Controlling Biological Activity with Light: Diarylethene-Containing Cyclic Peptidomimetics
Photobiological processes in nature are usually triggered by nonpeptidic chromophores or by modified side chains. A system is presented in which the polypeptide backbone itself can be conformationally switched by light. An amino acid analogue was designed and synthesized based on a reversibly photoi...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2014-03, Vol.53 (13), p.3392-3395 |
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| creator | Babii, Oleg Afonin, Sergii Berditsch, Marina Reiβer, Sabine Mykhailiuk, Pavel K. Kubyshkin, Vladimir S. Steinbrecher, Thomas Ulrich, Anne S. Komarov, Igor V. |
| description | Photobiological processes in nature are usually triggered by nonpeptidic chromophores or by modified side chains. A system is presented in which the polypeptide backbone itself can be conformationally switched by light. An amino acid analogue was designed and synthesized based on a reversibly photoisomerizable diarylethene scaffold. This analogue was incorporated into the cyclic backbone of the antimicrobial peptide gramicidin S at several sites. The biological activity of the resulting peptidomimetics could then be effectively controlled by ultraviolet/visible light within strictly defined spatial and temporal limits.
Making light work: An amino acid analogue based on a reversibly photoisomerizable diarylethene scaffold was incorporated into the cyclic backbone of the antimicrobial peptide gramicidin S. The biological activity of the resulting peptidomimetics could be effectively controlled by ultraviolet/visible light within strictly defined spatial and temporal limits. |
| doi_str_mv | 10.1002/anie.201310019 |
| format | Article |
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Making light work: An amino acid analogue based on a reversibly photoisomerizable diarylethene scaffold was incorporated into the cyclic backbone of the antimicrobial peptide gramicidin S. The biological activity of the resulting peptidomimetics could be effectively controlled by ultraviolet/visible light within strictly defined spatial and temporal limits.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201310019</identifier><identifier>PMID: 24554486</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Amino acids ; Analogue ; Antiinfectives and antibacterials ; antimicrobial agents ; Backbone ; Biological ; Biological activity ; diarylethenes ; Ethylenes - chemistry ; gramicidin S ; Light ; Models, Molecular ; Molecular Conformation ; Peptides, Cyclic - chemistry ; peptidomimetics ; Peptidomimetics - chemistry ; Photochemistry ; Scaffolds ; Structure-Activity Relationship ; Temporal logic ; Ultraviolet</subject><ispartof>Angewandte Chemie International Edition, 2014-03, Vol.53 (13), p.3392-3395</ispartof><rights>2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4819-3b482d2de2b3e4dfce5b732d166dfcb7997f2acecc3353c93fd01f4a40b1dece3</citedby><cites>FETCH-LOGICAL-c4819-3b482d2de2b3e4dfce5b732d166dfcb7997f2acecc3353c93fd01f4a40b1dece3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201310019$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201310019$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27929,27930,45579,45580</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24554486$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Babii, Oleg</creatorcontrib><creatorcontrib>Afonin, Sergii</creatorcontrib><creatorcontrib>Berditsch, Marina</creatorcontrib><creatorcontrib>Reiβer, Sabine</creatorcontrib><creatorcontrib>Mykhailiuk, Pavel K.</creatorcontrib><creatorcontrib>Kubyshkin, Vladimir S.</creatorcontrib><creatorcontrib>Steinbrecher, Thomas</creatorcontrib><creatorcontrib>Ulrich, Anne S.</creatorcontrib><creatorcontrib>Komarov, Igor V.</creatorcontrib><title>Controlling Biological Activity with Light: Diarylethene-Containing Cyclic Peptidomimetics</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>Photobiological processes in nature are usually triggered by nonpeptidic chromophores or by modified side chains. A system is presented in which the polypeptide backbone itself can be conformationally switched by light. An amino acid analogue was designed and synthesized based on a reversibly photoisomerizable diarylethene scaffold. This analogue was incorporated into the cyclic backbone of the antimicrobial peptide gramicidin S at several sites. The biological activity of the resulting peptidomimetics could then be effectively controlled by ultraviolet/visible light within strictly defined spatial and temporal limits.
