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A Role for the Orphan Human Cytochrome P450 2S1 in Polyunsaturated Fatty Acid ω-1 Hydroxylation Using an Untargeted Metabolomic Approach.

Fekry MI, Xiao Y, Berg JZ, Guengerich FP.

Drug Metab Dispos. 2019 Sep 11. pii: dmd.119.089086. doi: 10.1124/dmd.119.089086. [Epub ahead of print]


Kinetic Modeling of Steady-State Situations in Cytochrome P450 Enzyme Reactions.

Guengerich FPP.

Drug Metab Dispos. 2019 Aug 19. pii: dmd.119.088732. doi: 10.1124/dmd.119.088732. [Epub ahead of print]


Human cytochrome P450 11B2 produces aldosterone by a processive mechanism due to the lactol form of the intermediate 18-hydroxycorticosterone.

Reddish MJ, Guengerich FP.

J Biol Chem. 2019 Aug 30;294(35):12975-12991. doi: 10.1074/jbc.RA119.009830. Epub 2019 Jul 11.


Human cytochrome P450 enzymes bind drugs and other substrates mainly through conformational-selection modes.

Guengerich FP, Wilkey CJ, Phan TTN.

J Biol Chem. 2019 Jul 12;294(28):10928-10941. doi: 10.1074/jbc.RA119.009305. Epub 2019 May 30.


Mitochondrially targeted cytochrome P450 2D6 is involved in monomethylamine-induced neuronal damage in mouse models.

Chattopadhyay M, Chowdhury AR, Feng T, Assenmacher CA, Radaelli E, Guengerich FP, Avadhani NG.

J Biol Chem. 2019 Jun 28;294(26):10336-10348. doi: 10.1074/jbc.RA119.008848. Epub 2019 May 20.


Mechanisms of Cytochrome P450-Catalyzed Oxidations.

Guengerich FP.

ACS Catal. 2018 Dec 7;8(12):10964-10976. doi: 10.1021/acscatal.8b03401. Epub 2018 Oct 18.


The abundant DNA adduct N 7-methyl deoxyguanosine contributes to miscoding during replication by human DNA polymerase η.

Njuma OJ, Su Y, Guengerich FP.

J Biol Chem. 2019 Jun 28;294(26):10253-10265. doi: 10.1074/jbc.RA119.008986. Epub 2019 May 17.


Conformational selection dominates binding of steroids to human cytochrome P450 17A1.

Guengerich FP, Wilkey CJ, Glass SM, Reddish MJ.

J Biol Chem. 2019 Jun 28;294(26):10028-10041. doi: 10.1074/jbc.RA119.008860. Epub 2019 May 9.


Judy L. Bolton, 1962-2019.

Guengerich FP.

Chem Res Toxicol. 2019 Jun 17;32(6):944-945. doi: 10.1021/acs.chemrestox.9b00157. Epub 2019 Apr 30. No abstract available.


Drug Metabolism and Toxicology Special Issue Call for Papers.

Guengerich FP, Georg GI, Wang S.

J Med Chem. 2019 Feb 14;62(3):1077. doi: 10.1021/acs.jmedchem.9b00005. Epub 2019 Jan 11. No abstract available.


Oxidation of Flavone, 5-Hydroxyflavone, and 5,7-Dihydroxyflavone to Mono-, Di-, and Tri-Hydroxyflavones by Human Cytochrome P450 Enzymes.

Nagayoshi H, Murayama N, Kakimoto K, Tsujino M, Takenaka S, Katahira J, Lim YR, Kim D, Yamazaki H, Komori M, Guengerich FP, Shimada T.

Chem Res Toxicol. 2019 Jun 17;32(6):1268-1280. doi: 10.1021/acs.chemrestox.9b00078. Epub 2019 Apr 17.


Isotopic tagging of oxidized and reduced cysteines (iTORC) for detecting and quantifying sulfenic acids, disulfides, and free thiols in cells.

Albertolle ME, Glass SM, Trefts E, Guengerich FP.

J Biol Chem. 2019 Apr 19;294(16):6522-6530. doi: 10.1074/jbc.AC118.007225. Epub 2019 Mar 8.


Human DNA polymerase η has reverse transcriptase activity in cellular environments.

Su Y, Ghodke PP, Egli M, Li L, Wang Y, Guengerich FP.

J Biol Chem. 2019 Apr 12;294(15):6073-6081. doi: 10.1074/jbc.RA119.007925. Epub 2019 Mar 6.


Celebrating the scientific legacy of Herbert Tabor.

Gierasch LM, Guengerich FP.

