Role of microsomal steroid hydroxylases in Δ7-steroid biosynthesis
Abstract
CYP17 (steroid 17α-hydroxylase/17,20-lyase) is a key enzyme in steroid hormone biosynthesis. It catalyzes two independent reactions at the same active center and has a unique ability to differentiate Δ(4)-steroids and Δ(5)-steroids in the 17,20-lyase reaction. The present work presents a complex experimental analysis of the role of CYP17 in the metabolism of 7-dehydrosteroids. The data indicate the existence of a possible alternative pathway of steroid hormone biosynthesis using 7-dehydrosteroids. The major reaction products of CYP17 catalyzed hydroxylation of 7-dehydropregnenolone have been identified. Catalytic activity of CYP17 from different species with 7-dehydropregnenolone has been estimated. It is shown that CYP21 cannot use Δ(5)-Δ(7) steroids as a substrate.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
7DHP serves as a substrate for CYP17A1, producing 17(OH)7DHP and Δ7-dehydroepiandrosterone.
“Further support for 7DHP serving as a substrate for CYP17A1 is the production of 17(OH)7DHP and Δ7-dehydroepiandrosterone [65].”
From Novel activities of CYP11A1 and their potential physiological significance (2015) · cites this paper as [65]
Cites
The Carbon Monoxide-binding Pigment of Liver Microsomes
Omura, T., & Sato, R. (1964) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(20)82244-3 · Cited by 11,781 · see citing works
HIGH-RESOLUTION CRYSTAL STRUCTURE OF CYTOCHROME P450-CAM
Poulos, T. L., Finzel, B. C., & Howard, A. J. (1987) · Journal of Molecular Biology · doi:10.1016/0022-2836(87)90190-2 · Cited by 1,414 · see citing works
Neuroendocrinology of the Skin1
Slominski, A., & Wortsman, J. (2000) · Endocrine Reviews · doi:10.1210/edrv.21.5.0410 · Cited by 727 · see citing works
Barnes, H. J., Arlotto, M. P., & Waterman, M. R. (1991) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.88.13.5597 · Cited by 559 · see citing works
Neuroendocrinology of the Skin
Slominski, A. T. (2000) · Endocrine Reviews · doi:10.1210/er.21.5.457 · Cited by 503 · see citing works
Nishihara, K., Kanemori, M., Kitagawa, M., Yanagi, H., & Yura, T. (1998) · Applied and Environmental Microbiology · doi:10.1128/aem.64.5.1694-1699.1998 · Cited by 440 · see citing works
Expression of Bovine 17α-Hydroxylase Cytochrome P-450 cDNA in Nonsteroidogenic (COS 1) Cells
Zuber, M. X., Simpson, E. R., & Waterman, M. R. (1986) · Science · doi:10.1126/science.3535074 · Cited by 388 · see citing works
Smith-Lemli-Opitz Syndrome Is Caused by Mutations in the 7-Dehydrocholesterol Reductase Gene
Waterham, H. R., Wijburg, F. A., Hennekam, R. C. M., Vreken, P., Poll-The, B. T., Dorland, L., Duran, M., Jira, P. E., Smeitink, J. A. M., Wevers, R. A., et al. (1998) · The American Journal of Human Genetics · doi:10.1086/301982 · Cited by 296 · see citing works
Conley, A. J., & Bird, I. M. (1997) · Biology of Reproduction · doi:10.1095/biolreprod56.4.789 · Cited by 295 · see citing works
Gower, D. B. (1972) · Journal of Steroid Biochemistry · doi:10.1016/0022-4731(72)90011-8 · Cited by 259 · see citing works
Slominski, A., Zjawiony, J., Wortsman, J., Semak, I., Stewart, J., Pisarchik, A., Sweatman, T., Marcos, J., Dunbar, C., & C. Tuckey, R. (2004) · European Journal of Biochemistry · doi:10.1111/j.1432-1033.2004.04356.x · Cited by 243 · see citing works
ACTH receptor, CYP11A1, CYP17 and CYP21A2 genes are expressed in skin.
