SrasV1, Ncbi, Merge, bibRecord, 002F55

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

Identifieur interne : 002F55 ( Ncbi/Merge ); précédent : 002F54; suivant : 002F56

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

Links toward previous steps (curation, corpus...)

to stream PubMed, to step Corpus: 000985
to stream PubMed, to step Curation: 000985
to stream PubMed, to step Checkpoint: 000957

Links to Exploration step

pubmed:30102451

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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 =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.</AbstractText>
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<MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D010456" MajorTopicYN="N">Peptides, Cyclic</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
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<MeshHeading><DescriptorName UI="D060327" MajorTopicYN="N">Solid-Phase Synthesis Techniques</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName>
</MeshHeading>
</MeshHeadingList>
<KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="Y">cyclic peptides</Keyword>
<Keyword MajorTopicYN="Y">macrolactamization</Keyword>
<Keyword MajorTopicYN="Y">proline</Keyword>
<Keyword MajorTopicYN="Y">reniochalistatins</Keyword>
<Keyword MajorTopicYN="Y">solid-phase peptide synthesis</Keyword>
</KeywordList>
</MedlineCitation>
<PubmedData><History><PubMedPubDate PubStatus="received"><Year>2018</Year>
<Month>08</Month>
<Day>06</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="pubmed"><Year>2018</Year>
<Month>8</Month>
<Day>14</Day>
<Hour>6</Hour>
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<PubMedPubDate PubStatus="medline"><Year>2019</Year>
<Month>9</Month>
<Day>17</Day>
<Hour>6</Hour>
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<PubMedPubDate PubStatus="entrez"><Year>2018</Year>
<Month>8</Month>
<Day>14</Day>
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<PublicationStatus>ppublish</PublicationStatus>
<ArticleIdList><ArticleId IdType="pubmed">30102451</ArticleId>
<ArticleId IdType="doi">10.1002/cmdc.201800529</ArticleId>
</ArticleIdList>
</PubmedData>
</pubmed>
<affiliations><list><country><li>République populaire de Chine</li>
</country>
</list>
<tree><country name="République populaire de Chine"><noRegion><name sortKey="Zhou, Rong" sort="Zhou, Rong" uniqKey="Zhou R" first="Rong" last="Zhou">Rong Zhou</name>
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<name sortKey="Feng, Pengju" sort="Feng, Pengju" uniqKey="Feng P" first="Pengju" last="Feng">Pengju Feng</name>
<name sortKey="Li, Hangbin" sort="Li, Hangbin" uniqKey="Li H" first="Hangbin" last="Li">Hangbin Li</name>
<name sortKey="Liao, Xiaojian" sort="Liao, Xiaojian" uniqKey="Liao X" first="Xiaojian" last="Liao">Xiaojian Liao</name>
<name sortKey="Long, Weili" sort="Long, Weili" uniqKey="Long W" first="Weili" last="Long">Weili Long</name>
<name sortKey="Sun, Yueguang" sort="Sun, Yueguang" uniqKey="Sun Y" first="Yueguang" last="Sun">Yueguang Sun</name>
<name sortKey="Xu, Shihai" sort="Xu, Shihai" uniqKey="Xu S" first="Shihai" last="Xu">Shihai Xu</name>
</country>
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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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