J Biol Chem. 2019 Feb 1;294(5):1635-1637. doi: 10.1074/jbc.TME119.007427. Review. No abstract available.


Glutamine-451 Confers Sensitivity to Oxidative Inhibition and Heme-Thiolate Sulfenylation of Cytochrome P450 4B1.

Albertolle ME, Song HD, Wilkey CJ, Segrest JP, Guengerich FP.

Chem Res Toxicol. 2019 Mar 18;32(3):484-492. doi: 10.1021/acs.chemrestox.8b00353. Epub 2019 Feb 11.


Synthesis and Characterization of Site-Specific O6 -Alkylguanine DNA-Alkyl Transferase-Oligonucleotide Crosslinks.

Ghodke PP, Albertolle ME, Johnson KM, Guengerich FP.

Curr Protoc Nucleic Acid Chem. 2019 Mar;76(1):e74. doi: 10.1002/cpnc.74. Epub 2019 Jan 18.


Happy centennial birthday to Herb Tabor, pillar of JBC.

Gierasch LM, Guengerich FP.

J Biol Chem. 2018 Nov 30;293(48):18803. doi: 10.1074/jbc.E118.006720. No abstract available.


FEMA GRAS assessment of natural flavor complexes: Citrus-derived flavoring ingredients.

Cohen SM, Eisenbrand G, Fukushima S, Gooderham NJ, Guengerich FP, Hecht SS, Rietjens IMCM, Bastaki M, Davidsen JM, Harman CL, McGowen M, Taylor SV.

Food Chem Toxicol. 2019 Feb;124:192-218. doi: 10.1016/j.fct.2018.11.052. Epub 2018 Nov 24.


Sterol 14α-Demethylase Structure-Based Optimization of Drug Candidates for Human Infections with the Protozoan Trypanosomatidae.

Friggeri L, Hargrove TY, Rachakonda G, Blobaum AL, Fisher P, de Oliveira GM, da Silva CF, Soeiro MNC, Nes WD, Lindsley CW, Villalta F, Guengerich FP, Lepesheva GI.

J Med Chem. 2018 Dec 13;61(23):10910-10921. doi: 10.1021/acs.jmedchem.8b01671. Epub 2018 Nov 30.


Binding of a physiological substrate causes large-scale conformational reorganization in cytochrome P450 51.

Hargrove TY, Wawrzak Z, Fisher PM, Child SA, Nes WD, Guengerich FP, Waterman MR, Lepesheva GI.

J Biol Chem. 2018 Dec 14;293(50):19344-19353. doi: 10.1074/jbc.RA118.005850. Epub 2018 Oct 16.


The safety evaluation of food flavouring substances: the role of metabolic studies.

Smith RL, Cohen SM, Fukushima S, Gooderham NJ, Hecht SS, Guengerich FP, Rietjens IMCM, Bastaki M, Harman CL, McGowen MM, Taylor SV.

Toxicol Res (Camb). 2018 Mar 28;7(4):618-646. doi: 10.1039/c7tx00254h. eCollection 2018 Jul 1. Review.


Site-specific oxidation of flavanone and flavone by cytochrome P450 2A6 in human liver microsomes.

Nagayoshi H, Murayama N, Kakimoto K, Takenaka S, Katahira J, Lim YR, Kim V, Kim D, Yamazaki H, Komori M, Guengerich FP, Shimada T.

Xenobiotica. 2019 Jul;49(7):791-802. doi: 10.1080/00498254.2018.1505064. Epub 2018 Sep 28.


The Cytochrome P450 Slow Metabolizers CYP2C9*2 and CYP2C9*3 Directly Regulate Tumorigenesis via Reduced Epoxyeicosatrienoic Acid Production.

Sausville LN, Gangadhariah MH, Chiusa M, Mei S, Wei S, Zent R, Luther JM, Shuey MM, Capdevila JH, Falck JR, Guengerich FP, Williams SM, Pozzi A.

Cancer Res. 2018 Sep 1;78(17):4865-4877. doi: 10.1158/0008-5472.CAN-17-3977. Epub 2018 Jul 16.


Formation and Cleavage of C-C Bonds by Enzymatic Oxidation-Reduction Reactions.

Guengerich FP, Yoshimoto FK.

Chem Rev. 2018 Jul 25;118(14):6573-6655. doi: 10.1021/acs.chemrev.8b00031. Epub 2018 Jun 22. Review.


Sterol 14α-Demethylase Structure-Based Design of VNI (( R)- N-(1-(2,4-Dichlorophenyl)-2-(1 H-imidazol-1-yl)ethyl)-4-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamide)) Derivatives To Target Fungal Infections: Synthesis, Biological Evaluation, and Crystallographic Analysis.