Slominski, A., Ermak, G., & Mihm, M. (1996) · The Journal of Clinical Endocrinology & Metabolism · doi:10.1210/jcem.81.7.8675607 · Cited by 216 · see citing works
Nakajin, S., Shinoda, M., Haniu, M., Shively, J. E., & Hall, P. F. (1984) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(17)43191-7 · Cited by 212 · see citing works
Auchus, R. J., & Miller, W. L. (1999) · Molecular Endocrinology · doi:10.1210/mend.13.7.0326 · Cited by 185 · see citing works
Kominami, S., Ochi, H., Kobayashi, Y., & Takemori, S. (1980) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(19)85711-3 · Cited by 171 · see citing works
Guryev, O., Carvalho, R. A., Usanov, S., Gilep, A., & Estabrook, R. W. (2003) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.2336107100 · Cited by 170 · see citing works
Fevold, H. R., Lorence, M. C., McCarthy, J. L., Trant, J. M., Kagimoto, M., Waterman, M. R., & Mason, J. I. (1989) · Molecular Endocrinology · doi:10.1210/mend-3-6-968 · Cited by 159 · see citing works
Imai, T., Globerman, H., Gertner, J. M., Kagawa, N., & Waterman, M. R. (1993) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(19)36570-6 · Cited by 153 · see citing works
Lee-Robichaud, P., Wright, J. N., Akhtar, M. E., & Akhtar, M. (1995) · Biochemical Journal · doi:10.1042/bj3080901 · Cited by 145 · see citing works
Ouellet, H., Guan, S., Johnston, J. B., Chow, E. D., Kells, P. M., Burlingame, A. L., Cox, J. S., Podust, L. M., & de Montellano, P. R. O. (2010) · Molecular Microbiology · doi:10.1111/j.1365-2958.2010.07243.x · Cited by 132 · see citing works
The cholesterol side-chain cleavage system of the adrenal cortex: A mixed-function oxidase
Simpson, E. R., & Boyd, G. S. (1966) · Biochemical and Biophysical Research Communications · doi:10.1016/0006-291x(66)90402-5 · Cited by 124 · see citing works
The Structure of Mycobacterium tuberculosis CYP125
McLean, K. J., Lafite, P., Levy, C., Cheesman, M. R., Mast, N., Pikuleva, I. A., Leys, D., & Munro, A. W. (2009) · Journal of Biological Chemistry · doi:10.1074/jbc.m109.032706 · Cited by 116 · see citing works
Swart, P., Swart, A. C., Waterman, M. R., Estabrook, R. W., & Mason, J. I. (1993) · The Journal of Clinical Endocrinology & Metabolism · doi:10.1210/jcem.77.1.8325965 · Cited by 106 · see citing works
Slominski, A., Semak, I., Wortsman, J., Zjawiony, J., Li, W., Zbytek, B., & Tuckey, R. C. (2006) · The FEBS Journal · doi:10.1111/j.1742-4658.2006.05302.x · Cited by 98 · see citing works
Slominski, A. T., Zmijewski, M. A., Semak, I., Sweatman, T., Janjetovic, Z., Li, W., Zjawiony, J. K., & Tuckey, R. C. (2009) · PLoS ONE · doi:10.1371/journal.pone.0004309 · Cited by 90 · see citing works
Suhara, K., Fujimura, Y., Shiroo, M., & Katagiri, M. (1984) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(17)47213-9 · Cited by 88 · see citing works
5α-Reduced C21 steroids are substrates for human cytochrome P450c17
Gupta, M. K., Guryev, O. L., & Auchus, R. J. (2003) · Archives of Biochemistry and Biophysics · doi:10.1016/j.abb.2003.07.003 · Cited by 84 · see citing works
