The synthesis of a c(RGDyK) targeted SN38 prodrug with an indolequinone structure for bioreductive drug release

Org Lett. 2010 Apr 2;12(7):1384-7. doi: 10.1021/ol1002626.

Abstract

Preparation of a novel c(RGDyK) targeted SN38 prodrug incorporating an indolequinone structure for bioreductively triggered drug release is described. This design yields a prodrug that targets surface molecules on tumor cells (alpha(v)beta(3) integrins) and releases drug under bioreductive conditions. There are three moieties in the prodrug design, namely a therapeutic drug SN38, an indolequinone structure serving as a drug releasing trigger, and an alpha(v)beta(3) integrin targeting peptide c(RGDyK). Preliminary studies showed that SN38 is released in the presence of a bioreductive enzyme (DT-diaphorase).

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Camptothecin / analogs & derivatives*
  • Camptothecin / chemistry
  • Camptothecin / metabolism
  • Camptothecin / pharmacokinetics
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Female
  • Humans
  • Indolequinones / chemistry*
  • Integrin alphaVbeta3 / antagonists & inhibitors
  • Integrin alphaVbeta3 / metabolism*
  • KB Cells
  • Molecular Structure
  • NAD(P)H Dehydrogenase (Quinone) / chemistry
  • NAD(P)H Dehydrogenase (Quinone) / metabolism
  • Oxidation-Reduction
  • Peptides, Cyclic / chemistry*
  • Prodrugs / chemical synthesis*
  • Prodrugs / chemistry
  • Prodrugs / pharmacokinetics*
  • Structure-Activity Relationship
  • Time Factors
  • Uterine Cervical Neoplasms / chemistry
  • Uterine Cervical Neoplasms / drug therapy*
  • Uterine Cervical Neoplasms / metabolism

Substances

  • Indolequinones
  • Integrin alphaVbeta3
  • Peptides, Cyclic
  • Prodrugs
  • SN38-Glu
  • cyclo(Arg-Gly-Asp-Tyr-Lys)
  • NAD(P)H Dehydrogenase (Quinone)
  • Camptothecin