新型香豆素标记的环二肽在溶液中的光物理性质：通过 TICT 模型感应与 SDS 胶束的相互作用。

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

机构信息

Department of Chemistry, Center for Heterocyclic Compounds, University of Florida, Gainesville, FL 32611-7200, USA.

出版信息

Amino Acids. 2013 Jul;45(1):159-70. doi: 10.1007/s00726-013-1483-3. Epub 2013 Apr 4.

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.

摘要

N-酰基苯并三唑能够实现蓝色到绿色荧光香豆素标记的去端肽 8a-f（产率 69-92%）和去端三肽 12a-d（产率 0.02-0.96）的合成（量子产率 0.004-0.97）。报告了对极性质子和非质子溶剂中荧光香豆素标记的去端肽 8a-f 和 12a-d 的详细光物理研究。7-甲氧基和 7-二乙氨基香豆素-3-羰基去端肽 8c、f 和 12d 对溶剂非常敏感。这些高荧光化合物可用于肽分析。进一步对 SDS 胶束微环境中的 7-二乙氨基香豆素标记的去端肽 8c、12d 的光物理研究反映了它们与生物膜结合的能力，这表明它们在生物和药物化学领域有潜在的应用。