476
Views
46
CrossRef citations to date
0
Altmetric
Research Article

Mechanism and Role of Covalent Heme Binding in the CYP4 Family of P450 Enzymes and the Mammalian Peroxidases

Pages 405-426 | Published online: 09 Oct 2008

Keep up to date with the latest research on this topic with citation updates for this article.

Read on this site (1)

Elise D. Rivett, Lim Heo, Michael Feig & Eric L. Hegg. (2021) Biosynthesis and trafficking of heme o and heme a: new structural insights and their implications for reaction mechanisms and prenylated heme transfer. Critical Reviews in Biochemistry and Molecular Biology 56:6, pages 640-668.
Read now

Articles from other publishers (45)

Robert D. Pelletier, Allan E. Rettie & John P. Kowalski. (2023) Improved methods for the detection of heme and protoporphyrin IX adducts and quantification of heme B from cytochrome P450 containing systems. Journal of Chromatography B 1231, pages 123921.
Crossref
Elise D. Rivett, Hannah G. Addis, Jonathan V. Dietz, Jayda A. Carroll-Deaton, Shipra Gupta, Koji L. Foreman, Minh Anh Dang, Jennifer L. Fox, Oleh Khalimonchuk & Eric L. Hegg. (2023) Evidence that the catalytic mechanism of heme a synthase involves the formation of a carbocation stabilized by a conserved glutamate. Archives of Biochemistry and Biophysics 744, pages 109665.
Crossref
Kanae Yanai, Masahiko Hada & Hiroshi Fujii. (2023) Electric field effect of positive and negative charges of substituents on electronic structure and reactivity of oxoiron(IV) porphyrin π-cation radical complex. Journal of Inorganic Biochemistry 244, pages 112208.
Crossref
Annika Röder, Saskia Hüsken, Michael C. Hutter, Allan E. Rettie, Helmut Hanenberg, Constanze Wiek & Marco Girhard. (2023) Spotlight on CYP4B1. International Journal of Molecular Sciences 24:3, pages 2038.
Crossref
Lei Chen, Hong Yuan, Xiao‐Juan Wang, Lianzhi Li, Xiangshi Tan & Ying‐Wu Lin. (2022) Engineering Human Neuroglobin into a Cytochrome c ‐Like Protein with a Single Thioether Bond in Non‐native State . ChemBioChem 23:23.
Crossref
Yuna Suzuki, Masahiko Hada & Hiroshi Fujii. (2021) Synthesis, characterization, and reactivity of oxoiron(IV) porphyrin π-cation radical complexes bearing cationic N-methyl-2-pyridinium group. Journal of Inorganic Biochemistry 223, pages 111542.
Crossref
Kanako Ueno, Yuri Ishimizu & Hiroshi Fujii. (2021) Significant Solvent Effect on Reactivity of Oxoiron(IV) Porphyrin π-Cation Radical Complex: Activation in n -Alkane Solvent . Inorganic Chemistry 60:13, pages 9243-9247.
Crossref
Nami Fukui, Kanako Ueno, Masahiko Hada & Hiroshi Fujii. (2021) meso -Substitution Activates Oxoiron(IV) Porphyrin π-Cation Radical Complex More Than Pyrrole-β-Substitution for Atom Transfer Reaction . Inorganic Chemistry 60:5, pages 3207-3217.
Crossref
SYM Lim, M Alshagga, CE Ong, JY Chieng & Y Pan. (2020) Cytochrome P450 4B1 (CYP4B1) as a target in cancer treatment. Human & Experimental Toxicology 39:6, pages 785-796.
Crossref
Florian A. Thesseling, Michael C. Hutter, Constanze Wiek, John P. Kowalski, Allan E. Rettie & Marco Girhard. (2020) Novel insights into oxidation of fatty acids and fatty alcohols by cytochrome P450 monooxygenase CYP4B1. Archives of Biochemistry and Biophysics 679, pages 108216.
Crossref
William C. Wright, Jude Chenge & Taosheng Chen. (2019) Structural perspectives of the CYP3A family and their small molecule modulators in drug metabolism. Liver Research 3:3-4, pages 132-142.
Crossref
Hyoung-Goo Park, Vitchan Kim, Harim Kim, Rowoon Lee, Myung-A. Cho, Sung-Woo Park, Young-Jin Chun & Donghak Kim. (2019) CYP52A23 from Candida albicans and its Substrate Preference for Fatty Acid Hydroxylation. Archives of Biochemistry and Biophysics 671, pages 27-34.
Crossref
Can Liu, Hong Yuan, Fei Liao, Chuan-Wan Wei, Ke-Jie Du, Shu-Qin Gao, Xiangshi Tan & Ying-Wu Lin. (2019) Unique Tyr-heme double cross-links in F43Y/T67R myoglobin: an artificial enzyme with a peroxidase activity comparable to that of native peroxidases. Chemical Communications 55:46, pages 6610-6613.
