RRC ID |
71897
|
Author |
Nakagami A, Mao Q, Gouhier G, Arima H, Kitagishi H.
|
Title |
FRET-Based In-Cell Detection of Highly Selective Supramolecular Complexes of meso-Tetraarylporphyrin with Peptide/BODIPY-Modified Per-O-Methyl-β-Cyclodextrins.
|
Journal |
Chembiochem
|
Abstract |
Artificial supramolecular systems capable of self-assembly and that precisely function in biological media are in high demand. Herein, we demonstrate a highly specific host-guest-pair system that functions in living cells. A per-O-methyl-β-cyclodextrin derivative (R8-B-CDMe ) bearing both an octaarginine peptide chain and a BODIPY dye was synthesized as a fluorescent intracellular delivery tool. R8-B-CDMe was efficiently taken up by HeLa cells through both endocytosis and direct transmembrane pathways. R8-B-CDMe formed a 2 : 1 inclusion complex with tetrakis(4-sulfonatophenyl)porphyrin (TPPS) as a guest molecule in water, from which fluorescence resonance energy transfer (FRET) from R8-B-CDMe to TPPS was observed. The FRET phenomenon was clearly detected in living cells using confocal microscopy techniques, which revealed that the formed supramolecular R8-B-CDMe /TPPS complex was maintained within the cells. The R8-B-CDMe cytotoxicity assay revealed that the addition of TPPS counteracts the strong cytotoxicity (IC50 =16 μM) of the CD cavity due to complexation within the cells. A series of experiments demonstrated the bio-orthogonality of the supramolecular per-O-methyl-β-CD/tetraarylporphyrin host-guest pair in living cells.
|
Volume |
22(22)
|
Pages |
3190-3198
|
Published |
2021-11-16
|
DOI |
10.1002/cbic.202100380
|
PMID |
34467611
|
MeSH |
Boron Compounds / chemistry*
Fluorescence Resonance Energy Transfer*
HeLa Cells
Humans
Macromolecular Substances / chemistry
Mesoporphyrins / chemistry*
Molecular Structure
Peptides / chemistry*
Spectrometry, Fluorescence
beta-Cyclodextrins / chemistry*
|
IF |
2.576
|
Resource |
Human and Animal Cells |
HeLa(RCB0007) |