Serine- and threonine-derived diamine equivalents for site-specific incorporation of platinum centers in peptides, and the anticancer potential of these conjugates
A modular strategy that allows introduction of one or more reactive platinum units at chosen locations along a peptide sequence is presented. This makes use of diazides generated from serine and threonine as diamine equivalents which can be conjugated to the peptide under standard coupling condition...
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| Veröffentlicht in: | New journal of chemistry 2018, Vol.42 (4), p.2450-2458 |
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| container_end_page | 2458 |
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| container_issue | 4 |
| container_start_page | 2450 |
| container_title | New journal of chemistry |
| container_volume | 42 |
| creator | Kumbhakonam, Sateeshkumar Vellaisamy, Kasipandi Saroj, Soumya Venkatesan, Nalini D., Karunagaran Kannoth Manheri, Muraleedharan |
| description | A modular strategy that allows introduction of one or more reactive platinum units at chosen locations along a peptide sequence is presented. This makes use of diazides generated from serine and threonine as diamine equivalents which can be conjugated to the peptide under standard coupling conditions. Reduction of these diazides using Pd/C and H
2
followed by platination affords the final products in good yields. Following this, we prepared a new class of peptide–platinum conjugates and carried out preliminary cytotoxicity evaluation and DNA interaction studies. Inclusion of lysine residues in the sequence was found to improve DNA interaction and anticancer activities compared to analogous conjugates with hydrophobic side chains. |
| doi_str_mv | 10.1039/C7NJ03999A |
| format | Article |
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2
followed by platination affords the final products in good yields. Following this, we prepared a new class of peptide–platinum conjugates and carried out preliminary cytotoxicity evaluation and DNA interaction studies. Inclusion of lysine residues in the sequence was found to improve DNA interaction and anticancer activities compared to analogous conjugates with hydrophobic side chains.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/C7NJ03999A</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Anticancer properties ; Cancer ; Conjugates ; Deoxyribonucleic acid ; DNA ; Equivalence ; Lysine ; Peptides ; Platinum ; Toxicity</subject><ispartof>New journal of chemistry, 2018, Vol.42 (4), p.2450-2458</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c259t-b5fce7c83b489f189641193a763ffdf96a5b6639359b8c9051894477fc5d51593</citedby><cites>FETCH-LOGICAL-c259t-b5fce7c83b489f189641193a763ffdf96a5b6639359b8c9051894477fc5d51593</cites><orcidid>0000-0001-9331-8947 ; 0000-0001-5711-3557</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,4009,27902,27903,27904</link.rule.ids></links><search><creatorcontrib>Kumbhakonam, Sateeshkumar</creatorcontrib><creatorcontrib>Vellaisamy, Kasipandi</creatorcontrib><creatorcontrib>Saroj, Soumya</creatorcontrib><creatorcontrib>Venkatesan, Nalini</creatorcontrib><creatorcontrib>D., Karunagaran</creatorcontrib><creatorcontrib>Kannoth Manheri, Muraleedharan</creatorcontrib><title>Serine- and threonine-derived diamine equivalents for site-specific incorporation of platinum centers in peptides, and the anticancer potential of these conjugates</title><title>New journal of chemistry</title><description>A modular strategy that allows introduction of one or more reactive platinum units at chosen locations along a peptide sequence is presented. This makes use of diazides generated from serine and threonine as diamine equivalents which can be conjugated to the peptide under standard coupling conditions. Reduction of these diazides using Pd/C and H
2
