Highly efficient photocontrol of mitotic kinesin Eg5 ATPase activity using a novel photochromic compound composed of two azobenzene derivatives
Mitotic kinesin Eg5 plays an important physiological role in cell division. Several small-molecule inhibitors of Eg5 are the focus of cancer therapies. Azobenzene is a photochromic compound exhibiting cis-trans isomerization upon ultraviolet (UV) and visible (VIS) light irradiation. Photochromic com...
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| Veröffentlicht in: | Journal of biochemistry (Tokyo) 2018-10, Vol.164 (4), p.295-301 |
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| creator | Sadakane, Kei Alrazi, Islam M D Maruta, Shinsaku |
| description | Mitotic kinesin Eg5 plays an important physiological role in cell division. Several small-molecule inhibitors of Eg5 are the focus of cancer therapies. Azobenzene is a photochromic compound exhibiting cis-trans isomerization upon ultraviolet (UV) and visible (VIS) light irradiation. Photochromic compounds of azobenzene derivatives, mimicking Eg5-specific inhibitors of STLC, indicated photoreversible inhibitory effects on Eg5 ATPase activity; however, the photoreversible switching efficiency was not significant. This study presents a novel synthesized photochromic Eg5 inhibitor 2, 3-bis[(2,5-dioxo-1-{4-[(E)-2-phenyldiazen-1-yl]phenyl}pyrrolidin-3-yl)sulfanyl] butanedioic acid (BDPSB), which is composed of two azobenzenes. BDPSB exhibited cis-trans isomerization with UV and VIS light irradiation. The trans form of BDPSB significantly inhibited microtubule-dependent ATPase activity of Eg5, with an IC50 of 74 μM. Cis BDPSB showed weak effects on the microtubule-dependent ATPase activity. The results suggest that the novel photochromic Eg5 inhibitor BDPSB, which exhibits highly efficient photoswitching, shows a switch 'ON' and 'OFF' behaviour with VIS and UV light irradiation. |
| doi_str_mv | 10.1093/jb/mvy051 |
| format | Article |
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Several small-molecule inhibitors of Eg5 are the focus of cancer therapies. Azobenzene is a photochromic compound exhibiting cis-trans isomerization upon ultraviolet (UV) and visible (VIS) light irradiation. Photochromic compounds of azobenzene derivatives, mimicking Eg5-specific inhibitors of STLC, indicated photoreversible inhibitory effects on Eg5 ATPase activity; however, the photoreversible switching efficiency was not significant. This study presents a novel synthesized photochromic Eg5 inhibitor 2, 3-bis[(2,5-dioxo-1-{4-[(E)-2-phenyldiazen-1-yl]phenyl}pyrrolidin-3-yl)sulfanyl] butanedioic acid (BDPSB), which is composed of two azobenzenes. BDPSB exhibited cis-trans isomerization with UV and VIS light irradiation. The trans form of BDPSB significantly inhibited microtubule-dependent ATPase activity of Eg5, with an IC50 of 74 μM. Cis BDPSB showed weak effects on the microtubule-dependent ATPase activity. The results suggest that the novel photochromic Eg5 inhibitor BDPSB, which exhibits highly efficient photoswitching, shows a switch 'ON' and 'OFF' behaviour with VIS and UV light irradiation.