Friggeri L, Hargrove TY, Wawrzak Z, Blobaum AL, Rachakonda G, Lindsley CW, Villalta F, Nes WD, Botta M, Guengerich FP, Lepesheva GI.

J Med Chem. 2018 Jul 12;61(13):5679-5691. doi: 10.1021/acs.jmedchem.8b00641. Epub 2018 Jun 25.


Association of pharmacokinetic profiles of lenalidomide in human plasma simulated using pharmacokinetic data in humanized-liver mice with liver toxicity detected by human serum albumin RNA.

Murayama N, Suemizu H, Uehara S, Kusama T, Mitsui M, Kamiya Y, Shimizu M, Guengerich FP, Yamazaki H.

J Toxicol Sci. 2018;43(6):369-375. doi: 10.2131/jts.43.369.


Cytochrome P450 research and The Journal of Biological Chemistry.

Guengerich FP.

J Biol Chem. 2019 Feb 1;294(5):1671-1680. doi: 10.1074/jbc.TM118.004144. Epub 2019 Feb 1. Review.


Biological chemistry without borders.

Guengerich FP.

J Biol Chem. 2018 Jun 1;293(22):8720-8721. doi: 10.1074/jbc.E118.004007. No abstract available.


Introduction to Metals in Biology 2018: Copper homeostasis and utilization in redox enzymes.

Guengerich FP.

J Biol Chem. 2018 Mar 30;293(13):4603-4605. doi: 10.1074/jbc.TM118.002255. Epub 2018 Feb 7. Review.


Sulfenylation of Human Liver and Kidney Microsomal Cytochromes P450 and Other Drug-Metabolizing Enzymes as a Response to Redox Alteration.

Albertolle ME, Phan TTN, Pozzi A, Guengerich FP.

Mol Cell Proteomics. 2018 May;17(5):889-900. doi: 10.1074/mcp.RA117.000382. Epub 2018 Jan 26.


Updated procedure for the safety evaluation of natural flavor complexes used as ingredients in food.

Cohen SM, Eisenbrand G, Fukushima S, Gooderham NJ, Guengerich FP, Hecht SS, Rietjens IMCM, Davidsen JM, Harman CL, Taylor SV.

Food Chem Toxicol. 2018 Mar;113:171-178. doi: 10.1016/j.fct.2018.01.021. Epub 2018 Jan 31.


Cytochrome P450 2A6 and other human P450 enzymes in the oxidation of flavone and flavanone.

Kakimoto K, Murayama N, Takenaka S, Nagayoshi H, Lim YR, Kim V, Kim D, Yamazaki H, Komori M, Guengerich FP, Shimada T.

Xenobiotica. 2019 Feb;49(2):131-142. doi: 10.1080/00498254.2018.1426133. Epub 2018 Jan 29.


Development and Uses of Offline and Web-Searchable Metabolism Databases - The Case of Benzo[a]pyrene.

Rendic SP, Guengerich FP.

Curr Drug Metab. 2018;19(1):3-46. doi: 10.2174/1389200219666171207123939. Review.


Inherent steroid 17α,20-lyase activity in defunct cytochrome P450 17A enzymes.

Gonzalez E, Johnson KM, Pallan PS, Phan TTN, Zhang W, Lei L, Wawrzak Z, Yoshimoto FK, Egli M, Guengerich FP.

J Biol Chem. 2018 Jan 12;293(2):541-556. doi: 10.1074/jbc.RA117.000504. Epub 2017 Dec 6.


7-ketocholesterol and 27-hydroxycholesterol decreased doxorubicin sensitivity in breast cancer cells: estrogenic activity and mTOR pathway.

Wang CW, Huang CC, Chou PH, Chang YP, Wei S, Guengerich FP, Chou YC, Wang SF, Lai PS, Souček P, Ueng YF.

Oncotarget. 2017 Aug 2;8(39):66033-66050. doi: 10.18632/oncotarget.19789. eCollection 2017 Sep 12.


Human DNA polymerase η accommodates RNA for strand extension.

Su Y, Egli M, Guengerich FP.

J Biol Chem. 2017 Nov 3;292(44):18044-18051. doi: 10.1074/jbc.M117.809723. Epub 2017 Sep 26.


Selective changes in cholesterol metabolite levels in plasma of breast cancer patients after tumor removal.

Soucek P, Vrana D, Ueng YF, Wei S, Kozevnikovova R, Guengerich FP.

Clin Chem Lab Med. 2018 Feb 23;56(3):e78-e81. doi: 10.1515/cclm-2017-0409. No abstract available.


