title: Structure-Activity Relationships of Methylquercetin on Anti-migration and Anti-proliferation Activity in B16 Melanoma Cells.
abstract: Melanoma is a malignant skin tumor and quercetin has been reported to inhibit metastasis. A quercetin glycoside and 7 methylquercetins were synthesized from rutin to investigate structure-activity relationships.
  
  
  
  We evaluated the anti-proliferative and anti-migration activity of quercetin glycoside and 7 methylquercetins in murine B16 melanoma cells by commercially available kits. We also examined the effect of these compounds on growth of human fibroblast cells to evaluate cytotoxicity.
  
  
  
  3-O-methylquercetin (2) exhibited 30, 38, 45% migration activity at 25, 12.5, 6.25 μM respectively. Furthermore, 3,4',7-O-trimethylquercetin (5) and 3,4'-O-dimethylquercetin (3) inhibited migration more potent than 2 with no cytotoxicity. 3-hydroxymethylquercetin and quercetin glycoside exhibited no anti-migration activity. Furthermore, the3and4inhibited melanoma proliferation with no cytotoxicity.
  
  
  
  The methoxyl group at the C-3 position plays an important role in inhibiting the migration of B16 melanoma cells.
authors.affiliation: Department of Medical Physiology, Texas A&M Health Science Center College of Medicine, Temple, TX, U.S.A.
authors.forename: Kosei
authors.initials: K
authors.lastname: Yamauchi
authors.affiliation: United Graduate School of Agricultural Science, Gifu University, Gifu, Japan.
authors.forename: Tohru
authors.initials: T
authors.lastname: Mitsunaga
authors.affiliation: Department of Medical Physiology, Texas A&M Health Science Center College of Medicine, Temple, TX, U.S.A.
authors.forename: Syeda H
authors.initials: SH
authors.lastname: Afroze
authors.affiliation: Department of Obstetrics and Gynecology, Baylor Scott & White Health/Texas A&M Health Science Center College of Medicine, Temple, TX, U.S.A. Mohammad.Uddin1@BSWHealth.org.|Department of Pediatrics, Baylor Scott & White Health/Texas A&M Health Science Center College of Medicine, Temple, TX, U.S.A.|Department of Internal Medicine, Baylor Scott & White Health/Texas A&M Health Science Center College of Medicine, Temple, TX, U.S.A.
authors.forename: Mohammad N
authors.initials: MN
authors.lastname: Uddin
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000494:pharmacology*; D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects*; D002465:Cell Movement / Q000187:drug effects*; D049109:Cell Proliferation / Q000187:drug effects*; D002478:Cells, Cultured; D004305:Dose-Response Relationship, Drug; D005347:Fibroblasts / Q000187:drug effects / Q000473:pathology; D006801:Humans; D008546:Melanoma, Experimental / Q000188:drug therapy / Q000473:pathology*; D051379:Mice; D011794:Quercetin / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D000975:Antioxidants; D011794:Quercetin
keywords: B16 melanoma cells; anti-migration; anti-proliferation; methylquercetin