Zhao, B., Li, L., Kagawa, N., Sundaramoorthy, M., Banerjee, S., Nagy, L. D., Guengerich, F. P., & Waterman, M. R. (2012) · Journal of Biological Chemistry · doi:10.1074/jbc.m111.323501 · Cited by 80 · see citing works
Porter, T. D., Wilson, T. E., & Kasper, C. B. (1987) · Archives of Biochemistry and Biophysics · doi:10.1016/0003-9861(87)90111-1 · Cited by 72 · see citing works
Cytochrome P-450 C21scc: One enzyme with two actions: Hydroxylase and lyase
Hall, P. F. (1991) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/0960-0760(91)90272-7 · Cited by 70 · see citing works
The Saga of the Ring B Unsaturated Equine Estrogens*
Bhavnani, B. R. (1988) · Endocrine Reviews · doi:10.1210/edrv-9-4-396 · Cited by 67 · see citing works
Nakajin, S., Takahashi, M., Shinoda, M., & Hall, P. F. (1985) · Biochemical and Biophysical Research Communications · doi:10.1016/0006-291x(85)91190-8 · Cited by 64 · see citing works
Tremblay, Y., Fleury, A., Beaudoin, C., Vallée, M., & BÉLANGER, A. (1994) · DNA and Cell Biology · doi:10.1089/dna.1994.13.1199 · Cited by 52 · see citing works
Liu, Y., Yao, Z., & Papadopoulos, V. (2005) · Molecular Endocrinology · doi:10.1210/me.2004-0271 · Cited by 48 · see citing works
Equine Type Estrogens Produced by a Pregnant Woman Carrying a Smith-Lemli-Opitz Syndrome Fetus
Shackleton, C. H. L., Roitman, E., Kratz, L. E., & Kelley, R. I. (1999) · The Journal of Clinical Endocrinology & Metabolism · doi:10.1210/jcem.84.3.5660 · Cited by 37 · see citing works
Soucy, P., Lacoste, L., & Luu‐The, V. (2003) · European Journal of Biochemistry · doi:10.1046/j.1432-1033.2003.03508.x · Cited by 27 · see citing works
Gilep, A. A., Estabrook, R. W., & Usanov, S. A. (2003) · Biochemistry (Moscow) · doi:10.1023/a:1022101703670 · Cited by 23 · see citing works
Cloutier, M., Fleury, A., Courtemanche, J., Ducharme, L., Mason, J. I., & Lehoux, J. (1997) · DNA and Cell Biology · doi:10.1089/dna.1997.16.357 · Cited by 23 · see citing works
Gilep, A. A., Guryev, O. L., Usanov, S. A., & Estabrook, R. W. (2001) · Biochemical and Biophysical Research Communications · doi:10.1006/bbrc.2001.5075 · Cited by 21 · see citing works
Shet, M. S., Fisher, C., Tremblay, Y., Bélanger, A., Conley, A. J., Mason, J. I., & Estabrook, R. W. (2007) · Drug Metabolism Reviews · doi:10.1080/03602530701468391 · Cited by 21 · see citing works
Sushko, T. A., Gilep, A. A., & Usanov, S. A. (2012) · Biochemistry (Moscow) · doi:10.1134/s0006297912060041 · Cited by 17 · see citing works
Foster, S. J., Marshall, D. E., Houghton, E., & Gower, D. B. (2002) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/s0960-0760(02)00224-8 · Cited by 12 · see citing works
Beaudoin, C., Lavallée, B., Tremblay, Y., Hum, D. W., Breton, R., de Launoit, Y., & BÉLANGER, A. (1998) · DNA and Cell Biology · doi:10.1089/dna.1998.17.707 · Cited by 10 · see citing works
Flagged first, then by citations
1 of the 44 references couldn’t be matched to a known paper.
