hydantoins

Summary

Summary: Compounds based on imidazolidine dione. Some derivatives are ANTICONVULSANTS.

Top Publications

  1. Ma Z, Luo Y, Michailides T. Molecular characterization of the two-component histidine kinase gene from Monilinia fructicola. Pest Manag Sci. 2006;62:991-8 pubmed
    ..Comparison of DNA sequences of the Mfos-1 from LIR mutants and the wild-type sensitive (S) isolate showed that LIR mutants had single point mutations in the coiled coil region of Mfos-1. ..
  2. Kador P, Hamada T, Reinhardt R, Blessing K. Effect of an aldose reductase inhibitor on alveolar bone loss associated with periodontitis in diabetic rats. Postgrad Med. 2010;122:138-44 pubmed publisher
    ..05). These results suggest that the sorbitol pathway plays a critical role in the pathophysiological mechanism(s) of diabetic periodontitis and that AR may be a direct pharmacological target for the treatment for this disease...
  3. Gasparutto D, Muller E, Boiteux S, Cadet J. Excision of the oxidatively formed 5-hydroxyhydantoin and 5-hydroxy-5-methylhydantoin pyrimidine lesions by Escherichia coli and Saccharomyces cerevisiae DNA N-glycosylases. Biochim Biophys Acta. 2009;1790:16-24 pubmed publisher
    ..The study provides new insights into the substrate specificity of DNA N-glycosylases involved in the base excision repair of oxidized bases, together with complementary information on the biological role of hydantoin type lesions. ..
  4. Opacić N, Barbarić M, Zorc B, Cetina M, Nagl A, Frkovic D, et al. The novel L- and D-amino acid derivatives of hydroxyurea and hydantoins: synthesis, X-ray crystal structure study, and cytostatic and antiviral activity evaluations. J Med Chem. 2005;48:475-82 pubmed
    ..2 microg/mL; 6m, EC(50) = 4.0 microg/mL). However, these compounds showed also rather expressed cytotoxicity (4m, CC(50) = 43.4 microg/mL; 6m, CC(50) = 12.5 microg/mL(-1)). ..
  5. Ananda Kumar C, Kavitha C, Vinaya K, Benaka Prasad S, Thimmegowda N, Chandrappa S, et al. Synthesis and in vitro cytotoxic evaluation of novel diazaspiro bicyclo hydantoin derivatives in human leukemia cells: a SAR study. Invest New Drugs. 2009;27:327-37 pubmed publisher
    ..The position and number of substituents in benzyl group attached to N-8 of diazaspiro bicyclo hydantoin nucleus interacted selectively with specific targets leading to the difference of biochemical and pharmacological effects. ..
  6. Rolseth V, Krokeide S, Kunke D, Neurauter C, Suganthan R, Sejersted Y, et al. Loss of Neil3, the major DNA glycosylase activity for removal of hydantoins in single stranded DNA, reduces cellular proliferation and sensitizes cells to genotoxic stress. Biochim Biophys Acta. 2013;1833:1157-64 pubmed publisher
    ..b>Hydantoins are products of 8-oxoG oxidation and as 8-oxoG, they have been shown to be mutagenic lesions...
  7. Menor Salván C, Marin Yaseli M. A new route for the prebiotic synthesis of nucleobases and hydantoins in water/ice solutions involving the photochemistry of acetylene. Chemistry. 2013;19:6488-97 pubmed publisher
    ..Here, we report a new explanation for the origin of hydantoins, purines, and pyrimidines in eutectic water/ice/urea solutions driven by ultraviolet irradiation (in the 185-254?..
  8. Rivière J, Bergeron F, Tremblay S, Gasparutto D, Cadet J, Wagner J. Oxidation of 5-hydroxy-2'-deoxyuridine into isodialuric acid, dialuric acid, and hydantoin products. J Am Chem Soc. 2004;126:6548-9 pubmed
    ..Studies of a trinucleotide containing 5-hydroxyuracil suggest that the reactions described herein for the monomer can be extrapolated to DNA. ..
  9. Zhao X, Krishnamurthy N, Burrows C, David S. Mutation versus repair: NEIL1 removal of hydantoin lesions in single-stranded, bulge, bubble, and duplex DNA contexts. Biochemistry. 2010;49:1658-66 pubmed publisher
    ..Depending on the context, the glycosylase activity of NEIL1 may stall replication and prevent mutations or lead to inappropriate removal that may contribute to the mutational spectrum of these unusual lesions. ..
  10. Dry I, Yuan K, Hutton D. Dicarboximide resistance in field isolates of Alternaria alternata is mediated by a mutation in a two-component histidine kinase gene. Fungal Genet Biol. 2004;41:102-8 pubmed
    ..alternata isolates confirmed the presence of mutations leading to premature termination of the translated HK protein. The possible role of the two-component HK in the development of dicarboximide resistance in A. alternata is discussed. ..

