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Chemical Compound Review

AC1MXIRZ     2-sulfanylidene-5H-pyrimidin- 4-one

Synonyms: NSC-1905, NSC1905, CTK8I8992
 
 
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Disease relevance of NSC1905

 

High impact information on NSC1905

 

Chemical compound and disease context of NSC1905

 

Biological context of NSC1905

  • Photosensitized damage to supercoiled plasmid DNA induced by 334-nm radiation in the presence of 2-thiouracil consists of alkali- and piperidine-labile sites as well as frank strand breaks [15].
  • Induction of cell killing, mutation and umu gene expression by 6-mercaptopurine or 2-thiouracil with UVA irradiation [11].
  • The hybridization affinity and base pair recognition ability of oligonucleotides having 2-thiouracil moieties with both the complementary RNAs and DNAs were also studied in detail [16].
 

Anatomical context of NSC1905

  • Several 5-diethylaminomethyl derivatives and nitrogen mustards of uracil and 2-thiouracil have been synthesized and tested for their potential anticancer activity in vitro on KB cells and in vivo on Ehrlich carcinoma [17].
  • From 6 to 12 weeks of age, four lambs in the treatment group received 15 mg kg(-1) body weight per day of 6-propyl 2-thiouracil orally to suppress normal thyroid function [18].
 

Associations of NSC1905 with other chemical compounds

 

Gene context of NSC1905

  • To obtain a more definitive estimate of the relative stabilities for 2-thiouracil tautomers in the gas phase, single-point MP2/6-31+G** calculations were performed on the HF/6-31+G** optimized geometries [23].
  • ESR of irradiated 2-thiouracil single crystals. A 3alpha-hydrogen radical [24].
 

