Targeted dendrimeric anticancer prodrug: a methotrexate-folic acid-poly(amidoamine) conjugate and a novel, rapid, "one pot" synthetic approach

Bioconjug Chem. 2010 Mar 17;21(3):489-95. doi: 10.1021/bc9003958. Epub 2010 Feb 3.

Abstract

A targeted dendrimeric anticancer prodrug, a conjugate of generation 5 (G5) polyamidoamine (PAMAM) dendrimer, folic acid (FA), and methotrexate (MTX), has been successfully synthesized by using a novel "one pot" approach which is simple, reproducible, and feasible for large-scale synthesis. All dendrimer products have been characterized by (1)H NMR, MALDI-TOF, GPC, and HPLC. With this new method, the ratio of FA versus MTX attached to the dendrimer can be easily tuned to achieve the desired therapeutic effect. A new analytical approach for calculating the numbers of FA and MTX attached to the dendrimer has been established. In vitro studies performed on FA receptor-expressing KB cells show that the new conjugate has a similar affinity and cytotoxic potency to G5-FA-MTX synthesized using the traditional multiple-step approach.

Publication types

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

MeSH terms

  • Antineoplastic Agents / administration & dosage*
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Survival / drug effects
  • Dendrimers / chemical synthesis
  • Dendrimers / chemistry*
  • Dose-Response Relationship, Drug
  • Drug Delivery Systems*
  • Folic Acid / chemistry*
  • Humans
  • KB Cells
  • Methotrexate / chemistry
  • Methotrexate / pharmacology*
  • Molecular Structure
  • Polyamines / chemistry*
  • Prodrugs / administration & dosage
  • Prodrugs / chemical synthesis*
  • Prodrugs / chemistry
  • Prodrugs / pharmacology
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Dendrimers
  • Poly(amidoamine)
  • Polyamines
  • Prodrugs
  • Folic Acid
  • Methotrexate