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Chemical Compound Review

AC1MO44G     3-ethylamino-4-methylamino- cyclobutane-1,2...

Synonyms: 2221-EP2301536A1, 2221-EP2301538A1, 2221-EP2311455A1, 2221-EP2316452A1
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Disease relevance of Squaric acid

  • In conclusion, alopecia areata-like hair loss in C3H/HeJ mice responded to treatment with the contact sensitizer squaric acid dibutylester analogous to human alopecia areata [1].
  • In 12 C3H/HeJ mice with alopecia areata an allergic contact dermatitis was induced and elicited weekly on one side of the back by topical applications of squaric acid dibutylester [1].
  • The concentration of squaric acid was varied as needed to maintain a moderate dermatitis [2].
  • In order to clarify the relation between the reactivity of the leaving groups in cisplatin-like complexes and their activity / toxicity, six new complexes of the formula Pt(NH3)2X and Pt(dach)X (where X is selenato, anion of squaric acid, or demethylcantharic acid) have been synthesized and compared [3].
  • Di-through the pentasaccharide that mimic the upstream terminus of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Ogawa were synthesized in the form of 5-methoxycarbonylpentyl glycosides and linked to BSA using squaric acid diester chemistry [4].

High impact information on Squaric acid


Chemical compound and disease context of Squaric acid


Biological context of Squaric acid


Anatomical context of Squaric acid

  • The response to mitogens and to IL-2 was related to the response to the topical sensitizer SADBE (squaric acid dibutylester) and patients with no allergic reaction to this substance showed a marked reduction in lymphocyte stimulation, especially with IL-2 [15].
  • In this study we examined the effects of squaric acid dibutylester treatment on hair follicles and the associated leukocyte infiltrate in alopecia areata mice by light and transmission electron microscopic analysis [16].

Associations of Squaric acid with other chemical compounds


Gene context of Squaric acid

  • Squaric acid as an internal standard for temperature measurements in 13C MAS NMR [13].
  • Preliminary results on radiation damage in catalase at 400, 600 and 800 kV and images of catalase and squaric acid are included [20].
  • Comparison of such shifts with those observed for the squaric acid (H2Sq)/4,4'-bipyridine (Bipy) charge transfer (CT) complex reveals that the interaction is much stronger in the aggregate, a clear effect of the restrict geometry [19].

