Synthesis of a pH-sensitive nitrilotriacetic linker to peptide transduction domains to enable intracellular delivery of histidine imidazole ring-containing macromolecules

J Am Chem Soc. 2010 Aug 11;132(31):10680-2. doi: 10.1021/ja1040418.

Abstract

Intracellular delivery of functional macromolecules using peptide transduction domains (PTDs) is an exciting technology with both experimental and therapeutic applications. Recent data indicate that PTD-mediated transduction occurs via fluid-phase macropinocytosis involving an intracellular pH drop to approximately 5. Nitrilotriacetic acid (NTA)-coordinated metals avidly bind hexahistidine-tagged macromolecules, including peptides and proteins. Histidine's imidazole ring has a pK(a) of 6, making this an attractive target for the biological pH drop of PTD-mediated macropinocytotic delivery. The objective of this study was to develop a pH-sensitive PTD delivery peptide (NTA(3)-PTD). We demonstrate the in vitro function of this novel peptide by delivering fluorescently labeled peptides (1.6 kDa) and functional enzymes, beta-galactosidase (119 kDa) and Cre recombinase (37 kDa). Furthermore, the NTA(3)-PTD peptide was able to deliver functional Cre recombinase in an in vivo mouse model.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Disease Models, Animal
  • Drug Carriers / chemistry
  • Drug Delivery Systems*
  • Gene Expression Regulation, Enzymologic / drug effects
  • Histidine / chemistry*
  • Humans
  • Hydrogen-Ion Concentration
  • Imidazoles / chemistry*
  • Luciferases / genetics
  • Luciferases / metabolism
  • Macromolecular Substances / chemistry
  • Mice
  • Mice, Transgenic
  • Nitrilotriacetic Acid / chemistry*
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry
  • Organometallic Compounds / pharmacology*
  • Peptides / chemistry*

Substances

  • Drug Carriers
  • Imidazoles
  • Macromolecular Substances
  • Organometallic Compounds
  • Peptides
  • Histidine
  • imidazole
  • Luciferases
  • Nitrilotriacetic Acid