(4-Methoxy-benzylidene)-(3-methoxy-phenyl)-amine, a Nitrogen Analog of Stilbene as a Potent Inhibitor of Melanin Production
The current study was carried out to investigate in vitro the effects of (4-methoxy-benzylidene)-(3-methoxy-phenyl)-amine on melanin biosynthesis which is closely related to hyper-pigmentation. (4-Methoxy-benzylidene)-(3-methoxy-phenyl)-amine, a nitrogen analog of stilbene, was synthesized by a sing...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2002, Vol.50(4), pp.450-452 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | Choi, Sang Yoon Kim, Sanghee Kim, Hocheol Suk, Kyoungho Hwang, Jae Sung Lee, Byeong Gon Kim, Ae-Jung Kim, Sun Yeou |
| description | The current study was carried out to investigate in vitro the effects of (4-methoxy-benzylidene)-(3-methoxy-phenyl)-amine on melanin biosynthesis which is closely related to hyper-pigmentation. (4-Methoxy-benzylidene)-(3-methoxy-phenyl)-amine, a nitrogen analog of stilbene, was synthesized by a single step process. This compound inhibited the tyrosinase activity, which converts dopa to dopachrome in the biosynthetic process of melanin, and showed a UV-blocking effect at UV-B band. The compound also exhibited SOD-like activity, which is involved in the protection against auto-oxidation and inhibited melanin production in melan-a cell line. Our results suggest the possibility that (4-methoxy-benzylidene)-(3-methoxy-phenyl)-amine might be used as a skin whitening agent. |
| doi_str_mv | 10.1248/cpb.50.450 |
| format | Article |
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(4-Methoxy-benzylidene)-(3-methoxy-phenyl)-amine, a nitrogen analog of stilbene, was synthesized by a single step process. This compound inhibited the tyrosinase activity, which converts dopa to dopachrome in the biosynthetic process of melanin, and showed a UV-blocking effect at UV-B band. The compound also exhibited SOD-like activity, which is involved in the protection against auto-oxidation and inhibited melanin production in melan-a cell line. Our results suggest the possibility that (4-methoxy-benzylidene)-(3-methoxy-phenyl)-amine might be used as a skin whitening agent.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.50.450</identifier><identifier>PMID: 11963989</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Animals ; Biological and medical sciences ; Cell Line ; Cell Survival - drug effects ; Medical sciences ; Melanins - antagonists & inhibitors ; Melanins - biosynthesis ; Mice ; Mice, Inbred C57BL ; Monophenol Monooxygenase - antagonists & inhibitors ; oxyresveratrol ; Pharmacology. Drug treatments ; Skin Pigmentation - drug effects ; Skin, nail, hair, dermoskeleton ; stilbene ; Stilbenes - chemical synthesis ; Stilbenes - pharmacology ; Stilbenes - toxicity ; Sunscreening Agents - chemical synthesis ; Sunscreening Agents - pharmacology ; Sunscreening Agents - toxicity ; Superoxide Dismutase - metabolism ; Superoxides - antagonists & inhibitors ; Ultraviolet Rays ; whitening agent</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2002, Vol.50(4), pp.450-452</ispartof><rights>2002 The Pharmaceutical Society of Japan</rights><rights>2002 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 2002</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c625t-65ad50fd5308fb98e9b8debeec212e5ed92ba44cb5107473200a287bb37ec97f3</citedby><cites>FETCH-LOGICAL-c625t-65ad50fd5308fb98e9b8debeec212e5ed92ba44cb5107473200a287bb37ec97f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14185126$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11963989$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Choi, Sang Yoon</creatorcontrib><creatorcontrib>Kim, Sanghee</creatorcontrib><creatorcontrib>Kim, Hocheol</creatorcontrib><creatorcontrib>Suk, Kyoungho</creatorcontrib><creatorcontrib>Hwang, Jae