Analytical, diagnostic and therapeutic context of Squaric acid


  1. Successful treatment of alopecia areata-like hair loss with the contact sensitizer squaric acid dibutylester (SADBE) in C3H/HeJ mice. Freyschmidt-Paul, P., Sundberg, J.P., Happle, R., McElwee, K.J., Metz, S., Boggess, D., Hoffmann, R. J. Invest. Dermatol. (1999) [Pubmed]
  2. Treatment of alopecia areata with squaric acid dibutylester. Caserio, R.J. Archives of dermatology. (1987) [Pubmed]
  3. Synthesis, antitumor activity and acute toxicity of diammine/diamino-cyclohexane platinum(II) complexes with oxygen-ligating leaving group. Zou, J., Dou, P.Y., Wang, K. J. Inorg. Biochem. (1997) [Pubmed]
  4. One-pot preparation of a series of glycoconjugates with predetermined antigen-carrier ratio from oligosaccharides that mimic the O-PS of Vibrio cholerae O:1, serotype Ogawa. Saksena, R., Ma, X., Kovác, P. Carbohydr. Res. (2003) [Pubmed]
  5. Squaric acid-based peptidic inhibitors of matrix metalloprotease-1. Onaran, M.B., Comeau, A.B., Seto, C.T. J. Org. Chem. (2005) [Pubmed]
  6. Comparative study on cytogenetic effects by diplatinum complexes of the ligands of naphthazarine and squaric acid in human lymphocytes. Lialiaris, T., Mourelatos, D., Boutis, L., Papageorgiou, A., Christianopoulou, M., Papageorgiou, V., Dozi-Vassiliades, J. J. Pharmacol. Exp. Ther. (1989) [Pubmed]
  7. Molecular structure, infrared spectrum, and photochemistry of squaric Acid dimethyl ester in solid argon. Breda, S., Reva, I., Lapinski, L., Fausto, R. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2006) [Pubmed]
  8. Chronic delayed-type hypersensitivity reaction as a means to treat alopecia areata. Zöller, M., Freyschmidt-Paul, P., Vitacolonna, M., McElwee, K.J., Hummel, S., Hoffmann, R. Clin. Exp. Immunol. (2004) [Pubmed]
  9. Squaric acid dibutylester: indications for use and efficacy in alopecia areata. Pardasani, A.G., Turner, E., McMichael, A.J. Archives of dermatology. (2001) [Pubmed]
  10. Diphencyprone in the treatment of alopecia areata. Happle, R., Hausen, B.M., Wiesner-Menzel, L. Acta Derm. Venereol. (1983) [Pubmed]
  11. Thymopentin in the treatment of severe alopecia areata. Tosti, A., Manuzzi, P., Gasponi, A. Dermatologica (1988) [Pubmed]
  12. Determination of the sildenafil effect on alopecia areata in childhood: An open-pilot comparison study. Sarifakioglu, E., Tuncer Degim, I., Gorpelioglu, C. The Journal of dermatological treatment. (2006) [Pubmed]
  13. Squaric acid as an internal standard for temperature measurements in 13C MAS NMR. Klymachyov, A.N., Dalal, N.S. Solid state nuclear magnetic resonance. (1996) [Pubmed]
  14. A new class of semisynthetic anthracycline glycoside antibiotics incorporating a squaric acid moiety. Sztaricskai, F., Sum, A., Roth, E., Pelyvás, I.F., Sándor, S., Batta, G., Herczegh, P., Reményi, J., Miklán, Z., Hudecz, F. J. Antibiot. (2005) [Pubmed]
  15. Decreased in vitro lymphocyte stimulation and reduced sensitivity to IL-2 in patients with alopecia areata. Orecchia, G., Capelli, E., Martinetti, M., Cuccia Belvedere, M., Rabbiosi, G. Arch. Dermatol. Res. (1988) [Pubmed]
  16. Normalisation of hair follicle morphology in C3H/HeJ alopecia areata mice after treatment with squaric acid dibutylester. Gardner, S., Freyschmidt-Paul, P., Hoffmann, R., Sundberg, J.P., Happle, R., Lindsey, N.J., Tobin, D.J. European journal of dermatology : EJD. (2000) [Pubmed]
  17. Squaric acid and esters: analysis for contaminants and stability in solvents. Wilkerson, M.G., Henkin, J., Wilkin, J.K., Smith, R.G. J. Am. Acad. Dermatol. (1985) [Pubmed]
  18. The chirality selectivity in the uptake of platinum (II) complexes with 1,2-cyclohexanediamine isomers as carrier ligand by human erythrocytes. Zou, J., Yang, X.G., Li, R.C., Lu, J.F., Wang, K. Biometals (1997) [Pubmed]
  19. The squaric acid aggregate in mordenite investigated by Raman spectroscopy. Lopes, J.G., de Oliveira, L.F., Santos, P.S. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. (2001) [Pubmed]
  20. An HVEM for high resolution low-dose studies of biomacromolecules. Pawley, J. Ultramicroscopy. (1984) [Pubmed]
  21. Contact immunotherapy with squaric acid dibutylester for the treatment of recalcitrant warts. Lee, A.N., Mallory, S.B. J. Am. Acad. Dermatol. (1999) [Pubmed]
  22. Experimental and computational studies of the structure and vibrational spectra of pyridinium-betaine of squaric acid. Kolev, T.M., Yancheva, D.Y., Stamboliyska, B.A. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. (2003) [Pubmed]
  23. Photochemotherapy plus squaric acid dibutylester in alopecia areata treatment. Orecchia, G., Perfetti, L., Borroni, G., Rabbiosi, G. Dermatologica (1990) [Pubmed]
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