Loading…
Trichormamides C and D, antiproliferative cyclic lipopeptides from the cultured freshwater cyanobacterium cf. Oscillatoria sp. UIC 10045
[Display omitted] Extract from the cultured freshwater cf. Oscillatoria sp. UIC 10045 showed antiproliferative activity against HT-29 cell line. Bioassay-guided fractionation led to the isolation of two new cyclic lipopeptides, named trichormamides C (1) and D (2). The planar structures were determi...
Saved in:
Published in: | Bioorganic & medicinal chemistry 2015-07, Vol.23 (13), p.3153-3162 |
---|---|
Main Authors: | , , , , , , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
cited_by | cdi_FETCH-LOGICAL-c521t-1a7951dde4b83d6c8df126a6a8eae7ebbd43bf399f77c85881054744ef8f90563 |
---|---|
cites | cdi_FETCH-LOGICAL-c521t-1a7951dde4b83d6c8df126a6a8eae7ebbd43bf399f77c85881054744ef8f90563 |
container_end_page | 3162 |
container_issue | 13 |
container_start_page | 3153 |
container_title | Bioorganic & medicinal chemistry |
container_volume | 23 |
creator | Luo, Shangwen Kang, Hahk-Soo Krunic, Aleksej Chen, Wei-Lun Yang, Jilai Woodard, John L. Fuchs, James R. Hyun Cho, Sang Franzblau, Scott G. Swanson, Steven M. Orjala, Jimmy |
description | [Display omitted]
Extract from the cultured freshwater cf. Oscillatoria sp. UIC 10045 showed antiproliferative activity against HT-29 cell line. Bioassay-guided fractionation led to the isolation of two new cyclic lipopeptides, named trichormamides C (1) and D (2). The planar structures were determined by combined analyses of HRESIMS, Q-TOF ESIMS/MS, and 1D and 2D NMR spectra. The absolute configurations of the amino acid residues were assigned by advanced Marfey’s analysis after partial and complete acid hydrolysis. Trichormamides C (1) is a cyclic undecapeptide and D (2) is a cyclic dodecapeptide, both containing a lipophilic β-aminodecanoic acid residue. Trichormamide C (1) displayed antiproliferative activities against HT-29 and MDA-MB-435 cancer cell lines with IC50 values of 1.7 and 1.0μM, respectively, as well as anti-Mycobacterium tuberculosis activity with MIC value of 23.8μg/mL (17.3μM). Trichormamide D (2) was found to be less potent against both HT-29 and MDA-MB-435 cancer cell lines with IC50 values of 11.5 and 11.7μM, respectively. |
doi_str_mv | 10.1016/j.bmc.2015.04.073 |
format | article |
fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_4469202</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0968089615003818</els_id><sourcerecordid>1686995250</sourcerecordid><originalsourceid>FETCH-LOGICAL-c521t-1a7951dde4b83d6c8df126a6a8eae7ebbd43bf399f77c85881054744ef8f90563</originalsourceid><addsrcrecordid>eNp9kc9u1DAQxi0EokvhAbggHzmwYZw4TiwkJLT8q1Spl_ZsOfaY9SqJg-0s6hvw2LhsqeDCaSzP931jz4-QlwwqBky8PVTDZKoaWFsBr6BrHpEN44Jvm0ayx2QDUvRb6KU4I89SOgBAzSV7Ss5qAcAaXm_Iz-vozT7ESU_eYqI7qmdLP74pJfslhtE7jDr7I1Jza0Zv6OiXsOCSf8tdDBPN-9Jcx7xGtOUG0_6HzhiLQc9h0Kac_TpR4yp6lYwfR51D9JqmpaI3FzvKAHj7nDxxekz44r6ek5vPn653X7eXV18udh8ut6atWd4y3cmWWYt86BsrTG8dq4UWukeNHQ6D5c3gGild15m-7XsGLe84R9c7Ca1ozsn7U-6yDhNag3OOelRL9JOOtypor_7tzH6vvoWj4lzIGuoS8Po-IIbvK6asJp8Mll_NGNakmOiFlG3dQpGyk9TEkFJE9zCGgbojqA6qEFR3BBVwVQgWz6u_3_fg-IOsCN6dBFi2dPQYVdkpzgatj2iyssH_J_4XbO2uow</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1686995250</pqid></control><display><type>article</type><title>Trichormamides C and D, antiproliferative cyclic lipopeptides from the cultured freshwater