Photophysics of novel coumarin-labeled depsipeptides in solution: sensing interactions with SDS micelle via TICT model

Biswas S., Avan I., Basak A. K., Abo-Dya N. E., Asiri A., Katritzky A. R.

AMINO ACIDS, vol.45, no.1, pp.159-170, 2013 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 45 Issue: 1
  • Publication Date: 2013
  • Doi Number: 10.1007/s00726-013-1483-3
  • Journal Name: AMINO ACIDS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.159-170
  • Keywords: Coumarin, Peptidomimetics, Depsipeptides, SDS, Micelle, TICT, LASER-DYES, FLUORESCENT PEPTIDES, AMINO-ACIDS, SOLID-PHASE, IN-VITRO, PROTEIN, EMISSION, MECHANISM, SYSTEMS, PROBES
  • Anadolu University Affiliated: Yes

Abstract

N-Acylbenzotriazoles enable the synthesis (69-92 % yield) of blue to green fluorescent coumarin-labeled depsidipeptides 8a-f (quantum yields 0.004-0.97) and depsitripeptides 12a-d (quantum yields 0.02-0.96). Detailed photophysical studies of fluorescent coumarin-labeled depsipeptides 8a-f and 12a-d are reported for both polar protic and polar aprotic solvents. 7-Methoxy and 7-diethylaminocoumarin-3-ylcarbonyl depsipeptides 8c,f and 12d are highly solvent sensitive. These highly fluorescent compounds could be useful for peptide assays. Further photophysical studies of 7-diethylaminocoumarin-labeled depsipeptides 8c,12d within the micellar microenvironment of SDS reflect their ability to bind with the biological membrane, suggesting potential applications in the fields of bio- and medicinal chemistry.