Synthesis and evaluation of photolabile insulin prodrugs. Academic Article uri icon

Overview

abstract

  • We have developed two photolabile insulin prodrugs, insulin-2P and insulin-3P. These prodrugs were synthesized by protecting GlyA1 (N(alphaA1)), and one or both of the PheB1 (N(alphaB1)) and LysB29 (N(epsilonB29)) amino groups in insulin using 5'-(alpha-methyl-nitro-piperonyl)oxy-carbonyl as the protecting group. These insulin prodrugs were efficiently activated by exposure to longwave UV light to produce insulin quantitatively. Using 2-deoxyglucose uptake assays, both di- and tri-protected compounds were less active than native insulin in the protected state, and showed comparable activity to native insulin upon photoactivation.

publication date

  • September 1, 2005

Research

keywords

  • Insulin
  • Prodrugs

Identity

Scopus Document Identifier

  • 23244448933

Digital Object Identifier (DOI)

  • 10.1016/j.bmcl.2005.05.112

PubMed ID

  • 15993597

Additional Document Info

volume

  • 15

issue

  • 17