PMID-sentid Pub_year Sent_text comp_official_name comp_offsetprotein_name organism prot_offset 28278026-0 2018 7,8-benzoflavone binding to human cytochrome P450 3A4 reveals complex fluorescence quenching, suggesting binding at multiple protein sites. alpha-naphthoflavone 0-16 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 34-53 33790108-3 2021 The Michaelis constants (Km) for progesterone 6beta-hydroxylation by CYP3A5 were markedly decreased in the presence of dehydroepiandrosterone (DHEA) and alpha-naphthoflavone (ANF), whereas progesterone and DHEA competitively inhibited testosterone 6beta-hydroxylation mediated by CYP3A4, and progesterone competitively inhibited CYP3A5-mediated activity, which was weaker than that for CYP3A4. alpha-naphthoflavone 153-173 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 280-286 33790108-3 2021 The Michaelis constants (Km) for progesterone 6beta-hydroxylation by CYP3A5 were markedly decreased in the presence of dehydroepiandrosterone (DHEA) and alpha-naphthoflavone (ANF), whereas progesterone and DHEA competitively inhibited testosterone 6beta-hydroxylation mediated by CYP3A4, and progesterone competitively inhibited CYP3A5-mediated activity, which was weaker than that for CYP3A4. alpha-naphthoflavone 153-173 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 386-392 33790108-3 2021 The Michaelis constants (Km) for progesterone 6beta-hydroxylation by CYP3A5 were markedly decreased in the presence of dehydroepiandrosterone (DHEA) and alpha-naphthoflavone (ANF), whereas progesterone and DHEA competitively inhibited testosterone 6beta-hydroxylation mediated by CYP3A4, and progesterone competitively inhibited CYP3A5-mediated activity, which was weaker than that for CYP3A4. alpha-naphthoflavone 175-178 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 280-286 33790108-3 2021 The Michaelis constants (Km) for progesterone 6beta-hydroxylation by CYP3A5 were markedly decreased in the presence of dehydroepiandrosterone (DHEA) and alpha-naphthoflavone (ANF), whereas progesterone and DHEA competitively inhibited testosterone 6beta-hydroxylation mediated by CYP3A4, and progesterone competitively inhibited CYP3A5-mediated activity, which was weaker than that for CYP3A4. alpha-naphthoflavone 175-178 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 386-392 33790108-4 2021 ANF noncompetitively inhibited testosterone 6beta-hydroxylation mediated by both CYP3A4 and CYP3A5. alpha-naphthoflavone 0-3 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 81-87 23651100-0 2013 Pivotal role of P450-P450 interactions in CYP3A4 allostery: the case of alpha-naphthoflavone. alpha-naphthoflavone 72-92 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 42-48 23651100-1 2013 We investigated the relationship between oligomerization of CYP3A4 (cytochrome P450 3A4) and its response to ANF (alpha-naphthoflavone), a prototypical heterotropic activator. alpha-naphthoflavone 114-134 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 60-66 23651100-1 2013 We investigated the relationship between oligomerization of CYP3A4 (cytochrome P450 3A4) and its response to ANF (alpha-naphthoflavone), a prototypical heterotropic activator. alpha-naphthoflavone 114-134 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 68-87 23434495-9 2013 Both quercetin (CYP2C8 inhibitor) and ketoconazole (CYP3A4 inhibitor) showed 60-100% inhibition of M1-M4 and M6 formations in HLMs, while M5 formation was mainly inhibited by alpha-naphthoflavone (CYP1A2 inhibitor, 70-80%) and quercetin (90%). alpha-naphthoflavone 175-195 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 52-58 17573349-5 2007 We explore the energetics of four ligands (6-(p-toluidino)-2-naphthalenesulfonic acid (TNS), alpha-naphthoflavone (ANF), miconazole, and bromocriptine) binding to CYP3A4 incorporated into Nanodiscs. alpha-naphthoflavone 93-113 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 163-169 22004098-0 2011 Allosteric activation of cytochrome P450 3A4 by alpha-naphthoflavone: branch point regulation revealed by isotope dilution analysis. alpha-naphthoflavone 48-68 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 25-44 21177853-0 2011 Analysis