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Chemical Compound Review

Cyanidine     1,3,5-triazine

Synonyms: Vedita, s-Triazine, sym-Triazine, Vedita 250, CHEMBL15698, ...
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Disease relevance of NSC56189

  • Cloning and analysis of s-triazine catabolic genes from Pseudomonas sp. strain NRRLB-12227 [1].
  • We used degenerate oligodeoxyribonucleotides derived from the N-terminal sequence of the s-triazine hydrolase from Rhodococcus corallinus NRRL B-15444R in an amplification reaction to isolate a DNA segment containing a 57-bp fragment from the trzA gene [2].
  • The TrzN protein, which is involved in s-triazine herbicide catabolism by Arthrobacter aurescens TC1, was cloned and expressed in Escherichia coli as a His-tagged protein [3].
  • In spite of clinical activity in heavily-pretreated ovarian cancer, the antitumour s-triazine trimelamol [TM; tris(hydroxymethyl)-tris(methyl)melamine] had to be withdrawn from further clinical studies due to formulation difficulties related to instability [4].
  • The genetic toxicity of atrazine, a member of the s-triazine herbicides, was reviewed with the objective of classifying the chemical [5].

High impact information on NSC56189


Chemical compound and disease context of NSC56189


Biological context of NSC56189

  • The s-triazine hydrolase activity of the recombinant strains carrying the trzA plasmid were compared with that of the R. corallinus strain from which it was derived [2].
  • AtzB had 25% amino acid identity with TrzA, a protein that catalyzes a hydrolytic deamination of the s-triazine substrate melamine [14].
  • On a weight basis, the s-triazine, commonly named triazine amine (TAM), constitutes approx. half of several sulfonylurea herbicides and is formed after hydrolysis of these herbicides [15].
  • This technique may be useful in determining the bioavailability of other s-triazine compounds in soils [16].
  • The second and third clone originated from the molecular evolution of the s-triazine selective antibody IPR-7 [17].

Anatomical context of NSC56189


Associations of NSC56189 with other chemical compounds


Gene context of NSC56189

  • Carbonic anhydrase inhibitors: novel sulfonamides incorporating 1,3,5-triazine moieties as inhibitors of the cytosolic and tumour-associated carbonic anhydrase isozymes I, II and IX [27].
  • Therefore, P450 1A2 alone is likely to be responsible for the hepatic oxidative phase-I metabolism of the s-triazine derivatives in exposed humans [28].
  • The compounds having imidazolyl and tertiary amino groups as substituents in the 1,3,5-triazine ring showed significant aromatase-inhibitory activity [29].
  • The replacement of the bound [(14)C]atrazine by 1,3,5-triazines was tested to determine whether the novel 1,3,5-triazine analogues exhibit the same binding pattern at the D1-protein as atrazine [30].
  • Effects of s-triazine herbicides on hormone-receptor complex formation, 5 alpha-reductase and 3 alpha-hydroxysteroid dehydrogenase activity at the anterior pituitary level [31].

Analytical, diagnostic and therapeutic context of NSC56189

  • Restriction mapping and Southern hybridization analyses of these cloned DNA fragments suggested that these s-triazine catabolic genes may be located on a transposable element, the ends of which are identical 2.2-kb insertion sequences [1].
  • A concept based on the Peroxidase-chip (P-chip), antibody co-immobilization, competitive and enzyme-channeling principle was exploited to develop an integrated flow-through amperometric biosensor for detection of environmental pollutants such as s-triazine herbicides [32].
  • Synthesis and evaluation of a new biselector s-triazine based chiral stationary phase for enantioselective HPLC: potentiality of the approach and perspectives [33].


