Metabolism and covalent binding of 1-(o-chlorophenyl)-1-(p-chlorophenyl)-2,2-dichloroethane (o,p,'-DDD). Correlation between adrenocorticolytic activity and metabolic activation by adrenocortical mitochondria

Adrenocortical carcinoma

Else, T., Kim, A. C., Sabolch, A., Raymond, V. M., Kandathil, A., Caoili, E. M., Jolly, S., Miller, B. S., Giordano, T. J., & Hammer, G. D. (2014) · Endocrine Reviews · doi:10.1210/er.2013-1029 · Cited by 892 · see citing works

The Steroid Hormone Biosynthesis Pathway as a Target for Endocrine-Disrupting Chemicals

Sanderson, J. T. (2006) · Toxicological Sciences · doi:10.1093/toxsci/kfl051 · Cited by 518 · see citing works

Plasma concentrations of o,p'DDD, o,p'DDA, and o,p'DDE as predictors of tumor response to mitotane in adrenocortical carcinoma: results of a retrospective ENS@T multicenter study

Hermsen, I. G., Fassnacht, M., Terzolo, M., Houterman, S., den Hartigh, J., Leboulleux, S., Daffara, F., Berruti, A., Chadarevian, R., Schlumberger, M., et al. (2011) · The Journal of Clinical Endocrinology & Metabolism · doi:10.1210/jc.2010-2676 · Cited by 173 · see citing works

Disruption of androgen receptor signaling in males by environmental chemicals

Luccio-Camelo, D., & Prins, G. S. (2011) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2011.04.004 · Cited by 169 · see citing works

Intersection of the Roles of Cytochrome P450 Enzymes with Xenobiotic and Endogenous Substrates: Relevance to Toxicity and Drug Interactions

Guengerich, F. P. (2016) · Chemical Research in Toxicology · doi:10.1021/acs.chemrestox.6b00226 · Cited by 135 · see citing works

Mitotane has a strong and a durable inducing effect on CYP3A4 activity

van Erp, N. P., Guchelaar, H.-J., Ploeger, B. A., Romijn, J. A., Hartigh, J. D., & Gelderblom, H. (2011) · European Journal of Endocrinology · doi:10.1530/eje-10-0956 · Cited by 118 · see citing works

Metabolic activation and toxicity of a DDT-metabolite, 3-methylsulphonyl-DDE, in the adrenal Zona fasciculata in mice

Lund, B., Bergman, Å., & Brandt, I. (1988) · Chemico-Biological Interactions · doi:10.1016/0009-2797(88)90028-2 · Cited by 94 · see citing works

Morphofunctional effects of mitotane on mitochondria in human adrenocortical cancer cells

Poli, G., Guasti, D., Rapizzi, E., Fucci, R., Canu, L., Bandinelli, A., Cini, N., Bani, D., Mannelli, M., & Luconi, M. (2013) · Endocrine Related Cancer · doi:10.1530/erc-13-0150 · Cited by 88 · see citing works

Steroid and xenobiotic effects on the adrenal cortex: mediation by oxidative and other mechanisms

Hornsby, P. J. (1989) · Free Radical Biology and Medicine · doi:10.1016/0891-5849(89)90163-9 · Cited by 83 · see citing works

Pharmacological profile and effects of mitotane in adrenocortical carcinoma

Corso, C. R., Acco, A., Bach, C., Bonatto, S. J. R., de Figueiredo, B. C., & de Souza, L. M. (2020) · British Journal of Clinical Pharmacology · doi:10.1111/bcp.14721 · Cited by 67 · see citing works

Targeting Estrogen Receptor-α Reduces Adrenocortical Cancer (ACC) Cell Growth<i>in Vitro</i>and<i>in Vivo</i>: Potential Therapeutic Role of Selective Estrogen Receptor Modulators (SERMs) for ACC Treatment

Sirianni, R., Zolea, F., Chimento, A., Ruggiero, C., Cerquetti, L., Fallo, F., Pilon, C., Arnaldi, G., Carpinelli, G., Stigliano, A., et al. (2012) · The Journal of Clinical Endocrinology &amp; Metabolism · doi:10.1210/jc.2012-2374 · Cited by 58 · see citing works

Metabolic Activation and Binding of Mitotane in Adrenal Cortex Homogenates

Cai, W., Counsell, R. E., Djanegara, T., SCHTEINGART, D. E., Sinsheimer, J. E., & Wotring, L. L. (1995) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.2600840203 · Cited by 56 · see citing works

Treating canine Cushing’s syndrome: Current options and future prospects

Sanders, K., Kooistra, H. S., & Galac, S. (2018) · The Veterinary Journal · doi:10.1016/j.tvjl.2018.09.014 · Cited by 56 · see citing works

Modulation of proteomic profile in H295R adrenocortical cell line induced by mitotane