cyanobacterium cf. Oscillatoria sp. UIC 10045</title><source>Elsevier</source><creator>Luo, Shangwen ; Kang, Hahk-Soo ; Krunic, Aleksej ; Chen, Wei-Lun ; Yang, Jilai ; Woodard, John L. ; Fuchs, James R. ; Hyun Cho, Sang ; Franzblau, Scott G. ; Swanson, Steven M. ; Orjala, Jimmy</creator><creatorcontrib>Luo, Shangwen ; Kang, Hahk-Soo ; Krunic, Aleksej ; Chen, Wei-Lun ; Yang, Jilai ; Woodard, John L. ; Fuchs, James R. ; Hyun Cho, Sang ; Franzblau, Scott G. ; Swanson, Steven M. ; Orjala, Jimmy</creatorcontrib><description>[Display omitted]
Extract from the cultured freshwater cf. Oscillatoria sp. UIC 10045 showed antiproliferative activity against HT-29 cell line. Bioassay-guided fractionation led to the isolation of two new cyclic lipopeptides, named trichormamides C (1) and D (2). The planar structures were determined by combined analyses of HRESIMS, Q-TOF ESIMS/MS, and 1D and 2D NMR spectra. The absolute configurations of the amino acid residues were assigned by advanced Marfey’s analysis after partial and complete acid hydrolysis. Trichormamides C (1) is a cyclic undecapeptide and D (2) is a cyclic dodecapeptide, both containing a lipophilic β-aminodecanoic acid residue. Trichormamide C (1) displayed antiproliferative activities against HT-29 and MDA-MB-435 cancer cell lines with IC50 values of 1.7 and 1.0μM, respectively, as well as anti-Mycobacterium tuberculosis activity with MIC value of 23.8μg/mL (17.3μM). Trichormamide D (2) was found to be less potent against both HT-29 and MDA-MB-435 cancer cell lines with IC50 values of 11.5 and 11.7μM, respectively.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2015.04.073</identifier><identifier>PMID: 26001342</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - isolation & purification ; Anti-Bacterial Agents - pharmacology ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - isolation & purification ; Antineoplastic Agents - pharmacology ; Antiproliferative activity ; Cell Line, Tumor ; Cell Survival - drug effects ; cf. Oscillatoria sp ; Cyanobacteria ; Cyanobacteria - chemistry ; Cyclic lipopeptides ; Drug Design ; Drug Screening Assays, Antitumor ; HT-29 ; HT29 Cells ; Humans ; Inhibitory Concentration 50 ; Lipopeptides - chemistry ; Lipopeptides - isolation & purification ; Lipopeptides - pharmacology ; MDA-MB-435 ; Microbial Sensitivity Tests ; Mycobacterium tuberculosis - drug effects ; Mycobacterium tuberculosis - growth & development ; Peptides, Cyclic - chemistry ; Peptides, Cyclic - isolation & purification ; Peptides, Cyclic - pharmacology ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry, 2015-07, Vol.23 (13), p.3153-3162</ispartof><rights>2015 Elsevier Ltd</rights><rights>Copyright © 2015 Elsevier Ltd. All rights reserved.</rights><rights>2015 Published by Elsevier Ltd. 2015</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c521t-1a7951dde4b83d6c8df126a6a8eae7ebbd43bf399f77c85881054744ef8f90563</citedby><cites>FETCH-LOGICAL-c521t-1a7951dde4b83d6c8df126a6a8eae7ebbd43bf399f77c85881054744ef8f90563</cites><orcidid>0000-0002-4420-2048</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,778,782,883,27907,27908</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26001342$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Luo, Shangwen</creatorcontrib><creatorcontrib>Kang, Hahk-Soo</creatorcontrib><creatorcontrib>Krunic, Aleksej</creatorcontrib><creatorcontrib>Chen, Wei-Lun</creatorcontrib><creatorcontrib>Yang, Jilai</creatorcontrib><creatorcontrib>Woodard, John L.