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Open AccessArticle

Characterization and Antiproliferative Activity of a Novel 2-Aminothiophene Derivative-β-Cyclodextrin Binary System

1
Department of Pharmacy, Federal University of Rio Grande do Norte, Av. General Cordeiro de Farias, s/n, Petrópolis, Natal, Rio Grande do Norte 59012-570, Brazil
2
Department of Clinical and Toxicological Analysis, Federal University of Rio Grande do Norte, Av. General Cordeiro de Faria, s/n, Petrópolis, Natal, Rio Grande do Norte 59012-570, Brazil
3
Department of Biochemistry, Federal University of Rio Grande do Norte, Av. Senador Salgado Filho, 3000, Lagoa Nova, Natal, Rio Grande do Norte 59078-970, Brazil
4
Graduate Program of Biotechnology, Laureate International Universities—Universidade Potiguar (UnP), Av. Sen. Salgado Filho, 1610, Lagoa Nova, Natal, Rio Grande do Norte 59056-000, Brazil
5
Department of Biological Sciences, State University of Paraíba, Rua Horácio Trajano de Oliveira, s/n, Cristo Redentor, João Pessoa 58071-160, Brazil
*
Author to whom correspondence should be addressed.
Academic Editor: Bernard Martel
Molecules 2018, 23(12), 3130; https://doi.org/10.3390/molecules23123130
Received: 10 October 2018 / Revised: 8 November 2018 / Accepted: 10 November 2018 / Published: 29 November 2018
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
The novel 2-aminothiophene derivative 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile (6CN) has shown potential anti-proliferative activity in human cancer cell lines. However, the poor aqueous solubility of 6CN impairs its clinical use. This work aimed to develop binary 6CN-β-cyclodextrin (βCD) systems with the purpose of increasing 6CN solubility in water and therefore, to improve its pharmacological activity. The 6CN-βCD binary systems were prepared by physical mixing, kneading and rotary evaporation methods and further characterized by FTIR, XRD, DSC, TG and SEM. In addition, molecular modeling and phase solubility studies were performed. Finally, MTT assays were performed to investigate the cytostatic and anti-proliferative effects of 6CN-βCD binary systems. The characterization results show evident changes in the physicochemical properties of 6CN after the formation of the binary systems with βCD. In addition, 6CN was associated with βCD in aqueous solution and the solid state, which was confirmed by molecular modeling and the aforementioned characterization techniques. Phase solubility studies indicated that βCD forms stable 1:1 complexes with 6CN. The MTT assay demonstrated the cytostatic and anti-proliferative activities of 6CN-βCD binary systems and therefore, these might be considered as promising candidates for new anticancer drugs. View Full-Text
Keywords: 2-aminothiophene derivative; β-cyclodextrin; antitumor; anti-proliferative; cytostatic 2-aminothiophene derivative; β-cyclodextrin; antitumor; anti-proliferative; cytostatic
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Ferreira, E.B.; Da Silva Júnior, W.F.; De Oliveira Pinheiro, J.G.; Da Fonseca, A.G.; Moura Lemos, T.M.A.; De Oliveira Rocha, H.A.; De Azevedo, E.P.; Mendonça Junior, F.J.B.; Neves de Lima, Á.A. Characterization and Antiproliferative Activity of a Novel 2-Aminothiophene Derivative-β-Cyclodextrin Binary System. Molecules 2018, 23, 3130.

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