  1. Cloning and analysis of s-triazine catabolic genes from Pseudomonas sp. strain NRRLB-12227. Eaton, R.W., Karns, J.S. J. Bacteriol. (1991) [Pubmed]
  2. Cloning and expression of the s-triazine hydrolase gene (trzA) from Rhodococcus corallinus and development of Rhodococcus recombinant strains capable of dealkylating and dechlorinating the herbicide atrazine. Shao, Z.Q., Seffens, W., Mulbry, W., Behki, R.M. J. Bacteriol. (1995) [Pubmed]
  3. Substrate specificity and colorimetric assay for recombinant TrzN derived from Arthrobacter aurescens TC1. Shapir, N., Rosendahl, C., Johnson, G., Andreina, M., Sadowsky, M.J., Wackett, L.P. Appl. Environ. Microbiol. (2005) [Pubmed]
  4. Stable analogues of the antitumour agent trimelamol retain in vitro cytotoxicity in drug-sensitive and resistant rodent and human cell lines. Coley, H.M., Jarman, M., Brooks, N., Thornton, T.J., Judson, I.R. Eur. J. Cancer (1994) [Pubmed]
  5. An assessment of the genetic toxicity of atrazine: relevance to human health and environmental effects. Brusick, D.J. Mutat. Res. (1994) [Pubmed]
  6. Anion-aromatic bonding: a case for anion recognition by pi-acidic rings. Mascal, M., Armstrong, A., Bartberger, M.D. J. Am. Chem. Soc. (2002) [Pubmed]
  7. A new series of estrogen receptor modulators that display selectivity for estrogen receptor beta. Henke, B.R., Consler, T.G., Go, N., Hale, R.L., Hohman, D.R., Jones, S.A., Lu, A.T., Moore, L.B., Moore, J.T., Orband-Miller, L.A., Robinett, R.G., Shearin, J., Spearing, P.K., Stewart, E.L., Turnbull, P.S., Weaver, S.L., Williams, S.P., Wisely, G.B., Lambert, M.H. J. Med. Chem. (2002) [Pubmed]
  8. Purification and characterization of allophanate hydrolase (AtzF) from Pseudomonas sp. strain ADP. Shapir, N., Sadowsky, M.J., Wackett, L.P. J. Bacteriol. (2005) [Pubmed]
  9. Regulation of the Pseudomonas sp. strain ADP cyanuric acid degradation operon. García-González, V., Govantes, F., Porrúa, O., Santero, E. J. Bacteriol. (2005) [Pubmed]
  10. Arthrobacter aurescens TC1 metabolizes diverse s-triazine ring compounds. Strong, L.C., Rosendahl, C., Johnson, G., Sadowsky, M.J., Wackett, L.P. Appl. Environ. Microbiol. (2002) [Pubmed]
  11. Degradation of cyanuric acid in soil by Pseudomonas sp. NRRL B-12227 using bioremediation with self-immobilization system. Shiomi, N., Yamaguchi, Y., Nakai, H., Fujita, T., Katsuda, T., Katoh, S. J. Biosci. Bioeng. (2006) [Pubmed]
  12. Anti-inflammatory effect of LA 2851 and reference drugs on some models of inflammation. Investigation of the mechanism of action. Junien, J.L., Lakatos, C., Brohon, J., Guillaume, M., Sterne, J. Agents Actions (1982) [Pubmed]
  13. In vitro cytotoxicity of imidazolyl-1,3,5-triazine derivatives. Yaguchi, S., Izumisawa, Y., Sato, M., Nakagane, T., Koshimizu, I., Sakita, K., Kato, M., Yoshioka, K., Sakato, M., Kawashima, S. Biol. Pharm. Bull. (1997) [Pubmed]
  14. The atzB gene of Pseudomonas sp. strain ADP encodes the second enzyme of a novel atrazine degradation pathway. Boundy-Mills, K.L., de Souza, M.L., Mandelbaum, R.T., Wackett, L.P., Sadowsky, M.J. Appl. Environ. Microbiol. (1997) [Pubmed]
  15. Isolation and characterisation of Rhodococcus erythropolis TA57 able to degrade the triazine amine product from hydrolysis of sulfonylurea pesticides in soils. Andersen, S.M., Mortensen, H.S., Bossi, R., Jacobsen, C.S. Syst. Appl. Microbiol. (2001) [Pubmed]
  16. Influence of soil aging on sorption and bioavailability of simazine. Regitano, J.B., Koskinen, W.C., Sadowsky, M.J. J. Agric. Food Chem. (2006) [Pubmed]
  17. Cloning, functional expression and kinetic characterization of pesticide-selective Fab fragment variants derived by molecular evolution of variable antibody genes. Rau, D., Kramer, K., Hock, B. Analytical and bioanalytical chemistry. (2002) [Pubmed]