Detail Information

Publications62

  1. Ma Z, Luo Y, Michailides T. Molecular characterization of the two-component histidine kinase gene from Monilinia fructicola. Pest Manag Sci. 2006;62:991-8 pubmed
    ..Comparison of DNA sequences of the Mfos-1 from LIR mutants and the wild-type sensitive (S) isolate showed that LIR mutants had single point mutations in the coiled coil region of Mfos-1. ..
  2. Kador P, Hamada T, Reinhardt R, Blessing K. Effect of an aldose reductase inhibitor on alveolar bone loss associated with periodontitis in diabetic rats. Postgrad Med. 2010;122:138-44 pubmed publisher
    ..05). These results suggest that the sorbitol pathway plays a critical role in the pathophysiological mechanism(s) of diabetic periodontitis and that AR may be a direct pharmacological target for the treatment for this disease...
  3. Gasparutto D, Muller E, Boiteux S, Cadet J. Excision of the oxidatively formed 5-hydroxyhydantoin and 5-hydroxy-5-methylhydantoin pyrimidine lesions by Escherichia coli and Saccharomyces cerevisiae DNA N-glycosylases. Biochim Biophys Acta. 2009;1790:16-24 pubmed publisher
    ..The study provides new insights into the substrate specificity of DNA N-glycosylases involved in the base excision repair of oxidized bases, together with complementary information on the biological role of hydantoin type lesions. ..
  4. Opacić N, Barbarić M, Zorc B, Cetina M, Nagl A, Frkovic D, et al. The novel L- and D-amino acid derivatives of hydroxyurea and hydantoins: synthesis, X-ray crystal structure study, and cytostatic and antiviral activity evaluations. J Med Chem. 2005;48:475-82 pubmed
    ..2 microg/mL; 6m, EC(50) = 4.0 microg/mL). However, these compounds showed also rather expressed cytotoxicity (4m, CC(50) = 43.4 microg/mL; 6m, CC(50) = 12.5 microg/mL(-1)). ..
  5. Ananda Kumar C, Kavitha C, Vinaya K, Benaka Prasad S, Thimmegowda N, Chandrappa S, et al. Synthesis and in vitro cytotoxic evaluation of novel diazaspiro bicyclo hydantoin derivatives in human leukemia cells: a SAR study. Invest New Drugs. 2009;27:327-37 pubmed publisher
    ..The position and number of substituents in benzyl group attached to N-8 of diazaspiro bicyclo hydantoin nucleus interacted selectively with specific targets leading to the difference of biochemical and pharmacological effects. ..
  6. Rolseth V, Krokeide S, Kunke D, Neurauter C, Suganthan R, Sejersted Y, et al. Loss of Neil3, the major DNA glycosylase activity for removal of hydantoins in single stranded DNA, reduces cellular proliferation and sensitizes cells to genotoxic stress. Biochim Biophys Acta. 2013;1833:1157-64 pubmed publisher
    ..b>Hydantoins are products of 8-oxoG oxidation and as 8-oxoG, they have been shown to be mutagenic lesions...
  7. Menor Salván C, Marin Yaseli M. A new route for the prebiotic synthesis of nucleobases and hydantoins in water/ice solutions involving the photochemistry of acetylene. Chemistry. 2013;19:6488-97 pubmed publisher
    ..Here, we report a new explanation for the origin of hydantoins, purines, and pyrimidines in eutectic water/ice/urea solutions driven by ultraviolet irradiation (in the 185-254?..
  8. Rivière J, Bergeron F, Tremblay S, Gasparutto D, Cadet J, Wagner J. Oxidation of 5-hydroxy-2'-deoxyuridine into isodialuric acid, dialuric acid, and hydantoin products. J Am Chem Soc. 2004;126:6548-9 pubmed
    ..Studies of a trinucleotide containing 5-hydroxyuracil suggest that the reactions described herein for the monomer can be extrapolated to DNA. ..
  9. Zhao X, Krishnamurthy N, Burrows C, David S. Mutation versus repair: NEIL1 removal of hydantoin lesions in single-stranded, bulge, bubble, and duplex DNA contexts. Biochemistry. 2010;49:1658-66 pubmed publisher
    ..Depending on the context, the glycosylase activity of NEIL1 may stall replication and prevent mutations or lead to inappropriate removal that may contribute to the mutational spectrum of these unusual lesions. ..
