Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Fluorescent Peptides Labeled with Environment-Sensitive 7-Aminocoumarins and Their Interactions with Lipid Bilayer Membranes and Living Cells
Tokiko MuraseToshitada YoshiharaKeiichi YamadaSeiji Tobita
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2013 Volume 86 Issue 4 Pages 510-519


The photophysical properties of protected nonnatural amino acids Boc–L-Dap(7DEAC)–OMe (7DEAC: 7-diethylaminocoumarin) and Boc–L-Dap(C343)–OMe (C343: coumarin 343) were investigated to evaluate the suitability of these amino acids as fluorescent units in peptide-based fluorescent biosensors. The absorption and fluorescence spectra of Boc–L-Dap(7DEAC)–OMe and Boc–L-Dap(C343)–OMe exhibited significant red shifts with increasing solvent polarity. The fluorescence quantum yield and lifetime of Boc–L-Dap(7DEAC)–OMe solutions decreased remarkably with increasing solvent polarity, whereas those of Boc–L-Dap(C343)–OMe were slightly affected by the solvent polarity. Fluorescent peptides H–Dap(7DEAC)–LLA–OMe (1), H–Dap(7DEAC)–KLA–OMe (2), and H–Dap(7DEAC)–ELA–OMe (3) labeled with environment-sensitive 7DEAC were synthesized to examine the interactions of these labeled peptides with lipid membranes and living cells. Neutral 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) and anionic 1,2-dimyristoyl-sn-glycero-3-[phospho-rac-(1-glycerol)] (DMPG) liposomes were used to investigate peptide–membrane interactions. Hydrophobic peptide 1 exhibited high affinities to both DMPC and DMPC/DMPG mixed membranes. Of the three peptides, cationic peptide 2 exhibited the strongest affinity to DMPC/DMPG membranes, whereas anionic peptide 3 showed a much lower affinity to DMPC/DMPG membranes. These results could be interpreted based on hydrophobic and electrostatic interactions between the peptides and membranes. Peptide 1 was efficiently internalized into HeLa cells, whereas peptides 2 and 3 showed a much lower intracellular delivery.

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© 2013 The Chemical Society of Japan
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