Analytical, diagnostic and therapeutic context of NSC1905

References

  1. Pseudouridine-deficient transfer RNAs from Escherichia coli B and their use as substrates for pseudouridine synthetase. Kwong, L.K., Moore, V.G., Kaiser, I.I. J. Biol. Chem. (1977) [Pubmed]
  2. Mechanism of selective incorporation of the melanoma seeker 2-thiouracil into growing melanin. Napolitano, A., Palumbo, A., d'Ischia, M., Prota, G. J. Med. Chem. (1996) [Pubmed]
  3. Boron-containing thiouracil derivatives for neutron-capture therapy of melanoma. Tjarks, W., Gabel, D. J. Med. Chem. (1991) [Pubmed]
  4. Alterations of cardiac alpha 1-adrenoceptor subtypes in hypothyroid rats. Zhang, Y., Xu, K., Han, C. Clin. Exp. Pharmacol. Physiol. (1997) [Pubmed]
  5. Effect of 2-thiouracil on RNA and protein synthesis in synchronous and asynchronous infections of tobacco mosaic virus. Dawson, W.O., Grantham, G.L. Intervirology (1983) [Pubmed]
  6. An aspartate transcarbamylase lacking catalytic subunit interactions. Study of conformational changes by ultraviolet absorbance and circular dichroism spectroscopy. Kerbiriou, D., Hervé, G. J. Biol. Chem. (1977) [Pubmed]
  7. Modified bases in RNA reduce secondary structure and enhance hybridization. Gamper, H.B., Gewirtz, A., Edwards, J., Hou, Y.M. Biochemistry (2004) [Pubmed]
  8. Synthesis and antiviral activity of deoxy analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) as potent and selective anti-HIV-1 agents. Tanaka, H., Takashima, H., Ubasawa, M., Sekiya, K., Nitta, I., Baba, M., Shigeta, S., Walker, R.T., De Clercq, E., Miyasaka, T. J. Med. Chem. (1992) [Pubmed]
  9. A new class of propylthiouracil analogs: comparison of 5'-deiodinase inhibition and antithyroid activity. Nogimori, T., Braverman, L.E., Taurog, A., Fang, S.L., Wright, G., Emerson, C.H. Endocrinology (1986) [Pubmed]
  10. Affinity therapeutics. 1. Selective incorporation of 2-thiouracil derivatives in murine melanomas. Cytostatic activity of 2-thiouracil arotinoids, 2-thiouracil retinoids, arotinoids, and retinoids. Wätjen, F., Buchardt, O., Langvad, E. J. Med. Chem. (1982) [Pubmed]
  11. Induction of cell killing, mutation and umu gene expression by 6-mercaptopurine or 2-thiouracil with UVA irradiation. Komeda, K., Iwamoto, S., Kominami, S., Ohnishi, T. Photochem. Photobiol. (1997) [Pubmed]
  12. Time-course of actinomycin D inhibition of tobacco mosaic virus multiplication relative to the rate of spread of the infection. Dawson, W.O. Intervirology (1978) [Pubmed]
  13. Effects of selection for growth and selection diet on eggshell quality and embryonic development in Japanese quail. Peebles, E.D., Marks, H.L. Poult. Sci. (1991) [Pubmed]
  14. Effect of orally administered antithyroid thioureylenes on PCNA and P53 expression in psoriatic lesions. Elias, A.N., Barr, R.J., Rohan, M.K., Dangaran, K. International journal of dermatology. (1995) [Pubmed]
  15. Photosensitized damage to supercoiled plasmid DNA induced by 334-nm radiation in the presence of 2-thiouracil consists of alkali- and piperidine-labile sites as well as frank strand breaks. Churchill, M.E., Schmitz, A.M., Peak, J.G., Peak, M.J. Photochem. Photobiol. (1990) [Pubmed]
  16. SNPs analysis by use of oligonucleotides containing 2'-O-methyl-2-thiouridines. Okamoto, I., Seio, K., Sekine, M. Nucleic acids symposium series (2004) (2005) [Pubmed]
  17. Synthesis and anticancer activity of 5-diethylaminomethyl derivatives and nitrogen mustards of uracil and 2-thiouracils. Fabrissin, S., de Nardo, M., Nisi, C., Morasca, L., Dolfini, E., Franchi, G. J. Med. Chem. (1976) [Pubmed]
  18. Effect of transient early hyperthyroidism on onset of puberty in Suffolk ram lambs. Fallah-Rad, A.H., Connor, M.L., Del Vecchio, R.P. Reproduction (2001) [Pubmed]
  19. The binding of thioureylene compounds to human serum albumin. Zatón, A., Martinez, A., Manuel de Gandarias, J. Biochem. Pharmacol. (1988) [Pubmed]
  20. Probucol, but not MaxEPA fish oil, inhibits mononuclear cell adhesion to the aortic intima in the rat model of atherosclerosis. Barbeau, M.L., Whitman, S.C., Rogers, K.A. Biochem. Cell Biol. (1995) [Pubmed]
  21. Intra- and intermolecular interactions in small bioactive molecules: cooperative features from experimental and theoretical charge-density analysis. Munshi, P., Guru Row, T.N. Acta Crystallogr., B (2006) [Pubmed]
  22. The concerted effects of thyroid function and dietary protein on growth and protein metabolism in mice at different growth stages. Hayashi, K., Akiba, Y., Tomita, Y., Matsumoto, T. J. Nutr. Sci. Vitaminol. (1984) [Pubmed]
  23. Ab initio study on tautomerism of 2-thiouracil in the gas phase and in solution. Yekeler, H. J. Comput. Aided Mol. Des. (2000) [Pubmed]
  24. ESR of irradiated 2-thiouracil single crystals. A 3alpha-hydrogen radical. Jørgensen, J.P., Sagstuen, E. Radiat. Res. (1981) [Pubmed]
  25. Flow injection analysis system equipped with a newly designed electrochemiluminescent detector and its application for detection of 2-thiouracil. Chi, Y., Duan, J., Lin, S., Chen, G. Anal. Chem. (2006) [Pubmed]
  26. Effects of thyroid hormone on the renal dopaminergic system. Del Compare, J.A., Aguirre, J.A., Ibarra, F.R., Barontini, M., Armando, I. Endocrine (2001) [Pubmed]
  27. Effects of L-thyroxine and zinc therapy on wound healing in hypothyroid rats. Erdoğan, M., Ilhan, Y.S., Akkuş, M.A., Caboğlu, S.A., Ozercan, I., Ilhan, N., Yaman, M. Acta chirurgica Belgica. (1999) [Pubmed]
  28. Effect of iodobenzene therapy on mitochondrial activity in 2-thiouracil-induced hypothyroidism in weanling rats. Visvanathan, A., Narayanan, U., Shanmugasundaram, K.R. Res. Commun. Chem. Pathol. Pharmacol. (1983) [Pubmed]
 
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