Oxidation of Indole by Cytochrome P450 Enzymes

P450 superfamily: update on new sequences, gene mapping, accession numbers and nomenclature

Nelson, D. R., Koymans, L. M. H., Kamataki, T., Stegeman, J. J., Feyereisen, R., Waxman, D. J., Waterman, M. R., Gotoh, O., Coon, M. J., Estabrook, R. W., et al. (1996) · Pharmacogenetics · doi:10.1097/00008571-199602000-00002 · Cited by 2,946 · see citing works

Cytochrome P450

de Montellano, P. R. O. (1995) · Springer eBooks · doi:10.1007/978-1-4757-2391-5 · Cited by 594 · see citing works

Principles and methods of toxicology

Krebs, H. C. (1995) · Toxicon · doi:10.1016/0041-0101(95)90106-x · Cited by 327 · see citing works

A cytochrome b 5 is required for full activity of flavonoid 3′,5′-hydroxylase, a cytochrome P450 involved in the formation of blue flower colors

de Vetten, N., ter Horst, J., van Schaik, H., de Boer, A., Mol, J. N. M., & Koes, R. E. (1999) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.96.2.778 · Cited by 182 · see citing works

Physical Methods in Heterocyclic Chemistry

Barton, J. W. (1972) · Journal of Chromatography A · doi:10.1016/s0021-9673(01)91924-7 · Cited by 136 · see citing works

The blue diaper syndrome: Familial hypercalcemia with nephrocalcinosis and indicanuria

Drummond, K. N., Michael, A. F., Ulstrom, R. A., & Good, R. A. (1964) · The American Journal of Medicine · doi:10.1016/0002-9343(64)90134-2 · Cited by 129 · see citing works

The oxidation of manganese by peroxidase systems

Kenten, R. H., & Mann, P. J. (1950) · Biochemical Journal · doi:10.1042/bj0460067 · Cited by 93 · see citing works

Identification of molecular aggregates containing glycoproteins III, J, K (carboxypeptidase H), and H (Kex2-related proteases) in the soluble and membrane fractions of adrenal medullary chromaffin granules.

Palmer, D. J., & Christie, D. L. (1992) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(19)88625-8 · Cited by 85 · see citing works

Formation of both methylenedioxy groups in the alkaloid (S)-stylopine is catalyzed by cytochrome P-450 enzymes

Bauer, W., & Zenk, M. H. (1989) · Tetrahedron Letters · doi:10.1016/s0040-4039(01)93756-6 · Cited by 42 · see citing works

Biotechnology, bioremediation, and blue genes

Bialy, H. (1997) · Nature Biotechnology · doi:10.1038/nbt0297-110 · Cited by 33 · see citing works

Pigments derived from tryptophan: (1) urorosein, (2) tryptochrome

Fearon, W. R., & Boggust, W. A. (1950) · Biochemical Journal · doi:10.1042/bj0460062 · Cited by 31 · see citing works

Contribution to the chemistry of leucaemic urine

Friedmann, E., Marrian, D. H., & Perutz, M. F. (1950) · Biochimica et Biophysica Acta · doi:10.1016/0006-3002(50)90145-4 · Cited by 13 · see citing works

Magnetic Circular Dichroism Studies XXIII [1] Magnetic Circular Dichroism Spectra of Indole Alkaloids

Barth, G., Linder, R. E., Bunnenberg, E., & Djerassi, C. (1972) · Helvetica Chimica Acta · doi:10.1002/hlca.19720550637 · Cited by 12 · see citing works

The Microbiota-Gut-Brain Axis

Cryan, J. F., O'Riordan, K. J., Cowan, C. S. M., Sandhu, K. V., Bastiaanssen, T. F. S., Boehme, M., Codagnone, M. G., Cussotto, S., Fulling, C., Golubeva, A. V., et al. (2019) · Physiological Reviews · doi:10.1152/physrev.00018.2018 · Cited by 5,286 · see citing works

Activation of the Aryl Hydrocarbon Receptor by Structurally Diverse Exogenous and Endogenous Chemicals

Denison, M. S., & Nagy, S. R. (2003) · Annual Review of Pharmacology and Toxicology · doi:10.1146/annurev.pharmtox.43.100901.135828 · Cited by 1,895 · see citing works

Indole as an intercellular signal in microbial communities

Lee, J.-H., & Lee, J. (2010) · FEMS Microbiology Reviews · doi:10.1111/j.1574-6976.2009.00204.x · Cited by 1,059 · see citing works

Regulation of the immune response by the aryl hydrocarbon receptor

Gutiérrez-Vázquez, C., & Quintana, F. J. (2018) · Immunity · doi:10.1016/j.immuni.2017.12.012 · Cited by 985 · see citing works