Stigliano, A., Cerquetti, L., Borro, M., et al. (2008) · Endocrine Related Cancer · doi:10.1677/erc-07-0003 · Cited by 50 · see citing works

Adrenocortical toxicity of 3-methylsulfonyl-DDE in mice II. Mitochondrial changes following ecologically relevant doses

Jönsson, C. (1991) · Fundamental and Applied Toxicology · doi:10.1016/0272-0590(91)90121-j · Cited by 45 · see citing works

Adrenocortical Cancer

Wandoloski, M., Bussey, K. J., & Demeure, M. J. (2009) · Surgical Clinics of North America · doi:10.1016/j.suc.2009.06.019 · Cited by 39 · see citing works

Comparison of the adrenalytic activity of mitotane and a methylated homolog on normal adrenal cortex and adrenal cortical carcinoma

Schteingart, D. E., Sinsheimer, J. E., Counsell, R. E., Abrams, G. D., McClellan, N., Djanegara, T., Hines, J., Ruangwises, N., Benitez, R., & Wotring, L. L. (1993) · Cancer Chemotherapy and Pharmacology · doi:10.1007/bf00685036 · Cited by 38 · see citing works

Bovine adrenal cortex transformations of mitotane [1-(2-chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloroethane; o,p′-DDD] and its p,p′- and m,p′-isomers

Cai, W., Benitez, R., Counsell, R. E., Djanegara, T., SCHTEINGART, D. E., Sinsheimer, J. E., & Wotring, L. L. (1995) · Biochemical Pharmacology · doi:10.1016/0006-2952(95)00028-x · Cited by 36 · see citing works

Adrenocorticolytic DDT-metabolites: studies in mink, Mustela vison and otter, Lutra lutra

J�nsson, C.-J., Lund, B., & Brandt, I. (1993) · Ecotoxicology · doi:10.1007/bf00058213 · Cited by 37 · see citing works

Determination of Mitotane (o,p`-DDD) and its Metabolites o,p`-DDA and o,p`-DDE in Plasma by High-Performance Liquid Chromatography

Andersen, A., Kasperlik-Zaluska, A. A., & Warren, D. J. (1999) · Therapeutic Drug Monitoring · doi:10.1097/00007691-199906000-00020 · Cited by 36 · see citing works

In vitro adrenal bio activation and effects on steroid metabolism of DDT, PCBs and their metabolites in the gray seal (Halichoerus grypus)

Lund, B. (1994) · Environmental Toxicology and Chemistry · doi:10.1002/etc.5620130609 · Cited by 36 · see citing works

The organochlorine o,p′-DDD disrupts the adrenal steroidogenic signaling pathway in rainbow trout (Oncorhynchus mykiss)

Lacroix, M., & Hontela, A. (2003) · Toxicology and Applied Pharmacology · doi:10.1016/s0041-008x(03)00168-6 · Cited by 35 · see citing works

Fluorodesoxyglucose uptake in the remaining adrenal glands during the follow-up of patients with adrenocortical carcinoma: do not consider it as malignancy

Leboulleux, S., Deandreis, D., Escourrou, C., Ghuzlan, A. A., Bidault, F., Auperin, A., Travagli, J. P., Lumbroso, J., Schlumberger, M. J., & Baudin, É. (2010) · European Journal of Endocrinology · doi:10.1530/eje-10-0666 · Cited by 31 · see citing works

Regional distribution of microsomal drug and steroid metabolism in the guinea pig adrenal cortex

Eacho, P. I., & Colby, H. D. (1983) · Life Sciences · doi:10.1016/0024-3205(83)90117-0 · Cited by 31 · see citing works

Molecular Mechanisms of Mitotane Action in Adrenocortical Cancer Based on In Vitro Studies

Iacono, M. L., Puglisi, S., Perotti, P., Saba, L., Petiti, J., Giachino, C., Reimondo, G., & Terzolo, M. (2021) · Cancers · doi:10.3390/cancers13215255 · Cited by 30 · see citing works

Metabolism and toxicity of xenobiotics in the adrenal cortex, with particular reference to 7,12‐dimethylbenz(a) anthracene

Hallberg, E. (1990) · Journal of Biochemical and Molecular Toxicology · doi:10.1002/jbt.2570050202 · Cited by 28 · see citing works

Biphasic hormonal responses to the adrenocorticolytic DDT metabolite 3-methylsulfonyl-DDE in human cells

Asp, V., Ullerås, E., Lindström, V., Bergström, U., Oskarsson, A., & Brandt, I. (2009) · Toxicology and Applied Pharmacology · doi:10.1016/j.taap.2009.10.018 · Cited by 26 · see citing works