Sung</creatorcontrib><creatorcontrib>Lee, Byeong Gon</creatorcontrib><creatorcontrib>Kim, Ae-Jung</creatorcontrib><creatorcontrib>Kim, Sun Yeou</creatorcontrib><title>(4-Methoxy-benzylidene)-(3-methoxy-phenyl)-amine, a Nitrogen Analog of Stilbene as a Potent Inhibitor of Melanin Production</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>The current study was carried out to investigate in vitro the effects of (4-methoxy-benzylidene)-(3-methoxy-phenyl)-amine on melanin biosynthesis which is closely related to hyper-pigmentation. (4-Methoxy-benzylidene)-(3-methoxy-phenyl)-amine, a nitrogen analog of stilbene, was synthesized by a single step process. This compound inhibited the tyrosinase activity, which converts dopa to dopachrome in the biosynthetic process of melanin, and showed a UV-blocking effect at UV-B band. The compound also exhibited SOD-like activity, which is involved in the protection against auto-oxidation and inhibited melanin production in melan-a cell line. Our results suggest the possibility that (4-methoxy-benzylidene)-(3-methoxy-phenyl)-amine might be used as a skin whitening agent.</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Cell Line</subject><subject>Cell Survival - drug effects</subject><subject>Medical sciences</subject><subject>Melanins - antagonists & inhibitors</subject><subject>Melanins - biosynthesis</subject><subject>Mice</subject><subject>Mice, Inbred C57BL</subject><subject>Monophenol Monooxygenase - antagonists & inhibitors</subject><subject>oxyresveratrol</subject><subject>Pharmacology. Drug treatments</subject><subject>Skin Pigmentation - drug effects</subject><subject>Skin, nail, hair, dermoskeleton</subject><subject>stilbene</subject><subject>Stilbenes - chemical synthesis</subject><subject>Stilbenes - pharmacology</subject><subject>Stilbenes - toxicity</subject><subject>Sunscreening Agents - chemical synthesis</subject><subject>Sunscreening Agents - pharmacology</subject><subject>Sunscreening Agents - toxicity</subject><subject>Superoxide Dismutase - metabolism</subject><subject>Superoxides - antagonists & inhibitors</subject><subject>Ultraviolet Rays</subject><subject>whitening agent</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpF0F1rFDEUBuAgil2rN_4AGRChLc2az5nJlZSitdBqQb0eksyZ3SyzyTbJgmv_vFl26N4kkDw5b3gRek_JnDLRfrYbM5dkLiR5gWaUiwZLxvhLNCOEKMx4zU_Qm5RWhDBJGv4anVCqaq5aNUNPZwLfQ16GvztswP_bja4HD-f4jOP1dL5Zgt-N51ivnYfLSlc_XI5hAb668noMiyoM1a_sxvIeKp0KeAgZfK5u_dIZl0Pci3sYtXe-eoih39rsgn-LXg16TPBu2k_Rn29ff19_x3c_b26vr-6wrZnMuJa6l2ToJSftYFQLyrQ9GADLKAMJvWJGC2GNpKQRDWeEaNY2xvAGrGoGfoo-HuZuYnjcQsrdKmxj-XrqqKgJF0yRuqiLg7IxpBRh6DbRrXXcdZR0-5670nMnSVd6LvjDNHJr1tAf6VRsAZ8moJPV4xC1ty4dnaCtpGyf-uXgVinrBTwDHbOzIzxnHpYSfbxZ6tiB5_8BQOScTQ</recordid><startdate>20020401</startdate><enddate>20020401</enddate><creator>Choi, Sang Yoon</creator><creator>Kim, Sanghee</creator><creator>Kim, Hocheol</creator><creator>Suk, Kyoungho</creator><creator>Hwang, Jae Sung</creator><creator>Lee, Byeong Gon</creator><creator>Kim, Ae-Jung</creator><creator>Kim, Sun Yeou</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</general><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><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope></search><sort><creationdate>20020401</creationdate><title>(4-Methoxy-benzylidene)-(3-methoxy-phenyl)-amine, a Nitrogen Analog of Stilbene as a Potent Inhibitor of Melanin Production</title><author>Choi, Sang Yoon ; Kim, Sanghee ; Kim, Hocheol ; Suk, Kyoungho ; Hwang, Jae Sung ; Lee, Byeong Gon ; Kim, Ae-Jung ; Kim, Sun Yeou</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c625t-65ad50fd5308fb98e9b8debeec212e5ed92ba44cb5107473200a287bb37ec97f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Cell