Crossref
Matthew E. Albertolle, Hyun D. Song, Clayton J. Wilkey, Jere P. Segrest & F. Peter Guengerich. (2019) Glutamine-451 Confers Sensitivity to Oxidative Inhibition and Heme-Thiolate Sulfenylation of Cytochrome P450 4B1. Chemical Research in Toxicology 32:3, pages 484-492.
Crossref
Yi Liu, Karan Gautam Kaval, Ambro van Hoof & Danielle A. Garsin. (2019) Heme peroxidase HPX-2 protects Caenorhabditis elegans from pathogens. PLOS Genetics 15:1, pages e1007944.
Crossref
Junhao Li, Hongxiao Zhang, Guixia Liu, Yun Tang, Yaoquan Tu & Weihua Li. (2018) Computational Insight Into Vitamin K1 ω-Hydroxylation by Cytochrome P450 4F2. Frontiers in Pharmacology 9.
Crossref
Gareth K. Jennings, Mei-Hui Hsu, Lisa S. Shock, Eric F. Johnson & John C Hackett. (2018) Noncovalent interactions dominate dynamic heme distortion in cytochrome P450 4B1. Journal of Biological Chemistry 293:29, pages 11433-11446.
Crossref
Hui-Min Cheng, Hong Yuan, Xiao-Juan Wang, Jia-Kun Xu, Shu-Qin Gao, Ge-Bo Wen, Xiangshi Tan & Ying-Wu Lin. (2018) Formation of Cys-heme cross-link in K42C myoglobin under reductive conditions with molecular oxygen. Journal of Inorganic Biochemistry 182, pages 141-149.
Crossref
Ying-Wu Lin. (2018) Structure and function of heme proteins regulated by diverse post-translational modifications. Archives of Biochemistry and Biophysics 641, pages 1-30.
Crossref
Loai Basheer, Keren Schultz, Yelena Guttman & Zohar Kerem. (2017) In silico and in vitro inhibition of cytochrome P450 3A by synthetic stilbenoids. Food Chemistry 237, pages 895-903.
Crossref
Andrei L. Kleschyov. (2017) The NO-heme signaling hypothesis. Free Radical Biology and Medicine 112, pages 544-552.
Crossref
Mei-Hui Hsu, Brian R. Baer, Allan E. Rettie & Eric F. Johnson. (2017) The Crystal Structure of Cytochrome P450 4B1 (CYP4B1) Monooxygenase Complexed with Octane Discloses Several Structural Adaptations for ω-Hydroxylation. Journal of Biological Chemistry 292:13, pages 5610-5621.
Crossref
Martina Paumann-Page, Romy-Sophie Katz, Marzia Bellei, Irene Schwartz, Eva Edenhofer, Benjamin Sevcnikar, Monika Soudi, Stefan Hofbauer, Gianantonio Battistuzzi, Paul G. Furtmüller & Christian Obinger. (2017) Pre-steady-state Kinetics Reveal the Substrate Specificity and Mechanism of Halide Oxidation of Truncated Human Peroxidasin 1. Journal of Biological Chemistry 292:11, pages 4583-4592.
Crossref
Katharina Roellecke, Vera D. Jäger, Veselin H. Gyurov, John P. Kowalski, Stephanie Mielke, Allan E. Rettie, Helmut Hanenberg, Constanze Wiek & Marco Girhard. (2017) Ligand characterization of CYP4B1 isoforms modified for high-level expression in Escherichia coli and HepG2 cells . Protein Engineering Design and Selection.
Crossref
Loai Basheer, Keren Schultz & Zohar Kerem. (2016) Inhibition of cytochrome P450 3A by acetoxylated analogues of resveratrol in in vitro and in silico models. Scientific Reports 6:1.
Crossref
Paul R. Ortiz de Montellano. 2015. Heme Peroxidases. Heme Peroxidases 1 30 .
Loai Basheer, Keren Schultz, Merav Fichman & Zohar Kerem. (2015) Use of In Vitro and Predictive In Silico Models to Study the Inhibition of Cytochrome P4503A by Stilbenes. PLOS ONE 10:10, pages e0141061.
Crossref
Ying-Wu Lin. (2015) The broad diversity of heme-protein cross-links: An overview. Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics 1854:8, pages 844-859.
Crossref
Dao-Jing Yan, Hong Yuan, Wei Li, Yu Xiang, Bo He, Chang-Ming Nie, Ge-Bo Wen, Ying-Wu Lin & Xiangshi Tan. (2015) How a novel tyrosine–heme cross-link fine-tunes the structure and functions of heme proteins: a direct comparitive study of L29H/F43Y myoglobin. Dalton Transactions 44:43, pages 18815-18822.
Crossref
Paul R. Ortiz de Montellano. 2015. Cytochrome P450. Cytochrome P450 111 176 .
