Preparation and Biological Activity of Amino Acid and Peptide Conjugates of Antitumor Hydroxymethylacylfulvene
The primary hydroxyl group in hydroxymethylacylfulvene, a potent antitumor drug, is readily replaced by thiols including cysteine, N-acetylcysteine, homocysteine, and glutathione. Best yields are obtained when reaction is carried out in the presence of dilute sulfuric acid. A variety of sulfur-conta...
Gespeichert in:
| Veröffentlicht in: | Journal of medicinal chemistry 2000-09, Vol.43 (19), p.3577-3580 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3580 |
|---|---|
| container_issue | 19 |
| container_start_page | 3577 |
| container_title | Journal of medicinal chemistry |
| container_volume | 43 |
| creator | McMorris, Trevor C Yu, Jian Ngo, Huan-Tony Wang, Haixia Kelner, Michael J |
| description | The primary hydroxyl group in hydroxymethylacylfulvene, a potent antitumor drug, is readily replaced by thiols including cysteine, N-acetylcysteine, homocysteine, and glutathione. Best yields are obtained when reaction is carried out in the presence of dilute sulfuric acid. A variety of sulfur-containing analogues have been prepared, and their toxicity to tumor cells was examined. |
| doi_str_mv | 10.1021/jm0000315 |
| format | Article |
| fullrecord | <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_jm0000315</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>a561944513</sourcerecordid><originalsourceid>FETCH-LOGICAL-a378t-26ae3fef8ef89a7df36643f937dbd917bd49cf790fc2dc6ca81808cbecbda8e63</originalsourceid><addsrcrecordid>eNpt0MtqGzEUBmBRUmon7aIvUGaRLrKYRBqN57J0hqYpMcSlKV2KM7o4cmYkI2mM5-0jX0g2FQLBOZ-kw4_QV4KvCc7IzbrHcVEy-4CmZJbhNK9wfoamGGdZmhUZnaBz79cHk9FPaELI_gKhU2SWTm7AQdDWJGBEcqttZ1eaQ5fMedBbHcbEqmTea2NjRYuDWspN0EImjTXrYQVB-gMyQYehty65H4Wzu7GX4XnsgI-dGrqtNPIz-qig8_LL6bxAf-9-PDX36eLx569mvkiBllWIM4OkSqoq7hpKoWhR5FTVtBStqEnZirzmqqyx4pngBYeKVLjireStgEoW9AJdHd_lznrvpGIbp3twIyOY7TNjb5lF--1oN0PbS_EuTyFFcHkC4GMuyoHh2r-7GSFFvv8zPTLtg9y9tcG9sKKk5Yw9Lf-wf81Dgxe_C0ai_370wD1b28GZmMh_5nsFWzGQ7Q</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Preparation and Biological Activity of Amino Acid and Peptide Conjugates of Antitumor Hydroxymethylacylfulvene</title><source>MEDLINE</source><source>ACS Publications</source><creator>McMorris, Trevor C ; Yu, Jian ; Ngo, Huan-Tony ; Wang, Haixia ; Kelner, Michael J</creator><creatorcontrib>McMorris, Trevor C ; Yu, Jian ; Ngo, Huan-Tony ; Wang, Haixia ; Kelner, Michael J</creatorcontrib><description>The primary hydroxyl group in hydroxymethylacylfulvene, a potent antitumor drug, is readily replaced by thiols including cysteine, N-acetylcysteine, homocysteine, and glutathione. Best yields are obtained when reaction is carried out in the presence of dilute sulfuric acid. A variety of sulfur-containing analogues have been prepared, and their toxicity to tumor cells was examined.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm0000315</identifier><identifier>PMID: 11000013</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Amino Acids - chemistry ; Animals ; Antineoplastic agents ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Drug Screening Assays, Antitumor ; General aspects ; Inhibitory Concentration 50 ; Medical sciences ; Peptides - chemistry ; Pharmacology. Drug treatments ; Rats ; Sesquiterpenes - chemistry ; Sesquiterpenes - pharmacology ; Tumor Cells, Cultured</subject><ispartof>Journal of medicinal chemistry, 2000-09, Vol.43 (19), p.3577-3580</ispartof><rights>Copyright © 2000 American Chemical Society</rights><rights>2000 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a378t-26ae3fef8ef89a7df36643f937dbd917bd49cf790fc2dc6ca81808cbecbda8e63</citedby><cites>FETCH-LOGICAL-a378t-26ae3fef8ef89a7df36643f937dbd917bd49cf790fc2dc6ca81808cbecbda8e63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm0000315$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm0000315$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27074,27922,27923,56736,56786</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1511646$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11000013$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>McMorris, Trevor C</creatorcontrib><creatorcontrib>Yu, Jian</creatorcontrib><creatorcontrib>Ngo, Huan-Tony</creatorcontrib><creatorcontrib>Wang, Haixia</creatorcontrib><creatorcontrib>Kelner, Michael J</creatorcontrib><title>Preparation and Biological Activity of Amino Acid and Peptide Conjugates of Antitumor Hydroxymethylacylfulvene</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>The primary hydroxyl group in hydroxymethylacylfulvene, a potent antitumor drug, is readily replaced by thiols including cysteine, N-acetylcysteine, homocysteine, and glutathione. Best yields are obtained when reaction is carried out in the presence of dilute sulfuric acid. A variety of sulfur-containing analogues have been prepared, and their toxicity to tumor cells was examined.