Ligand-directed acyl imidazole chemistry for labeling of membrane-bound proteins on live cells

Journal of the American Chemical Society

Volumn 134, Issue 9, 2012, Pages 3961-3964

  Fujishima, Sho Hei ^a   Yasui, Ryosuke ^a   Miki, Takayuki ^a   Ojida, Akio ^b   Hamachi, Itaru ^a  

^a KYOTO UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CELL SURFACES; DIHYDROFOLATE REDUCTASE; FOLATE RECEPTOR; IN-SITU; IN-VITRO; LIGAND BINDING; LIVE CELL; LIVING CELL; MEMBRANE-BOUND PROTEINS; NATURAL PROTEINS; PROTEIN LABELING;

BINDING ENERGY; BIOSENSORS; CELL MEMBRANES; PROTEINS; SULFUR COMPOUNDS;

LIGANDS;

ALKYLOXYACYL IMIDAZOLE; DIHYDROFOLATE REDUCTASE; FLUORESCEIN; FOLATE RECEPTOR; FOLIC ACID; IMIDAZOLE DERIVATIVE; LIGAND DIRECTED ACYL IMIDAZOLE; MEMBRANE BOUND PROTEIN; MEMBRANE PROTEIN; METHOTREXATE; TOLUENESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BIOSENSOR; CELL ENGINEERING; CELL SURFACE; CELLS; CHEMISTRY; LIGAND BINDING; LIVE CELL; PROTEIN MODIFICATION;

FLUORESCENCE; FOLATE RECEPTORS, GPI-ANCHORED; HUMANS; IMIDAZOLES; KB CELLS; LIGANDS; MEMBRANE PROTEINS; MICROSCOPY, FLUORESCENCE; MOLECULAR STRUCTURE; STAINING AND LABELING; TETRAHYDROFOLATE DEHYDROGENASE;

EID: 84857850984     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2108855     Document Type: Article

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33. The fluorescence signal was clearly detected even after cells were washed with FA (25 μM) (Figure S4), indicating that FR on KB cells was covalently labeled by 2.
34. Dissociation constants of FR for FA and the reduced FA derivatives (H2FA and H4FA) were reported to be <1 nM and 1-10 nM, respectively (Keleman, L. E. Int. J. Cancer 2006, 119, 243) . Since the binding affinities for PT, MTX, and TMP were not reported, we roughly evaluated them by the competitive labeling experiment (Figure S8).
35. The fluorescence spectrum of Fl-labeled FR on the cell surface was almost identical with that of 1 alone in its wavelength (Figure S9).