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Chemical Compound Review

Aldeform     1,3,5-trioxane

Synonyms: Marvosan, Triformol, Trioxan, Trioxin, Paraformal, ...
 
 
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Disease relevance of Aldeform

  • Preclinical evaluation of this water-soluble synthetic trioxane 8a in rodents shows it to have at least as good a therapeutic index (efficacy/toxicity) as that of water-soluble semisynthetic trioxane artelinic acid (5) [1].
  • In the transgenic adenocarcinoma of mouse prostate model, some of the trioxane dimers had potent anticancer activity [2].
  • Biological mechanisms of action of novel C-10 non-acetal trioxane dimers in prostate cancer cell lines [3].
  • Trioxane numbered 9 produced a similar outcome: 12 mg/kg suppressed parasitemia in two monkeys but was not curative; however, 48 mg/kg cured infections in all four monkeys treated [4].
  • Trioxane numbered 8 at 12 mg/kg cleared parasitemia in two monkeys, but recrudescence occurred in one animal [4].
 

Psychiatry related information on Aldeform

  • Transitional depression of exploratory locomotor activity in female offspring and a decrease of active avoidance acquisition were observed in adult male and female offspring from the 0.58 g/kg group, whereas a dose of 0.19 g trioxane /kg did not affect the behavioral performance of progeny [5].
 

High impact information on Aldeform

  • This simplified acetal trioxane carboxylic acid 8a is thermally stable, and it is hydrolytically stable in water even at 40 degrees C and pH 7.4 for at least 7 days [1].
  • These results provide the first direct characterization of the antimalarial mode of action of artemisinin and its trioxane analog, and suggest that artemisinin appears to react with heme molecules that have been incorporated into hemozoin and subsequently the heme performs cytochrome P450-type chemistry [6].
  • The mutagenic activity of trioxane and dioxolane was investigated in 5 histidine-requiring strains of S. typhimurium: TA1535, TA1537, TA1538, TA98 and TA100 with and without activation by liver microsomes [7].
  • Other desirable features beneficial to clinical uses such as bioavailability, drug stability and water solubility have been considered, and portions of the trioxane skeleton have been added or modified to accommodate these parameters accordingly [8].
  • I.p. administration of trioxane produced no chromosomal damage resulting in erythrocyte micronucleus formation, even at highly toxic doses [9].
 

Biological context of Aldeform

 

Analytical, diagnostic and therapeutic context of Aldeform

  • Fourier transform infrared (FTIR) and resonance Raman (RR) spectroscopies have been employed to investigate the reductive cleavage of the O-O bond of the endoperoxide moiety of the antimalarial drug artemisinin and its analog trioxane alcohol by hemin dimer [6].

References

  1. Antimalarial simplified 3-aryltrioxanes: synthesis and preclinical efficacy/toxicity testing in rodents. Posner, G.H., Jeon, H.B., Parker, M.H., Krasavin, M., Paik, I.H., Shapiro, T.A. J. Med. Chem. (2001) [Pubmed]
  2. Anticancer and antimalarial efficacy and safety of artemisinin-derived trioxane dimers in rodents. Posner, G.H., McRiner, A.J., Paik, I.H., Sur, S., Borstnik, K., Xie, S., Shapiro, T.A., Alagbala, A., Foster, B. J. Med. Chem. (2004) [Pubmed]
  3. Biological mechanisms of action of novel C-10 non-acetal trioxane dimers in prostate cancer cell lines. Alagbala, A.A., McRiner, A.J., Borstnik, K., Labonte, T., Chang, W., D'Angelo, J.G., Posner, G.H., Foster, B.A. J. Med. Chem. (2006) [Pubmed]
  4. New, antimalarial, tricyclic 1,2,4-trioxanes: evaluations in mice and monkeys. Posner, G.H., Oh, C.H., Webster, H.K., Ager, A.L., Rossan, R.N. Am. J. Trop. Med. Hyg. (1994) [Pubmed]
  5. Effects of maternal exposure to trioxane on postnatal development in rats. Sitarek, K., Barański, B. Polish journal of occupational medicine. (1990) [Pubmed]
  6. Ferryl-oxo heme intermediate in the antimalarial mode of action of artemisinin. Kapetanaki, S., Varotsis, C. FEBS Lett. (2000) [Pubmed]
  7. Absence of mutagenicity of trioxane and dioxolane in Salmonella typhimurium. Kowalski, Z., Spiechowicz, E., Barański, B. Mutat. Res. (1984) [Pubmed]
  8. Development of artemisinin and its structurally simplified trioxane derivatives as antimalarial drugs. Ploypradith, P. Acta Trop. (2004) [Pubmed]
  9. Genotoxic effects of dioxolane and trioxane in mice evaluated by the micronucleus test. Przybojewska, B., Dziubałtowska, E., Kowalski, Z. Toxicol. Lett. (1984) [Pubmed]
  10. Alkylation of manganese(II) tetraphenylporphyrin by a synthetic antimalarial trioxane. Berrien, J.F., Provot, O., Mayrargue, J., Coquillay, M., Cicéron, L., Gay, F., Danis, M., Robert, A., Meunier, B. Org. Biomol. Chem. (2003) [Pubmed]
  11. Quantitative NMR spectroscopy of complex technical mixtures using a virtual reference: chemical equilibria and reaction kinetics of formaldehyde-water-1,3,5-trioxane. Maiwald, M., Grützner, T., Ströfer, E., Hasse, H. Analytical and bioanalytical chemistry. (2006) [Pubmed]
 
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