Loading…
In vitro and in vivo evaluation of select kahalalide F analogs with antitumor and antifungal activities
Kahalalide F (KF) and the regioisomer isoKF are novel anticancer drugs of marine origin and currently under clinical investigation. Here we report the synthesis of two new KF analogs with significant in vitro and in vivo antifungal and antitumor activities. The primary amine hydrogen of ornithine in...
Saved in:
| Published in: | Bioorganic & medicinal chemistry 2011-11, Vol.19 (22), p.6628-6632 |
|---|---|
| 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-c506t-35885971033b06c5b671078655d3e677f97e794392928e504ae580c51a77be433 |
|---|---|
| cites | cdi_FETCH-LOGICAL-c506t-35885971033b06c5b671078655d3e677f97e794392928e504ae580c51a77be433 |
| container_end_page | 6632 |
| container_issue | 22 |
| container_start_page | 6628 |
| container_title | Bioorganic & medicinal chemistry |
| container_volume | 19 |
| creator | Shilabin, Abbas Gholipour Hamann, Mark T. |
| description | Kahalalide F (KF) and the regioisomer isoKF are novel anticancer drugs of marine origin and currently under clinical investigation. Here we report the synthesis of two new KF analogs with significant in vitro and in vivo antifungal and antitumor activities. The primary amine hydrogen of ornithine in KF has been replaced with 4-fluoro-3-methylbenzyl and morpholin-4-yl-benzyl via reductive N-alkylation. The TGI of these analogs using the NCI-60 cell line screening revealed promising results when compared to paclitaxel. The result of in vivo hollow fiber and animal toxicity assays are presented. |
| doi_str_mv | 10.1016/j.bmc.2011.06.050 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_3523750</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0968089611004901</els_id><sourcerecordid>904493972</sourcerecordid><originalsourceid>FETCH-LOGICAL-c506t-35885971033b06c5b671078655d3e677f97e794392928e504ae580c51a77be433</originalsourceid><addsrcrecordid>eNp9kc1u1DAURiMEokPhAdhAdqwSruOfxEJCQhWFSpVYQNeW49xkPDhxsZ0g3h5Pp1SwYWV_8vHxlb-ieEmgJkDE20Pdz6ZugJAaRA0cHhU7wgSrKJXkcbEDKboKOinOimcxHgCgYZI8Lc4a0lEpGOyK6WopN5uCL_UylPYYNl_ipt2qk_VL6ccyokOTyu96r512dsDyMtPa-SmWP23a55BsWmcf7iTHNK7LpF2pTbLZbjE-L56M2kV8cb-eFzeXH79dfK6uv3y6uvhwXRkOIlWUdx2XLQFKexCG9yLv205wPlAUbTvKFlvJqGxk0yEHppF3YDjRbdsjo_S8eH_y3q79jIPBJQXt1G2wsw6_lNdW_Xuy2L2a_KYob2jLIQve3AuC_7FiTGq20aBzekG_RiWBMUll22SSnEgTfIwBx4dXCKhjP-qgcj_q2I8CoeDO_urv8R5u_CkkA69PwKi90lOwUd18zQYOQEB2lGXi3YnA_I2bxaCisbgYHGzINanB2_8M8BuD_apF</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>904493972</pqid></control><display><type>article</type><title>In vitro and in vivo evaluation of select kahalalide F analogs with antitumor and antifungal activities</title><source>ScienceDirect Journals</source><creator>Shilabin, Abbas Gholipour ; Hamann, Mark T.</creator><creatorcontrib>Shilabin, Abbas Gholipour ; Hamann, Mark T.</creatorcontrib><description>Kahalalide F (KF) and the regioisomer isoKF are novel anticancer drugs of marine origin and currently under clinical investigation. Here we report the synthesis of two new KF analogs with significant in vitro and in vivo antifungal and antitumor activities. The primary amine hydrogen of ornithine in KF has been replaced with 4-fluoro-3-methylbenzyl and morpholin-4-yl-benzyl via reductive N-alkylation. The TGI of these analogs using the NCI-60 cell line screening revealed promising results when compared to paclitaxel. The result of in vivo hollow fiber and animal toxicity assays are presented.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2011.06.050</identifier><identifier>PMID: 21839640</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>amines ; animal fibers ; Animals ; Anti-cancer ; Anti-infective ; anticarcinogenic activity ; Antifungal activity ; Antifungal Agents - chemistry ; Antifungal Agents - pharmacology ; antifungal properties ; antineoplastic agents ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Antitumor activity ; Antitumor agents ; chemistry ; Depsipeptides - chemistry ; Depsipeptides - pharmacology ; Drug Screening Assays, Antitumor ; Fibers ; Humans ; Hydrogen ; in vivo studies ; Kahalalide F ; Marine natural products ; Mice ; Mice, Nude ; Microbial Sensitivity Tests ; ornithine ; Paclitaxel ; screening ; Structure-Activity Relationship ; Toxicity</subject><ispartof>Bioorganic & medicinal chemistry, 2011-11, Vol.19 (22), p.6628-6632</ispartof><rights>2011 Elsevier Ltd</rights><rights>Copyright © 2011 Elsevier Ltd. All rights reserved.