Line</topic><topic>Cell Survival - drug effects</topic><topic>Medical sciences</topic><topic>Melanins - antagonists & inhibitors</topic><topic>Melanins - biosynthesis</topic><topic>Mice</topic><topic>Mice, Inbred C57BL</topic><topic>Monophenol Monooxygenase - antagonists & inhibitors</topic><topic>oxyresveratrol</topic><topic>Pharmacology. Drug treatments</topic><topic>Skin Pigmentation - drug effects</topic><topic>Skin, nail, hair, dermoskeleton</topic><topic>stilbene</topic><topic>Stilbenes - chemical synthesis</topic><topic>Stilbenes - pharmacology</topic><topic>Stilbenes - toxicity</topic><topic>Sunscreening Agents - chemical synthesis</topic><topic>Sunscreening Agents - pharmacology</topic><topic>Sunscreening Agents - toxicity</topic><topic>Superoxide Dismutase - metabolism</topic><topic>Superoxides - antagonists & inhibitors</topic><topic>Ultraviolet Rays</topic><topic>whitening agent</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Choi, Sang Yoon</creatorcontrib><creatorcontrib>Kim, Sanghee</creatorcontrib><creatorcontrib>Kim, Hocheol</creatorcontrib><creatorcontrib>Suk, Kyoungho</creatorcontrib><creatorcontrib>Hwang, Jae Sung</creatorcontrib><creatorcontrib>Lee, Byeong Gon</creatorcontrib><creatorcontrib>Kim, Ae-Jung</creatorcontrib><creatorcontrib>Kim, Sun Yeou</creatorcontrib><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><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Choi, Sang Yoon</au><au>Kim, Sanghee</au><au>Kim, Hocheol</au><au>Suk, Kyoungho</au><au>Hwang, Jae Sung</au><au>Lee, Byeong Gon</au><au>Kim, Ae-Jung</au><au>Kim, Sun Yeou</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>(4-Methoxy-benzylidene)-(3-methoxy-phenyl)-amine, a Nitrogen Analog of Stilbene as a Potent Inhibitor of Melanin Production</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2002-04-01</date><risdate>2002</risdate><volume>50</volume><issue>4</issue><spage>450</spage><epage>452</epage><pages>450-452</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>The current study was carried out to investigate in vitro the effects of (4-methoxy-benzylidene)-(3-methoxy-phenyl)-amine on melanin biosynthesis which is closely related to hyper-pigmentation. (4-Methoxy-benzylidene)-(3-methoxy-phenyl)-amine, a nitrogen analog of stilbene, was synthesized by a single step process. This compound inhibited the tyrosinase activity, which converts dopa to dopachrome in the biosynthetic process of melanin, and showed a UV-blocking effect at UV-B band. The compound also exhibited SOD-like activity, which is involved in the protection against auto-oxidation and inhibited melanin production in melan-a cell line. Our results suggest the possibility that (4-methoxy-benzylidene)-(3-methoxy-phenyl)-amine might be used as a skin whitening agent.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>11963989</pmid><doi>10.1248/cpb.50.450</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Animals Biological and medical sciences Cell Line Cell Survival - drug effects Medical sciences Melanins - antagonists & inhibitors Melanins - biosynthesis Mice Mice, Inbred C57BL Monophenol Monooxygenase - antagonists & inhibitors oxyresveratrol Pharmacology. Drug treatments Skin Pigmentation - drug effects Skin, nail, hair, dermoskeleton stilbene Stilbenes - chemical synthesis Stilbenes - pharmacology Stilbenes - toxicity Sunscreening Agents - chemical synthesis Sunscreening Agents - pharmacology Sunscreening Agents - toxicity Superoxide Dismutase - metabolism Superoxides - antagonists & inhibitors Ultraviolet Rays whitening agent |
| title | (4-Methoxy-benzylidene)-(3-methoxy-phenyl)-amine, a Nitrogen Analog of Stilbene as a Potent Inhibitor of Melanin Production |
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