Summary of information on human CYP enzymes: human P450 metabolism data

Rendić, S. (2002) · Drug Metabolism Reviews · doi:10.1081/dmr-120001392 · Cited by 819 · see citing works

GSK-3-Selective Inhibitors Derived from Tyrian Purple Indirubins

Meijer, L., Skaltsounis, A., Magiatis, P., Polychronopoulos, P., Knockaert, M., Leost, M., Ryan, X. P., Vonica, A., Brivanlou, A. H., Dajani, R., et al. (2003) · Chemistry & Biology · doi:10.1016/j.chembiol.2003.11.010 · Cited by 814 · see citing works

Indole and Tryptophan Metabolism: Endogenous and Dietary Routes to Ah Receptor Activation

Hubbard, T. D., Murray, I. A., & Perdew, G. H. (2015) · Drug Metabolism and Disposition · doi:10.1124/dmd.115.064246 · Cited by 646 · see citing works

Indole is an inter-species biofilm signal mediated by SdiA

Lee, J., Jayaraman, A., & Wood, T. K. (2007) · BMC Microbiology · doi:10.1186/1471-2180-7-42 · Cited by 471 · see citing works

Complex reactions catalyzed by cytochrome P450 enzymes

Isin, E. M., & Guengerich, F. P. (2006) · Biochimica et Biophysica Acta (BBA) - General Subjects · doi:10.1016/j.bbagen.2006.07.003 · Cited by 446 · see citing works

Indirubin and Indigo Are Potent Aryl Hydrocarbon Receptor Ligands Present in Human Urine

Adachi, J., Mori, Y., Matsui, S., Takigami, H., Fujino, J., Kitagawa, H., Miller, C. A., Kato, T., Saeki, K., & Matsuda, T. (2001) · Journal of Biological Chemistry · doi:10.1074/jbc.c100238200 · Cited by 407 · see citing works

Structural Basis for the Synthesis of Indirubins as Potent and Selective Inhibitors of Glycogen Synthase Kinase-3 and Cyclin-Dependent Kinases

Polychronopoulos, P., Magiatis, P., Skaltsounis, A., Myrianthopoulos, V., Mikros, E., Tarricone, A., Musacchio, A., Roe, S. M., Pearl, L. H., Leost, M., et al. (2004) · Journal of Medicinal Chemistry · doi:10.1021/jm031016d · Cited by 382 · see citing works

Lactobacillus gallinarum -derived metabolites boost anti-PD1 efficacy in colorectal cancer by inhibiting regulatory T cells through modulating IDO1/Kyn/AHR axis

Fong, W., Li, Q., Ji, F., Liang, W., Lau, H. C.-H., Kang, X., Liu, W., To, K. K. W., Zuo, Z., Li, X., et al. (2023) · Gut · doi:10.1136/gutjnl-2023-329543 · Cited by 325 · see citing works

Modulation of a Circulating Uremic Solute via Rational Genetic Manipulation of the Gut Microbiota

Devlin, A. S., Marcobal, A. M., Dodd, D., Nayfach, S., Plummer, N. S., Meyer, T., Pollard, K. S., Sonnenburg, J. L., & Fischbach, M. A. (2016) · Cell Host & Microbe · doi:10.1016/j.chom.2016.10.021 · Cited by 300 · see citing works

Formation and Cleavage of C–C Bonds by Enzymatic Oxidation–Reduction Reactions

Guengerich, F. P., & Yoshimoto, F. K. (2018) · Chemical Reviews · doi:10.1021/acs.chemrev.8b00031 · Cited by 296 · see citing works

New Insights Into Gut-Bacteria-Derived Indole and Its Derivatives in Intestinal and Liver Diseases

Li, X., Zhang, B., Hu, Y., & Zhao, Y. (2021) · Frontiers in Pharmacology · doi:10.3389/fphar.2021.769501 · Cited by 235 · see citing works

Cytochrome p450 enzymes in the generation of commercial products

Guengerich, F. P. (2002) · Nature Reviews Drug Discovery · doi:10.1038/nrd792 · Cited by 223 · see citing works

Human Cytochrome P450 Enzymes

Guengerich, F. P. (2007) · Springer eBooks · doi:10.1007/0-387-27447-2_10 · Cited by 220 · see citing works

Formation of Volatile Tea Constituent Indole During the Oolong Tea Manufacturing Process

Zeng, L., Zhou, Y., Gui, J., Fu, X., Mei, X., Zhen, Y., Ye, T.-X., Du, B., Dong, F., Watanabe, N., et al. (2016) · Journal of Agricultural and Food Chemistry · doi:10.1021/acs.jafc.6b01742 · Cited by 186 · see citing works