Kinetic Deuterium Isotope Effects in Cytochrome P450 Reactions.

Guengerich FP.

Methods Enzymol. 2017;596:217-238. doi: 10.1016/bs.mie.2017.06.036. Epub 2017 Jul 18.


The Dihydroxy Metabolite of the Teratogen Thalidomide Causes Oxidative DNA Damage.

Wani TH, Chakrabarty A, Shibata N, Yamazaki H, Guengerich FP, Chowdhury G.

Chem Res Toxicol. 2017 Aug 21;30(8):1622-1628. doi: 10.1021/acs.chemrestox.7b00127. Epub 2017 Aug 2.


Human mitochondrial cytochrome P450 27C1 is localized in skin and preferentially desaturates trans-retinol to 3,4-dehydroretinol.

Johnson KM, Phan TTN, Albertolle ME, Guengerich FP.

J Biol Chem. 2017 Aug 18;292(33):13672-13687. doi: 10.1074/jbc.M116.773937. Epub 2017 Jul 12.


Kinetic processivity of the two-step oxidations of progesterone and pregnenolone to androgens by human cytochrome P450 17A1.

Gonzalez E, Guengerich FP.

J Biol Chem. 2017 Aug 11;292(32):13168-13185. doi: 10.1074/jbc.M117.794917. Epub 2017 Jul 6.


Oxidation of 1-chloropyrene by human CYP1 family and CYP2A subfamily cytochrome P450 enzymes: catalytic roles of two CYP1B1 and five CYP2A13 allelic variants.

Shimada T, Murayama N, Kakimoto K, Takenaka S, Lim YR, Yeom S, Kim D, Yamazaki H, Guengerich FP, Komori M.

Xenobiotica. 2018 Jun;48(6):565-575. doi: 10.1080/00498254.2017.1347306. Epub 2017 Jul 21.


In vitro cytochrome P450 46A1 (CYP46A1) activation by neuroactive compounds.

Mast N, Anderson KW, Johnson KM, Phan TTN, Guengerich FP, Pikuleva IA.

J Biol Chem. 2017 Aug 4;292(31):12934-12946. doi: 10.1074/jbc.M117.794909. Epub 2017 Jun 22.


Introduction to Metals in Biology 2017: Iron transport, storage, and the ramifications.

Guengerich FP.

J Biol Chem. 2017 Aug 4;292(31):12725-12726. doi: 10.1074/jbc.R117.801332. Epub 2017 Jun 14.


Functional analysis of human cytochrome P450 21A2 variants involved in congenital adrenal hyperplasia.

Wang C, Pallan PS, Zhang W, Lei L, Yoshimoto FK, Waterman MR, Egli M, Guengerich FP.

J Biol Chem. 2017 Jun 30;292(26):10767-10778. doi: 10.1074/jbc.M117.792465. Epub 2017 May 24.


Heme-thiolate sulfenylation of human cytochrome P450 4A11 functions as a redox switch for catalytic inhibition.

Albertolle ME, Kim D, Nagy LD, Yun CH, Pozzi A, Savas Ü, Johnson EF, Guengerich FP.

J Biol Chem. 2017 Jul 7;292(27):11230-11242. doi: 10.1074/jbc.M117.792200. Epub 2017 May 22.


Induction of human cytochrome P450 3A enzymes in cultured placental cells by thalidomide and relevance to bioactivation and toxicity.

Murayama N, Kazuki Y, Satoh D, Arata K, Harada T, Shibata N, Guengerich FP, Yamazaki H.

J Toxicol Sci. 2017;42(3):343-348. doi: 10.2131/jts.42.343.


The Role of Oxysterols in Human Cancer.

Kloudova A, Guengerich FP, Soucek P.

Trends Endocrinol Metab. 2017 Jul;28(7):485-496. doi: 10.1016/j.tem.2017.03.002. Epub 2017 Apr 12. Review.


Formation of S-[2-(N6-Deoxyadenosinyl)ethyl]glutathione in DNA and Replication Past the Adduct by Translesion DNA Polymerases.

Sedgeman CA, Su Y, Guengerich FP.

Chem Res Toxicol. 2017 May 15;30(5):1188-1196. doi: 10.1021/acs.chemrestox.7b00022. Epub 2017 Apr 14.


7,8-benzoflavone binding to human cytochrome P450 3A4 reveals complex fluorescence quenching, suggesting binding at multiple protein sites.

Marsch GA, Carlson BT, Guengerich FP.

J Biomol Struct Dyn. 2018 Mar;36(4):841-860. doi: 10.1080/07391102.2017.1301270. Epub 2017 Mar 20.

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