Cytochrome P450 11A1 Bioactivation of a Kinase Inhibitor in Rats: Use of Radioprofiling, Modulation of Metabolism, and Adrenocortical Cell Lines to Evaluate Adrenal Toxicity

Zhang, D., Flint, O. P., Wang, L., et al. (2012) · Chemical Research in Toxicology · doi:10.1021/tx200524d · Cited by 27 · see citing works

In vitro bioactivation of the environmental pollutant 3-methylsulphonyl-2,2-bis(4-chlorophenyl)-1,1-dichloroethene in the human adrenal gland

Jönsson, C., & LUND, B. (1994) · Toxicology Letters · doi:10.1016/0378-4274(94)90177-5 · Cited by 27 · see citing works

Effects of mitotane treatment on human steroid metabolism: implications for patient management

Ghataore, L., Chakraborti, I., Aylwin, S. J. B., Schulte, K., Dorota Dworakowska, B., Coskeran, P., & Taylor, N. (2012) · Endocrine Connections · doi:10.1530/ec-12-0028 · Cited by 26 · see citing works

The Lack of Antitumor Effects of o,p′DDA Excludes Its Role as an Active Metabolite of Mitotane for Adrenocortical Carcinoma Treatment

Hescot, S., Paci, A., Seck, A., Slama, A., Viengchareun, S., Trabado, S., Brailly‐Tabard, S., Ghuzlan, A. A., Young, J., Baudin, É., et al. (2014) · Hormones and Cancer · doi:10.1007/s12672-014-0189-7 · Cited by 24 · see citing works

Comparative CYP-dependent binding of the adrenocortical toxicants 3-methylsulfonyl–DDE and o,p′-DDD in Y-1 adrenal cells

Hermansson, V., Asp, V., Bergman, Å., Bergström, U., & Brandt, I. (2007) · Archives of Toxicology · doi:10.1007/s00204-007-0206-5 · Cited by 19 · see citing works

Genomic and Expression Profiling of Adrenocortical Carcinoma: Application to Diagnosis, Prognosis and Treatment

Bussey, K. J., & Demeure, M. J. (2009) · Future Oncology · doi:10.2217/fon.09.45 · Cited by 17 · see citing works

o,p′-DDD in the mouse lung: Selective uptake, covalent binding and effect on drug metabolism

Lund, B., Klasson‐Wehler, E., & Brandt, I. (1986) · Chemico-Biological Interactions · doi:10.1016/0009-2797(86)90022-0 · Cited by 16 · see citing works

DDT and its Analogs

Smith, A. G. (2001) · Elsevier eBooks · doi:10.1016/b978-012426260-7.50063-x · Cited by 16 · see citing works

Pharmacokinetics of the adrenocorticolytic compounds 3-methylsulphonyl-DDE and o,p′-DDD (mitotane) in Minipigs

Hermansson, V., Cantillana, T., Hovander, L., et al. (2007) · Cancer Chemotherapy and Pharmacology · doi:10.1007/s00280-007-0468-x · Cited by 13 · see citing works

Developmental and Reproductive Toxicity of Persistent Environmental Pollutants

Brandt, I., Berg, C., Halldin, K., et al. (1998) · Archives of toxicology. Supplement · doi:10.1007/978-3-642-46856-8_10 · Cited by 12 · see citing works

In vitro macromolecular binding of 2-(2-chlorophenyl)-2-(4-chlorophenyl)-1,1-dichloroethane (o,p′-DDD) in the mouse lung and liver

Lund, B., Bergman, Å., & Brandt, I. (1989) · Chemico-Biological Interactions · doi:10.1016/0009-2797(89)90063-x · Cited by 12 · see citing works

Covalent Binding of Four DDD Isomers in the Mouse Lung: Lack of Structure Specificity

Lund, B., Ghantous, H. N., Bergman, Å., et al. (1989) · Pharmacology & Toxicology · doi:10.1111/j.1600-0773.1989.tb01174.x · Cited by 12 · see citing works

Metabolism of xenobiotics in the human adrenal gland

Papadopoulos, D., Seidegård, J., & Rydström, J. (1984) · Cancer Letters · doi:10.1016/0304-3835(84)90039-9 · Cited by 12 · see citing works

Chiral effects in adrenocorticolytic action ofo,p′-DDD (mitotane) in human adrenal cells

Asp, V., Cantillana, T., Bergman, Å., et al. (2010) · Xenobiotica · doi:10.3109/00498250903470230 · Cited by 10 · see citing works

Toxicology of DDT and Some Analogues

Smith, A. G. (2009) · Elsevier eBooks · doi:10.1016/b978-0-12-374367-1.00093-8 · Cited by 11 · see citing works

Isolation and Use of Primary Adrenocortical Cells from Guinea Pigs, Dogs and Monkeys forIn Vitro Toxicity Studies

Wolfgang, G. H. I., Vernetti, L. A., & MacDonald, J. R. (1994) · Toxicology Methods · doi:10.3109/15376519409041600 · Cited by 8 · see citing works

Are Chlorinated Pesticides a Causation in Maternal Mitochondrial DNA (mtDNA) Mutations?

Thrasher, J. D. (2000) · Archives of Environmental Health An International Journal · doi:10.1080/00039890009604018 · Cited by 8 · see citing works

Metabolism of 4-chlorobiphenyl by guinea pig adrenocortical and hepatic microsomes

Eacho, P. I., O’Donnell, J. P., & Colby, H. D. (1984) · Biochemical Pharmacology · doi:10.1016/0006-2952(84)90148-5 · Cited by 7 · see citing works

Mechanisms of endocrine disruption

Greathouse, K. L., & Walker, C. L. (2010) · Cambridge University Press eBooks · doi:10.1017/cbo9780511674686.007 · Cited by 5 · see citing works

Toxicologically important DDT metabolites : Synthesis, enantioselective analysis and kinetics

Cantillana, T. (2009) · DiVA (Stockholm University) · Cited by 5 · see citing works

Metabolic effects of pharmaceuticals in fish

Yeh, A., Meador, J. P., Lunsman, T. D., Mayfield, D. B., & Verslycke, T. A. (2021) · Elsevier eBooks · doi:10.1016/b978-0-08-102971-8.00013-5 · Cited by 6 · see citing works

Adrenal Bioactivation and Toxicity of 3-Meso2-Dde, O,P'-Ddd and Dmba Investigated in Tissue Slice Culture

Lindhe, Ö. (2001) · KTH Publication Database DiVA (KTH Royal Institute of Technology) · Cited by 4 · see citing works

Effects of o,p’-DDE, a Mitotane Metabolite, in an Adrenocortical Carcinoma Cell Line

Bach, C., Corso, C. R., Veiga, A. D. A., Paraizo, M. M., & de Souza, L. M. (2022) · Pharmaceuticals · doi:10.3390/ph15121486 · Cited by 3 · see citing works

Mitotane treatment in adrenocortical carcinoma: mechanisms of action and predictive markers of response to therapy

ALTIERI, B., Lalli, E., & Faggiano, A. (2021) · Minerva Endocrinology · doi:10.23736/s2724-6507.21.03601-0 · Cited by 5 · see citing works

DDT and Other Chlorinated Insecticides

Smith, A. G. (2012) · Royal Society of Chemistry eBooks · doi:10.1039/9781849733007-00037 · Cited by 1 · see citing works

Biochemical mechanism of the o,p’-DDD effect on the adrenal cortex

As, M., & Ковзун, О. І. (2017) · The Ukrainian Biochemical Journal · doi:10.15407/ubj89.05.005 · Cited by 1 · see citing works

Effects of two DDT metabolites and one synthetic DDE-analogue on testicular steroidogenesis in primary porcine Leydig cells in vitro during neonatal development

Sørvik, I. B. (2010) · NORA - Norwegian Open Research Archives

Two-dimensional chromatography for enantiomeric analysis of mitotane and its metabolite o,p′-DDA in patients with adrenocortical carcinoma indicates enantioselective metabolism

Stadler, G., Veiga, A. D. A., Corso, C. R., de Assis, C. B., Nogueira, B. D. T., Martins, L. R. R., Bonk, B. C., Pontes, F. L. D., de Figueiredo, B. C., & de Souza, L. M. (2023) · Bioorganic Chemistry · doi:10.1016/j.bioorg.2023.106835

Covalent and non-covalent binding in vanadium–protein adducts

Ugone, V., Sanna, D., Ruggiu, S., et al. (2020) · Inorganic Chemistry Frontiers · doi:10.1039/d0qi01308k · Cited by 23 · see citing works

Covalent and non-covalent albumin binding of Au(i) bis-NHCs via post-synthetic amide modification†

Sen, S., Perrin, M. W., Sedgwick, A. C., Lynch, V., Sessler, J., & Arambula, J. (2021) · Chemical Science · doi:10.1039/d1sc01055g · Cited by 12 · see citing works

The Reactions of Disulphide Dyes for the Covalent Coloration of Keratin

Asquith, R. S., Carthew, P., & FRANCIS, T. T. (1973) · Journal of the Society of Dyers and Colourists · doi:10.1111/j.1478-4408.1973.tb03144.x · Cited by 4 · see citing works

Covalent and Non-covalent Binding of Tetrathiafulvalene to Carbon Nanotubes

Guldi, D. M. (2012) · ECS Meeting Abstracts · doi:10.1149/ma2012-01/29/1108

[Research progress of the small molecule covalent inhibitors].

Yang, B., Wang, W., & Li, L. (2014) · PubMed · Cited by 1 · see citing works