Interactions of safrole and isosafrole and their metabolites with cytochromes P-450.

Abstract:

:The structural features which determine interaction of safrole and related methylenedioxyphenyl compounds with cytochromes P-450 or P-448, and determine the induction of these two classes of the cytochrome, have been studied. All methylenedioxyphenyl compounds studied interact with both cytochromes P-450 and P-448 eliciting type I spectral changes and it has been found that the allyl 4-substituent is important in these interactions. Methylenedioxyphenyl compounds with an oxidised allyl 4-substituent exhibited higher affinity for cytochrome P-448 while those possessing an intact allyl or methylvinyl group generally showed higher affinity for cytochrome P-450. Compounds possessing intact allyl and methylenedioxyphenyl groups (safrole, isosafrole and myristicine) were the most potent inducers of cytochromes P-450 and P-448; compounds containing an intact allyl group only (estragole, allybenzene and eugenol methyl ether) or an oxidized allyl group and an intact methylenedioxyphenyl group (epoxysafrole) were inducers of P-448 only.

journal_name

Chem Biol Interact

authors

Ioannides C,Delaforge M,Parke DV

doi

10.1016/s0009-2797(85)80106-x

subject

Has Abstract

pub_date

1985-05-01 00:00:00

pages

303-11

issue

3

eissn

0009-2797

issn

1872-7786

journal_volume

53

pub_type

杂志文章
  • Template properties of DNA alkylated with N-methyl-N-nitrosourea and N-ethyl-N-nitrosourea.

    abstract::Alkylation of DNA with N-methyl-N-nitrosourea (MeNU) and N-ethyl-N-nitrosourea (EtNU) reduces its ability to support RNA synthesis catalyzed by exogenously added RNA polymerase. It is likely that 7-alkylguanine and alkyl phosphotriester in DNA are mainly responsible for the inhibition of RNA synthesis. The inhibitory ...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/0009-2797(83)90027-3

    authors: Marushige K,Marushige Y

    更新日期:1983-09-01 00:00:00

  • Response of Drosophila melanogaster to selection for P450-mediated resistance to isoquinoline alkaloids.

    abstract::Several species of columnar cacti in the Sonoran Desert contain isoquinoline alkaloids that are toxic to all but the resident drosophilids that feed and breed in necrotic stems. Cytochrome P450 enzymes are known to be involved in the metabolic detoxification of these alkaloids by the desert Drosophila and are conseque...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/s0009-2797(99)00161-1

    authors: Fogleman JC

    更新日期:2000-03-01 00:00:00

  • Lycium barbarum polysaccharides reduce intestinal ischemia/reperfusion injuries in rats.

    abstract::Inflammation and oxidative stress exert important roles in intestinal ischemia-reperfusion injury (IRI). Lycium barbarum polysaccharides (LBPs) have shown effective antioxidative and immunomodulatory functions in different models. The purpose of the present study was to assess the effects and potential mechanisms of L...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/j.cbi.2013.05.010

    authors: Yang X,Bai H,Cai W,Li J,Zhou Q,Wang Y,Han J,Zhu X,Dong M,Hu D

    更新日期:2013-08-25 00:00:00

  • Mercury inhibition of avian fatty acid synthetase complex.

    abstract::(1) Subcutaneous or intra-abdominal injections of 8 mg of HgCl2/100 g body weight markedly depressed hepatic fatty acid synthetase activity of chicks at 1 h post-injection. The depression occurred despite the fact that the chicks continued to eat up until the time they were killed. Under these same conditions, the hep...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/0009-2797(75)90003-4

    authors: Donaldson WE

    更新日期:1975-11-01 00:00:00

  • Induction of rat liver O6-alkylguanine-DNA alkyltransferase by bleomycin.

