Dendritic hexadecapeptide as a cathepsin B degradable carrier for delivery of HSP90 inhibitor

Bioorg Med Chem Lett. 2015 Sep 1;25(17):3744-7. doi: 10.1016/j.bmcl.2015.06.012. Epub 2015 Jun 11.

Abstract

Biodegradable vehicles that degrade specifically at tumor sites are highly desirable since they can cause selective exposure of highly toxic drugs at tumor sites whereas keep the conjugates stable during blood circulation. Here, we evaluate the utility of a dendritic hexadecapeptide comprised of four arms, each having a tetrapeptide sequence recognized by an enzyme cathepsin B as a carrier system for heat shock protein 90 (HSP90) inhibitor geldanamycin (GDM). We report the synthesis of a carrier having GDM conjugated to the terminal end of each arm (>55% wt/wt drug). We further report the stability of the GDM containing peptidic dendrimer in various buffers and in the presence of serum along with its ability to release free drug in the presence of cathepsin B, the enzyme overexpressed in a variety of tumors. Using androgen-independent prostate cancer cell line (DU-145) we further demonstrate that the geldanamycin containing peptidic dendrimer has antiproliferative property similar to the free drug derivative.

Keywords: Cathepsin B; Degradable polymer; Geldanamycin; HSP90 inhibitor; Peptidic dendrimer.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Antibiotics, Antineoplastic / administration & dosage
  • Antibiotics, Antineoplastic / pharmacokinetics
  • Benzoquinones / administration & dosage*
  • Benzoquinones / pharmacokinetics
  • Cathepsin B / administration & dosage
  • Cathepsin B / chemistry
  • Cathepsin B / metabolism*
  • Cell Line, Tumor / drug effects
  • Dendrimers / administration & dosage*
  • Dendrimers / chemistry
  • Drug Carriers / administration & dosage*
  • Drug Carriers / chemistry
  • Drug Carriers / pharmacokinetics
  • Drug Stability
  • HSP90 Heat-Shock Proteins / antagonists & inhibitors*
  • Humans
  • Inhibitory Concentration 50
  • Lactams, Macrocyclic / administration & dosage*
  • Lactams, Macrocyclic / pharmacokinetics
  • Male
  • Peptides / administration & dosage*
  • Peptides / chemistry*
  • Peptides / pharmacokinetics
  • Prostatic Neoplasms / drug therapy
  • Prostatic Neoplasms / pathology

Substances

  • Antibiotics, Antineoplastic
  • Benzoquinones
  • Dendrimers
  • Drug Carriers
  • HSP90 Heat-Shock Proteins
  • Lactams, Macrocyclic
  • Peptides
  • Cathepsin B
  • geldanamycin