Tram Kim Lam, Melissa Rotunno, Brid M. Ryan, Angela C. Pesatori, Pier Alberto Bertazzi, Margaret Spitz, Neil E. Caporaso & Maria Teresa Landi. (2014) Heme-related gene expression signatures of meat intakes in lung cancer tissues. Molecular Carcinogenesis 53:7, pages 548-556.
Crossref
George R Tiller & Danielle A Garsin. (2014) The SKPO-1 Peroxidase Functions in the Hypodermis to Protect Caenorhabditis elegans From Bacterial Infection . Genetics 197:2, pages 515-526.
Crossref
Zhi‐Yi Zhang. 2014. Handbook of Metabolic Pathways of Xenobiotics. Handbook of Metabolic Pathways of Xenobiotics 1 4 .
Zhi‐Yi Zhang. 2014. Handbook of Metabolic Pathways of Xenobiotics. Handbook of Metabolic Pathways of Xenobiotics 1 5 .
Markus Auer, Clemens Gruber, Marzia Bellei, Katharina F. Pirker, Marcel Zamocky, Daniela Kroiss, Stefan A. Teufer, Stefan Hofbauer, Monika Soudi, Gianantonio Battistuzzi, Paul G. Furtmüller & Christian Obinger. (2013) A Stable Bacterial Peroxidase with Novel Halogenating Activity and an Autocatalytically Linked Heme Prosthetic Group. Journal of Biological Chemistry 288:38, pages 27181-27199.
Crossref
Júlio S. Rebouças & Brian R. James. (2013) Molecular Recognition Using Ruthenium(II) Porphyrin Thiol Complexes as Probes. Inorganic Chemistry 52:2, pages 1084-1098.
Crossref
Thuy T. B. Ly, Yogan Khatri, Josef Zapp, Michael C. Hutter & Rita Bernhardt. (2012) CYP264B1 from Sorangium cellulosum So ce56: a fascinating norisoprenoid and sesquiterpene hydroxylase. Applied Microbiology and Biotechnology 95:1, pages 123-133.
Crossref
Kieran F. Geoghegan, Alison H. Varghese, Xidong Feng, Andrew J. Bessire, James J. Conboy, Roger B. Ruggeri, Kay Ahn, Samantha N. Spath, Sergey V. Filippov, Steven J. Conrad, Philip A. Carpino, Cristiano R. W. Guimarães & Felix F. Vajdos. (2012) Deconstruction of Activity-Dependent Covalent Modification of Heme in Human Neutrophil Myeloperoxidase by Multistage Mass Spectrometry (MS 4 ) . Biochemistry 51:10, pages 2065-2077.
Crossref
Xiao-Li Sun, Xu-Ri Huang, Ji-Lai Li, Rui-Ping Huo & Chia-Chung Sun. (2012) Mechanism Insights of Ethane C–H Bond Activations by Bare [Fe III ═O] + : Explicit Electronic Structure Analysis . The Journal of Physical Chemistry A 116:5, pages 1475-1485.
Crossref
Gianantonio Battistuzzi, Johanna Stampler, Marzia Bellei, Jutta Vlasits, Monika Soudi, Paul G. Furtmüller & Christian Obinger. (2011) Influence of the Covalent Heme–Protein Bonds on the Redox Thermodynamics of Human Myeloperoxidase. Biochemistry 50:37, pages 7987-7994.
Crossref
Jonathan B. Johnston, Hugues Ouellet, Larissa M. Podust & Paul R. Ortiz de Montellano. (2011) Structural control of cytochrome P450-catalyzed ω-hydroxylation. Archives of Biochemistry and Biophysics 507:1, pages 86-94.
Crossref
Markus Zollinger, Hans-Peter Gschwind, Yi Jin, Claudia Sayer, Frédéric Zécri & Stefan Hartmann. (2011) Absorption and Disposition of the Sphingosine 1-Phosphate Receptor Modulator Fingolimod (FTY720) in Healthy Volunteers: A Case of Xenobiotic Biotransformation Following Endogenous Metabolic Pathways. Drug Metabolism and Disposition 39:2, pages 199-207.
Crossref
Yi Jin, Markus Zollinger, Hubert Borell, Alfred Zimmerlin & Christopher J. Patten. (2011) CYP4F Enzymes Are Responsible for the Elimination of Fingolimod (FTY720), a Novel Treatment of Relapsing Multiple Sclerosis. Drug Metabolism and Disposition 39:2, pages 191-198.
Crossref
Timothy N. Waltham, Hazel M. Girvan, Christopher F. Butler, Stuart R. Rigby, Adrian J. Dunford, Robert A. Holt & Andrew W. Munro. (2011) Analysis of the oxidation of short chain alkynes by flavocytochrome P450 BM3. Metallomics 3:4, pages 369.
Crossref
Song-Hee Han, Chang-Yong Eun, Jung-Soo Han, Young-Jin Chun, Dong-Hyun Kim, Chul-Ho Yun & Dong-Hak Kim. (2009) Self-Sufficient Catalytic System of Human Cytochrome P450 4A11 and NADPH-P450 Reductase. Biomolecules and Therapeutics 17:2, pages 156-161.
Crossref

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.