Biodegradation and Biotransformation of Indole: Advances and Perspectives

Ma, Q., Zhang, X., & Qu, Y. (2018) · Frontiers in Microbiology · doi:10.3389/fmicb.2018.02625 · Cited by 177 · see citing works

Production of Indole and Indole-Related Compounds by the Intestinal Microbiota and Consequences for the Host: The Good, the Bad, and the Ugly

Tennoune, N., Andriamihaja, M., & Blachier, F. (2022) · Microorganisms · doi:10.3390/microorganisms10050930 · Cited by 159 · see citing works

Hepatic microsomal metabolism of indole to indoxyl, a precursor of indoxyl sulfate

Banoğlu, E., Jha, G. G., & King, R. J. (2001) · European Journal of Drug Metabolism and Pharmacokinetics · doi:10.1007/bf03226377 · Cited by 153 · see citing works

Does Enzymatic Hydrolysis of Glycosidically Bound Volatile Compounds Really Contribute to the Formation of Volatile Compounds During the Oolong Tea Manufacturing Process?

Gui, J., Fu, X., Zhou, Y., Katsuno, T., Mei, X., Deng, R., Xu, X., Zhang, L., Dong, F., Watanabe, N., et al. (2015) · Journal of Agricultural and Food Chemistry · doi:10.1021/acs.jafc.5b02741 · Cited by 151 · see citing works

Human Cytochrome P450 Enzymes

Guengerich, F. P. (2015) · Springer eBooks · doi:10.1007/978-3-319-12108-6_9 · Cited by 150 · see citing works

Reactivities of Oxo and Peroxo Intermediates Studied by Hemoprotein Mutants

Watanabe, Y., Nakajima, H., & Ueno, T. (2007) · Accounts of Chemical Research · doi:10.1021/ar600046a · Cited by 146 · see citing works

Indole: a signaling molecule or a mere metabolic byproduct that alters bacterial physiology at a high concentration?

Kim, J., & Park, W. (2015) · The Journal of Microbiology · doi:10.1007/s12275-015-5273-3 · Cited by 146 · see citing works

Cytochromes P450 and drug discovery

Lamb, D. C., Waterman, M. R., Kelly, S. L., & Guengerich, F. P. (2007) · Current Opinion in Biotechnology · doi:10.1016/j.copbio.2007.09.010 · Cited by 141 · see citing works

The role of the indoles in microbiota-gut-brain axis and potential therapeutic targets: A focus on human neurological and neuropsychiatric diseases

Zhou, Y., Chen, Y., He, H., Peng, M., Zeng, M., & Sun, H. (2023) · Neuropharmacology · doi:10.1016/j.neuropharm.2023.109690 · Cited by 141 · see citing works

Guanine-Rich RNAs and DNAs That Bind Heme Robustly Catalyze Oxygen Transfer Reactions

Poon, L. C.-H., Methot, S. P., Morabi-Pazooki, W., Pio, F., Bennet, A. J., & Sen, D. (2011) · Journal of the American Chemical Society · doi:10.1021/ja108571a · Cited by 137 · see citing works

Nutritional Influences on Skatole Formation and Skatole Metabolism in the Pig

Wesoly, R., & Weiler, U. (2012) · Animals · doi:10.3390/ani2020221 · Cited by 127 · see citing works

Isatin: Role in stress and anxiety

Medvedev, A. E., Igosheva, N., Crumeyrolle‐Arias, M., & Glover, V. A. S. (2005) · Stress · doi:10.1080/10253890500342321 · Cited by 127 · see citing works

Protein engineering of toluene ortho-monooxygenase of Burkholderia cepacia G4 for regiospecific hydroxylation of indole to form various indigoid compounds

Rui, L., Reardon, K. F., & Wood, T. K. (2004) · Applied Microbiology and Biotechnology · doi:10.1007/s00253-004-1698-z · Cited by 125 · see citing works

Monooxygenase, Peroxidase and Peroxygenase Properties and Reaction Mechanisms of Cytochrome P450 Enzymes

Hrycay, E. G., & Bandiera, S. M. (2015) · Advances in experimental medicine and biology · doi:10.1007/978-3-319-16009-2_1 · Cited by 124 · see citing works

Reactivities of Oxo and Peroxo Intermediates Studied by Hemoprotein Mutants

Watanabe, Y., Nakajima, H., & Ueno, T. (2007) · ChemInform · doi:10.1002/chin.200741272 · Cited by 115 · see citing works

Tryptophan metabolites in depression: Modulation by gut microbiota

Lukić, I., Ivković, S., Mitić, M., & Adžić, M. (2022) · Frontiers in Behavioral Neuroscience · doi:10.3389/fnbeh.2022.987697 · Cited by 110 · see citing works

Early immunocastration of male pigs with Improvac® – Effect on boar taint, hormones and reproductive organs

