title: Structure-activity relationship of novel menaquinone-4 analogues: modification of the side chain affects their biological activities.
abstract: We synthesized new vitamin K analogues with demethylation or reduction of the double bonds of the side chain of menaquinone-4 (MK-4) and evaluated their SXR-mediated transcriptional activity as well as the extent of their conversion to MK-4. The results indicated that the analogue with the methyl group deleted at the 7' site of the side chain part affected conversion activity to MK-4. In contrast, a decrease in the number of the double bonds in the side chain moiety appeared to decrease the SXR-mediated transcriptional activity.
authors.affiliation: Laboratory of Environmental Sciences, Yokohama College of Pharmacy, 601 Matano-cho, Totsuka-ku, Yokohama 245-0066, Japan.
authors.forename: Yoshitomo
authors.initials: Y
authors.lastname: Suhara
authors.forename: Norika
authors.initials: N
authors.lastname: Hanada
authors.forename: Takashi
authors.initials: T
authors.lastname: Okitsu
authors.forename: Miho
authors.initials: M
authors.lastname: Sakai
authors.forename: Masato
authors.initials: M
authors.lastname: Watanabe
authors.forename: Kimie
authors.initials: K
authors.lastname: Nakagawa
authors.forename: Akimori
authors.initials: A
authors.lastname: Wada
authors.forename: Kazuyoshi
authors.initials: K
authors.lastname: Takeda
authors.forename: Kazuhiko
authors.initials: K
authors.lastname: Takahashi
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Tokiwa
authors.forename: Toshio
authors.initials: T
authors.lastname: Okano
mesh_terms: D045744:Cell Line, Tumor; D003903:Deuterium; D017930:Genes, Reporter; D006801:Humans; D008156:Luciferases / Q000096:biosynthesis / Q000235:genetics; D000077297:Pregnane X Receptor; D011485:Protein Binding; D055503:Protein Multimerization; D011987:Receptors, Steroid / Q000235:genetics / Q000378:metabolism*; D047488:Retinoid X Receptors / Q000378:metabolism; D013329:Structure-Activity Relationship; D014158:Transcription, Genetic / Q000187:drug effects*; D024482:Vitamin K 2 / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000077297:Pregnane X Receptor; D011987:Receptors, Steroid; D047488:Retinoid X Receptors; D024482:Vitamin K 2; C030814:menatetrenone; D003903:Deuterium; D008156:Luciferases