Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2022 Jan 26;20(2):103.
doi: 10.3390/md20020103.

Chitosan-Based Films with 2-Aminothiophene Derivative: Formulation, Characterization and Potential Antifungal Activity

Verônica da Silva Oliveira  1 , Meriângela Miranda da Cruz  1 , Gabriela Suassuna Bezerra  1 , Natan Emanuell Sobral E Silva  1 , Fernando Henrique Andrade Nogueira  1 , Guilherme Maranhão Chaves  1 , José Lamartine Soares Sobrinho  2 , Francisco Jaime Bezerra Mendonça-Junior  3 , Bolívar Ponciano Goulart de Lima Damasceno  4 , Attilio Converti  5 , Ádley Antonini Neves de Lima  1
Affiliations

Chitosan-Based Films with 2-Aminothiophene Derivative: Formulation, Characterization and Potential Antifungal Activity

Verônica da Silva Oliveira et al. Mar Drugs. .

Abstract

In this study, films of chitosan and 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile (6CN), a 2-aminothiophene derivative with great pharmacological potential, were prepared as a system for a topical formulation. 6CN-chitosan films were characterized by physicochemical analyses, such as Fourier-transform infrared spectroscopy (FTIR), differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), X-ray diffraction (XRD), and scanning electronic microscopy (SEM). Additionally, the antifungal potential of the films was evaluated in vitro against three species of Candida (C. albicans, C. tropicalis, and C. parapsilosis). The results of the FTIR and thermal analysis showed the incorporation of 6CN in the polymer matrix. In the diffractogram, the 6CN-chitosan films exhibited diffraction halos that were characteristic of amorphous structures, while the micrographs showed that 6CN particles were dispersed in the chitosan matrix, exhibiting pores and cracks on the film surface. In addition, the results of antifungal investigation demonstrated that 6CN-chitosan films were effective against Candida species showing potential for application as a new antifungal drug.

Keywords: 2-aminothiophene derivative; antifungal activity; chitosan; films.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structural representation of (A) 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile (6CN); (B) chitosan.
Figure 2
Figure 2
FTIR spectra of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile (6CN), blank chitosan film (CF), and 6CN-chitosan films with 6CN concentrations of 0.48 mg·mL−1 (F3), 0.80 mg·mL−1 (F5), and 1.28 mg·mL−1 (F8). (▲) C≡N stretching.
Figure 3
Figure 3
Representation of the possible interactions of 6CN with the polymeric matrix.
Figure 4
Figure 4
Differential scanning calorimetric curves of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile (6CN), blank chitosan film (CF), and 6CN-chitosan films with 6CN concentrations of 0.48 mg·mL−1 (F3), 0.80 mg·mL−1 (F5), and 1.28 mg·mL−1 (F8).
Figure 5
Figure 5
Thermogravimetric curves of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile (6CN), blank chitosan film (CF), and 6CN-chitosan films with 6CN concentrations of 0.48 mg·mL−1 (F3), 0.80 mg·mL−1 (F5), and 1.28 mg·mL−1 (F8).
Figure 6
Figure 6
X-ray diffraction patterns of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile (6CN), blank chitosan film (CF), and 6CN-chitosan films with 6CN concentrations of 0.48 mg·mL−1 (F3), 0.80 mg·mL−1 (F5), and 1.28 mg·mL−1 (F8).
Figure 7
Figure 7
SEM micrographs of blank chitosan film at (A) 100× and (B) 500×; of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile (6CN) at (C) 150× and (D) 500×; of 6CN-chitosan films with 6CN concentration of 0.48 mg·mL−1 (F3) at (E) 100×, (F) 500×, (G) 1000×, and (H) 10,000×; of 6CN-chitosan films with 6CN concentration of 0.80 mg·mL−1 (F5) at (I) 100×, (J) 500×, (K) 1000×, and (L) 10,000×; of 6CN-chitosan films with 6CN concentration of 1.28 mg·mL−1 (F8) at (M) 100×, (N) 500×, (O) 1000×, and (P) 10,000×.
Figure 8
Figure 8
Diameter of the inhibition zones that were caused by 6CN-chitosan films (F3, F5, and F8) against Candida albicans, Candida tropicalis, and Candida parapsilosis. Values were expressed as the mean ± standard error of mean. (n = 3, * p < 0.05).
See this image and copyright information in PMC

References

    1. Thamban Chandrika N., Shrestha S.K., Ngo H.X., Howard K.C., Garneau-Tsodikova S. Novel fluconazole derivatives with promising antifungal activity. Bioorg. Med. Chem. 2018;26:573–580. doi: 10.1016/j.bmc.2017.12.018. - DOI - PMC - PubMed
    1. Kummari L.K., Butler M.S., Furlong E., Blundell R., Nouwens A., Silva A.B., Kappler U., Fraser J.A., Kobe B., Cooper M.A., et al. Antifungal benzo[b]thiophene 1,1-dioxide IMPDH inhibitors exhibit pan- assay interference (PAINS) profiles. Bioorg. Med. Chem. 2018;26:5408–5419. doi: 10.1016/j.bmc.2018.09.004. - DOI - PubMed
    1. Scotti L., Scotti M.T., De Oliveira Lima E., Da Silva M.S., Do Carmo Alves De Lima M., Da Rocha Pitta I., De Moura R.O., De Oliveira J.G.B., Da Cruz R.M.D., Mendonça F.J.B. Experimental methodologies and evaluations of computer-aided drug design methodologies applied to a series of 2-aminothiophene derivatives with antifungal activities. Molecules. 2012;17:2298–2315. doi: 10.3390/molecules17032298. - DOI - PMC - PubMed
    1. Mendonça F.J.B., Lima-Neto R.G., de Oliveira T.B., de Lima M.C.A., Pitta I.R., Galdino S.L., da Cruz R.M.D., de Araújo R.S.A., Neves R.P. Synthesis and evaluation of the antifungal activity of 2-(substituted-amino)-4,5-dialkyl-thiophene-3-carbonitrile derivatives. Lat. Am. J. Pharm. 2011;30:1492–1499.
    1. de Araújo Neto L.N., do Carmo Alves de Lima M., de Oliveira J.F., de Souza E.R., Buonafina M.D.S., Vitor Anjos M.N., Brayner F.A., Alves L.C., Neves R.P., Mendonça-Junior F.J.B. Synthesis, cytotoxicity and antifungal activity of 5-nitro-thiophene-thiosemicarbazones derivatives. Chem. Biol. Interact. 2017;272:172–181. doi: 10.1016/j.cbi.2017.05.005. - DOI - PubMed

MeSH terms

LinkOut - more resources