</rights><rights>2011 Elsevier Ltd. All rights reserved. 2011</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c506t-35885971033b06c5b671078655d3e677f97e794392928e504ae580c51a77be433</citedby><cites>FETCH-LOGICAL-c506t-35885971033b06c5b671078655d3e677f97e794392928e504ae580c51a77be433</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,776,780,881,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21839640$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shilabin, Abbas Gholipour</creatorcontrib><creatorcontrib>Hamann, Mark T.</creatorcontrib><title>In vitro and in vivo evaluation of select kahalalide F analogs with antitumor and antifungal activities</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>Kahalalide F (KF) and the regioisomer isoKF are novel anticancer drugs of marine origin and currently under clinical investigation. Here we report the synthesis of two new KF analogs with significant in vitro and in vivo antifungal and antitumor activities. The primary amine hydrogen of ornithine in KF has been replaced with 4-fluoro-3-methylbenzyl and morpholin-4-yl-benzyl via reductive N-alkylation. The TGI of these analogs using the NCI-60 cell line screening revealed promising results when compared to paclitaxel. The result of in vivo hollow fiber and animal toxicity assays are presented.</description><subject>amines</subject><subject>animal fibers</subject><subject>Animals</subject><subject>Anti-cancer</subject><subject>Anti-infective</subject><subject>anticarcinogenic activity</subject><subject>Antifungal activity</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - pharmacology</subject><subject>antifungal properties</subject><subject>antineoplastic agents</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antitumor activity</subject><subject>Antitumor agents</subject><subject>chemistry</subject><subject>Depsipeptides - chemistry</subject><subject>Depsipeptides - pharmacology</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Fibers</subject><subject>Humans</subject><subject>Hydrogen</subject><subject>in vivo studies</subject><subject>Kahalalide F</subject><subject>Marine natural products</subject><subject>Mice</subject><subject>Mice, Nude</subject><subject>Microbial Sensitivity Tests</subject><subject>ornithine</subject><subject>Paclitaxel</subject><subject>screening</subject><subject>Structure-Activity Relationship</subject><subject>Toxicity</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNp9kc1u1DAURiMEokPhAdhAdqwSruOfxEJCQhWFSpVYQNeW49xkPDhxsZ0g3h5Pp1SwYWV_8vHxlb-ieEmgJkDE20Pdz6ZugJAaRA0cHhU7wgSrKJXkcbEDKboKOinOimcxHgCgYZI8Lc4a0lEpGOyK6WopN5uCL_UylPYYNl_ipt2qk_VL6ccyokOTyu96r512dsDyMtPa-SmWP23a55BsWmcf7iTHNK7LpF2pTbLZbjE-L56M2kV8cb-eFzeXH79dfK6uv3y6uvhwXRkOIlWUdx2XLQFKexCG9yLv205wPlAUbTvKFlvJqGxk0yEHppF3YDjRbdsjo_S8eH_y3q79jIPBJQXt1G2wsw6_lNdW_Xuy2L2a_KYob2jLIQve3AuC_7FiTGq20aBzekG_RiWBMUll22SSnEgTfIwBx4dXCKhjP-qgcj_q2I8CoeDO_urv8R5u_CkkA69PwKi90lOwUd18zQYOQEB2lGXi3YnA_I2bxaCisbgYHGzINanB2_8M8BuD_apF</recordid><startdate>20111115</startdate><enddate>20111115</enddate><creator>Shilabin, Abbas Gholipour</creator><creator>Hamann, Mark T.</creator><general>Elsevier Ltd</general><scope>FBQ</scope><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>7QO</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>M7N</scope><scope>P64</scope><scope>5PM</scope></search><sort><creationdate>20111115</creationdate><title>In vitro and in vivo evaluation of select kahalalide F analogs with antitumor and antifungal activities</title><author>Shilabin, Abbas Gholipour ; Hamann, Mark T.