of heterotropic cooperativity in cytochrome P450 3A4 using alpha-naphthoflavone and testosterone. alpha-naphthoflavone 68-88 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 42-61 21177853-1 2011 Cytochrome P450 3A4 (CYP3A4) displays non-Michaelis-Menten kinetics for many of the substrates it metabolizes, including testosterone (TST) and alpha-naphthoflavone (ANF). alpha-naphthoflavone 144-164 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 0-19 21177853-1 2011 Cytochrome P450 3A4 (CYP3A4) displays non-Michaelis-Menten kinetics for many of the substrates it metabolizes, including testosterone (TST) and alpha-naphthoflavone (ANF). alpha-naphthoflavone 144-164 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 21-27 21177853-1 2011 Cytochrome P450 3A4 (CYP3A4) displays non-Michaelis-Menten kinetics for many of the substrates it metabolizes, including testosterone (TST) and alpha-naphthoflavone (ANF). alpha-naphthoflavone 166-169 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 0-19 21177853-1 2011 Cytochrome P450 3A4 (CYP3A4) displays non-Michaelis-Menten kinetics for many of the substrates it metabolizes, including testosterone (TST) and alpha-naphthoflavone (ANF). alpha-naphthoflavone 166-169 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 21-27 19299527-5 2009 Upon addition of alpha-naphthoflavone (25 microM), human CYP3A4 showed a slightly decreased substrate concentration at which 50% of the maximal rate V(max) is reached for 7-BFC, whereas chimpanzee CYP3A4 showed a >2-fold increase. alpha-naphthoflavone 17-37 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 57-63 21218106-4 2008 The aim of this study was to evaluate the efficiency of different in vitro systems containing individual enzymes of the mixed-function monooxygenase system to oxidize two model substrates of CYP3A enzymes, exogenous and endogenous compounds, alpha-naphtoflavone (alpha-NF) and testosterone, respectively. alpha-naphthoflavone 242-261 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 191-196 17573349-7 2007 The dissociation constants for binding to the active site in CYP3A4-Nanodiscs were 4.0 microm for TNS, 5.8 microm for ANF, 0.45 microm for miconazole, and 0.45 microm for bromocriptine. alpha-naphthoflavone 118-121 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 61-67 17459328-0 2007 Energetics of heterotropic cooperativity between alpha-naphthoflavone and testosterone binding to CYP3A4. alpha-naphthoflavone 49-69 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 98-104 17459328-2 2007 Heterotropic cooperativity of drug binding to CYP3A4 was examined with the flavanoid, alpha-naphthoflavone (ANF) and the steroid, testosterone (TST). alpha-naphthoflavone 86-106 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 46-52 17459328-2 2007 Heterotropic cooperativity of drug binding to CYP3A4 was examined with the flavanoid, alpha-naphthoflavone (ANF) and the steroid, testosterone (TST). alpha-naphthoflavone 108-111 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 46-52 15870379-1 2005 The role of cytochrome b(5) (b(5)) in the alpha-naphthoflavone (alpha-NF)-mediated inhibition of H(2)O(2)-supported 7-benzyloxyquinoline (7-BQ) debenzylation by heterologously expressed and purified cytochrome P450 3A4 (CYP3A4) was studied. alpha-naphthoflavone 42-62 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 199-218 17198380-0 2007 Mechanism of interactions of alpha-naphthoflavone with cytochrome P450 3A4 explored with an engineered enzyme bearing a fluorescent probe. alpha-naphthoflavone 29-49 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 55-74 15870379-1 2005 The role of cytochrome b(5) (b(5)) in the alpha-naphthoflavone (alpha-NF)-mediated inhibition of H(2)O(2)-supported 7-benzyloxyquinoline (7-BQ) debenzylation by heterologously expressed and purified cytochrome P450 3A4 (CYP3A4) was studied. alpha-naphthoflavone 42-62 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 220-226 15870379-1 2005 The role of cytochrome b(5) (b(5)) in the alpha-naphthoflavone (alpha-NF)-mediated inhibition of H(2)O(2)-supported 7-benzyloxyquinoline (7-BQ) debenzylation by heterologously expressed and purified cytochrome P450 3A4 (CYP3A4) was studied. alpha-naphthoflavone 64-72 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 199-218 15870379-1 2005 The role of cytochrome b(5) (b(5)) in the alpha-naphthoflavone (alpha-NF)-mediated inhibition of H(2)O(2)-supported 7-benzyloxyquinoline (7-BQ) debenzylation by heterologously expressed and purified cytochrome P450 3A4 (CYP3A4) was studied. alpha-naphthoflavone 64-72 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 220-226 15546903-7 2005 24-Hydroxylase activity in recombinant CYP3A4 and pooled human liver microsomes showed dose-dependent inhibition by ketoconazole, troleandomycin, alpha-naphthoflavone, and isoniazid, known inhibitors of CYP3A4. alpha-naphthoflavone 146-166 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 39-45 15546903-7 2005 24-Hydroxylase activity in recombinant CYP3A4 and pooled human liver microsomes showed dose-dependent inhibition by ketoconazole, troleandomycin, alpha-naphthoflavone, and isoniazid, known inhibitors of CYP3A4. alpha-naphthoflavone 146-166 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 203-209 10821163-10 2000 Furafylline, quinidine and alpha-naphthoflavone activated CYP3A4-catalysed phenanthrene metabolism by 1.7-, 2- and 15-fold respectively. alpha-naphthoflavone 27-47 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 58-64 15005856-14 2004 Activity in recombinant CYP3A4 and pooled liver microsomes was dose-dependently inhibited by ketoconazole, troleandomycin, isoniazid, and alpha-naphthoflavone, known inhibitors of CYP3A4. alpha-naphthoflavone 138-158 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 24-30 15005856-14 2004 Activity in recombinant CYP3A4 and pooled liver microsomes was dose-dependently inhibited by ketoconazole, troleandomycin, isoniazid, and alpha-naphthoflavone, known inhibitors of CYP3A4. alpha-naphthoflavone 138-158 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 180-186 12893521-7 2003 Additionally, 7-benzyloxyresorufin O-debenzylation by recombinant CYP3A4 was increased by the addition of alpha-naphthoflavone, testosterone and progesterone but not by quinidine, whereas no chemicals tested could activate the O-debenzylation of 7-benzyloxyresorufin by CYP2B6. alpha-naphthoflavone 106-126 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 66-72 12067248-11 2002 alpha-Naphthoflavone (alpha-NF), a well-known activator of CYP3A4, did not stimulate 7-BQ oxidation by A245T, although the S(50) value for alpha-NF binding to wild-type P450eryF was similar to P450 3A4. alpha-naphthoflavone 0-20 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 59-65 12067248-11 2002 alpha-Naphthoflavone (alpha-NF), a well-known activator of CYP3A4, did not stimulate 7-BQ oxidation by A245T, although the S(50) value for alpha-NF binding to wild-type P450eryF was similar to P450 3A4. alpha-naphthoflavone 22-30 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 59-65 11054425-2 2001 In the present study, we observed that alpha-naphthoflavone (alpha-NF) exhibited a differential effect on CYP3A4-mediated product formation as shown by an increase and decrease, respectively, of the carboxylic acid (P(2)) and omega-3-hydroxylated (P(1)) metabolites of losartan, while losartan was found to be an inhibitor of the formation of the 5,6-epoxide of alpha-NF. alpha-naphthoflavone 39-59 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 106-112 11054425-2 2001 In the present study, we observed that alpha-naphthoflavone (alpha-NF) exhibited a differential effect on CYP3A4-mediated product formation as shown by an increase and decrease, respectively, of the carboxylic acid (P(2)) and omega-3-hydroxylated (P(1)) metabolites of losartan, while losartan was found to be an inhibitor of the formation of the 5,6-epoxide of alpha-NF. alpha-naphthoflavone 61-69 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 106-112 10385214-7 1999 alpha-Naphthoflavone, a CYP 3A activator, increased metabolite formation. alpha-naphthoflavone 0-20 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 24-30 10548449-4 1999 The activation of POD activity in human liver microsomes by alphanaphthoflavone was inhibited by 100 microM aniline, anti-CYP2E1 antibody, 1 microM