    abstract::Alkyl adducts at the O6-position of guanine constitute promutagenic DNA lesions likely to be involved in the initiation of malignant transformation. They can be removed by a cellular acceptor protein termed O6-alkylguanine-DNA alkyltransferase (AT). In rat liver this repair enzyme can be induced by a variety of hepato...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/0009-2797(86)90060-8

    authors: Schmerold I,Spath A

    更新日期:1986-12-01 00:00:00

  • Comparison of methods used for the determination of cholinesterase activity in whole blood.

    abstract::Cholinesterases (ChEs) are classified as either acetylcholinesterase (AChE) or butyrylcholinesterase (BChE) based on their substrate and inhibitor specificity. Organophosphate and carbamate compounds commonly represented by herbicides, pesticides, and nerve gases irreversibly inhibit ChEs. Therefore, exposure to organ...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/j.cbi.2008.05.002

    authors: Naik RS,Doctor BP,Saxena A

    更新日期:2008-09-25 00:00:00

  • Germanium oxide inhibits the transition from G2 to M phase of CHO cells.

    abstract::We report here for the first time that germanium oxide (GeO(2)) blocks cell progression. GeO(2) is not genotoxic to Chinese hamster ovary (CHO) cells and has limited cytotoxicity. However, GeO(2) arrests cells at G2/M phase. The proportion of cells stopped at G2/M phase increased dose-dependently up to 5 mM GeO(2) whe...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/s0009-2797(02)00072-8

    authors: Chiu SJ,Lee MY,Chen HW,Chou WG,Lin LY

    更新日期:2002-10-20 00:00:00

  • Cadmium induces the activation of cell wall integrity pathway in budding yeast.

    abstract::MAP kinases are important signaling molecules regulating cell survival, proliferation and differentiation, and can be activated by cadmium stress. In this study, we demonstrate that cadmium induces phosphorylation of the yeast cell wall integrity (CWI) pathway_MAP kinase Slt2, and this cadmium-induced CWI activation i...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/j.cbi.2015.09.007

    authors: Xiong B,Zhang L,Xu H,Yang Y,Jiang L

    更新日期:2015-10-05 00:00:00

  • Association of variants of the -116 site of the butyrylcholinesterase BCHE gene to enzyme activity and body mass index.

    abstract::Butyrylcholinesterase (BChE) is coded by the BCHE gene that presents four exons. The non-codifying exon 1 presents two variants -116G and -116A, being -116A preferentially in cis conformation with the 539T variant (K) of exon 4 which was associated with lower BChE activity and lower body mass index (BMI) variance. Thi...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/j.cbi.2008.04.019

    authors: Furtado-Alle L,Andrade FA,Nunes K,Mikami LR,Souza RL,Chautard-Freire-Maia EA

    更新日期:2008-09-25 00:00:00

  • Tetraalkylammonium ions: protection of murine L1210 leukemia and bone marrow progenitor cells in vitro against mechlorethamine cytotoxicity and inhibition of the choline transport system.

    abstract::In the series of tetraalkylammonium ions from tetramethylammonium to tetra-n-heptylammonium, tetra-n-pentylammonium ion was a potent protector of both murine L1210 leukemia and bone marrow progenitor cells against mechlorethamine cytotoxicity. It was also a non-competitive inhibitor of choline uptake. Phosphonium anal...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/0009-2797(82)90095-3

    authors: Naujokaitis SA,Fisher JM,Rabinovitz M

    更新日期:1982-06-01 00:00:00

  • A new post-intoxication treatment of paraoxon and parathion poisonings using an evolved PON1 variant and recombinant GOT1.

    abstract::Organophosphate (OP) based pesticides are highly toxic compounds that are still widely used in agriculture around the world. According to World Health Organization (WHO) data, it is estimated that between 250,000 and 370,000 deaths occur yearly around the globe as a result of acute intoxications by pesticides. Current...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/j.cbi.2016.05.034

    authors: Goldsmith M,Ashani Y,Margalit R,Nyska A,Mirelman D,Tawfik DS

    更新日期:2016-11-25 00:00:00

  • Effect of enzyme inducers on metabolism of 1-nitropyrene in human hepatoma cell line HepG2.