  10. Dry I, Yuan K, Hutton D. Dicarboximide resistance in field isolates of Alternaria alternata is mediated by a mutation in a two-component histidine kinase gene. Fungal Genet Biol. 2004;41:102-8 pubmed
    ..alternata isolates confirmed the presence of mutations leading to premature termination of the translated HK protein. The possible role of the two-component HK in the development of dicarboximide resistance in A. alternata is discussed. ..
  11. Ajouz S, Decognet V, Nicot P, Bardin M. Microsatellite stability in the plant pathogen Botrytis cinerea after exposure to different selective pressures. Fungal Biol. 2010;114:949-54 pubmed publisher
    ..This is the first study that reveals long-term stability of microsatellite markers of a spore-producing fungus exposed to different stresses. ..
  12. Hazra T, Muller J, Manuel R, Burrows C, Lloyd R, Mitra S. Repair of hydantoins, one electron oxidation product of 8-oxoguanine, by DNA glycosylases of Escherichia coli. Nucleic Acids Res. 2001;29:1967-74 pubmed
    ..In contrast, MutY does not significantly inhibit Nei for any Gh(Sp) base pair. These results suggest a protective function for MutY in preventing mutation as a result of A (G) incorporation opposite Gh(Sp) during DNA replication. ..
  13. Fonn Pfister R, Chemla P, Ward E, Girardet M, Kreuz K, Honzatko R, et al. The mode of action and the structure of a herbicide in complex with its target: binding of activated hydantocidin to the feedback regulation site of adenylosuccinate synthetase. Proc Natl Acad Sci U S A. 1996;93:9431-6 pubmed
    ..This work provides the first crystal structure of a herbicide-target complex reported to date...
  14. Somsak L, Kovacs L, Toth M, Osz E, Szilagyi L, Györgydeák Z, et al. Synthesis of and a comparative study on the inhibition of muscle and liver glycogen phosphorylases by epimeric pairs of d-gluco- and d-xylopyranosylidene-spiro-(thio)hydantoins and N-(d-glucopyranosyl) amides. J Med Chem. 2001;44:2843-8 pubmed
    D-Gluco- and D-xylopyranosylidene-spiro-hydantoins and -thiohydantoins were prepared from the parent sugars in a six-step, highly chemo-, regio-, and stereoselective procedure...
  15. Walters E, Lee S, Niderman T, Bernasconi P, Subramanian M, Siehl D. Adenylosuccinate synthetase from maize. Purification, properties, and mechanism of inhibition by 5'-phosphohydantocidin. Plant Physiol. 1997;114:549-55 pubmed
    ..Inhibition of AdSS by 5'-PH was competitive with IMP, with an apparent Ki of 22 nM. Apparently, 5'-PH inhibits the enzyme by binding to the IMP site and forming a tight, dead-end complex. ..
  16. Siehl D, Subramanian M, Walters E, Lee S, Anderson R, Toschi A. Adenylosuccinate synthetase: site of action of hydantocidin, a microbial phytotoxin. Plant Physiol. 1996;110:753-8 pubmed
    ..These results identify the site of action of hydantocidin and establish adenylosuccinate synthetase as an herbicide target of commercial potential. ..
  17. Schmitzer P, Graupner P, Chapin E, Fields S, Gilbert J, Gray J, et al. Ribofuranosyl triazolone: a natural product herbicide with activity on adenylosuccinate synthetase following phosphorylation. J Nat Prod. 2000;63:777-81 pubmed
    ..Metabolite reversal studies suggested the target site was adenylosuccinate synthetase, which was confirmed by direct measurement of the activity of the 5'-phosphorylated derivative on the isolated enzyme. ..
  18. Sekulic T, Keleman S, Tot K, Tot J, Trišović N, Uscumlic G. In Silico Study of Chromatographic Lipophilicity Parameters of 3-(4-Substituted Benzyl)-5-Phenylhydantoins. Comb Chem High Throughput Screen. 2016;19:437-43 pubmed
    ..nitro, methoxy and tert-butyl group in the molecule is indicated as unfavorable for the oral bioavailability of hydantoins. Multivariate exploratory analysis was used in order to visualize grouping patterns among molecular descriptors ..
  19. Durham T, Marimuthu J, Toth J, Liu C, Adams L, Mudra D, et al. A Highly Selective Hydantoin Inhibitor of Aggrecanase-1 and Aggrecanase-2 with a Low Projected Human Dose. J Med Chem. 2017;60:5933-5939 pubmed publisher