Brunius, C. F., Zamaratskaia, G., Andersson, K., Chen, G., Norrby, M., Madej, A., & Lundström, K. (2011) · Vaccine · doi:10.1016/j.vaccine.2011.10.014 · Cited by 110 · see citing works

An overview of microbial indigo-forming enzymes

Fabara, A. N., & Fraaije, M. W. (2019) · Applied Microbiology and Biotechnology · doi:10.1007/s00253-019-10292-5 · Cited by 105 · see citing works

Structure of the Human Lung Cytochrome P450 2A13

Smith, B. D., Sanders, J. L., Porubsky, P. R., Lushington, G. H., Stout, C. D., & Scott, E. E. (2007) · Journal of Biological Chemistry · doi:10.1074/jbc.m702361200 · Cited by 100 · see citing works

Biological targets for isatin and its analogues: Implications for therapy.

Medvedev, A. E., Бунеева, О. А., & Glover, V. A. S. (2007) · PubMed Central · Cited by 99 · see citing works

Recombinant Enzymes Overexpressed in Bacteria Show Broad Catalytic Specificity of Human Cytochrome P450 2W1 and Limited Activity of Human Cytochrome P450 2S1

Wu, Z., Sohl, C. D., Shimada, T., & Guengerich, F. P. (2006) · Molecular Pharmacology · doi:10.1124/mol.106.023648 · Cited by 99 · see citing works

Biodegradation of indole by a newly isolated Cupriavidus sp. SHE

Qu, Y., Shen, E., Ma, Q., Zhang, Z., Liu, Z., Shen, W., Wang, J., Li, D., Li, H., & Zhou, J. (2015) · Journal of Environmental Sciences · doi:10.1016/j.jes.2015.01.023 · Cited by 98 · see citing works

Independent actions on cyclin-dependent kinases and aryl hydrocarbon receptor mediate the antiproliferative effects of indirubins

Knockaert, M., Blondel, M., Bach, S., Leost, M., Elbi, C., Hager, G. L., Nagy, S. R., Han, D., Denison, M. S., Ffrench, M., et al. (2004) · Oncogene · doi:10.1038/sj.onc.1207535 · Cited by 97 · see citing works

Aryl hydrocarbon receptor response to indigoids in vitro and in vivo

Guengerich, F. P., Martin, M. V., McCormick, W. A., Nguyen, L. P., Glover, E. A., & Bradfield, C. A. (2004) · Archives of Biochemistry and Biophysics · doi:10.1016/j.abb.2004.01.002 · Cited by 95 · see citing works

Enzymatic Processing of Fumiquinazoline F: A Tandem Oxidative-Acylation Strategy for the Generation of Multicyclic Scaffolds in Fungal Indole Alkaloid Biosynthesis

Ames, B. D., Liu, X., & Walsh, C. T. (2010) · Biochemistry · doi:10.1021/bi1012029 · Cited by 94 · see citing works

Host-microbe co-metabolism via MCAD generates circulating metabolites including hippuric acid

Pruss, K. M., Chen, H., Liu, Y., Treuren, W. V., Higginbottom, S. K., Jarman, J. B., Fischer, C. R., Mak, J., Wong, B. T., Cowan, T. M., et al. (2023) · Nature Communications · doi:10.1038/s41467-023-36138-3 · Cited by 92 · see citing works

The effect of age on distribution of skatole and indole levels in entire male pigs in four breeds: Yorkshire, Landrace, Hampshire and Duroc

Babol, J., Zamaratskaia, G., Juneja, R., & Lundström, K. (2004) · Meat Science · doi:10.1016/j.meatsci.2003.11.008 · Cited by 91 · see citing works

Kinetic Analysis of Oxidation of Coumarins by Human Cytochrome P450 2A6

Yun, C., Kim, K., Calcutt, M. W., & Guengerich, F. P. (2005) · Journal of Biological Chemistry · doi:10.1074/jbc.m411019200 · Cited by 90 · see citing works

Characterisation of odorant compounds and their biochemical formation in green tea with a low temperature storage process

Katsuno, T., Kasuga, H., Kusano, Y., Yaguchi, Y., Tomomura, M., Cui, J., Yang, Z., Baldermann, S., Nakamura, Y., Ohnishi, T., et al. (2013) · Food Chemistry · doi:10.1016/j.foodchem.2013.10.069 · Cited by 87 · see citing works

Mutations of Toluene-4-Monooxygenase That Alter Regiospecificity of Indole Oxidation and Lead to Production of Novel Indigoid Pigments

McClay, K. R., Boss, C., Keresztes, I., & Steffan, R. J. (2005) · Applied and Environmental Microbiology · doi:10.1128/aem.71.9.5476-5483.2005 · Cited by 86 · see citing works

