title: Enantioselective Fluorescent Imaging of Free Amino Acids in Living Cells.
abstract: 1,1'-Spirobiindane-7,7'-diol (SPINOL)-based chiral aldehydes (R)- and (S)-3, in combination with Zn2+, are highly enantioselective fluorescent sensors for structurally diverse chiral amino acids. Application of this enantiomeric sensor pair in HeLa cells containing a free amino acid shows that the chirality-matched sensor-amino acid interaction leads to strong blue emission and chirality mismatch gives only weak fluorescence. This allows a quick determination of the chiral configuration of the free amino acid in the cells. It represents the first enantioselective fluorescent imaging of free amino acids in living cells.
authors.affiliation: Key Laboratory of Cluster Science of Ministry of Education, Beijing Key Laboratory of Photoelectronic/Electrophotonic, Conversion Materials, School of Chemistry, Beijing Institute of Technology, 5 Zhongguancun Road, Beijing, 100081, P.R. China.
authors.forename: Chaoyuan
authors.initials: C
authors.lastname: Zeng
authors.affiliation: Key Laboratory of Cluster Science of Ministry of Education, Beijing Key Laboratory of Photoelectronic/Electrophotonic, Conversion Materials, School of Chemistry, Beijing Institute of Technology, 5 Zhongguancun Road, Beijing, 100081, P.R. China.
authors.forename: Xiaoling
authors.initials: X
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, University of Virginia, Charlottesville, VA, 22904, USA.
authors.forename: Lin
authors.initials: L
authors.lastname: Pu
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D006367:HeLa Cells; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D018613:Microscopy, Confocal; D013050:Spectrometry, Fluorescence; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D005456:Fluorescent Dyes; D015032:Zinc
keywords: amino acids; enantioselectivity; fluorescence; imaging agents; sensors