    ..The projected human dose required to achieve sustained plasma levels ?10 times the hADAMTS-5 IC50 is 5 mg q.d. ..
  20. Hamann L, Manfredi M, Sun C, Krystek S, Huang Y, Bi Y, et al. Tandem optimization of target activity and elimination of mutagenic potential in a potent series of N-aryl bicyclic hydantoin-based selective androgen receptor modulators. Bioorg Med Chem Lett. 2007;17:1860-4 pubmed
    ..Subsequent concurrent optimization for target activity and avoidance of mutagenicity led to the identification of a pharmacologically superior clinical candidate without mutagenic potential. ..
  21. Ribeiro M. Effects of thyroid hormone analogs on lipid metabolism and thermogenesis. Thyroid. 2008;18:197-203 pubmed publisher
    ..The available studies indicate that achieving selective activation of different TR-mediated pathways is a promising strategy for treating lipid disorders and obesity. ..
  22. Wong J, Webster M, Halverson C, Hengel M, Ngim K, Ebeler S. Multiresidue pesticide analysis in wines by solid-phase extraction and capillary gas chromatography-mass spectrometric detection with selective ion monitoring. J Agric Food Chem. 2003;51:1148-61 pubmed
  23. Hammad H, de Heer H, Soullie T, Hoogsteden H, Trottein F, Lambrecht B. Prostaglandin D2 inhibits airway dendritic cell migration and function in steady state conditions by selective activation of the D prostanoid receptor 1. J Immunol. 2003;171:3936-40 pubmed
  24. Ebersberger A, Natura G, Eitner A, Halbhuber K, Rost R, Schaible H. Effects of prostaglandin D2 on tetrodotoxin-resistant Na+ currents in DRG neurons of adult rat. Pain. 2011;152:1114-26 pubmed publisher
    ..Thus, the net effect of PGD(2) on DRG neurons is pronociceptive, although the magnitude of the TTX-R Na(+) currents depends on the balance of DP1 and DP2 receptor activation. ..
  25. de Groot A, White I, Flyvholm M, Lensen G, Coenraads P. Formaldehyde-releasers in cosmetics: relationship to formaldehyde contact allergy. Part 1. Characterization, frequency and relevance of sensitization, and frequency of use in cosmetics. Contact Dermatitis. 2010;62:2-17 pubmed publisher
  26. Tang Y, Xu X, Liu X, Huang X, Chen Y, Wang W, et al. Development of a lateral flow immunoassay (LFA) strip for the rapid detection of 1-aminohydantoin in meat samples. J Food Sci. 2011;76:T138-43 pubmed publisher
    ..This developed gold nanoparticle based LFA had a good specificity, sensitivity, stability, and reliability. It was potentially suitable for on-the-spot large-scale screening of meat samples, and even more other applications...
  27. Schuligoi R, Sedej M, Waldhoer M, Vukoja A, Sturm E, Lippe I, et al. Prostaglandin H2 induces the migration of human eosinophils through the chemoattractant receptor homologous molecule of Th2 cells, CRTH2. J Leukoc Biol. 2009;85:136-45 pubmed publisher
    ..These data indicate that PGH2 causes activation of the PGD2 receptors CRTH2 and DP via a dual mechanism: by interacting directly with the receptors and/or by giving rise to PGD2 after catalytic conversion by plasma proteins. ..
  28. Wu L, Wang Q, Liang X, Andreasson K. Divergent effects of prostaglandin receptor signaling on neuronal survival. Neurosci Lett. 2007;421:253-8 pubmed
  29. Ocasio C, Scanlan T. Design and characterization of a thyroid hormone receptor alpha (TRalpha)-specific agonist. ACS Chem Biol. 2006;1:585-93 pubmed
    ..Herein, we report the synthesis and biological evaluation of CO23, the first potent thyromimetic with TRalpha-specific effects in vitro and in vivo . ..
  30. Samuele A, Kataropoulou A, Viola M, Zanoli S, La Regina G, Piscitelli F, et al. Non-nucleoside HIV-1 reverse transcriptase inhibitors di-halo-indolyl aryl sulfones achieve tight binding to drug-resistant mutants by targeting the enzyme-substrate complex. Antiviral Res. 2009;81:47-55 pubmed publisher
  31. Latacz G, Pekala E, Ciopińska A, Kiec Kononowicz K. Unnatural D-amino acids as building blocks of new peptidomimetics. Acta Pol Pharm. 2006;63:430-3 pubmed