Whole-cell biocatalysis using cytochrome P450 monooxygenases for biotransformation of sustainable bioresources (fatty acids, fatty alkanes, and aromatic amino acids)

Park, H., Park, G., Jeon, W., Ahn, J., Yang, Y., & Choi, K. (2020) · Biotechnology Advances · doi:10.1016/j.biotechadv.2020.107504 · Cited by 85 · see citing works

Transient induction of cytochromes P450 1A1 and 1B1 in MCF-7 human breast cancer cells by indirubin

Spink, B. C., Hussain, M. M., Katz, B. H., Eisele, L. E., & Spink, D. C. (2003) · Biochemical Pharmacology · doi:10.1016/j.bcp.2003.08.019 · Cited by 82 · see citing works

Filling a Hole in Cytochrome P450 BM3 Improves Substrate Binding and Catalytic Efficiency

Huang, W., Westlake, A. C. G., Maréchal, J., Joyce, M. G., Moody, P. C. E., & Roberts, G. C. K. (2007) · Journal of Molecular Biology · doi:10.1016/j.jmb.2007.08.015 · Cited by 81 · see citing works

The scent of age

Osada, K., Yamazaki, K., Curran, M., Bard, J., Smith, B. P. C., & Beauchamp, G. K. (2003) · Proceedings of the Royal Society B Biological Sciences · doi:10.1098/rspb.2002.2308 · Cited by 80 · see citing works

Random Mutagenesis of Human Cytochrome P450 2A6 and Screening with Indole Oxidation Products1

Nakamura, K., Martin, M. V., & Guengerich, F. P. (2001) · Archives of Biochemistry and Biophysics · doi:10.1006/abbi.2001.2569 · Cited by 80 · see citing works

Analysis of Coumarin 7-Hydroxylation Activity of Cytochrome P450 2A6 using Random Mutagenesis

Kim, D., Wu, Z., & Guengerich, F. P. (2005) · Journal of Biological Chemistry · doi:10.1074/jbc.m508171200 · Cited by 78 · see citing works

Directed evolution of cytochrome P450 enzymes for biocatalysis: exploiting the catalytic versatility of enzymes with relaxed substrate specificity

Behrendorff, J. B. Y. H., Huang, W., & Gillam, E. M. J. (2015) · Biochemical Journal · doi:10.1042/bj20141493 · Cited by 77 · see citing works

Aryl hydrocarbon receptor-mediated induction of microsomal drug-metabolizing enzyme activity by indirubin and indigo

Sugihara, K., Kitamura, S., Yamada, T., Okayama, T., Ohta, S., Yamashita, K. H., Yasuda, M., Fujii‐Kuriyama, Y., Saeki, K., Matsui, S., et al. (2004) · Biochemical and Biophysical Research Communications · doi:10.1016/j.bbrc.2004.04.066 · Cited by 77 · see citing works

Correlation of tryptophan metabolites with connectivity of extended central reward network in healthy subjects

Osadchiy, V., Labus, J. S., Gupta, A., Jacobs, J. P., Ashe-McNalley, C., Hsiao, E. Y., & Mayer, E. A. (2018) · PLoS ONE · doi:10.1371/journal.pone.0201772 · Cited by 76 · see citing works

Expansion of Substrate Specificity of Cytochrome P450 2A6 by Random and Site-directed Mutagenesis*

Wu, Z., Podust, L. M., & Guengerich, F. P. (2005) · Journal of Biological Chemistry · doi:10.1074/jbc.m508182200 · Cited by 73 · see citing works

Human Carbonyl Reductases

Malátková, P., Maser, E., & Wsól, V. (2010) · Current Drug Metabolism · doi:10.2174/138920010794233530 · Cited by 73 · see citing works

Hydroxylation of Indole by Laboratory-evolved 2-Hydroxybiphenyl 3-Monooxygenase

Meyer, A., ̈rsten, M. W., Schmid, A., Kohler, H. E., & Witholt, B. (2002) · Journal of Biological Chemistry · doi:10.1074/jbc.m205621200 · Cited by 71 · see citing works

Metabolomics-Driven Discovery of a Prenylated Isatin Antibiotic Produced byStreptomycesSpecies MBT28

Wu, C., Du, C., Gubbens, J., Choi, Y. H., & van Wezel, G. P. (2015) · Journal of Natural Products · doi:10.1021/acs.jnatprod.5b00276 · Cited by 71 · see citing works

Interactions of mammalian cytochrome P450, NADPH-cytochrome P450 reductase, and cytochrome b5 enzymes

Shimada, T., Mernaugh, R. L., & Guengerich, F. P. (2004) · Archives of Biochemistry and Biophysics · doi:10.1016/j.abb.2004.12.008 · Cited by 70 · see citing works