ketoconazole and anti-CYP3A4 antibody. alpha-naphthoflavone 60-79 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 170-176 10548449-8 1999 The activation of POD activity by alpha-naphthoflavone was observed for CYP3A4, but not for CYP2E1. alpha-naphthoflavone 34-54 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 72-78 10548449-9 1999 Co-expression of b5 with CYP3A4 enhanced the activation of POD activity by alpha-naphthoflavone. alpha-naphthoflavone 75-95 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 25-31 9825830-8 1998 CPHP and haloperidol formation were, moreover, enhanced by alpha-naphthoflavone, an effect known for CYP3A4 mediated reactions. alpha-naphthoflavone 59-79 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 101-107 10022752-0 1998 Human cytochrome P450 3A (CYP3A) mediated midazolam metabolism: the effect of assay conditions and regioselective stimulation by alpha-naphthoflavone, terfenadine and testosterone. alpha-naphthoflavone 129-149 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 6-24 9521735-5 1998 7, 8-Benzoflavone activation of phenanthrene metabolism by CYP3A4 and dapsone activation of flurbiprofen and naproxen metabolism by CYP2C9 were also observed. alpha-naphthoflavone 0-17 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 59-65 10022752-0 1998 Human cytochrome P450 3A (CYP3A) mediated midazolam metabolism: the effect of assay conditions and regioselective stimulation by alpha-naphthoflavone, terfenadine and testosterone. alpha-naphthoflavone 129-149 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 26-31 10022752-1 1998 The effect of ionic strength, assay constituents, alpha-naphthoflavone (aNF), terfenadine and testosterone on human CYP3A mediated midazolam (MDZ) 1"-hydroxylation (MDZ 1"-OH) and 4-hydroxylation (MDZ 4-OH) in vitro was examined. alpha-naphthoflavone 50-70 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 116-121 10022752-1 1998 The effect of ionic strength, assay constituents, alpha-naphthoflavone (aNF), terfenadine and testosterone on human CYP3A mediated midazolam (MDZ) 1"-hydroxylation (MDZ 1"-OH) and 4-hydroxylation (MDZ 4-OH) in vitro was examined. alpha-naphthoflavone 72-75 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 116-121 9220969-1 1997 Cassette mutagenesis and site-directed mutagenesis were used to investigate the importance of individual amino acid residues at positions 364-377 of cytochrome P450 3A4 in determining steroid hydroxylation or stimulation by alpha-naphthoflavone. alpha-naphthoflavone 224-244 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 149-168 9473295-0 1998 Analysis of four residues within substrate recognition site 4 of human cytochrome P450 3A4: role in steroid hydroxylase activity and alpha-naphthoflavone stimulation. alpha-naphthoflavone 133-153 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 71-90 9431830-6 1997 The CYP3A inducer, alpha-naphthoflavone, increased N-demethylation rates. alpha-naphthoflavone 19-39 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 4-9 9223567-9 1997 Some inhibition was produced by alpha-naphthoflavone, a chemical that inhibits CYP1As and also interacts with CYP3A4. alpha-naphthoflavone 32-52 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 110-116 9202751-3 1997 In the presence of flavonoids such as alpha-naphthoflavone and flavone, both CYP3A4 and CYP3A5 have also been shown to play a minor role in the activation of food-derived heterocyclic amines. alpha-naphthoflavone 38-58 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 77-83 7833826-1 1994 7,8-Benzoflavone(ANF) is a potent in vitro inhibitor of CYP1A2 but is an in vitro activator of CYP3A4. alpha-naphthoflavone 0-16 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 95-101 8886602-9 1996 alpha-Naphthoflavone stimulated 1"-OH metabolite formation in human and cDNA-expressed human CYP3A4 microsomes at low concentration (10 microM). alpha-naphthoflavone 0-20 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 93-99 7883227-10 1995 In addition to those localisation studies, the capacity of expressed CYP3A4 and CYP3A5 to activate the dietary heterocyclic amine MeIQ in the presence of alpha-naphthoflavone was