followed by platination affords the final products in good yields. Following this, we prepared a new class of peptide–platinum conjugates and carried out preliminary cytotoxicity evaluation and DNA interaction studies. Inclusion of lysine residues in the sequence was found to improve DNA interaction and anticancer activities compared to analogous conjugates with hydrophobic side chains.</description><subject>Anticancer properties</subject><subject>Cancer</subject><subject>Conjugates</subject><subject>Deoxyribonucleic acid</subject><subject>DNA</subject><subject>Equivalence</subject><subject>Lysine</subject><subject>Peptides</subject><subject>Platinum</subject><subject>Toxicity</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpFkU1OwzAQhS0EEqWw4QSW2CECdhw78bKq-FUFC2Aduc4YXKV2ajuVOA8XxVUrsXrzZr43sxiELim5pYTJu3n9-pJVytkRmlAmZCFLQY9zTauqILwSp-gsxhUhlNaCTtDvOwTroMDKdTh9B_BuZ7vc3UKHO6vW2WPYjHarenApYuMDjjZBEQfQ1liNrdM-DD6oZL3D3uChz6Ub11jnBISYCTzAkGwH8eZwCrImq5XTEPDgUyat6nfpPIuAtXer8UsliOfoxKg-wsVBp-jz4f5j_lQs3h6f57NFoUsuU7HkRkOtG7asGmloI0VFqWSqFsyYzkih-FIIJhmXy0ZLwjNSVXVtNO845ZJN0dV-7xD8ZoSY2pUfg8sn25JQ0jSkKetMXe8pHXyMAUw7BLtW4aelpN09of1_AvsDoTh8zg</recordid><startdate>2018</startdate><enddate>2018</enddate><creator>Kumbhakonam, Sateeshkumar</creator><creator>Vellaisamy, Kasipandi</creator><creator>Saroj, Soumya</creator><creator>Venkatesan, Nalini</creator><creator>D., Karunagaran</creator><creator>Kannoth Manheri, Muraleedharan</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><orcidid>https://orcid.org/0000-0001-9331-8947</orcidid><orcidid>https://orcid.org/0000-0001-5711-3557</orcidid></search><sort><creationdate>2018</creationdate><title>Serine- and threonine-derived diamine equivalents for site-specific incorporation of platinum centers in peptides, and the anticancer potential of these conjugates</title><author>Kumbhakonam, Sateeshkumar ; Vellaisamy, Kasipandi ; Saroj, Soumya ; Venkatesan, Nalini ; D., Karunagaran ; Kannoth Manheri, Muraleedharan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c259t-b5fce7c83b489f189641193a763ffdf96a5b6639359b8c9051894477fc5d51593</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Anticancer properties</topic><topic>Cancer</topic><topic>Conjugates</topic><topic>Deoxyribonucleic acid</topic><topic>DNA</topic><topic>Equivalence</topic><topic>Lysine</topic><topic>Peptides</topic><topic>Platinum</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kumbhakonam, Sateeshkumar</creatorcontrib><creatorcontrib>Vellaisamy, Kasipandi</creatorcontrib><creatorcontrib>Saroj, Soumya</creatorcontrib><creatorcontrib>Venkatesan, Nalini</creatorcontrib><creatorcontrib>D., Karunagaran</creatorcontrib><creatorcontrib>Kannoth Manheri, Muraleedharan</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kumbhakonam, Sateeshkumar</au><au>Vellaisamy, Kasipandi</au><au>Saroj, Soumya</au><au>Venkatesan, Nalini</au><au>D., Karunagaran</au><au>Kannoth Manheri, Muraleedharan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Serine- and threonine-derived diamine equivalents for site-specific incorporation of platinum centers in peptides, and the anticancer potential of these conjugates</atitle><jtitle>New journal of chemistry</jtitle><date>2018</date><risdate>2018</risdate><volume>42</volume><issue>4</issue><spage>2450</spage><epage>2458</epage><pages>2450-2458</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>A modular strategy that allows introduction of one or more reactive platinum units at chosen locations along a peptide sequence is presented. This makes use of diazides generated from serine and threonine as diamine equivalents which can be conjugated to the peptide under standard coupling conditions. Reduction of these diazides using Pd/C and H
2
followed by platination affords the final products in good yields. Following this, we prepared a new class of peptide–platinum conjugates and carried out preliminary cytotoxicity evaluation and DNA interaction studies. Inclusion of lysine residues in the sequence was found to improve DNA interaction and anticancer activities compared to analogous conjugates with hydrophobic side chains.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/C7NJ03999A</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-9331-8947</orcidid><orcidid>https://orcid.org/0000-0001-5711-3557</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1144-0546 |
| ispartof | New journal of chemistry, 2018, Vol.42 (4), p.2450-2458 |
| issn | 1144-0546 1369-9261 |
| language | eng |
| recordid | cdi_proquest_journals_2010880827 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Anticancer properties Cancer Conjugates Deoxyribonucleic acid DNA Equivalence Lysine Peptides Platinum Toxicity |
| title | Serine- and threonine-derived diamine equivalents for site-specific incorporation of platinum centers in peptides, and the anticancer potential of these conjugates |
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