The yin and yang of intracellular delivery of amphipathic optical probes using n -butyl charge masking

Hitesh K. Agarwal, Radoslav Janicek, Jun Zhao, Karthik Sambath, Marcel Egger, Ernst Niggli, Graham C.R. Ellis-Davies

Research output: Contribution to journalArticlepeer-review

Abstract

Monitoring and manipulation of ionized intracellular calcium concentrations within intact, living cells using optical probes with organic chromophores is a core method for cell physiology. Since all these probes have multiple negative charges, they must be smuggled through the plasma membrane in a transiently neutral form, with intracellular esterases used to deprotect the masked anions. Here we explore the ability of the synthetically easily accessible n-butyl ester protecting group to deliver amphipathic cargoes to the cytosol. We show that the size of the caging chromophore conditions the ability of intracellular probe delivery and esterase charge unmasking.

Original languageEnglish (US)
Pages (from-to)2826-2829
Number of pages4
JournalChemical Communications
Volume58
Issue number17
DOIs
StatePublished - Feb 28 2022
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • General Chemistry
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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