Skip to main content
Log in

Comparative metabolism and carcinogenicity of ring-halogenated 3,3-dimethyl-1-phenyltriazenes

  • Original Papers
  • Published:
Journal of Cancer Research and Clinical Oncology Aims and scope Submit manuscript

Summary

The objective of this study was to compare urinary metabolism of parent 3,3-dimethyl-1-phenyltriazene with that of its ring-substituted 1-(4-chlorophenyl)-3,3-dimethyltriazene and 1-(2,4,6-trichlorophenyl)-3,3-dimethyltriazene congeners, in an attempt to evaluate the molecular requirements for systemic carcinogenic activity. Complementary carcinogenicity assays were conducted at low equimolar dose levels using both 4- und 2,4,6-chlorinated and brominated analogues. Ring halogenation was found to prolong metabolic detoxification and to reduce carcinogenic activity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Abbreviations

4-Br-PDMT:

1-(4-bromophenyl)-3,3-dimethyltriazene

2,4,6-Br3-PDMT:

1-(2,4,6-tribromophenyl)-3,3-dimethyltriazene

4-Cl-BANEN:

4-(4-chlorobenzeneazo)-N-ethyl-1-naphthylamine

4-Cl-2-HO-BANEN:

4-(4-chloro-2-hydroxybenzeneazo)-N-ethyl-1-naphthylamine

4-Cl-PDMT:

1-(4-chlorophenyl)-3,3-dimethyltriazene

2,4,6-Cl3-BANEN:

4-(2,4,6-trichlorobenzeneazo)-N-ethyl-1-naphthylamine

2,4,6-Cl3-PDMT:

1-(2,4,6-trichlorophenyl)-3,3-dimethyltriazene

DMPT:

3,3-dimethyl-1-phenyltriazene

MFO:

mixed-function oxidase

NEN:

N-ethyl-1-naphthylamine reagent

References

  • Druckrey H, Ivankovic S, Preussmann R (1967a) Neurotrope carcinogene Wirkung von Phenyl-dimethyl-triazen an Ratten. Naturwissenschaften 54:171

    Google Scholar 

  • Druckrey H, Ivankovic S, Preussmann R, Brunner U (1967b) Teratogene Wirkung von 1-Phenyl-3,3-dimethyltriazen; Erzeugung von Gaumenspalten bei BD-Ratten. Experientia 23:1042–1043

    Google Scholar 

  • Elks J, Hey DH (1943) Union of aryl nuclei. VI. Reactions with 1-aryl-3,3-dimethyltriazenes. J Chem Soc 441–445

  • Hunter L (1937) The azo group as a chelating group. II. The structure of the diazoamino-compounds. J Chem Soc 320–324

  • Johnson AW (1946) Synthesis of 2-arylfurans. J Chem Soc 895–899

  • Kolar GF (1984) Triazenes, In: Searle CE (ed) Chemical carcinogens, 2nd edn., American Chemical Society, Washington (in press) (ASC monograph 173)

    Google Scholar 

  • Kolar GF, Carubelli R (1979) Urinary metabolite of 1-(2,4,6-trichlorophenyl)-3,3-dimethyltriazene with an intact diazoamino structure. Cancer Lett 7:209–214

    Google Scholar 

  • Kolar GF, Preussmann R (1971) Validity of a linear Hammett plot for the stability of some carcinogenic 1-aryl-3,3-dimethyltriazenes in an aqueous system. Z Naturforsch [B] 26:950–953

    Google Scholar 

  • Kolar GF, Schlesiger J (1975) Biotransformation of 1-(4-chlorophenyl)-3,3-dimethyltriazene into 3-chloro-4-hydroxyaniline. Intramolecular hydroxylation-induced chlorine migration during a catabolic degradation of a chemical carcinogen. Cancer Lett 1:43–47

    Google Scholar 

  • Kolar GF, Schlesiger J (1976) Urinary metabolites of 3,3-dimethyl-1-phenyltriazene. Chem Biol Interact 14:301–311

    Google Scholar 

  • Margison GP, Likhachev AJ, Kolar GF (1979) In vivo alkylation of foetal, maternal, and normal rat tissue nucleic acids by 3-methyl-1-phenyltriazene. Chem Biol Interact 25:345–353

    Google Scholar 

  • Preussmann R, von Hodenberg A (1970) Mechanism of carcinogenesis with 1-aryl-3,3-dialkyltriazenes. II. In vivo alkylation of guanosine, RNY, and DNA with aryl-monoalkyltriazenes to form 7-alkylguanine. Biochem Pharmacol 19:1505–1508

    Google Scholar 

  • Preussmann R, von Hodenberg A, Hengy H (1968) Mechanism of carcinogenesis with 1-aryl-3,3-dialkyltriazenes. Enzymatic dealkylation by rat liver microsomal fraction in vitro. Biochem Pharmacol 18:1–13

    Google Scholar 

  • Preussmann R, Ivankovic S, Landschütz C, Gimmy J, Flohr E, Griesbach U (1974) Carcinogene Wirkung von 13 Aryldialkyltriazenen an BD-Ratten. Z Krebforsch 81:285–310

    Google Scholar 

  • Rondestvedt CS, Davis SJ (1957) 1-Aryl-3,3-dialkyltriazenes as tumor inhibitors. J Organ Chem 22:200–203

    Google Scholar 

  • Schlesiger J (1977) Stoffwechseluntersuchung ausgewählter 1-Aryl-3,3-dimethyltriazene. Dissertation, Naturwissenschaftliche Gesamtfakultät der Universität Heidelberg

Download references

Author information

Authors and Affiliations

Authors

Additional information

Dedicated to Professor Hermann Druckrey on the occasion of his 80th birthday

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kolar, G.F., Habs, M. Comparative metabolism and carcinogenicity of ring-halogenated 3,3-dimethyl-1-phenyltriazenes. J Cancer Res Clin Oncol 108, 71–75 (1984). https://doi.org/10.1007/BF00390976

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00390976

Key words

Navigation