    abstract::We measured the response of HepG2 cells to the classic cytochrome (cyt.) P-450 inducers 3-methylcholanthrene (3-MC) and phenobarbital (PB), by evaluating oxidative and/or reductive metabolism of the nitroarenes, 1-NP and 1,6-dinitropyrene (1,6-DNP), in control and induced cells. In HepG2 cells, 3-MC induces ring-hydro...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/0009-2797(91)90057-e

    authors: Belisario MA,Arena AR,Pecce R,Borgia R,Staiano N,De Lorenzo F

    更新日期:1991-01-01 00:00:00

  • Inhibition of stage-specific DNA synthesis in rat spermatogenic cells by polycyclic aromatic hydrocarbons.

    abstract::Changes in the rate of DNA synthesis in spermatogenic cells after treatment of segments of rat seminiferous tubule at defined stages of epithelial cycle with benzo[a]pyrene (BP) or 7,12-methylbenz[a]anthracene (DMBA) were studied. The incorporation of labeled thymidine into DNA was used as a measure of the rate of DNA...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/0009-2797(89)90019-7

    authors: Georgellis A,Parvinen M,Rydström J

    更新日期:1989-01-01 00:00:00

  • Interactions of pyrethroids with phosphatidylcholine bilayers: comparisons in liposomal systems exhibiting large or small radii of curvature.

    abstract::Pyrethroid interactions with dipalmitoyl phosphatidylcholine (DPPC) vesicles have been characterized in bilayers having large and small radii of curvature. The abilities of pyrethroids to alter the gel-fluid phase transition profiles were determined by steady state fluorescence anisotropy and phase-modulation lifetime...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/s0009-2797(85)80156-3

    authors: Stelzer KJ,Gordon MA

    更新日期:1985-06-01 00:00:00

  • Joint toxic effects of the type-2 alkene electrophiles.

    abstract::Human populations are exposed to complex environmental mixtures of acrolein, methylvinyl ketone (MVK) and other type-2 alkenes. Many members of this chemical class are electrophiles that possess a common molecular mechanism of toxicity; i.e., protein inactivation via formation of stable cysteine adducts. Therefore, ac...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/j.cbi.2016.06.014

    authors: Zhang L,Geohagen BC,Gavin T,LoPachin RM

    更新日期:2016-07-25 00:00:00

  • Butyrylcholinesterase radioligands to image Alzheimer's disease brain.

    abstract::Butyrylcholinesterase (BuChE) is found to have a brain distribution pattern that is distinct from that of acetylcholinesterase (AChE). Neurons containing BuChE are particularly located in the amygdala, hippocampal formation and the thalamus, structures involved in the normal functions of cognition and behavior that ty...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/j.cbi.2012.08.009

    authors: Darvesh S

    更新日期:2013-03-25 00:00:00

  • Non-enzymatic modifications of prostaglandin H synthase 1 affect bifunctional enzyme activity - Implications for the sensitivity of blood platelets to acetylsalicylic acid.

    abstract::Due to its ability to inhibit the blood platelet PGHS-1, acetylsalicylic acid (ASA, Aspirin(®)) is widely used as a preventive agent in atherothrombotic diseases. However, its beneficial effects seem to be lower in diabetic patients, suggesting that protein glycation may impair effective ASA-mediated acetylation proce...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/j.cbi.2016.04.021

    authors: Kassassir H,Siewiera K,Talar M,Stec-Martyna E,Pawlowska Z,Watala C

    更新日期:2016-06-25 00:00:00

  • The affinity of cytochrome P-450 for ethyl isocyanide: an explanation of double soret spectra.