  18. Low central nervous system penetration of N2,N4,N6,-trihydroxymethyl-N2,N4,N6,-trimethylmelamine (Trimelamol): a cytotoxic s-triazine with reduced neurotoxicity. Judson, I.R., Rutty, C.J., Abel, G., Graham, M.A. Br. J. Cancer (1986) [Pubmed]
  19. In vitro metabolism of atrazine, terbuthylazine, ametryne, and terbutryne in rats, pigs, and humans. Lang, D., Criegee, D., Grothusen, A., Saalfrank, R.W., Böcker, R.H. Drug Metab. Dispos. (1996) [Pubmed]
  20. Evaluation of in-vitro anti-inflammatory activity of some 2-alkyl-4,6-dimethoxy-1,3,5-triazines. Dianzani, C., Collino, M., Gallicchio, M., Samaritani, S., Signore, G., Menicagli, R., Fantozzi, R. J. Pharm. Pharmacol. (2006) [Pubmed]
  21. Photosynthetic electron transport inhibition by 2-substituted 4-alkyl-6-benzylamino-1,3,5-triazines with thylakoids from wild-type and atrazine-resistant Chenopodium album. Okano, R., Ohki, A., Ohki, S., Kohno, H., van Rensen, J.J., Böger, P., Wakabayashi, K. Z. Naturforsch., C, J. Biosci. (2002) [Pubmed]
  22. Complete nucleotide sequence and organization of the atrazine catabolic plasmid pADP-1 from Pseudomonas sp. strain ADP. Martinez, B., Tomkins, J., Wackett, L.P., Wing, R., Sadowsky, M.J. J. Bacteriol. (2001) [Pubmed]
  23. Hexamethylmelamine: a critical review of an active drug. Foster, B.J., Harding, B.J., Leyland-Jones, B., Hoth, D. Cancer Treat. Rev. (1986) [Pubmed]
  24. Aromatic dienophiles. 1. A theoretical study of an inverse-electron demand Diels-Alder reaction between 2-aminopyrrole and 1,3,5-triazine. Yu, Z.X., Dang, Q., Wu, Y.D. J. Org. Chem. (2001) [Pubmed]
  25. Coupling of m-aminophenylboronic acid to s-triazine-activated Sephacryl: use in the affinity chromatography of glycated hemoglobins. Bisse, E., Wieland, H. J. Chromatogr. (1992) [Pubmed]
  26. Moisture-triggered 1,3,5-triazine-based Cu(II) molecular switch: a combined X-ray single-crystal and powder diffraction study. Casellas, H., Gamez, P., Reedijk, J., Mutikainen, I., Turpeinen, U., Masciocchi, N., Galli, S., Sironi, A. Inorganic chemistry. (2005) [Pubmed]
  27. Carbonic anhydrase inhibitors: novel sulfonamides incorporating 1,3,5-triazine moieties as inhibitors of the cytosolic and tumour-associated carbonic anhydrase isozymes I, II and IX. Garaj, V., Puccetti, L., Fasolis, G., Winum, J.Y., Montero, J.L., Scozzafava, A., Vullo, D., Innocenti, A., Supuran, C.T. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  28. Identification of enzymes involved in the metabolism of atrazine, terbuthylazine, ametryne, and terbutryne in human liver microsomes. Lang, D.H., Rettie, A.E., Böcker, R.H. Chem. Res. Toxicol. (1997) [Pubmed]
  29. Synthesis and aromatase-inhibitory activity of imidazolyl-1,3,5-triazine derivatives. Matsuno, T., Kato, M., Tsuchida, Y., Takahashi, M., Yaguchi, S., Terada, S. Chem. Pharm. Bull. (1997) [Pubmed]
  30. Mode of action of novel 2-(benzylamino)-4-methyl-6-(trifluoro- methyl)-1,3,5-triazine herbicides: inhibition of photosynthetic electron transport and binding studies. Ohki, A., Kuboyama, N., Koizumi, K., Tanaka, A., Sato, Y., Kohno, H., Böger, P., Wakabayashi, K. J. Agric. Food Chem. (1999) [Pubmed]
  31. Effects of s-triazine herbicides on hormone-receptor complex formation, 5 alpha-reductase and 3 alpha-hydroxysteroid dehydrogenase activity at the anterior pituitary level. Kniewald, J., Mildner, P., Kniewald, Z. J. Steroid Biochem. (1979) [Pubmed]
  32. A highly sensitive flow-through amperometric immunosensor based on the Peroxidase chip and enzyme-channeling principle. Zeravik, J., Ruzgas, T., Fránek, M. Biosensors & bioelectronics. (2003) [Pubmed]
  33. Synthesis and evaluation of a new biselector s-triazine based chiral stationary phase for enantioselective HPLC: potentiality of the approach and perspectives. Lecci, C., Iuliano, A. Biomed. Chromatogr. (2005) [Pubmed]
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