Making light work: An amino acid analogue based on a reversibly photoisomerizable diarylethene scaffold was incorporated into the cyclic backbone of the antimicrobial peptide gramicidin S. The biological activity of the resulting peptidomimetics could be effectively controlled by ultraviolet/visible light within strictly defined spatial and temporal limits.</description><subject>Amino acids</subject><subject>Analogue</subject><subject>Antiinfectives and antibacterials</subject><subject>antimicrobial agents</subject><subject>Backbone</subject><subject>Biological</subject><subject>Biological activity</subject><subject>diarylethenes</subject><subject>Ethylenes - chemistry</subject><subject>gramicidin S</subject><subject>Light</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>Peptides, Cyclic - chemistry</subject><subject>peptidomimetics</subject><subject>Peptidomimetics - chemistry</subject><subject>Photochemistry</subject><subject>Scaffolds</subject><subject>Structure-Activity Relationship</subject><subject>Temporal logic</subject><subject>Ultraviolet</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc9v0zAYhiPExMbgyhFF4sIlnX_GDrcurGNSNThsQ9rFcpwvrYcTl9hl9L_HUUeFuOzk75Oe55X8vVn2DqMZRoic6cHCjCBM04arF9kJ5gQXVAj6Ms2M0kJIjo-z1yE8JF5KVL7KjgnjnDFZnmT3tR_i6J2zwyo_t975lTXa5XMT7S8bd_mjjet8aVfr-Cn_bPW4cxDXMEAxidoOk1fvjLMm_wabaFvf2x6iNeFNdtRpF-Dt03ua3S4ubuovxfLr5VU9XxaGSVwVtGGStKQF0lBgbWeAN4KSFpdlWhpRVaIj2oAxlHJqKtq1CHdMM9TgFgzQ0-zjPncz-p9bCFH1NhhwTg_gt0FhgdJxJJHV8yhHFcMEswn98B_64LfjkD4yUZLxEjOeqNmeMqMPYYRObUbbpyspjNRUkJoKUoeCkvD-KXbb9NAe8L-NJKDaA4_Wwe6ZODW_vrr4N7zYuzZE-H1w9fhDlYIKrr5fX6r7-maxXEih7ugfQGCsmg</recordid><startdate>20140324</startdate><enddate>20140324</enddate><creator>Babii, Oleg</creator><creator>Afonin, Sergii</creator><creator>Berditsch, Marina</creator><creator>Reiβer, Sabine</creator><creator>Mykhailiuk, Pavel K.</creator><creator>Kubyshkin, Vladimir S.</creator><creator>Steinbrecher, Thomas</creator><creator>Ulrich, Anne S.</creator><creator>Komarov, Igor V.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</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>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20140324</creationdate><title>Controlling Biological Activity with Light: Diarylethene-Containing Cyclic Peptidomimetics</title><author>Babii, Oleg ; Afonin, Sergii ; Berditsch, Marina ; Reiβer, Sabine ; Mykhailiuk, Pavel K. ; Kubyshkin, Vladimir S. ; Steinbrecher, Thomas ; Ulrich, Anne S. ; Komarov, Igor V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4819-3b482d2de2b3e4dfce5b732d166dfcb7997f2acecc3353c93fd01f4a40b1dece3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Amino acids</topic><topic>Analogue</topic><topic>Antiinfectives and antibacterials</topic><topic>antimicrobial agents</topic><topic>Backbone</topic><topic>Biological</topic><topic>Biological activity</topic><topic>diarylethenes</topic><topic>Ethylenes - chemistry</topic><topic>gramicidin S</topic><topic>Light</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>Peptides, Cyclic - chemistry</topic><topic>peptidomimetics</topic><topic>Peptidomimetics - chemistry</topic><topic>Photochemistry</topic><topic>Scaffolds</topic><topic>Structure-Activity Relationship</topic><topic>Temporal logic</topic><topic>Ultraviolet</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Babii, Oleg</creatorcontrib><creatorcontrib>Afonin, Sergii</creatorcontrib><creatorcontrib>Berditsch, Marina</creatorcontrib><creatorcontrib>Reiβer, Sabine</creatorcontrib><creatorcontrib>Mykhailiuk, Pavel K.</creatorcontrib><creatorcontrib>Kubyshkin, Vladimir S.</creatorcontrib><creatorcontrib>Steinbrecher, Thomas</creatorcontrib><creatorcontrib>Ulrich, Anne S.</creatorcontrib><creatorcontrib>Komarov, Igor V.</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Babii, Oleg</au><au>Afonin, Sergii</au><au>Berditsch, Marina</au><au>Reiβer, Sabine</au><au>Mykhailiuk, Pavel K.</au><au>Kubyshkin, Vladimir S.</au><au>Steinbrecher, Thomas</au><au>Ulrich, Anne S.</au><au>Komarov, Igor V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Controlling Biological Activity with Light: Diarylethene-Containing Cyclic Peptidomimetics</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2014-03-24</date><risdate>2014</risdate><volume>53</volume><issue>13</issue><spage>3392</spage><epage>3395</epage><pages>3392-3395</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>Photobiological processes in nature are usually triggered by nonpeptidic chromophores or by modified side chains. A system is presented in which the polypeptide backbone itself can be conformationally switched by light. An amino acid analogue was designed and synthesized based on a reversibly photoisomerizable diarylethene scaffold. This analogue was incorporated into the cyclic backbone of the antimicrobial peptide gramicidin S at several sites. The biological activity of the resulting peptidomimetics could then be effectively controlled by ultraviolet/visible light within strictly defined spatial and temporal limits.
Making light work: An amino acid analogue based on a reversibly photoisomerizable diarylethene scaffold was incorporated into the cyclic backbone of the antimicrobial peptide gramicidin S. The biological activity of the resulting peptidomimetics could be effectively controlled by ultraviolet/visible light within strictly defined spatial and temporal limits.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>24554486</pmid><doi>10.1002/anie.201310019</doi><tpages>4</tpages><edition>International ed. in English</edition></addata></record> |
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| subjects | Amino acids Analogue Antiinfectives and antibacterials antimicrobial agents Backbone Biological Biological activity diarylethenes Ethylenes - chemistry gramicidin S Light Models, Molecular Molecular Conformation Peptides, Cyclic - chemistry peptidomimetics Peptidomimetics - chemistry Photochemistry Scaffolds Structure-Activity Relationship Temporal logic Ultraviolet |
| title | Controlling Biological Activity with Light: Diarylethene-Containing Cyclic Peptidomimetics |
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