Design and synthesis of cell-permeable fluorescent nitrilotriacetic acid derivatives. Issue 20 (1st November 2018)

• Record Type: Journal Article
• Authors: Tsuji, Genichiro; Hattori, Takayuki; Kato, Masashi; Hakamata, Wataru; Inoue, Hideshi; Naito, Mikihiko; Kurihara, Masaaki; Demizu, Yosuke; Shoda, Takuji
• Is Part Of: Bioorganic & medicinal chemistry. Volume 26:Issue 20(2018)
• Page Start: 5494
• Page End: 5498
• Publication Date: 2018-11-01
• Subjects: BODIPY -- NTA -- Cell membrane permeability -- Acetoxymethyl group; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2018.09.028
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: 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.