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Novel 7-(dimethylamino)fluorene-based fluorescent probes and their binding to human serum albumin

Title
Novel 7-(dimethylamino)fluorene-based fluorescent probes and their binding to human serum albumin
Authors
Park K.K.Park J.W.Hamilton A.D.
Ewha Authors
박준우
SCOPUS Author ID
박준우scopusscopus
Issue Date
2009
Journal Title
Organic and Biomolecular Chemistry
ISSN
1477-0520JCR Link
Citation
vol. 7, no. 20, pp. 4225 - 4232
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
A novel solvatochromic fluorescent molecule, 9,9-dibutyl-7-(dimethylamino)- 2-fluorenesulfonate 2 was synthesized from 2-nitrofluorene in moderate yield. The fluorescence spectra of 2 and 7-(dimethylamino)-2-fluorenesulfonate 1 shift to shorter wavelengths as the polarity of the medium decreases. Both 1 and 2 bind to hydrophobic sites of human serum albumin (HSA). The apparent binding constants were determined by fluorescence titration to be 0.37 × 10 6 M-1 for 1 and 2.2 × 106 M-1 for 2. The energy of the Trp-214 fluorescence of HSA is transferred to the HSA-bound fluorophores with near 100% efficiency. The covalent bonding of acrylodan (AC) to Cys-34 has little effect on the binding affinity of 2 to HSA or fluorescent behavior of HSA-bound 2. Bound 2 also has little effect on the fluorescence of AC, but 2→AC and Trp-214→2→AC resonance energy transfers were observed. Competitive binding between the fluorene compounds and other ligands such as 1-anilino-8-naphthalenesulfonate, aspirin, S-(+)-ibuprofen and phenylbutazone were also studied fluorometrically. The results indicated that the primary binding site of 2 to HSA is site II in domain IIIA, whereas 1 binds to site I in domain IIA, but a different region from the phenylbutazone binding site. Because of its large molar absorptivity, strong fluorescence, sensitivity to its environment, and high binding constant to HSA, 2 can be used successfully in the study of proteins and their binding properties. © 2009 The Royal Society of Chemistry.
DOI
10.1039/b911605b
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자연과학대학 > 화학·나노과학전공 > Journal papers
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