Skip to main content
SpringerLink
Log in

Oligopeptides That Are Anticancer Drugs

  • Chapter
Molecular Orbital Calculations for Amino Acids and Peptides

  • 111 Accesses

Abstract

The peptidic bond is present in some molecules that have been found to possess anticancer activity. These oligopeptides have been termed “lexitropsins” or information-reading molecules. They are also antibiotics, and evidence from biochemical pharmacology indicates that they act to block the template function of DNA. They do so by binding selectively to adenine-thymine (AT) sequences in the minor groove (1).

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Hahn, F.E. In Antibiotics III. Mechanism of Action of Antimicrobial and Antitumor Agents. Corcoran, J.W., and Hahn, FE., (eds.) Springer-Verlag, N.Y., 1975.

    Google Scholar 

  2. Frederick, C.A., Grable, J., and Melia, M. Nature 309, 327, 1984.

    Article  PubMed  CAS  Google Scholar 

  3. Bishop, J.M. Cell 42, 23, 1985.

    Article  PubMed  CAS  Google Scholar 

  4. Suck, D., and Oefiner, C. Nature 321, 620, 1986.

    Article  PubMed  CAS  Google Scholar 

  5. Julia, M., and Preau-Joseph, N. Compt. Rend. des Séances de L’Académie de Sciences 275, 1115, 1963.

    Google Scholar 

  6. Arcamone, F., Orezzi, P.G., Barbieri, W., Nicolella, V., and Penco, S. Gazz. Chim. Ital. 97, 1097, 1967.

    CAS  Google Scholar 

  7. Probst, G.W., Hoehn, M.M., and Woods, B.L. Antimicrob. Agents. Chemother. 789, 1965.

    Google Scholar 

  8. Takahashi, T., Sugawara, Y., and Susuki, M. Tetrahedron Lett. 1873, 1972.

    Google Scholar 

  9. Krowicki, K., and Lown, J.W. J. Org. Chem. 52, 3493, 1987.

    Article  CAS  Google Scholar 

  10. Kissinger, K., Krowicki, K., Dabrowiak, J.C., and Lown, J.W. Biochemistry 26, 5590, 1987.

    Article  PubMed  CAS  Google Scholar 

  11. Lee, M.S., Pon, R.T., Krowicki, K., and Lown, J.W. J. Biomol. Struct. Dyn. 5, 939, 1988.

    Article  PubMed  CAS  Google Scholar 

  12. Lown, J.W. Anti-Cancer Drug Design 3, 25, 1988.

    PubMed  CAS  Google Scholar 

  13. Lee, M., Shea, R.G., Hartley, J.A., Kissinger, K., Pon, R.T., Vesnaver, G., Breslauer, K.J., Dabrowiak, J.C., and Lown, J.W. J. Am. Chem. Soc. 111, 345, 1989.

    Article  CAS  Google Scholar 

  14. Schultz, P.G., and Dervan, P.B. J. Am. Chem. Soc. 105, 7748, 1983.

    Article  CAS  Google Scholar 

  15. Berman, H.M., Neidle, S., Zimmer, C., and Thrum, H. Biochem. Biophys. Acta 561, 124, 1979.

    Article  PubMed  CAS  Google Scholar 

  16. Gurskaya, G.V., Grokhovsky, S.L., Zhuze, A.L., and Gottikh, B.P. Biochem. Biophys. Acta 563, 336, 1979.

    Article  PubMed  CAS  Google Scholar 

  17. Remers, W.A., and Iyengar, B.S. In Cancer Chemotherapeutic Agents, Foye,W.O., (ed.) American Chemical Society, Washington, DC, 1995.