</description><subject>Amino Acids - chemistry</subject><subject>Animals</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General aspects</subject><subject>Inhibitory Concentration 50</subject><subject>Medical sciences</subject><subject>Peptides - chemistry</subject><subject>Pharmacology. Drug treatments</subject><subject>Rats</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - pharmacology</subject><subject>Tumor Cells, Cultured</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MtqGzEUBmBRUmon7aIvUGaRLrKYRBqN57J0hqYpMcSlKV2KM7o4cmYkI2mM5-0jX0g2FQLBOZ-kw4_QV4KvCc7IzbrHcVEy-4CmZJbhNK9wfoamGGdZmhUZnaBz79cHk9FPaELI_gKhU2SWTm7AQdDWJGBEcqttZ1eaQ5fMedBbHcbEqmTea2NjRYuDWspN0EImjTXrYQVB-gMyQYehty65H4Wzu7GX4XnsgI-dGrqtNPIz-qig8_LL6bxAf-9-PDX36eLx569mvkiBllWIM4OkSqoq7hpKoWhR5FTVtBStqEnZirzmqqyx4pngBYeKVLjireStgEoW9AJdHd_lznrvpGIbp3twIyOY7TNjb5lF--1oN0PbS_EuTyFFcHkC4GMuyoHh2r-7GSFFvv8zPTLtg9y9tcG9sKKk5Yw9Lf-wf81Dgxe_C0ai_370wD1b28GZmMh_5nsFWzGQ7Q</recordid><startdate>20000921</startdate><enddate>20000921</enddate><creator>McMorris, Trevor C</creator><creator>Yu, Jian</creator><creator>Ngo, Huan-Tony</creator><creator>Wang, Haixia</creator><creator>Kelner, Michael J</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</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></search><sort><creationdate>20000921</creationdate><title>Preparation and Biological Activity of Amino Acid and Peptide Conjugates of Antitumor Hydroxymethylacylfulvene</title><author>McMorris, Trevor C ; Yu, Jian ; Ngo, Huan-Tony ; Wang, Haixia ; Kelner, Michael J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a378t-26ae3fef8ef89a7df36643f937dbd917bd49cf790fc2dc6ca81808cbecbda8e63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Amino Acids - chemistry</topic><topic>Animals</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General aspects</topic><topic>Inhibitory Concentration 50</topic><topic>Medical sciences</topic><topic>Peptides - chemistry</topic><topic>Pharmacology. Drug treatments</topic><topic>Rats</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes - pharmacology</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>McMorris, Trevor C</creatorcontrib><creatorcontrib>Yu, Jian</creatorcontrib><creatorcontrib>Ngo, Huan-Tony</creatorcontrib><creatorcontrib>Wang, Haixia</creatorcontrib><creatorcontrib>Kelner, Michael J</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>McMorris, Trevor C</au><au>Yu, Jian</au><au>Ngo, Huan-Tony</au><au>Wang, Haixia</au><au>Kelner, Michael J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Preparation and Biological Activity of Amino Acid and Peptide Conjugates of Antitumor Hydroxymethylacylfulvene</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2000-09-21</date><risdate>2000</risdate><volume>43</volume><issue>19</issue><spage>3577</spage><epage>3580</epage><pages>3577-3580</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>The primary hydroxyl group in hydroxymethylacylfulvene, a potent antitumor drug, is readily replaced by thiols including cysteine, N-acetylcysteine, homocysteine, and glutathione. Best yields are obtained when reaction is carried out in the presence of dilute sulfuric acid. A variety of sulfur-containing analogues have been prepared, and their toxicity to tumor cells was examined.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>11000013</pmid><doi>10.1021/jm0000315</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 2000-09, Vol.43 (19), p.3577-3580 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_crossref_primary_10_1021_jm0000315 |
| source | MEDLINE; ACS Publications |
| subjects | Amino Acids - chemistry Animals Antineoplastic agents Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biological and medical sciences Drug Screening Assays, Antitumor General aspects Inhibitory Concentration 50 Medical sciences Peptides - chemistry Pharmacology. Drug treatments Rats Sesquiterpenes - chemistry Sesquiterpenes - pharmacology Tumor Cells, Cultured |
| title | Preparation and Biological Activity of Amino Acid and Peptide Conjugates of Antitumor Hydroxymethylacylfulvene |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-09T15%3A48%3A35IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Preparation%20and%20Biological%20Activity%20of%20Amino%20Acid%20and%20Peptide%20Conjugates%20of%20Antitumor%20Hydroxymethylacylfulvene&rft.jtitle=Journal%20of%20medicinal%20chemistry&rft.au=McMorris,%20Trevor%20C&rft.date=2000-09-21&rft.volume=43&rft.issue=19&rft.spage=3577&rft.epage=3580&rft.pages=3577-3580&rft.issn=0022-2623&rft.eissn=1520-4804&rft.coden=JMCMAR&rft_id=info:doi/10.1021/jm0000315&rft_dat=%3Cacs_cross%3Ea561944513%3C/acs_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/11000013&rfr_iscdi=true |