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Chemical Compound Review

Azunamic     azulene

Synonyms: Azulekeep, azulen, PubChem6349, AGN-PC-0DBGBJ, Azulene (JAN), ...
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Disease relevance of azulene


High impact information on azulene

  • Several novel azulene-containing retinoids were prepared and evaluated for their ability to suppress carcinogen-induced neoplastic transformation and to concomitantly up-regulate gap junctional communication in the in vitro mouse fibroblast C3H/10T1/2 cell bioassay [5].
  • The ESR measurement of anion radicals and a dianion diradical generated by the electrochemical reduction of amine 1b and diamine 2b revealed that the unpaired electron of these radicals delocalizes over the entire azulene ring including the central nitrogen atoms [6].
  • Fluorescence of Zn(II) porphyrin in the dyads is strongly quenched depending upon substitution position of azulene in order of 2 > 1 > 4 > 3 [7].
  • Energy transfer between polyatomic molecules. 3. Energy transfer quantities and probability density functions in self-collisions of benzene, toluene, p-xylene and azulene [8].
  • The purpose of this study was to evaluate the potential effectiveness of the topical external medicines used in clinical settings, and the authors investigated the effects of 1% azulene ointment, 0.12% dexamethasone ointment, and polaprezinc-sodium alginate suspension on an animal model for oral mucositis induced by chemotherapy [4].

Chemical compound and disease context of azulene


Biological context of azulene

  • This suggests that the photomutagenicity of azulene in S. typhimurium TA102 could be due to DNA fragmentation caused by the concurrent exposure to azulene and light [1].
  • When the cell suspensions are irradiated by light (UVA plus visible light) in the presence of azulene, an azulene dose-dependent cellular DNA damage is observed [1].
  • Further study revealed that the combination of light and azulene can cause single-strand cleavage on pure PhiX174 plasmid DNA in solution [1].
  • Butyl conformational reorganization as a possible explanation for the longitudinal flexibility of the binding site of bacteriorhodopsin. The azulene and C-22 retinoid analogs [11].
  • Simple guaiane-type compounds, such as (-)-guaiol and guaiazulene showed weak inhibitory effects on the 5 alpha-reductase activity with IC50 values of f 81.6 microM and 100.8 microM, respectively, while azulene was not active [12].

Anatomical context of azulene

  • We investigated 27 azulene derivatives for their relative cytotoxicity against three human normal cells and three human oral tumor cell lines [13].

Associations of azulene with other chemical compounds


Gene context of azulene

  • The ESR spectra of the neutral radical gave two hyperfine coupling constants: a(H) = 0.083 (6H) and 0.166 mT (9H) (g = 2.0024), indicating that an unpaired electron delocalizes over all three of the azulene rings [16].

Analytical, diagnostic and therapeutic context of azulene


  1. Phototoxicity and DNA damage induced by the cosmetic ingredient chemical azulene in human Jurkat T-cells. Wang, L., Yan, J., Wang, S., Cohly, H., Fu, P.P., Hwang, H.M., Yu, H. Mutat. Res. (2004) [Pubmed]
  2. Gargling with sodium azulene sulfonate reduces the postoperative sore throat after intubation of the trachea. Ogata, J., Minami, K., Horishita, T., Shiraishi, M., Okamoto, T., Terada, T., Sata, T. Anesth. Analg. (2005) [Pubmed]
  3. Azulene analogs of pharmacological agents III: acute toxicity and local anesthetic activity of azulylamides and azulenecarboxamides. Doukas, P.H., Speaker, T.J., Thompson, R.S. Journal of pharmaceutical sciences. (1975) [Pubmed]
  4. Evaluation of topical external medicine for 5-fluorouracil-induced oral mucositis in hamsters. Mitsuhashi, H., Suemaru, K., Li, B., Cui, R., Araki, H. Eur. J. Pharmacol. (2006) [Pubmed]
  5. Azulenic retinoids: novel nonbenzenoid aromatic retinoids with anticancer activity. Asato, A.E., Peng, A., Hossain, M.Z., Mirzadegan, T., Bertram, J.S. J. Med. Chem. (1993) [Pubmed]
  6. Azulene-substituted aromatic amines. synthesis and amphoteric redox behavior of N,N-Di(6-azulenyl)-p-toluidine and N,N,N',N'-tetra(6-azulenyl)-p-phenylenediamine and their derivatives. Ito, S., Kubo, T., Morita, N., Ikoma, T., Tero-Kubota, S., Kawakami, J., Tajiri, A. J. Org. Chem. (2005) [Pubmed]
  7. Synthesis of meso-azulenylporphyrins. Kurotobi, K., Osuka, A. Org. Lett. (2005) [Pubmed]
  8. Energy transfer between polyatomic molecules. 3. Energy transfer quantities and probability density functions in self-collisions of benzene, toluene, p-xylene and azulene. Bernshtein, V., Oref, I. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2006) [Pubmed]
  9. Photomutagenicity of cosmetic ingredient chemicals azulene and guaiazulene. Wang, L., Yan, J., Fu, P.P., Parekh, K.A., Yu, H. Mutat. Res. (2003) [Pubmed]
  10. Effect of sodium azulene sulfonate on capsaicin-induced pharyngitis in rats. Sakai, H., Misawa, M. Basic & clinical pharmacology & toxicology. (2005) [Pubmed]
  11. Butyl conformational reorganization as a possible explanation for the longitudinal flexibility of the binding site of bacteriorhodopsin. The azulene and C-22 retinoid analogs. Liu, R.S., Liu, C.W., Li, X.Y., Asato, A.E. Photochem. Photobiol. (1991) [Pubmed]
  12. Torilin from Torilis japonica, as a new inhibitor of testosterone 5 alpha-reductase. Park, W.S., Son, E.D., Nam, G.W., Kim, S.H., Noh, M.S., Lee, B.G., Jang, I.S., Kim, S.E., Lee, J.J., Lee, C.H. Planta Med. (2003) [Pubmed]
  13. Cytotoxic activity of azulenes against human oral tumor cell lines. Wakabayashi, H., Hashiba, K., Yokoyama, K., Hashimoto, K., Kikuchi, H., Nishikawa, H., Kurihara, T., Satoh, K., Shioda, S., Saito, S., Kusano, S., Nakashima, H., Motohashi, N., Sakagami, H. Anticancer Res. (2003) [Pubmed]
  14. Energy transfer between azulene and krypton: Comparison between experiment and computation. Bernshtein, V., Oref, I. The Journal of chemical physics. (2006) [Pubmed]
  15. PECT model analysis and predictions of experimental collisional energy transfer probabilities P(E',E) and moments <DeltaE> for azulene and biphenylene. Lenzer, T., Luther, K., Nilsson, D., Nordholm, S. The journal of physical chemistry. B, Condensed matter, materials, surfaces, interfaces & biophysical. (2005) [Pubmed]
  16. Synthesis, stabilities, and redox behavior of Di(1-azulenyl)(6-azulenyl)methylium hexafluorophosphates. Generation of a donor-acceptor-substituted neutral radical by azulenes. Ito, S., Kubo, T., Morita, N., Ikoma, T., Tero-Kubota, S., Tajiri, A. J. Org. Chem. (2003) [Pubmed]
  17. Supercollisions and energy transfer of highly vibrationally excited molecules. Liu, C.L., Hsu, H.C., Lyu, J.J., Ni, C.K. The Journal of chemical physics. (2005) [Pubmed]
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