</creatorcontrib><creatorcontrib>Fuchs, James R.</creatorcontrib><creatorcontrib>Hyun Cho, Sang</creatorcontrib><creatorcontrib>Franzblau, Scott G.</creatorcontrib><creatorcontrib>Swanson, Steven M.</creatorcontrib><creatorcontrib>Orjala, Jimmy</creatorcontrib><title>Trichormamides C and D, antiproliferative cyclic lipopeptides from the cultured freshwater cyanobacterium cf. Oscillatoria sp. UIC 10045</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>[Display omitted]
Extract from the cultured freshwater cf. Oscillatoria sp. UIC 10045 showed antiproliferative activity against HT-29 cell line. Bioassay-guided fractionation led to the isolation of two new cyclic lipopeptides, named trichormamides C (1) and D (2). The planar structures were determined by combined analyses of HRESIMS, Q-TOF ESIMS/MS, and 1D and 2D NMR spectra. The absolute configurations of the amino acid residues were assigned by advanced Marfey’s analysis after partial and complete acid hydrolysis. Trichormamides C (1) is a cyclic undecapeptide and D (2) is a cyclic dodecapeptide, both containing a lipophilic β-aminodecanoic acid residue. Trichormamide C (1) displayed antiproliferative activities against HT-29 and MDA-MB-435 cancer cell lines with IC50 values of 1.7 and 1.0μM, respectively, as well as anti-Mycobacterium tuberculosis activity with MIC value of 23.8μg/mL (17.3μM). Trichormamide D (2) was found to be less potent against both HT-29 and MDA-MB-435 cancer cell lines with IC50 values of 11.5 and 11.7μM, respectively.</description><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - isolation & purification</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - isolation & purification</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antiproliferative activity</subject><subject>Cell Line, Tumor</subject><subject>Cell Survival - drug effects</subject><subject>cf. Oscillatoria sp</subject><subject>Cyanobacteria</subject><subject>Cyanobacteria - chemistry</subject><subject>Cyclic lipopeptides</subject><subject>Drug Design</subject><subject>Drug Screening Assays, Antitumor</subject><subject>HT-29</subject><subject>HT29 Cells</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Lipopeptides - chemistry</subject><subject>Lipopeptides - isolation & purification</subject><subject>Lipopeptides - pharmacology</subject><subject>MDA-MB-435</subject><subject>Microbial Sensitivity Tests</subject><subject>Mycobacterium tuberculosis - drug effects</subject><subject>Mycobacterium tuberculosis - growth & development</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Peptides, Cyclic - isolation & purification</subject><subject>Peptides, Cyclic - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNp9kc9u1DAQxi0EokvhAbggHzmwYZw4TiwkJLT8q1Spl_ZsOfaY9SqJg-0s6hvw2LhsqeDCaSzP931jz4-QlwwqBky8PVTDZKoaWFsBr6BrHpEN44Jvm0ayx2QDUvRb6KU4I89SOgBAzSV7Ss5qAcAaXm_Iz-vozT7ESU_eYqI7qmdLP74pJfslhtE7jDr7I1Jza0Zv6OiXsOCSf8tdDBPN-9Jcx7xGtOUG0_6HzhiLQc9h0Kac_TpR4yp6lYwfR51D9JqmpaI3FzvKAHj7nDxxekz44r6ek5vPn653X7eXV18udh8ut6atWd4y3cmWWYt86BsrTG8dq4UWukeNHQ6D5c3gGild15m-7XsGLe84R9c7Ca1ozsn7U-6yDhNag3OOelRL9JOOtypor_7tzH6vvoWj4lzIGuoS8Po-IIbvK6asJp8Mll_NGNakmOiFlG3dQpGyk9TEkFJE9zCGgbojqA6qEFR3BBVwVQgWz6u_3_fg-IOsCN6dBFi2dPQYVdkpzgatj2iyssH_J_4XbO2uow</recordid><startdate>20150701</startdate><enddate>20150701</enddate><creator>Luo, Shangwen</creator><creator>Kang, Hahk-Soo</creator><creator>Krunic, Aleksej</creator><creator>Chen, Wei-Lun</creator><creator>Yang, Jilai</creator><creator>Woodard, John L.</creator><creator>Fuchs, James R.</creator><creator>Hyun Cho, Sang</creator><creator>Franzblau, Scott G.</creator><creator>Swanson, Steven M.</creator><creator>Orjala, Jimmy</creator><general>Elsevier Ltd</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-4420-2048</orcidid></search><sort><creationdate>20150701</creationdate><title>Trichormamides C and D, antiproliferative cyclic lipopeptides from the cultured freshwater cyanobacterium cf. Oscillatoria sp. UIC 10045</title><author>Luo, Shangwen ; Kang, Hahk-Soo ; Krunic, Aleksej ; Chen, Wei-Lun ; Yang, Jilai ; Woodard, John L. ; Fuchs, James R. ; Hyun Cho, Sang ; Franzblau, Scott G. ; Swanson, Steven M. ; Orjala, Jimmy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c521t-1a7951dde4b83d6c8df126a6a8eae7ebbd43bf399f77c85881054744ef8f90563</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - isolation & purification</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - isolation & purification</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Antiproliferative activity</topic><topic>Cell Line, Tumor</topic><topic>Cell Survival - drug effects</topic><topic>cf. Oscillatoria sp</topic><topic>Cyanobacteria</topic><topic>Cyanobacteria - chemistry</topic><topic>Cyclic lipopeptides</topic><topic>Drug Design</topic><topic>Drug Screening Assays, Antitumor</topic><topic>HT-29</topic><topic>HT29 Cells</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>Lipopeptides - chemistry</topic><topic>Lipopeptides - isolation & purification</topic><topic>Lipopeptides - pharmacology</topic><topic>MDA-MB-435</topic><topic>Microbial Sensitivity Tests</topic><topic>Mycobacterium tuberculosis - drug effects</topic><topic>Mycobacterium tuberculosis - growth & development</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Peptides, Cyclic - isolation & purification</topic><topic>Peptides, Cyclic - pharmacology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Luo, Shangwen</creatorcontrib><creatorcontrib>Kang, Hahk-Soo</creatorcontrib><creatorcontrib>Krunic, Aleksej</creatorcontrib><creatorcontrib>Chen, Wei-Lun</creatorcontrib><creatorcontrib>Yang, Jilai</creatorcontrib><creatorcontrib>Woodard, John L.</creatorcontrib><creatorcontrib>Fuchs, James R.</creatorcontrib><creatorcontrib>Hyun Cho, Sang</creatorcontrib><creatorcontrib>Franzblau, Scott G.</creatorcontrib><creatorcontrib>Swanson, Steven M.</creatorcontrib><creatorcontrib>Orjala, Jimmy</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Luo, Shangwen</au><au>Kang, Hahk-Soo</au><au>Krunic, Aleksej</au><au>Chen, Wei-Lun</au><au>Yang, Jilai</au><au>Woodard, John L.</au><au>Fuchs, James R.</au><au>Hyun Cho, Sang</au><au>Franzblau, Scott G.</au><au>Swanson, Steven M.</au><au>Orjala, Jimmy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Trichormamides C and D, antiproliferative cyclic lipopeptides from the cultured freshwater cyanobacterium cf. Oscillatoria sp. UIC 10045</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2015-07-01</date><risdate>2015</risdate><volume>23</volume><issue>13</issue><spage>3153</spage><epage>3162</epage><pages>3153-3162</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>[Display omitted]
