Inhibition of collagenase by aranciamycin and aranciamycin derivatives

J Med Chem. 1992 Jul 24;35(15):2768-71. doi: 10.1021/jm00093a008.


Aranciamycin (1), an anthracycline antibiotic, was found to be an inhibitor of Clostridium histolyticum collagenase, with an IC50 = 3.7 x 10(-7) M. Elastase and trypsin were not inhibited at concentrations less than or equal to 10(-5) M. A number of aranciamycin derivatives 2-13 were prepared and tested for collagenase inhibition. While loss of activity was found for derivatives modified in the sugar ring or rings B and D of the aglycone, increased potency was found when the tertiary alcohol at C-9 was esterified. All compounds 1-13 were found to inhibit DNA synthesis of Yoshida sarcoma tumor cells.

MeSH terms

  • Animals
  • Anthracyclines*
  • Antibiotics, Antineoplastic / chemistry
  • Antibiotics, Antineoplastic / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Microbial Collagenase / antagonists & inhibitors*
  • Pancreatic Elastase / antagonists & inhibitors
  • Rats
  • Sarcoma, Experimental
  • Streptomyces / chemistry
  • Trypsin Inhibitors / pharmacology
  • Tumor Cells, Cultured


  • Anthracyclines
  • Antibiotics, Antineoplastic
  • Trypsin Inhibitors
  • aranciamycin
  • Pancreatic Elastase
  • Microbial Collagenase