Cited by
Sorted by citations
Novel activities of CYP11A1 and their potential physiological significance
Slominski, A. T., Li, W., Kim, T.-K., Semak, I., Wang, J., Zjawiony, J. K., & Tuckey, R. C. (2015) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2014.11.010 · Cited by 292 · see citing works
Extra-adrenal glucocorticoid biosynthesis: implications for autoimmune and inflammatory disorders
Slominski, R. M., Tuckey, R. C., Manna, P. R., Jetten, A. M., Postlethwaite, A., Raman, C., & Slominski, A. T. (2020) · Genes & Immunity · doi:10.1038/s41435-020-0096-6 · Cited by 155 · see citing works
Zheng, K., Zhang, G., Jiang, N.-H., Yang, S., Li, C. L., Meng, Z., Guo, Q., & Long, G. (2014) · Genomics · doi:10.1016/j.ygeno.2014.07.013 · Cited by 24 · see citing works
Nikonovich, T., Hurski, A. L., Morozevich, G. E., Latysheva, А. S., Sushko, T. A., Strushkevich, N. V., Gilep, A. A., Misharin, A. Y., Zhabinskii, V. N., & Khripach, V. A. (2018) · Steroids · doi:10.1016/j.steroids.2018.08.004 · Cited by 18 · see citing works
Suzuki, R., Hirakawa, H., & Nagamune, T. (2014) · Biotechnology Journal · doi:10.1002/biot.201400007 · Cited by 18 · see citing works
Ajduković, J. J., Jakimov, D., Rárová, L., Strnad, M., Dzichenka, Y. U., Usanov, S. A., Škorić, D., Jovanović-Šanta, S., & Sakač, M. N. (2021) · RSC Advances · doi:10.1039/d1ra07613b · Cited by 17 · see citing works
Tuckey, R. C., Tang, E. K. Y., Chen, Y. A., & Slominski, A. T. (2021) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2021.105929 · Cited by 15 · see citing works
Modified bile acids and androstanes—Novel promising inhibitors of human cytochrome P450 17A1
Dzichenka, Y. U., Shapira, M. A., Yantsevich, A., Cherkesova, T., Grbović, L. M., Savić, M. P., Usanov, S. A., & Jovanović-Šanta, S. (2020) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2020.105777 · Cited by 10 · see citing works
Haidukevich, I. V., Sushko, T. A., Tumilovich, A. M., Grabovec, I. P., Usanov, S. A., & Gilep, A. A. (2018) · Toxicology in Vitro · doi:10.1016/j.tiv.2018.04.002 · Cited by 9 · see citing works
Volkova, Y. A., Scherbakov, A. M., Dzichenka, Y. U., Komkov, A., Bogdanov, F. B., Salnikova, D. I., Dmitrenok, A. S., Sachanka, A. B., Sorokin, D. V., & Zavarzin, I. V. (2024) · RSC Medicinal Chemistry · doi:10.1039/d4md00153b · Cited by 5 · see citing works
- Authors
- Sushko, T. A., Gilep, A. A., Yantsevich, A. V., & Usanov, S. A.
- Affiliations
- National Academy of Sciences of Belarus (BY)
- Corresponding author
- Sushko, T. A.
- Venue
- Biochemistry (Moscow)
- Publisher
- Pleiades Publishing Ltd
- Published
- 2013-03
- Volume
- 78
- Issue
- 3
- Pages
- 282-289
- ISSN
- 0006-2979 (ISSN-L)
- 1608-3040
- OpenAlex
- W2034077203
- Cited by
- 10
- References
- 44
- Citations by year
- 2024: 1 · 2021: 2 · 2020: 2 · 2018: 2 · 2014: 3
- FWCI
- 0.45
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- Biochemistry (Moscow) (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Steroid Chemistry and Biochemistry
- Health Sciences › Medicine › Endocrinology, Diabetes and Metabolism › Adrenal Hormones and Disorders
- Health Sciences › Medicine › Endocrinology, Diabetes and Metabolism › Hormonal Regulation and Hypertension
- Keywords
- CYP17, steroidogenesis
- MeSH terms
- Humans, Kinetics, Microsomes, Steroid 17-alpha-Hydroxylase, Steroid 21-Hydroxylase, Steroids, Substrate Specificity, Biocatalysis
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review