Extract from the cultured freshwater cf. Oscillatoria sp. UIC 10045 showed antiproliferative activity against HT-29 cell line. Bioassay-guided fractionation led to the isolation of two new cyclic lipopeptides, named trichormamides C (1) and D (2). The planar structures were determined by combined analyses of HRESIMS, Q-TOF ESIMS/MS, and 1D and 2D NMR spectra. The absolute configurations of the amino acid residues were assigned by advanced Marfey’s analysis after partial and complete acid hydrolysis. Trichormamides C (1) is a cyclic undecapeptide and D (2) is a cyclic dodecapeptide, both containing a lipophilic β-aminodecanoic acid residue. Trichormamide C (1) displayed antiproliferative activities against HT-29 and MDA-MB-435 cancer cell lines with IC50 values of 1.7 and 1.0μM, respectively, as well as anti-Mycobacterium tuberculosis activity with MIC value of 23.8μg/mL (17.3μM). Trichormamide D (2) was found to be less potent against both HT-29 and MDA-MB-435 cancer cell lines with IC50 values of 11.5 and 11.7μM, respectively.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>26001342</pmid><doi>10.1016/j.bmc.2015.04.073</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-4420-2048</orcidid><oa>free_for_read</oa></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0968-0896 |
ispartof | Bioorganic & medicinal chemistry, 2015-07, Vol.23 (13), p.3153-3162 |
issn | 0968-0896 1464-3391 |
language | eng |
recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_4469202 |
source | Elsevier |
subjects | Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - isolation & purification Anti-Bacterial Agents - pharmacology Antineoplastic Agents - chemistry Antineoplastic Agents - isolation & purification Antineoplastic Agents - pharmacology Antiproliferative activity Cell Line, Tumor Cell Survival - drug effects cf. Oscillatoria sp Cyanobacteria Cyanobacteria - chemistry Cyclic lipopeptides Drug Design Drug Screening Assays, Antitumor HT-29 HT29 Cells Humans Inhibitory Concentration 50 Lipopeptides - chemistry Lipopeptides - isolation & purification Lipopeptides - pharmacology MDA-MB-435 Microbial Sensitivity Tests Mycobacterium tuberculosis - drug effects Mycobacterium tuberculosis - growth & development Peptides, Cyclic - chemistry Peptides, Cyclic - isolation & purification Peptides, Cyclic - pharmacology Structure-Activity Relationship |
title | Trichormamides C and D, antiproliferative cyclic lipopeptides from the cultured freshwater cyanobacterium cf. Oscillatoria sp. UIC 10045 |
url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-16T15%3A21%3A41IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Trichormamides%20C%20and%20D,%20antiproliferative%20cyclic%20lipopeptides%20from%20the%20cultured%20freshwater%20cyanobacterium%20cf.%20Oscillatoria%20sp.%20UIC%2010045&rft.jtitle=Bioorganic%20&%20medicinal%20chemistry&rft.au=Luo,%20Shangwen&rft.date=2015-07-01&rft.volume=23&rft.issue=13&rft.spage=3153&rft.epage=3162&rft.pages=3153-3162&rft.issn=0968-0896&rft.eissn=1464-3391&rft_id=info:doi/10.1016/j.bmc.2015.04.073&rft_dat=%3Cproquest_pubme%3E1686995250%3C/proquest_pubme%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c521t-1a7951dde4b83d6c8df126a6a8eae7ebbd43bf399f77c85881054744ef8f90563%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1686995250&rft_id=info:pmid/26001342&rfr_iscdi=true |