    abstract::The 2 pH dependent peaks formed in the Soret region by the treatment of reduced hepatic microsomes or purified cytochrome P-448 with ethyl isocyanide do not exhibit identical dependence on ethyl isocyanide concentration. This behavior and other facts regarding double Soret spectra can be explained by a simple expostul...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/0009-2797(78)90051-0

    authors: Dahl AR,Hodgson E

    更新日期:1978-02-01 00:00:00

  • Conjugation of anti-dihydrodiol epoxides of benzo[a]pyrene, chrysene, benzo[c]phenanthrene and dibenz[a,h]anthracene with glutathione catalyzed by cytosol and by the Mu-class glutathione transferase HTP II from rat liver.

    abstract::The (+/-)-anti-dihydrodiol epoxides (DE) of benzo[a]pyrene (BP), chrysene (Chr), benzo[c]phenanthrene (BcPh) and dibenz[a,h]anthracene (DBA) were incubated in the presence of glutathione (GSH) with hepatic cytosol from untreated and Aroclor 1254 pretreated rats and with the Mu-class glutathione transferase (GST) HTP I...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/0009-2797(94)03357-9

    authors: Funk M,Gath I,Seidel A,Oesch F,Platt KL

    更新日期:1995-03-30 00:00:00

  • Dihydrotanshinone I inhibits the translational expression of hypoxia-inducible factor-1α.

    abstract::The hypoxia-inducible factor-1 (HIF-1) has been known to be correlated to the adaptation and proliferation of tumor cells; therefore HIF-1 has become an important target in the development of anticancer drugs. Dihydrotanshinone I (DHTS) is a phenanthrenequinone compound from Salvia miltiorrhiza Bunge, which has been u...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/j.cbi.2015.08.006

    authors: Li J,Mi C,Ma J,Wang KS,Lee JJ,Jin X

    更新日期:2015-10-05 00:00:00

  • CRKL promotes cell proliferation in gastric cancer and is negatively regulated by miR-126.

    abstract::V-crk avian sarcoma virus CT10 oncogene homolog-like (CRKL) is a member of CRK family and act as an adaptor protein participating in intra-cellular signal transduction. The role of CRKL in gastric cancer (GC) remains unclear. In this study, we show that CRKL was aberrantly highly expressed in both GC tumor specimens a...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/j.cbi.2013.09.003

    authors: Wang J,Chen X,Li P,Su L,Yu B,Cai Q,Li J,Yu Y,Liu B,Zhu Z

    更新日期:2013-11-25 00:00:00

  • Purification and characterization of two distinct aldehyde-oxidizing enzymes from the liver of black seabream.

    abstract::Two aldehyde dehydrogenases (ALDH) were purified from the liver of black seabream (Acanthopagrus schlegeli). Chromatography of the liver homogenate on an alpha-cyanocinnamate-Sepharose affinity column results in two activity peaks using acetaldehyde as the substrate. The eluate was subjected to another affinity chroma...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/s0009-2797(02)00200-4

    authors: Fong WP,Cheng CH,Tang WK

    更新日期:2003-02-01 00:00:00

  • Evidence that covalent binding of metabolically activated phenol to microsomal proteins is caused by oxidised products of hydroquinone and catechol.

    abstract::The metabolic activation of [14C]phenol resulting in covalent binding to proteins has been studied in rat liver microsomes. The covalent binding was dependent on microsomal enzymes and NADPH and showed saturation kinetics for phenol with a Km-value of 0.04 mM. The metabolites hydroquinone and catechol were formed at r...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/s0009-2797(85)80140-x

    authors: Wallin H,Melin P,Schelin C,Jergil B

    更新日期:1985-11-01 00:00:00

  • Radiomimetic property of furazolidone and the caffeine enhancement of its lethal action on the vibrios.

    abstract::Sensitivities of the strains belonging to four vibrio biotypes to the action of furazolidone were investigated. Vibrio cholerae (classical) was most and Vibrio parahaemolyticus least sensitive to this drug. Statistical analyses revealed significant differences between any two of the four types of vibrio in respect of ...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/0009-2797(81)90118-6

    authors: Banerjee SK,Chatterjee SN

    更新日期:1981-11-01 00:00:00

  • Gallic acid and ferulic acid protect the liver from thioacetamide-induced fibrosis in rats via differential expression of miR-21, miR-30 and miR-200 and impact on TGF-β1/Smad3 signaling.