shown. alpha-naphthoflavone 154-174 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 69-75 8010982-5 1994 Results of the study showed that: (1) purified CYP3A4 catalyzed 10,11-epoxidation; (2) cDNA-expressed CYP3A4 catalyzed 10,11-epoxidation (Vmax = 1730 pmol/min/nmol P450, Km = 442 microM); (3) the rate of 10,11-epoxidation correlated with CYP3A4 content in microsomes from sixteen human livers (r2 = 0.57, P < 0.001); (4) triacetyloleandomycin and anti-CYP3A4 IgG reduced 10,11-epoxidation to 31 +/- 6% (sixteen livers) and 43 +/- 2% (four livers) of control rates, respectively; and (5) microsomal 10,11-epoxidation but not phenol formation was activated 2- to 3-fold by alpha-naphthoflavone and progesterone and by carbamazepine itself (substrate activation). alpha-naphthoflavone 574-594 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 47-53 8010982-5 1994 Results of the study showed that: (1) purified CYP3A4 catalyzed 10,11-epoxidation; (2) cDNA-expressed CYP3A4 catalyzed 10,11-epoxidation (Vmax = 1730 pmol/min/nmol P450, Km = 442 microM); (3) the rate of 10,11-epoxidation correlated with CYP3A4 content in microsomes from sixteen human livers (r2 = 0.57, P < 0.001); (4) triacetyloleandomycin and anti-CYP3A4 IgG reduced 10,11-epoxidation to 31 +/- 6% (sixteen livers) and 43 +/- 2% (four livers) of control rates, respectively; and (5) microsomal 10,11-epoxidation but not phenol formation was activated 2- to 3-fold by alpha-naphthoflavone and progesterone and by carbamazepine itself (substrate activation). alpha-naphthoflavone 574-594 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 102-108 8010982-5 1994 Results of the study showed that: (1) purified CYP3A4 catalyzed 10,11-epoxidation; (2) cDNA-expressed CYP3A4 catalyzed 10,11-epoxidation (Vmax = 1730 pmol/min/nmol P450, Km = 442 microM); (3) the rate of 10,11-epoxidation correlated with CYP3A4 content in microsomes from sixteen human livers (r2 = 0.57, P < 0.001); (4) triacetyloleandomycin and anti-CYP3A4 IgG reduced 10,11-epoxidation to 31 +/- 6% (sixteen livers) and 43 +/- 2% (four livers) of control rates, respectively; and (5) microsomal 10,11-epoxidation but not phenol formation was activated 2- to 3-fold by alpha-naphthoflavone and progesterone and by carbamazepine itself (substrate activation). alpha-naphthoflavone 574-594 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 102-108 8010982-5 1994 Results of the study showed that: (1) purified CYP3A4 catalyzed 10,11-epoxidation; (2) cDNA-expressed CYP3A4 catalyzed 10,11-epoxidation (Vmax = 1730 pmol/min/nmol P450, Km = 442 microM); (3) the rate of 10,11-epoxidation correlated with CYP3A4 content in microsomes from sixteen human livers (r2 = 0.57, P < 0.001); (4) triacetyloleandomycin and anti-CYP3A4 IgG reduced 10,11-epoxidation to 31 +/- 6% (sixteen livers) and 43 +/- 2% (four livers) of control rates, respectively; and (5) microsomal 10,11-epoxidation but not phenol formation was activated 2- to 3-fold by alpha-naphthoflavone and progesterone and by carbamazepine itself (substrate activation). alpha-naphthoflavone 574-594 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 102-108 8204577-2 1994 It is reported that CYP3A4-catalyzed phenanthrene metabolism is activated by 7,8-benzoflavone and that 7,8-benzoflavone serves as a substrate for CYP3A4. alpha-naphthoflavone 77-93 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 20-26 8204577-2 1994 It is reported that CYP3A4-catalyzed phenanthrene metabolism is activated by 7,8-benzoflavone and that 7,8-benzoflavone serves as a substrate for CYP3A4. alpha-naphthoflavone 103-119 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 20-26 8204577-2 1994 It is reported that CYP3A4-catalyzed phenanthrene metabolism is activated by 7,8-benzoflavone and that 7,8-benzoflavone serves as a substrate for CYP3A4. alpha-naphthoflavone 103-119 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 146-152 8054246-11 1994 Proguanil activation was inhibited by R,S-mephenytoin, troleandomycin and by inhibitory anti-CYP3A antiserum and anti-CYP2C IgG and was activated by alpha-naphthoflavone. alpha-naphthoflavone 149-169 cytochrome P450 family 3 subfamily A member 4 Homo sapiens 93-98