SrasV1, Main, Exploration, bibRecord, 000C28

Synthesis and Biological Evaluation of Reniochalistatins A-E and a Reniochalistatin E Analogue.

Identifieur interne : 000C28 ( Main/Exploration ); précédent : 000C27; suivant : 000C29

Synthesis 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.

RBID : pubmed:30102451

Descripteurs français

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:

République populaire de Chine

Le document en format XML

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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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Synthesis and Biological Evaluation of Reniochalistatins A-E and a Reniochalistatin E Analogue.

Synthesis and Biological Evaluation of Reniochalistatins A-E and a Reniochalistatin E Analogue.

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Descripteurs français

English descriptors

Abstract

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Le document en format XML

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