    abstract::This study evaluates the possible protective effects of gallic acid (GaA) and ferulic acid (FeA) against an experimentally induced liver fibrosis by thioacetamide (TAA) in rats. Animals were divided into: Control group, GaA group (20 mg/kg/day, p.o), FeA (20 mg/kg/day, p.o), TAA group (receiving 250 mg/kg twice/week, ...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/j.cbi.2020.109098

    authors: Hussein RM,Anwar MM,Farghaly HS,Kandeil MA

    更新日期:2020-06-01 00:00:00

  • Nitrative modifications of α-enolase in hepatic proteins from diabetic rats: the involvement of myeloperoxidase.

    abstract::Many studies reported that oxidative and nitrative stress might be important in the pathogenesis of diabetes and the development of its complications. In this study, we showed that α-enolase (EC 4.2.1.11, 2-phospho-d-glycerate hydrolase) was identified as the important target for oxidative and nitrative modifications ...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/j.cbi.2014.05.021

    authors: Lu N,Li J,He Y,Tian R,Xiao Q

    更新日期:2014-09-05 00:00:00

  • Compounds with the dioxopyrimidine cycle inhibit cholinesterases from different groups of animals.

    abstract::We firstly synthesized derivatives of 6-methyluracil, alloxazine, and xanthine, containing omega-tetraalkylammonium (TAA) groups at the N(1) and N(3) atoms in a pyrimidine cycle and assayed their anticholinesterase activities. Compounds with triethylpentylammoniumalkyl groups behaved as typical reversible inhibitors o...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/j.cbi.2008.05.037

    authors: Anikienko KA,Bychikhin EA,Reznik VS,Akamsin D,Galyametdinova IV

    更新日期:2008-09-25 00:00:00

  • Acetaminophen hepatotoxicity and sterile inflammation: The mechanism of protection of Chlorogenic acid.

    abstract::Acetaminophen hepatotoxicity is characterized by extensive necrotic cell death and a sterile inflammatory response. A recent report suggested that a therapeutic intervention with chlorogenic acid, a dietary polyphenolic compound, protects against acetaminophen-induced liver injury by inhibiting the inflammatory injury...

    journal_title:Chemico-biological interactions

    pub_type: 信件

    doi:10.1016/j.cbi.2015.08.025

    authors: Jaeschke H

    更新日期:2016-01-05 00:00:00

  • Multiple mechanisms of cell death induced by chelidonine in MCF-7 breast cancer cell line.

    abstract::In a preliminary study screening anti-proliferative natural alkaloids, a very potent benzophenanthridine, chelidonine showed strong cytotoxicity in cancer cells. While several modes of death have been identified, most of anti-cancer attempts have focused on stimulation of cells to undergo apoptosis. Chelidonine seems ...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/j.cbi.2014.09.013

    authors: Noureini SK,Esmaili H

    更新日期:2014-11-05 00:00:00

  • The induction of Maspin expression by a glucosamine-derivative has an antiproliferative activity in prostate cancer cell lines.

    abstract::Mammary serine protease inhibitor or Maspin has been characterized as a class II tumor suppressor gene in several cancer types, among them prostate cancer (CaP). Androgen ablation is an effective therapy for CaP, but with short-term effectiveness, thus new therapeutic strategies are actively sought. The present study ...

    journal_title:Chemico-biological interactions

    pub_type: 杂志文章

    doi:10.1016/j.cbi.2019.01.014

    authors: Cocchiola R,Lopreiato M,Guazzo R,de Santi MM,Eufemi M,Scandurra R,Scotto d'Abusco A

    更新日期:2019-02-25 00:00:00