptides cycliques (pharmacologie), Peptides cycliques (synthèse chimique), Porifera (), Relation structure-activité, Sous-type H3N2 du virus de la grippe A (), Structure moléculaire, Techniques de synthèse en phase solide.
- MESH :
- métabolisme : Cyclooxygenase 1, Cyclooxygenase 2.
- pharmacologie : Anti-infectieux, Anti-inflammatoires, Antinéoplasiques, Peptides cycliques.
- synthèse chimique : Anti-infectieux, Anti-inflammatoires, Antinéoplasiques, Peptides cycliques.
- Animaux, Anti-infectieux, Anti-inflammatoires, Antinéoplasiques, Cyclisation, Humains, Lignée cellulaire tumorale, Peptides cycliques, Porifera, Relation structure-activité, Sous-type H3N2 du virus de la grippe A, Structure moléculaire, Techniques de synthèse en phase solide.
English descriptors
- KwdEn :
- Animals, Anti-Infective Agents (chemical synthesis), Anti-Infective Agents (chemistry), Anti-Infective Agents (pharmacology), Anti-Inflammatory Agents (chemical synthesis), Anti-Inflammatory Agents (chemistry), Anti-Inflammatory Agents (pharmacology), Antineoplastic Agents (chemical synthesis), Antineoplastic Agents (chemistry), Antineoplastic Agents (pharmacology), Cell Line, Tumor, Cyclization, Cyclooxygenase 1 (metabolism), Cyclooxygenase 2 (metabolism), Humans, Influenza A Virus, H3N2 Subtype (drug effects), Molecular Structure, Peptides, Cyclic (chemical synthesis), Peptides, Cyclic (chemistry), Peptides, Cyclic (pharmacology), Porifera (chemistry), Solid-Phase Synthesis Techniques, Structure-Activity Relationship.
- MESH :
- chemical , chemical synthesis : Anti-Infective Agents, Anti-Inflammatory Agents, Antineoplastic Agents, Peptides, Cyclic.
- chemical , chemistry : Anti-Infective Agents, Anti-Inflammatory Agents, Antineoplastic Agents, Peptides, Cyclic.
- chemical , metabolism : Cyclooxygenase 1, Cyclooxygenase 2.
- chemical , pharmacology : Anti-Infective Agents, Anti-Inflammatory Agents, Antineoplastic Agents, Peptides, Cyclic.
- chemistry : Porifera.
- drug effects : Influenza A Virus, H3N2 Subtype.
- Animals, Cell Line, Tumor, Cyclization, Humans, Molecular Structure, Solid-Phase Synthesis Techniques, Structure-Activity Relationship.
Abstract
The total synthesis of reniochalistatins A-E, along with a reniochalistatin E analogue (inverso-E) was successfully achieved through Fmoc-based solid-phase peptide synthesis and subsequent macrolactamization with PyBOP and DIEA. The biological activities of these reniochalistatins and a key linear peptide intermediate were systematically evaluated. Among these seven synthesized compounds, linear reniochalistatin B was found to have potent activity against several cancer cell lines not shown by the cyclic reniochalistatin B counterpart. In addition, linear reniochalistatin B was found to have antitubercular activity (IC50 =1.4 μm). Inverso-E possesses increasing cytotoxicity against the HeLa and LNCaP cell lines after simple alternation of the sequence of amino acids in reniochalistatin E. The results of these studies provide a feasible method to further investigate the structure-activity relationships (SARs) of reniochalistatins A-E.
DOI: 10.1002/cmdc.201800529
PubMed: 30102451
Affiliations:
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<front><div type="abstract" xml:lang="en">The total synthesis of reniochalistatins A-E, along with a reniochalistatin E analogue (inverso-E) was successfully achieved through Fmoc-based solid-phase peptide synthesis and subsequent macrolactamization with PyBOP and DIEA. The biological activities of these reniochalistatins and a key linear peptide intermediate were systematically evaluated. Among these seven synthesized compounds, linear reniochalistatin B was found to have potent activity against several cancer cell lines not shown by the cyclic reniochalistatin B counterpart. In addition, linear reniochalistatin B was found to have antitubercular activity (IC<sub>50</sub>
=1.4 μm). Inverso-E possesses increasing cytotoxicity against the HeLa and LNCaP cell lines after simple alternation of the sequence of amino acids in reniochalistatin E. The results of these studies provide a feasible method to further investigate the structure-activity relationships (SARs) of reniochalistatins A-E.</div>
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<name sortKey="Xu, Shihai" sort="Xu, Shihai" uniqKey="Xu S" first="Shihai" last="Xu">Shihai Xu</name>
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