Generation of New Protein Kinase Inhibitors Utilizing Cytochrome P450 Mutant Enzymes for Indigoid Synthesis

Guengerich, F. P., Sorrells, J. L., Schmitt, S., Krauser, J. A., Aryal, P., & Meijer, L. (2004) · Journal of Medicinal Chemistry · doi:10.1021/jm030561b · Cited by 70 · see citing works

Indole‐associated predator–prey interactions between the nematode C aenorhabditis elegans and bacteria

Lee, J., Kim, Y., Kim, M., Kim, E., Choi, H., Kim, Y., & Lee, J. (2016) · Environmental Microbiology · doi:10.1111/1462-2920.13649 · Cited by 69 · see citing works

Recent Highlights in the Development of Isatin-Based Anticancer Agents

Vine, K. L., Matesic, L., Locke, J. M., & Skropeta, D. (2013) · BENTHAM SCIENCE PUBLISHERS eBooks · doi:10.2174/9781608054961113020008 · Cited by 69 · see citing works

Indigogenic substrates for detection and localization of enzymes

Kiernan, J. A. (2007) · Biotechnic & Histochemistry · doi:10.1080/10520290701375278 · Cited by 69 · see citing works

Signal Mimics Derived from a Metagenomic Analysis of the Gypsy Moth Gut Microbiota

Guan, C., Ju, J., Borlee, B. R., Williamson, L. L., Shen, B., Raffa, K. F., & Handelsman, J. (2007) · Applied and Environmental Microbiology · doi:10.1128/aem.02617-06 · Cited by 69 · see citing works

Indoxyl-Sulfate-Induced Redox Imbalance in Chronic Kidney Disease

Lu, C., Zheng, C., Lu, K., Liao, M.-T., Wu, K., & Ma, M. (2021) · Antioxidants · doi:10.3390/antiox10060936 · Cited by 66 · see citing works

The therapeutic potential of dietary intervention: based on the mechanism of a tryptophan derivative-indole propionic acid on metabolic disorders

Niu, B., Pan, T., Xiao, Y., Wang, H., Zhu, J., Tian, F., Lu, W., & Chen, W. (2024) · Critical Reviews in Food Science and Nutrition · doi:10.1080/10408398.2023.2299744 · Cited by 66 · see citing works

Investigation of the Substrate Range of CYP199A4: Modification of the Partition between Hydroxylation and Desaturation Activities by Substrate and Protein Engineering

Bell, S. G., Zhou, R., Yang, W., Tan, A. B. H., Gentleman, A. S., Wong, L., & Zhou, W. (2012) · Chemistry - A European Journal · doi:10.1002/chem.201202776 · Cited by 65 · see citing works

Fenton chemistry enables the catalytic oxidative rearrangement of indoles using hydrogen peroxide

Zhao, G., Liang, L., Wang, E., Lou, S., Qi, R., & Tong, R. (2021) · Green Chemistry · doi:10.1039/d1gc00297j · Cited by 65 · see citing works

Tryptophan Metabolites at the Crossroad of Immune-Cell Interaction via the Aryl Hydrocarbon Receptor: Implications for Tumor Immunotherapy

Gargaro, M., Manni, G., Scalisi, G., Puccetti, P., & Fallarino, F. (2021) · International Journal of Molecular Sciences · doi:10.3390/ijms22094644 · Cited by 64 · see citing works

The pleiotropy of dioxin toxicity — Xenobiotic misappropriation of the aryl hydrocarbon receptor's alternative physiological roles

Furness, S. G. B., & Whelan, F. (2009) · Pharmacology & Therapeutics · doi:10.1016/j.pharmthera.2009.09.004 · Cited by 63 · see citing works

The Engagement of Cytochrome P450 Enzymes in Tryptophan Metabolism

Haduch, A., Bromek, E., Kuban, W., & Daniel, W. A. (2023) · Metabolites · doi:10.3390/metabo13050629 · Cited by 63 · see citing works

Environmental Chemical Diethylhexyl Phthalate Alters Intestinal Microbiota Community Structure and Metabolite Profile in Mice

Lei, M., Menon, R., Manteiga, S., Alden, N., Hunt, C. L., Alaniz, R. C., Lee, K., & Jayaraman, A. (2019) · mSystems · doi:10.1128/msystems.00724-19 · Cited by 62 · see citing works

Oxidative Metabolism as a Modulator of Kratom’s Biological Actions

Chakraborty, S., Uprety, R., Slocum, S. T., Irie, T., Rouzic, V. L., Li, X., Wilson, L., Scouller, B., Alder, A. F., Kruegel, A. C., et al. (2021) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.1c01111 · Cited by 61 · see citing works

