Molecules 2014, 19(5), 6106-6122; doi:10.3390/molecules19056106
Article

Molecular Docking and Fluorescence Characterization of Benzothieno[3,2-d]pyrimidin-4-one Sulphonamide Thio-Derivatives, a Novel Class of Selective Cyclooxygenase-2 Inhibitors

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Received: 15 January 2014; in revised form: 2 May 2014 / Accepted: 9 May 2014 / Published: 14 May 2014
(This article belongs to the Special Issue Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: The aims of this study were: (i) to explore the structure-activity relationship of some new anti-inflammatory benzothieno[3,2-d]pyrimidin-4-one sulphonamide thio-derivatives 111; and (ii) to evaluate the possibility of using the most active compounds as fluorescent probes to determine tumours or their progression. Therefore, to know the precise mechanism by which these compounds interact with cyclooxygenase (COX)-2 enzyme, a molecular docking study was carried out; to assess spectroscopic characteristics, their absorption and emission properties were determined. The results demonstrated that some derivatives of benzothieno[3,2-d] pyrimidine exhibit interesting anti-inflammatory properties related to interactions with active sites of COX-2 and are fluorescent. The antipyrine-bearing compound 4 displayed high COX-2 affinity (ΔG = −9.4) and good fluorescent properties (Φfl = 0.032). Thus, some members of this new class of anti-inflammatory may be promising for fluorescence imaging of cancer cells that express the COX-2 enzyme. Further in vitro and in vivo studies are needed to confirm this hypothesis.
Keywords: anti-inflammatory; antipyrine; cancer detection; COX-2; fluorescence
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MDPI and ACS Style

Barone, M.; Pannuzzo, G.; Santagati, A.; Catalfo, A.; De Guidi, G.; Cardile, V. Molecular Docking and Fluorescence Characterization of Benzothieno[3,2-d]pyrimidin-4-one Sulphonamide Thio-Derivatives, a Novel Class of Selective Cyclooxygenase-2 Inhibitors. Molecules 2014, 19, 6106-6122.

AMA Style

Barone M, Pannuzzo G, Santagati A, Catalfo A, De Guidi G, Cardile V. Molecular Docking and Fluorescence Characterization of Benzothieno[3,2-d]pyrimidin-4-one Sulphonamide Thio-Derivatives, a Novel Class of Selective Cyclooxygenase-2 Inhibitors. Molecules. 2014; 19(5):6106-6122.

Chicago/Turabian Style

Barone, Mariarita; Pannuzzo, Giovanna; Santagati, Andrea; Catalfo, Alfio; De Guidi, Guido; Cardile, Venera. 2014. "Molecular Docking and Fluorescence Characterization of Benzothieno[3,2-d]pyrimidin-4-one Sulphonamide Thio-Derivatives, a Novel Class of Selective Cyclooxygenase-2 Inhibitors." Molecules 19, no. 5: 6106-6122.

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