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c506t-35885971033b06c5b671078655d3e677f97e794392928e504ae580c51a77be433</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>amines</topic><topic>animal fibers</topic><topic>Animals</topic><topic>Anti-cancer</topic><topic>Anti-infective</topic><topic>anticarcinogenic activity</topic><topic>Antifungal activity</topic><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - pharmacology</topic><topic>antifungal properties</topic><topic>antineoplastic agents</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Antitumor activity</topic><topic>Antitumor agents</topic><topic>chemistry</topic><topic>Depsipeptides - chemistry</topic><topic>Depsipeptides - pharmacology</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Fibers</topic><topic>Humans</topic><topic>Hydrogen</topic><topic>in vivo studies</topic><topic>Kahalalide F</topic><topic>Marine natural products</topic><topic>Mice</topic><topic>Mice, Nude</topic><topic>Microbial Sensitivity Tests</topic><topic>ornithine</topic><topic>Paclitaxel</topic><topic>screening</topic><topic>Structure-Activity Relationship</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shilabin, Abbas Gholipour</creatorcontrib><creatorcontrib>Hamann, Mark T.</creatorcontrib><collection>AGRIS</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</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>Shilabin, Abbas Gholipour</au><au>Hamann, Mark T.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>In vitro and in vivo evaluation of select kahalalide F analogs with antitumor and antifungal activities</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2011-11-15</date><risdate>2011</risdate><volume>19</volume><issue>22</issue><spage>6628</spage><epage>6632</epage><pages>6628-6632</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>Kahalalide F (KF) and the regioisomer isoKF are novel anticancer drugs of marine origin and currently under clinical investigation. Here we report the synthesis of two new KF analogs with significant in vitro and in vivo antifungal and antitumor activities. The primary amine hydrogen of ornithine in KF has been replaced with 4-fluoro-3-methylbenzyl and morpholin-4-yl-benzyl via reductive N-alkylation. The TGI of these analogs using the NCI-60 cell line screening revealed promising results when compared to paclitaxel. The result of in vivo hollow fiber and animal toxicity assays are presented.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>21839640</pmid><doi>10.1016/j.bmc.2011.06.050</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 2011-11, Vol.19 (22), p.6628-6632 |
| issn | 0968-0896 1464-3391 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_3523750 |
| source | ScienceDirect Journals |
| subjects | amines animal fibers Animals Anti-cancer Anti-infective anticarcinogenic activity Antifungal activity Antifungal Agents - chemistry Antifungal Agents - pharmacology antifungal properties antineoplastic agents Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Antitumor activity Antitumor agents chemistry Depsipeptides - chemistry Depsipeptides - pharmacology Drug Screening Assays, Antitumor Fibers Humans Hydrogen in vivo studies Kahalalide F Marine natural products Mice Mice, Nude Microbial Sensitivity Tests ornithine Paclitaxel screening Structure-Activity Relationship Toxicity |
| title | In vitro and in vivo evaluation of select kahalalide F analogs with antitumor and antifungal activities |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-02T10%3A03%3A32IST&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=In%20vitro%20and%20in%20vivo%20evaluation%20of%20select%20kahalalide%20F%20analogs%20with%20antitumor%20and%20antifungal%20activities&rft.jtitle=Bioorganic%20&%20medicinal%20chemistry&rft.au=Shilabin,%20Abbas%20Gholipour&rft.date=2011-11-15&rft.volume=19&rft.issue=22&rft.spage=6628&rft.epage=6632&rft.pages=6628-6632&rft.issn=0968-0896&rft.eissn=1464-3391&rft_id=info:doi/10.1016/j.bmc.2011.06.050&rft_dat=%3Cproquest_pubme%3E904493972%3C/proquest_pubme%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c506t-35885971033b06c5b671078655d3e677f97e794392928e504ae580c51a77be433%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=904493972&rft_id=info:pmid/21839640&rfr_iscdi=true |