Design and synthesis of cell-permeable fluorescent nitrilotriacetic acid derivatives

Bioorg Med Chem. 2018 Nov 1;26(20):5494-5498. doi: 10.1016/j.bmc.2018.09.028. Epub 2018 Sep 24.

Abstract

Fluorescence labeling of the target molecules using a small molecule-based probe is superior than a method using genetically expressed green fluorescence protein (GFP) in terms of convenience in its preparation and functionalization. Fluorophore-nitrilotriacetic acid (NTA) conjugates with several ester protecting groups were synthesized and evaluated for their cell membrane permeability by fluorescence microscopy analysis. One of the derivatives, acetoxymethyl (AM)-protected NTA conjugate is hydrolyzed, resulting in intracellular accumulation, thus providing localized fluorescence intensity in cells. This modification is expected as an effective method for converting a non-cell membrane permeable NTA-BODIPY conjugates to a cell membrane permeable derivatives.

Keywords: Acetoxymethyl group; BODIPY; Cell membrane permeability; NTA.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boron Compounds / chemical synthesis
  • Boron Compounds / chemistry
  • Boron Compounds / metabolism
  • Cell Line
  • Cell Membrane Permeability
  • Fluorescence
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / metabolism*
  • Humans
  • Hydrolysis
  • Microscopy, Fluorescence
  • Nitrilotriacetic Acid / analogs & derivatives*
  • Nitrilotriacetic Acid / chemical synthesis
  • Nitrilotriacetic Acid / metabolism*

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Boron Compounds
  • Fluorescent Dyes
  • Nitrilotriacetic Acid