Cytochrome P450 BM-3 Evolved by Random and Saturation Mutagenesis as an Effective Indole-Hydroxylating Catalyst

Li, H., Mei, L., Urlacher, V. B., & Schmid, R. D. (2007) · Applied Biochemistry and Biotechnology · doi:10.1007/s12010-007-8002-5 · Cited by 60 · see citing works

Comparison of Gene Expression Patterns between 2,3,7,8-Tetrachlorodibenzo-p-dioxin and a Natural Arylhydrocarbon Receptor Ligand, Indirubin

Adachi, J. (2004) · Toxicological Sciences · doi:10.1093/toxsci/kfh129 · Cited by 59 · see citing works

Formation of Natural Indigo Derived from Woad (Isatis tinctoria L.) in Relation to Product Purity

García‐Macías, P., & John, P. (2004) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf0486803 · Cited by 58 · see citing works

Effects of sex, weight, diet and hCG administration on levels of skatole and indole in the liver and hepatic activities of cytochromes P4502E1 and P4502A6 in pigs

Zamaratskaia, G., Chen, G., & Lundström, K. (2005) · Meat Science · doi:10.1016/j.meatsci.2005.07.020 · Cited by 56 · see citing works

Characterization of a major form of human isatin reductase and the reduced metabolite

Usami, N., Kitahara, K., Ishikura, S., Nagano, M., Sakai, S., & Hara, A. (2001) · European Journal of Biochemistry · doi:10.1046/j.0014-2956.2001.02510.x · Cited by 56 · see citing works

12(R)-Hydroxy-5(Z),8(Z),10(E),14(Z)-eicosatetraenoic Acid [12(R)-HETE], an Arachidonic Acid Derivative, Is an Activator of the Aryl Hydrocarbon Receptor

Chiaro, C. R., Patel, R. D., & Perdew, G. H. (2008) · Molecular Pharmacology · doi:10.1124/mol.108.049379 · Cited by 56 · see citing works

Indole peroxygenase activity of indoleamine 2,3-dioxygenase

Kuo, H. H., & Mauk, A. G. (2012) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1207191109 · Cited by 53 · see citing works

An update on the dietary ligands of the AhR

Ashida, H., Nishiumi, S., & Fukuda, I. (2008) · Expert Opinion on Drug Metabolism & Toxicology · doi:10.1517/17425255.4.11.1429 · Cited by 53 · see citing works

Co-expression of P450 BM3 and glucose dehydrogenase by recombinant Escherichia coli and its application in an NADPH-dependent indigo production system

Lu, Y., & Mei, L. (2006) · Journal of Industrial Microbiology & Biotechnology · doi:10.1007/s10295-006-0193-1 · Cited by 52 · see citing works

Newer guar gum ester/chicken feather keratin interact films for tissue engineering

Das, A., Das, A., Basu, A., Datta, P., Gupta, M., & Mukherjee, A. (2021) · International Journal of Biological Macromolecules · doi:10.1016/j.ijbiomac.2021.03.034 · Cited by 51 · see citing works

Formation of the indigo precursor indican in genetically engineered tobacco plants and cell cultures

Warzecha, H., Frank, A., Peer, M., Gillam, E. M. J., Guengerich, F. P., & Unger, M. (2006) · Plant Biotechnology Journal · doi:10.1111/j.1467-7652.2006.00231.x · Cited by 51 · see citing works

A Series of Isatin-Hydrazones with Cytotoxic Activity and CDK2 Kinase Inhibitory Activity: A Potential Type II ATP Competitive Inhibitor

Al-Salem, H. S., Arifuzzaman, M., Alkahtani, H. M., Abdalla, A. N., Issa, I. S., Alqathama, A. A., Albalawi, F. S., & Rahman, A. F. M. M. (2020) · Molecules · doi:10.3390/molecules25194400 · Cited by 51 · see citing works

The Aryl Hydrocarbon Receptor Pathway and Sexual Differentiation of Neuroendocrine Functions

Petersen, S. L., Krishnan, S., & Hudgens, E. D. (2006) · Endocrinology · doi:10.1210/en.2005-1157 · Cited by 50 · see citing works

Application of a new versatile electron transfer system for cytochrome P450-based Escherichia coli whole-cell bioconversions

Ringle, M., Khatri, Y., Zapp, J., Hannemann, F., & Bernhardt, R. (2012) · Applied Microbiology and Biotechnology · doi:10.1007/s00253-012-4612-0 · Cited by 49 · see citing works

Peroxygenase and Oxidase Activities of Dehaloperoxidase-Hemoglobin from Amphitrite ornata

Barrios, D. A., D’Antonio, J., McCombs, N. L., Zhao, J., Franzen, S., Schmidt, A. C., Sombers, L. A., & Ghiladi, R. A. (2014) · Journal of the American Chemical Society · doi:10.1021/ja500293c · Cited by 49 · see citing works