    Google Scholar 

  18. Zimmer, C., Kakiuchi, N., and Guschlbauer, W. Nucl. Acids. Res. 10, 1721, 1982.

    Article  PubMed  CAS  Google Scholar 

  19. Zimmer, C., Marck, C., and Guschlbauer, W. FEBS Lett. 154, 156, 1983.

    Article  PubMed  CAS  Google Scholar 

  20. Goodsel, D., and Dickerson, R.E. J. Med. Chem. 29, 727, 1986.

    Article  Google Scholar 

  21. Zakrewska, K., Lavery, R., and Pullman, B. J. Biomol. Struct. Dyn. 4, 833, 1987.

    Article  Google Scholar 

  22. Pullman, B. Adv. Drug. Res. 18, 1, 1989.

    CAS  Google Scholar 

  23. Mazurek, R, Feng, W., Shukla, K., Sapse, A.M., and Lown, J.B. J. Biomol. Struc. Dyn. 9, 299, 1991.

    Article  CAS  Google Scholar 

  24. Martin, J.C., Wartell, R.M., and O’Shea, D.C. Proc. Natl. Acad. Sci. USA, 75, 5483, 1978.

    Article  PubMed  CAS  Google Scholar 

  25. Patel, D.J. Eur. J. Biochem. 99, 369, 1979.

    Article  PubMed  CAS  Google Scholar 

  26. Lown, J.W., Krowicki, B., Bhat, U.G., Skorogaty, A., Ward, B., and Dabrowiak, J.C. Biochemistry 25, 7408, 1986.

    Article  PubMed  CAS  Google Scholar 

  27. Bailly, C., Rommery, N., Houssin, R., and Hemchart, J.P. J. Pharm. Sci. 78, 910, 1989.

    Article  PubMed  CAS  Google Scholar 

  28. Sapse, A.M., Feng, W., Fugler-Domenico, L., Kabir, S., Joseph, T., and Lown, J.W. J. Biomol. Struct. Dyn. 10, 4, 709, 1993.

    Article  PubMed  CAS  Google Scholar 

  29. Kabir, S., and Sapse, A.M. J. Comp. Chem. 12, 1142, 1991.

    Article  CAS  Google Scholar 

  30. Zimmerman, J., Rao, K.E., Joseph, T., Sapse, A.M., and Lown, J.W. J. Biomol. Struct. Dyn. 9, 599,1991.

    Article  Google Scholar 

  31. Spatola, A.F. Chemistry and Biochemistry of Amino Acids, Peptides and Proteins, 7, 267, 1983.

    CAS  Google Scholar 

  32. Scheibye, S., Pederson, B.S., and Lawesson, S.O. Bull. Soc. Chim. Belg. 87, 229, 1978.

    Article  CAS  Google Scholar 

  33. Bartlett, P.A., Spear, K.L., and Jacobsen, N.E. Biochemistry 21, 1608, 1982.

    Article  PubMed  CAS  Google Scholar 

  34. Kopka, M.L., Yoon, C., Goodsell, D., Pjura, P, and Dickerson, R.E. Proc. Natl. Acad. Sci. USA 82, 1376, 1985.

    Article  PubMed  CAS  Google Scholar 

  35. Coll, M., Frederick, C.A., Wang, A.H.J., and Rich, A. Proc. Natl. Acad. Sci. USA 84, 8385, 1987.

    Article  PubMed  CAS  Google Scholar 

  36. Sapse, A.M., Kabir, S., and Snyder, G. THEOCHEM 339, 227, 1995.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. John Jay College and Graduate School, City University of New York, New York, NY, 10019, USA

    Anne-Marie Sapse

  2. Rockefeller University, New York, NY, 10021, USA

    Anne-Marie Sapse

Authors
  1. Anne-Marie Sapse
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

Copyright information

© 2000 Springer Science+Business Media New York

About this chapter

Cite this chapter

Sapse, AM. (2000). Oligopeptides That Are Anticancer Drugs. In: Molecular Orbital Calculations for Amino Acids and Peptides. Birkhäuser, Boston, MA. https://doi.org/10.1007/978-1-4612-1354-3_12

Download citation

  • DOI: https://doi.org/10.1007/978-1-4612-1354-3_12

  • Publisher Name: Birkhäuser, Boston, MA

  • Print ISBN: 978-1-4612-7109-3

  • Online ISBN: 978-1-4612-1354-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation