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Article

Unveiling a New Selenocyanate as a Multitarget Candidate with Anticancer, Antileishmanial and Antibacterial Potential

by
Sandra Ramos-Inza
1,2,
Andreina Henriquez-Figuereo
1,3,
Esther Moreno
1,2,3,
Melibea Berzosa
3,4,
Ignacio Encío
2,5,
Daniel Plano
1,2,3,* and
Carmen Sanmartín
1,2,3,*
1
Department of Pharmaceutical Technology and Chemistry, University of Navarra, Irunlarrea 1, E-31008 Pamplona, Spain
2
Instituto de Investigación Sanitaria de Navarra (IdiSNA), Irunlarrea 3, E-31008 Pamplona, Spain
3
Institute of Tropical Health of the University of Navarra (ISTUN), University of Navarra, Irunlarrea 1, E-31008 Pamplona, Spain
4
Department of Microbiology and Parasitology, University of Navarra, Irunlarrea 1, E-31008 Pamplona, Spain
5
Department of Health Sciences, Public University of Navarra, Avda. Barañain s/n, E-31008 Pamplona, Spain
*
Authors to whom correspondence should be addressed.
Molecules 2022, 27(21), 7477; https://doi.org/10.3390/molecules27217477
Submission received: 7 October 2022 / Revised: 25 October 2022 / Accepted: 28 October 2022 / Published: 2 November 2022
(This article belongs to the Special Issue Chalcogens in Medicinal Chemistry)
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Abstract

Currently, cancer, leishmaniasis and bacterial infections represent a serious public health burden worldwide. Six cinnamyl and benzodioxyl derivatives incorporating selenium (Se) as selenocyanate, diselenide, or selenide were designed and synthesized through a nucleophilic substitution and/or a reduction using hydrides. Ferrocene was also incorporated by a Friedel–Crafts acylation. All the compounds were screened in vitro for their antiproliferative, antileishmanial, and antibacterial properties. Their capacity to scavenge free radicals was also assessed as a first approach to test their antioxidant activity. Benzodioxyl derivatives 2a–b showed cytotoxicity against colon (HT-29) and lung (H1299) cancer cell lines, with IC50 values below 12 µM, and were also fairly selective when tested in nonmalignant cells. Selenocyanate compounds 1–2a displayed potent antileishmanial activity in L. major and L. infantum, with IC50 values below 5 µM. They also exhibited antibacterial activity in six bacterial strains, notably in S. epidermidis with MIC and MBC values of 12.5 µg/mL. Ferrocene-containing selenide 2c was also identified as a potent antileishmanial agent with radical scavenging activity. Remarkably, derivative 2a with a selenocyanate moiety was found to act as a multitarget compound with antiproliferative, leishmanicidal, and antibacterial activities. Thus, the current work showed that 2a could be an appealing scaffold to design potential therapeutic drugs for multiple pathologies.
Keywords: selenium; cytotoxicity; antileishmanial activity; antibacterial activity; antioxidant selenium; cytotoxicity; antileishmanial activity; antibacterial activity; antioxidant
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MDPI and ACS Style

Ramos-Inza, S.; Henriquez-Figuereo, A.; Moreno, E.; Berzosa, M.; Encío, I.; Plano, D.; Sanmartín, C. Unveiling a New Selenocyanate as a Multitarget Candidate with Anticancer, Antileishmanial and Antibacterial Potential. Molecules 2022, 27, 7477. https://doi.org/10.3390/molecules27217477

AMA Style

Ramos-Inza S, Henriquez-Figuereo A, Moreno E, Berzosa M, Encío I, Plano D, Sanmartín C. Unveiling a New Selenocyanate as a Multitarget Candidate with Anticancer, Antileishmanial and Antibacterial Potential. Molecules. 2022; 27(21):7477. https://doi.org/10.3390/molecules27217477

Chicago/Turabian Style

Ramos-Inza, Sandra, Andreina Henriquez-Figuereo, Esther Moreno, Melibea Berzosa, Ignacio Encío, Daniel Plano, and Carmen Sanmartín. 2022. "Unveiling a New Selenocyanate as a Multitarget Candidate with Anticancer, Antileishmanial and Antibacterial Potential" Molecules 27, no. 21: 7477. https://doi.org/10.3390/molecules27217477

APA Style

Ramos-Inza, S., Henriquez-Figuereo, A., Moreno, E., Berzosa, M., Encío, I., Plano, D., & Sanmartín, C. (2022). Unveiling a New Selenocyanate as a Multitarget Candidate with Anticancer, Antileishmanial and Antibacterial Potential. Molecules, 27(21), 7477. https://doi.org/10.3390/molecules27217477

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