</description><identifier>ISSN: 0021-924X</identifier><identifier>EISSN: 1756-2651</identifier><identifier>DOI: 10.1093/jb/mvy051</identifier><identifier>PMID: 29860530</identifier><language>eng</language><publisher>England</publisher><subject>Adenosine Triphosphatases - metabolism ; Azo Compounds - chemistry ; Azo Compounds - pharmacology ; Enzyme Activation - drug effects ; Enzyme Activation - radiation effects ; Kinesin - chemistry ; Kinesin - metabolism ; Light ; Molecular Structure ; Photochemistry ; Staining and Labeling ; Xenopus Proteins - metabolism</subject><ispartof>Journal of biochemistry (Tokyo), 2018-10, Vol.164 (4), p.295-301</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c402t-d210ec3320c886789f16c317a48f043f358f50fcd79ad7cf21cf0c76db4fc9413</citedby><cites>FETCH-LOGICAL-c402t-d210ec3320c886789f16c317a48f043f358f50fcd79ad7cf21cf0c76db4fc9413</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29860530$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sadakane, Kei</creatorcontrib><creatorcontrib>Alrazi, Islam M D</creatorcontrib><creatorcontrib>Maruta, Shinsaku</creatorcontrib><title>Highly efficient photocontrol of mitotic kinesin Eg5 ATPase activity using a novel photochromic compound composed of two azobenzene derivatives</title><title>Journal of biochemistry (Tokyo)</title><addtitle>J Biochem</addtitle><description>Mitotic kinesin Eg5 plays an important physiological role in cell division. Several small-molecule inhibitors of Eg5 are the focus of cancer therapies. Azobenzene is a photochromic compound exhibiting cis-trans isomerization upon ultraviolet (UV) and visible (VIS) light irradiation. Photochromic compounds of azobenzene derivatives, mimicking Eg5-specific inhibitors of STLC, indicated photoreversible inhibitory effects on Eg5 ATPase activity; however, the photoreversible switching efficiency was not significant. This study presents a novel synthesized photochromic Eg5 inhibitor 2, 3-bis[(2,5-dioxo-1-{4-[(E)-2-phenyldiazen-1-yl]phenyl}pyrrolidin-3-yl)sulfanyl] butanedioic acid (BDPSB), which is composed of two azobenzenes. BDPSB exhibited cis-trans isomerization with UV and VIS light irradiation. The trans form of BDPSB significantly inhibited microtubule-dependent ATPase activity of Eg5, with an IC50 of 74 μM. Cis BDPSB showed weak effects on the microtubule-dependent ATPase activity. The results suggest that the novel photochromic Eg5 inhibitor BDPSB, which exhibits highly efficient photoswitching, shows a switch 'ON' and 'OFF' behaviour with VIS and UV light irradiation.</description><subject>Adenosine Triphosphatases - metabolism</subject><subject>Azo Compounds - chemistry</subject><subject>Azo Compounds - pharmacology</subject><subject>Enzyme Activation - drug effects</subject><subject>Enzyme Activation - radiation effects</subject><subject>Kinesin - chemistry</subject><subject>Kinesin - metabolism</subject><subject>Light</subject><subject>Molecular Structure</subject><subject>Photochemistry</subject><subject>Staining and Labeling</subject><subject>Xenopus Proteins - metabolism</subject><issn>0021-924X</issn><issn>1756-2651</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kMtOwzAQRS0EoqWw4AeQl7AI9SPPZVUVilQJFkViFznOuHVJ7BI7Qe1P8MukamE1M7pnzuIidEvJIyUZH2-Kcd3tSETP0JAmURywOKLnaEgIo0HGwo8BunJuczgZ55dowLI0JhEnQ_Qz16t1tcOglJYajMfbtfVWWuMbW2GrcK299VriT23AaYNnqwhPlm_CARbS6077HW77YIUFNraD6mRYN7bu36Stt7Y15XFxUB6c_ttisbcFmD0YwCU0uhO9C9w1ulCicnBzmiP0_jRbTufB4vX5ZTpZBDIkzAclowQk54zINI2TNFM0lpwmIkwVCbniUaoiomSZZKJMpGJUKiKTuCxCJbOQ8hG6P3q3jf1qwfm81k5CVQkDtnU5I2GWhZwx0qMPR1Q21rkGVL5tdC2aXU5Jfug_3xT5sf-evTtp26KG8p_8K5z_AgejhO0</recordid><startdate>20181001</startdate><enddate>20181001</enddate><creator>Sadakane, Kei</creator><creator>Alrazi, Islam M D</creator><creator>Maruta, Shinsaku</creator><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></search><sort><creationdate>20181001</creationdate><title>Highly efficient photocontrol of mitotic kinesin Eg5 ATPase activity using a novel photochromic compound composed of two azobenzene derivatives</title><author>Sadakane, Kei ; Alrazi, Islam M D ; Maruta, Shinsaku</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c402t-d210ec3320c886789f16c317a48f043f358f50fcd79ad7cf21cf0c76db4fc9413</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Adenosine Triphosphatases - metabolism</topic><topic>Azo Compounds - chemistry</topic><topic>Azo Compounds - pharmacology</topic><topic>Enzyme Activation - drug effects</topic><topic>Enzyme Activation - radiation effects</topic><topic>Kinesin - chemistry</topic><topic>Kinesin - metabolism</topic><topic>Light</topic><topic>Molecular Structure</topic><topic>Photochemistry</topic><topic>Staining and Labeling</topic><topic>Xenopus Proteins - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sadakane, Kei</creatorcontrib><creatorcontrib>Alrazi, Islam M D</creatorcontrib><creatorcontrib>Maruta, Shinsaku</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><jtitle>Journal of biochemistry (Tokyo)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sadakane, Kei</au><au>Alrazi, Islam M D</au><au>Maruta, Shinsaku</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Highly efficient photocontrol of mitotic kinesin Eg5 ATPase activity using a novel photochromic compound composed of two azobenzene derivatives</atitle><jtitle>Journal of biochemistry (Tokyo)</jtitle><addtitle>J Biochem</addtitle><date>2018-10-01</date><risdate>2018</risdate><volume>164</volume><issue>4</issue><spage>295</spage><epage>301</epage><pages>295-301</pages><issn>0021-924X</issn><eissn>1756-2651</eissn><abstract>Mitotic kinesin Eg5 plays an important physiological role in cell division. Several small-molecule inhibitors of Eg5 are the focus of cancer therapies. Azobenzene is a photochromic compound exhibiting cis-trans isomerization upon ultraviolet (UV) and visible (VIS) light irradiation. Photochromic compounds of azobenzene derivatives, mimicking Eg5-specific inhibitors of STLC, indicated photoreversible inhibitory effects on Eg5 ATPase activity; however, the photoreversible switching efficiency was not significant. This study presents a novel synthesized photochromic Eg5 inhibitor 2, 3-bis[(2,5-dioxo-1-{4-[(E)-2-phenyldiazen-1-yl]phenyl}pyrrolidin-3-yl)sulfanyl] butanedioic acid (BDPSB), which is composed of two azobenzenes. BDPSB exhibited cis-trans isomerization with UV and VIS light irradiation. The trans form of BDPSB significantly inhibited microtubule-dependent ATPase activity of Eg5, with an IC50 of 74 μM. Cis BDPSB showed weak effects on the microtubule-dependent ATPase activity. The results suggest that the novel photochromic Eg5 inhibitor BDPSB, which exhibits highly efficient photoswitching, shows a switch 'ON' and 'OFF' behaviour with VIS and UV light irradiation.</abstract><cop>England</cop><pmid>29860530</pmid><doi>10.1093/jb/mvy051</doi><tpages>7</tpages></addata></record> |
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| ispartof | Journal of biochemistry (Tokyo), 2018-10, Vol.164 (4), p.295-301 |
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| source | MEDLINE; Oxford University Press Journals All Titles (1996-Current); Alma/SFX Local Collection |
| subjects | Adenosine Triphosphatases - metabolism Azo Compounds - chemistry Azo Compounds - pharmacology Enzyme Activation - drug effects Enzyme Activation - radiation effects Kinesin - chemistry Kinesin - metabolism Light Molecular Structure Photochemistry Staining and Labeling Xenopus Proteins - metabolism |
| title | Highly efficient photocontrol of mitotic kinesin Eg5 ATPase activity using a novel photochromic compound composed of two azobenzene derivatives |
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