FRET‐Based In‐Cell Detection of Highly Selective Supramolecular Complexes of <i>meso</i> ‐Tetraarylporphyrin with Peptide/BODIPY‐Modified Per‐ <i>O</i> ‐Methyl‐β‐Cyclodextrins - Archive ouverte HAL
Article Dans Une Revue ChemBioChem Année : 2021

FRET‐Based In‐Cell Detection of Highly Selective Supramolecular Complexes of meso ‐Tetraarylporphyrin with Peptide/BODIPY‐Modified Per‐ O ‐Methyl‐β‐Cyclodextrins

Atsuki Nakagami
  • Fonction : Auteur
Qiyue Mao
  • Fonction : Auteur
Hidetoshi Arima
  • Fonction : Auteur
Hiroaki Kitagishi

Résumé

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-CD Me) bearing both an octaarginine peptide chain and a BODIPY dye was synthesized as a fluorescent intracellular delivery tool. R8-B-CD Me was efficiently taken up by HeLa cells through both endocytosis and direct transmembrane pathways. R8-B-CD Me 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-CD Me 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-CD Me /TPPS complex was maintained within the cells. The R8-B-CD Me cytotoxicity assay revealed that the addition of TPPS counteracts the strong cytotoxicity (IC 50 = 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 hostguest pair in living cells.

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Chimie
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Dates et versions

hal-04045265 , version 1 (27-03-2023)

Identifiants

Citer

Atsuki Nakagami, Qiyue Mao, Géraldine Gouhier, Hidetoshi Arima, Hiroaki Kitagishi. FRET‐Based In‐Cell Detection of Highly Selective Supramolecular Complexes of meso ‐Tetraarylporphyrin with Peptide/BODIPY‐Modified Per‐ O ‐Methyl‐β‐Cyclodextrins. ChemBioChem, 2021, 22 (22), pp.3190 - 3198. ⟨10.1002/cbic.202100380⟩. ⟨hal-04045265⟩
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