Consumption of pasteurized human lysozyme transgenic goats’ milk alters serum metabolite profile in young pigs

Brundige, D. R., Maga, E. A., Klasing, K. C., & Murray, J. D. (2009) · Transgenic Research · doi:10.1007/s11248-009-9334-4 · Cited by 48 · see citing works

Indigo dyeing from Isatis tinctoria L.: From medieval to modern use

Mocquard, J., Lamer, A.-C. L., Fabre, P., Mathieu, C. E., Chastrette, C., Vitrai, A., & Vandenbossche, V. (2022) · Dyes and Pigments · doi:10.1016/j.dyepig.2022.110675 · Cited by 47 · see citing works

Metabolic mediators: microbial-derived metabolites as key regulators of anti-tumor immunity, immunotherapy, and chemotherapy

Lu, S., Wang, C., Ma, J., & Wang, Y. (2024) · Frontiers in Immunology · doi:10.3389/fimmu.2024.1456030 · Cited by 47 · see citing works

Unveiling the role of gut-brain axis in regulating neurodegenerative diseases: A comprehensive review

Yadav, H., Jaldhi, Bhardwaj, R., Anamika, A., Bakshi, A., Gupta, S., & Maurya, S. K. (2023) · Life Sciences · doi:10.1016/j.lfs.2023.122022 · Cited by 46 · see citing works

Regulation of CYP2A6 Protein Expression by Skatole, Indole, and Testicular Steroids in Primary Cultured Pig Hepatocytes

Chen, G., Cue, R.-A., Lundström, K., Wood, J. D., & Doran, O. (2007) · Drug Metabolism and Disposition · doi:10.1124/dmd.107.017285 · Cited by 46 · see citing works

mRNA Distribution and Heterologous Expression of Orphan Cytochrome P450 20A1

Stark, K., Wu, Z., Bartleson, C., & Guengerich, F. P. (2008) · Drug Metabolism and Disposition · doi:10.1124/dmd.108.022020 · Cited by 45 · see citing works

Biotransformation of indole by Cupriavidus sp. strain KK10 proceeds through N-heterocyclic- and carbocyclic-aromatic ring cleavage and production of indigoids

Fukuoka, K., Tanaka, K., Ozeki, Y., & Kanaly, R. A. (2014) · International Biodeterioration & Biodegradation · doi:10.1016/j.ibiod.2014.11.007 · Cited by 44 · see citing works

Biomimetic oxidation of indole by Mn(III)porphyrins

Linhares, M., Rebelo, S. L. H., Simões, M. M. Q., Silva, A. M. S., Neves, M. G. P. M. S., Cavaleiro, J. A. S., & Freire, C. (2013) · Applied Catalysis A General · doi:10.1016/j.apcata.2013.11.023 · Cited by 43 · see citing works

Indigo dye production by enzymatic mimicking based on an iron(III)porphyrin

Rebelo, S. L. H., Linhares, M., Simões, M. M. Q., Silva, A. M. S., Neves, M. G. P. M. S., Cavaleiro, J. A. S., & Freire, C. (2014) · Journal of Catalysis · doi:10.1016/j.jcat.2014.04.012 · Cited by 43 · see citing works

Oxidation of indole by human cytochrome P450 enzymes

Guengerich, F. P., Cai, H., Notley, L. M., Voss, J. J. D., & Gillam, E. M. J. (2000) · The FASEB Journal

Hepatic microsomal metabolism of indole to indoxyl, a precursor of indoxyl sulfate

Banoğlu, E., Jha, G. G., & King, R. J. (2001) · European Journal of Drug Metabolism and Pharmacokinetics · doi:10.1007/bf03226377 · Cited by 153 · see citing works

Formation of indigo by recombinant mammalian cytochrome P450

Kim, D., Gillam, E. M. J., Aguinaldo, A. M. A., Notley, L. M., Mundkowski, R. G., Волков, А. А., Arnold, F. H., Souček, P., Voss, J. J. D., & Guengerich, F. P. (2000) · The FASEB Journal · Cited by 2 · see citing works

Random Mutagenesis of Human Cytochrome P450 2A6 and Screening with Indole Oxidation Products1

Nakamura, K., Martin, M. V., & Guengerich, F. P. (2001) · Archives of Biochemistry and Biophysics · doi:10.1006/abbi.2001.2569 · Cited by 80 · see citing works

Expansion of Substrate Specificity of Cytochrome P450 2A6 by Random and Site-directed Mutagenesis*

Wu, Z., Podust, L. M., & Guengerich, F. P. (2005) · Journal of Biological Chemistry · doi:10.1074/jbc.m508182200 · Cited by 73 · see citing works