Total Synthesis of Cryptophycin A and Analogs

Abstract

The cryptophycins are antimitotic, cyanobacterial metabolites isolated from a blue- green algae. In vivo studies showed that the cryptophycins are active against breast, pancreatic and colon tumors, and retain their potency against the multi-drug resistant cancer cell lines. Total synthesis of two arenastatin A analogues containing the inverted C3 center were completed and preliminary biological testing of one of these isomers was conducted. The results revealed that the natural C3 S configuration is required for pM activity. Total synthesis of arenastatin A and four C10 analogues was completed and biological testing of analogues was conducted. Biological activity of the C10 analogues suggests that there is a specific interaction between the C3' site in the C10 side chain and cryptophycin's binding site.

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Document Details

Document Type
Technical Report
Publication Date
Jul 01, 2001
Accession Number
ADA391962

Entities

People

  • Gunda Georg
  • Suzanne B. Buck

Organizations

  • University of Kansas

Tags

Communities of Interest

  • Biomedical

DTIC Thesaurus Topics

  • Alcohols
  • Alkenes
  • Amino Acids
  • Cell Line
  • Cells
  • Chemical Synthesis
  • Chemistry
  • Column Chromatography
  • Cyanobacteria
  • Liquid Chromatography
  • Mass Spectrometry
  • Organic Chemistry
  • Students

Fields of Study

  • Chemistry

Readers

  • Molecular and Cellular Biochemistry
  • Oncology (Cancer Research).

Technology Areas

  • Fully Networked C3