Structure-activity relationships (SAR) and structure-metabolism relationships (SMR) affecting the teratogenicity of carboxylic acids.

(1990). Structure-Activity Relationships (Sar) and Structure-Metabolism Relationships (Smr) Affecting the Teratogenicity of Carboxylic Acids. Drug Metabolism Reviews: Vol. 22, No. 5, pp. 411-449.

[1]  N. A. Sörensen,et al.  Studies Related to Naturally Occurring Acetylene Compounds. XVII. Four New Polyacetylenes from Garden Varieties of Coreopsis. , 1954 .

[2]  C. Mackenzie,et al.  The binding sites of sarcosine oxidase. , 1955, The Journal of biological chemistry.

[3]  H. Wagner,et al.  Das biologische Verhalten von Fettsäuren mit Dreifachbindung I. Speicherung und Abbau von Stearolsäure bei der Ratte , 1966 .

[4]  G. Milne,et al.  Refsum's Disease: Nature of the Enzyme Defect , 1967, Science.

[5]  G. Milne,et al.  The nature of the metabolic defect in Refsum's disease. , 1968, Pathologia Europaea.

[6]  K Smith,et al.  Sweat in Schizophrenic Patients: Identification of the Odorous Substance , 1969, Science.

[7]  O. Stokke The degradation of a branched chain fatty acid by alternations between α- and β-oxidations , 1969 .

[8]  J. Wilson Mechanisms of teratogenesis. , 1973, The American journal of anatomy.

[9]  P. Mandel,et al.  Properties of ecto-(inoganic) pyrophosphatase of nervous system cells in culture. Activation upon partial release of sialic acid from the cell surface. , 1976, The Journal of biological chemistry.

[10]  E. Glover,et al.  Stereospecific, high affinity binding of 2,3,7,8-tetrachlorodibenzo-p-dioxin by hepatic cytosol. Evidence that the binding species is receptor for induction of aryl hydrocarbon hydroxylase. , 1976, The Journal of biological chemistry.

[11]  S. Fabro,et al.  Teratogenicity of valproic acid: In vivo and in vitro investigations , 1981 .

[12]  E. Freese Use of cultured cells in the identification of potential teratogens. , 1982, Teratogenesis, carcinogenesis, and mutagenesis.

[13]  F. J. D. Carlo Metabolism, Pharmacokinetics, and Toxicokinetics Defined , 1982 .

[14]  Teratogenesis of calcium valproate in rats. , 1983 .

[15]  H. Schulz Metabolism of 4-pentenoic acid and inhibition of thiolase by metabolites of 4-pentenoic acid. , 1983, Biochemistry.

[16]  R. Miller,et al.  Comparative metabolism and disposition of ethylene glycol monomethyl ether and propylene glycol monomethyl ether in male rats. , 1983, Toxicology and applied pharmacology.

[17]  J. Yonemoto,et al.  Effects of dimethoxyethyl phthalate, monomethoxyethyl phthalate, 2-methoxyethanol and methoxyacetic acid on post implantation rat embryos in culture. , 1984, Toxicology letters.

[18]  D. Lindhout,et al.  SPINA BIFIDA AND IN-UTERO EXPOSURE TO VALPROATE , 1984, The Lancet.

[19]  F. Mauguière,et al.  VALPROATE AND SPINA BIFIDA , 1984, The Lancet.

[20]  G. Granneman,et al.  Aspects of the metabolism of valproic acid. , 1984, Xenobiotica; the fate of foreign compounds in biological systems.

[21]  W. B. Howard,et al.  Structure-Activity Relationships of Retinoids in Developmental Toxicology , 1984 .

[22]  C C Willhite,et al.  Structure-activity relationships of retinoids in developmental toxicology. I. Studies on the nature of the polar terminus of the vitamin A molecule. , 1984, Toxicology and applied pharmacology.

[23]  R. Brent,et al.  Mechanisms of teratogenesis. , 1984, Annual review of pharmacology and toxicology.

[24]  R. Cook,et al.  Enzymatic properties of dimethylglycine dehydrogenase and sarcosine dehydrogenase from rat liver. , 1985, Archives of biochemistry and biophysics.

[25]  M. Boyd,et al.  Metabolic activation of 2-methylfuran by rat microsomal systems. , 1985, Toxicology and applied pharmacology.

[26]  D. MacGregor,et al.  Possible valproate teratogenicity. , 1985, Archives of neurology.

[27]  James L. Schardein,et al.  Chemically Induced Birth Defects , 1985 .

[28]  N A Brown,et al.  The teratogenic potential of alkoxy acids in post-implantation rat embryo culture: structure-activity relationships. , 1985, Toxicology letters.

[29]  D. Russell,et al.  Ornithine decarboxylase: a key regulatory enzyme in normal and neoplastic growth. , 1985, Drug metabolism reviews.

[30]  M. Coakley,et al.  Valproic acid teratogenicity: demonstration that the biochemical mechanism differs from that of valproate hepatotoxicity. , 1985, Biochemical Society transactions.

[31]  W. Scott,et al.  Teratogenicity of dimethoxyethyl phthalate and its metabolites methoxyethanol and methoxyacetic acid in the rat. , 1985, Teratology.

[32]  H. Nau,et al.  Predicting the human teratogenic potential of the anticonvulsant, valproic acid, from a non-human primate model. , 1986, Toxicology.

[33]  C. Auer,et al.  Structure-metabolism relationships (SMR) for the prediction of health hazards by the Environmental Protection Agency. II. Application to teratogenicity and other toxic effects caused by aliphatic acids. , 1986, Drug metabolism reviews.

[34]  T. Kuhara,et al.  Identification and quantification of octanoyl glucuronide in the urine of children who ingested medium-chain triglycerides. , 1986, Biomedical & environmental mass spectrometry.

[35]  P. Gove Webster's Third New International Dictionary , 1986 .

[36]  C. Auer,et al.  Structure-metabolism relationships (SMR) for the prediction of health hazards by the Environmental Protection Agency. I. Background for the practice of predictive toxicology. , 1986, Drug metabolism reviews.

[37]  O. Flint,et al.  Chemical teratogenesis: testing methods and the role of metabolism. , 1986, Drug metabolism reviews.

[38]  C C Willhite,et al.  Structure-activity relationships of retinoids in developmental toxicology. II. Influence of the polyene chain of the vitamin A molecule. , 1986, Toxicology and applied pharmacology.

[39]  H Nau,et al.  Pharmacologic evaluation of various metabolites and analogs of valproic acid: teratogenic potencies in mice. , 1986, Fundamental and applied toxicology : official journal of the Society of Toxicology.

[40]  R. Smith,et al.  Ethylene glycol monomethyl ether (EGME) inhibits rat embryo ornithine decarboxylase (ODC) activity. , 1986, Drug and chemical toxicology.

[41]  C. Willhite,et al.  Comparative teratogenic activity of cancer chemopreventive retinoidal benzoic acid congeners (arotinoids). , 1987, Journal of the National Cancer Institute.

[42]  W. B. Howard,et al.  Structure-toxicity relationships of the tetramethylated tetralin and indane analogs of retinoic acid. , 1987, Teratology.

[43]  V. Giguère,et al.  Identification of a receptor for the morphogen retinoic acid , 1987, Nature.

[44]  Pierre Chambon,et al.  A human retinoic acid receptor which belongs to the family of nuclear receptors , 1987, Nature.

[45]  W. Scott,et al.  Teratogenicity of di(2-ethylhexyl) phthalate, 2-ethylhexanol, 2-ethylhexanoic acid, and valproic acid, and potentiation by caffeine. , 1987, Teratology.

[46]  R. Miller Metabolism and disposition of glycol ethers. , 1987, Drug metabolism reviews.

[47]  B. Abbott,et al.  Teratogenicity of benzoic acid derivatives of retinoic acid in cultured mouse embryos. , 1988, Reproductive toxicology.

[48]  T. D. Stephens Proposed mechanisms of action in thalidomide embryopathy. , 1988, Teratology.

[49]  M. Rocher,et al.  Biological activity of retinoids correlates with affinity for nuclear receptors but not for cytosolic binding protein. , 1988, Skin pharmacology : the official journal of the Skin Pharmacology Society.

[50]  R. Evans,et al.  The steroid and thyroid hormone receptor superfamily. , 1988, Science.

[51]  H. Nau,et al.  Pharmacokinetic aspects of drug effects in vitro (II) placental transfer to the embryo and activity of some carboxylic acids structurally related to valproic acid in whole embryos in culture. , 1988, Toxicology in vitro : an international journal published in association with BIBRA.

[52]  C. Mebus,et al.  The possible role of one-carbon moieties in 2-methoxyethanol and 2-methoxyacetic acid-induced developmental toxicity. , 1989, Toxicology and applied pharmacology.

[53]  H. Nau,et al.  Teratogenicity and placental transfer of all-trans-, 13-cis-, 4-oxo-all-trans-, and 4-oxo-13-cis-retinoic acid after administration of a low oral dose during organogenesis in mice. , 1989, Toxicology and applied pharmacology.

[54]  M. Toyota,et al.  Terpenoid biotransformation in mammals. V. Metabolism of (+)-citronellal, (+-)-7-hydroxycitronellal, citral, (-)-perillaldehyde, (-)-myrtenal, cuminaldehyde, thujone, and (+-)-carvone in rabbits. , 1989, Xenobiotica; the fate of foreign compounds in biological systems.

[55]  H. Nau,et al.  Asymmetric synthesis and enantioselective teratogenicity of 2-n-propyl-4-pentenoic acid (4-en-VPA), an active metabolite of the anticonvulsant drug, valproic acid. , 1989, Toxicology letters.

[56]  L. Birnbaum,et al.  Cellular alterations and enhanced induction of cleft palate after coadministration of retinoic acid and TCDD. , 1989, Toxicology and applied pharmacology.

[57]  L. Newman,et al.  An in vitro assay for teratogens with cultures of rat embryo midbrain and limb bud cells. , 1989, Toxicology and applied pharmacology.

[58]  H. Nau,et al.  Asymmetric synthesis and teratogenic activity of (R)- and (S)-2-ethylhexanoic acid, a metabolite of the plasticizer di-(2-ethylhexyl)phthalate. , 1990, Life sciences.