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Retinylnitrones: A New Class of Retinoids with Chemopreventive Action

Abstract

Retinoids containing a polar nitrone end group have been synthesized. This new class of extensively conjugated, open chain nitrones has been found to be effective in reversing the keratinization in hamster tracheal organ cultures. The highest activity was displayed by the retinylnitrone bearing the least bulky N-alkyl substituent, i. e., methylnitrone 1; its activity level was comparable to that of all-trans retinoic acid.

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References

  1. Sporn, M. B. (1977) Nutr. Rev. 35, 65–69; Mayer, H., Bollag, W., Hänni, R., Rüegg, R. (1978) Experientia 34, 1105–1119; Sporn, M. B., Newton, D. L. (1981) In “Inhibition of Tumor Induction and Development”, (Zedeck, M. S., Lipkin, M. edits.), pp. 71–100, Plenum Press, New York; Modulation of Cellular Interactions by Vitamin A and Derivatives (Retinoids), (DeLuca, L. M., Shapiro, S. S. edits.), Ann. New York Acad. Sci. 359, 1–429; Hill, D. L., Grubs, C. J. (1982) Anticancer Res. 2, 111–124; Pawson, B. A., Ehmann, C. W. Itri, L. M., Sherman, M. I. (1982) J. Med. Chem. 25, 1269–1277; Bollag, W. (1982) In Psoriasis, Proc, Int. Symp., 3rd (Farber, E. M., Cox, A. J. edits.), pp. 175–183, Grune & Stratton, New York; Windhorst, P. B. (1982) In Psoriasis, Proc. Int. Symp., 3rd (Farber, E. M., Cox, A. J. edits.), pp. 185–189, Grune & Stratton, New York; Sporn, M. B. (1982) In Psoriasis, Proc. Int. Symp., 3rd (Farber, E. M., Cox, A. J. edits.), pp. 191–196, Grune & Stratton, New York.

    Google Scholar 

  2. Tufariello, J. J. (1979) Accts. Chem. Res. 12, 396–403; Asrof, A. Sk. Diss. Abstr. Int. B. (1980) 41 (5) 1766, 271 pp; Iwashita, T., Kusumi, T., Kakisawa, H. (1982) J. Org. Chem. 47, 230–233; Ingedoh, A. (1982) Pharm. Unserer Zeit 11, 48–56; Puglis, J. M. (1982) Diss. Abstr. Int. B. 43 (3), 732, 252 pp; Green, M. J. Tiberi, R. L., Friary, R., Lutsky, B. N., Berkenkoph, J. Fernandez, X., Monahan, M. (1982) J. Med. Chem. 25, 1492–1495.

    Google Scholar 

  3. Kliegel, W. (1977) Pharmazie 32 H11, 643–664.

    Google Scholar 

  4. Takeuchi, S., Kochi, M., Kawarada, A., Esumi, S., Sasaki, K., Kawabata, S., Saita, T., Inoue, Y., Yamamoto, M. (1980) Japan Kokai Tokyo Koho, JP 7926733; CA. 92 (18) 153148d.

  5. Rüdel, W. In Houben-Weyl, Methoden der organischen Chemie, 4th edit., by Müller, E., Vol. X/4, Georg Thieme Verlag, Stuttgart, 1968.

    Google Scholar 

  6. Spence, G. G., Taylor, E. C., Buchardt, O. (1970) Chem. Rev. 70, 231–265.

    Google Scholar 

  7. Bjorgo, J., Boyd, D. R., Neill, D. C., Jennings, W. B. (1977) J. Chem. Soc. Perkin Trans. 1 254–259.

    Google Scholar 

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Balogh-Nair, V., Nakanishi, K. Retinylnitrones: A New Class of Retinoids with Chemopreventive Action. Pharm Res 1, 93–95 (1984). https://doi.org/10.1023/A:1016359532649

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  • DOI: https://doi.org/10.1023/A:1016359532649

Keywords

  • High Activity
  • Retinoic Acid
  • Organ Culture
  • Retinoid
  • Nitrone