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

Park, K; Park, J; Hamilton, A

Journal article

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

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 x 10(6) M(-1) for 1 and 2.2 x 10(6) 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.

Publication status:: Published

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APA Style

Park, K., Park, J., & Hamilton, A. (2009). Novel 7-(dimethylamino)fluorene-based fluorescent probes and their binding to human serum albumin. Organic and Biomolecular Chemistry, 7(20), 4225–4232.

MLA Style

Park, K., et al. “Novel 7-(Dimethylamino)Fluorene-Based Fluorescent Probes and Their Binding to Human Serum Albumin.” Organic and Biomolecular Chemistry, vol. 7, no. 20, 2009, pp. 4225–32.

Chicago Style

Park, K, J Park, and A Hamilton. 2009. “Novel 7-(Dimethylamino)Fluorene-Based Fluorescent Probes and Their Binding to Human Serum Albumin.” Organic and Biomolecular Chemistry 7 (20): 4225–32.
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