期刊
DYES AND PIGMENTS
卷 173, 期 -, 页码 -出版社
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2019.107874
关键词
Solvatochromic fluorescent probe; Aminoquinoline derivative; One-pot synthesis; Albumin; Lysozyme; Amyloid fibril aggregates
资金
- Coordination for the Improvement of Higher Education Personnel
- National Council for Scientific and Technological Development (CNPq, Conselho Nacional de Desenvolvimento Cientifico e Tecnologico) [302793/2016-0, 305541/2017-0, 302769/2018-8]
- National Institute of Science and Technology -INCT BioNat [465637/2014-0]
- State of Sao Paulo Research Foundation (FAPESP, Fundacao de Amparo a Pesquisa do Estado de Sao Paulo) [2014/50926-0, 2015/22338-9, 2016/20549-5, 2015/00615-0, 2018/14506-7]
A novel aminoquinoline derivative (AQ) was synthesized and applied as a solvatochromic fluorescent probe to study proteins and their alterations. AQ is not fluorescent in aqueous solution but has its fluorescence quantum yield significantly increased upon binding to albumin. The generation of an induced circular dichroism signal in AQ confirmed the complexation. The Job's plot method revealed an 1:1 stoichiometry for the host-guest complex. The binding constant was determined by AQ fluorescence increase (2.7 x 10(5) mol(-1) L) and by protein intrinsic fluorescence quenching (5.1 x 10(5) mol(-1) L). The displacement of AQ from albumin by warfarin and ibuprofen showed that Sudlow's drug site-I is the preferential binding site. By applying the Bilot-Kawski solvatochromic model to the spectral shifts of fifteen solvents, the microenvironment dielectric constant at albumin site-I was estimated (epsilon = 14.8). In agreement, the average fluorescence lifetime of AQ complexed with albumin (6.11 ns) was close to dichloromethane (6.53 ns) and acetone (6.34 ns), which have dielectric constants of 8.9 and 21.0, respectively. Albumin was thermically treated to formation of amyloid fibril aggregates. AQ was able to differentiate the altered and native protein. Sodium dodecyl sulfate-induced aggregation of lysozyme to amyloid fibril was also efficiently detected by the AQ fluorescence increase. AQ was as efficient as the chromogenic bromocresol purple in the quantitative analysis of albumin. In conclusion, AQ can be considered a new solvatochromic fluorescent probe with several potential applications.
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