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Novel naphthoquinonyl derivatives: Potential structural components for the synthesis of cytotoxic peptides

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Summary

Syntheses and physicochemical properties are described of several novel naphthoquinonyl amino acid derivatives, which are potential components in cytotoxic peptide conjugates. These compounds include N ε- and N α-naphthoquinonyl derivatives of lysine as well as N-naphthoquinonyl-carboxylic derivatives. The former class of compounds can be employed as building blocks in a stepwise peptide synthesis, whereas the latter two are adequate for postpeptide chain-assembly modifications. The ability of the naphthoquinonyl derivatives to produce semiquinone radicals and hydroxyl radicals (•OH), using chemical (i.e. NaBH4) and enzymatic (i.e. NADPH-cytochrome P-450 reductase) routes, respectively, was evaluated employing electron spin resonance spectroscopy.

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References

  1. FitzGerald, D. and Pastan, I., J. Natl. Cancer Inst., 81 (1989) 1455.

    Google Scholar 

  2. Varga, J.M., Methods Enzymol., 112 (1985) 259.

    Google Scholar 

  3. Kreitman, R.J., FitzGerald, D. and Pastan, I., Int. J. Immunopharmacol., 14 (1992) 465.

    Google Scholar 

  4. Rich, P.R., Faraday Discuss. Chem. Soc., 74 (1982) 349.

    Google Scholar 

  5. Gutierrez, P.L., Free Radic. Biol. Med. 6 (1989) 405.

    Google Scholar 

  6. Colwell, C.A. and McCall, M., Science, 101 (1945) 592.

    Google Scholar 

  7. Ikeda, N., J. Pharm. Soc. Jpn., 75 (1955) 1073.

    Google Scholar 

  8. Ter Horst, W.P. and Felix, E.L., Ind. Eng. Chem., 35 (1943) 1255.

    Google Scholar 

  9. Lopez-Shirley, K., Zhang, F., Gosser, D., Scott, M. and Meshnick, S.R., J. Lab. Clin. Med., 123 (1994) 126.

    Google Scholar 

  10. Martin, Y.C., Bustard, T.M. and Lynn, K.R., J. Med. Chem., 16 (1973) 1089.

    Google Scholar 

  11. Prescott, B., J. Med. Chem., 12 (1969) 181.

    Google Scholar 

  12. Bajusz, S., Janaky, T., Csernus, V.J., Bokser, L., Fekete, M., Srkalovic, G., Redding, T.W. and Schally, A.V., Proc. Natl. Acad. Sci. USA, 86 (1989) 6313.

    Google Scholar 

  13. Bajusz, S., Janaky, T., Csernus, V.J., Bokser, L., Fekete, M., Srkalovic, G., Redding, T.W. and Schally, A.V., Proc. Natl. Acad. Sci. USA, 86 (1989) 6318.

    Google Scholar 

  14. Janaky, T., Juhasz, A., Bajusz, S., Csernus, V., Srkalovic, G., Bokser, L., Milovanovic, S., Redding, T.W., Rekasi, Z., Nagy, A. and Schally, A.V., Proc. Natl. Acad. Sci. USA, 89 (1992) 972.

    Google Scholar 

  15. Crooke, S.T., Duvernay, V.H. and Mong, S., In Sartorelli, A.C., Lazo, J.S. and Bertino, J.R. (Eds.) Molecular Actions and Targets for Cancer Chemotherapeutic Agents, Academic Press, New York, NY, U.S.A., 1981, pp. 137–160.

    Google Scholar 

  16. Tong, G.L., Wu, H.Y., Smith, T.H. and Henry, D.W., J. Med. Chem., 22 (1979) 912.

    Google Scholar 

  17. Tritton, T.R. and Yee, G., Science, 217 (1982) 248.

    Google Scholar 

  18. Pacifici, R.E. and Davies, K.J.A., Methods Enzymol., 186 (1990) 485.

    Google Scholar 

  19. Burkit, M.J., Fitchett, M. and Gilbert, B.C., In Hayaishi, O., Niki, E., Kondo, M. and Yoshikawa, T. (Eds.) Free-radical Damage to Nucleic Acid Components by the Fenton Reaction: An ESR Study, Elsevier, Amsterdam, The Netherlands 1989, pp. 63–70.

    Google Scholar 

  20. Stadtman, E.R., Annu. Rev. Biochem., 62 (1993) 797.

    Google Scholar 

  21. Neta, P., In Patai, S. and Rappoport, Z. (Eds.) The Chemistry of the Quininoid Compounds, Vol. 2, Part 2, Wiley, New York, NY, U.S.A., 1988, pp. 879–898.

    Google Scholar 

  22. Buettner, G.R. and Oberley, L.W., Biochem. Biophys. Res. Commun., 83 (1978) 69.

    Google Scholar 

  23. Phillips, A.H. and Langdon, R.G., J. Biol. Chem., 237 (1962) 2652.

    Google Scholar 

  24. Finley, K.T., In Patai, S. (Ed.) The Chemistry of the Quininoid Compounds, Wiley, New York, NY, U.S.A., 1974, pp. 877–1144.

    Google Scholar 

  25. Fieser, L.F. and Brown, R.H., J. Am. Chem. Soc., 71 (1949) 3609.

    Google Scholar 

  26. Fieser, L.F. and Turner, R.B., J. Am. Chem. Soc., 69 (1947) 2335.

    Google Scholar 

  27. Burton, H. and David, S.B., J. Chem. Soc., (1952) 2193.

  28. Okamoto, M. and Ohta, S., Chem. Pharm. Bull., 28 (1980) 1071.

    Google Scholar 

  29. Schreiber, J., Mottley, C., Sinha, B.K., Kalyanaraman, B. and Mason, R.P., J. Am. Chem. Soc., 109 (1987) 348.

    Google Scholar 

  30. Bullock, A.T. and Howard, C.B., Trans. Faraday Soc., 66 (1970) 1861.

    Google Scholar 

  31. Finkelstein, E., Rosen, G.M., and Raukman, E.Y., Arch. Biochem. Biophys., 200 (1980) 1.

    Google Scholar 

  32. Buettner, G.R., Free Radic. Biol. Med., 3 (1987) 259.

    Google Scholar 

  33. Pou, G., Hassett, D.J., Britigan, B.E., Cohen, M.S. and Rosen, G.M., Anal. Biochem., 177 (1989) 1.

    Google Scholar 

  34. Weiner, L.M., Methods Enzymol., 233 (1994) 92.

    Google Scholar 

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Authors and Affiliations

  1. Department of Organic Chemistry, The Weizmann Institute of Science, 76100, Rehovot, Israel

    Shai Rahimipour, Lev Weiner & Mati Fridkin

  2. Department of Chemistry, Ben Gurion University of the Negev, 84105, Beer Sheva, Israel

    Prativa Bade Shrestha-Dawadi & Shmuel Bittner

Authors
  1. Shai Rahimipour
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  2. Lev Weiner
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  3. Mati Fridkin
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  4. Prativa Bade Shrestha-Dawadi
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  5. Shmuel Bittner
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Rahimipour, S., Weiner, L., Fridkin, M. et al. Novel naphthoquinonyl derivatives: Potential structural components for the synthesis of cytotoxic peptides. Lett Pept Sci 3, 263–274 (1996). https://doi.org/10.1007/BF00127660

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  • DOI: https://doi.org/10.1007/BF00127660

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