title: A highly sensitive fluorogenic probe for cytochrome P450 activity in live cells.
abstract: A derivative of rhodamine 110 has been designed and assessed as a probe for cytochrome P450 activity. This probe is the first to utilize a 'trimethyl lock' that is triggered by cleavage of an ether bond. In vitro, fluorescence was manifested by the CYP1A1 isozyme with k(cat)/K(M)=8.8x10(3)M(-1)s(-1) and K(M)=0.09microM. In cellulo, the probe revealed the induction of cytochrome P450 activity by the carcinogen 2,3,7,8-tetrachlorodibenzo-p-dioxin, and its repression by the chemoprotectant resveratrol.
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706-1322, USA.
authors.forename: Melissa M
authors.initials: MM
authors.lastname: Yatzeck
authors.forename: Luke D
authors.initials: LD
authors.lastname: Lavis
authors.forename: Tzu-Yuan
authors.initials: TY
authors.lastname: Chao
authors.forename: Sunil S
authors.initials: SS
authors.lastname: Chandran
authors.forename: Ronald T
authors.initials: RT
authors.lastname: Raines
mesh_terms: D019363:Cytochrome P-450 CYP1A1 / Q000378:metabolism*; D003577:Cytochrome P-450 Enzyme System / Q000032:analysis* / Q000378:metabolism; D005456:Fluorescent Dyes; D006801:Humans; D007527:Isoenzymes; D015394:Molecular Structure; D000072317:Polychlorinated Dibenzodioxins / Q000494:pharmacology*; D011355:Prodrugs / Q000494:pharmacology; D000077185:Resveratrol; D012235:Rhodamines / Q000138:chemical synthesis* / Q000494:pharmacology; D013267:Stilbenes / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D005456:Fluorescent Dyes; D007527:Isoenzymes; D000072317:Polychlorinated Dibenzodioxins; D011355:Prodrugs; D012235:Rhodamines; D013267:Stilbenes; C049025:rhodamine 110; D003577:Cytochrome P-450 Enzyme System; D019363:Cytochrome P-450 CYP1A1; D000077185:Resveratrol