New N-allylthiourea derivatives: synthesis, molecular docking and in vitro cytotoxicity studies

Widiandani, Tri and Siswandono, Siswandono1 and Meiyanto, Edy and Sulistyowaty, Melanny Ika and Purwanto, Bambang Tri and Hardjono, Suko (2018) New N-allylthiourea derivatives: synthesis, molecular docking and in vitro cytotoxicity studies. Tropical Journal of Pharmaceutical Research, 17 (8). pp. 1607-1613. ISSN 1596-5996

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Official URL: http://dx.doi.org/10.4314/tjpr.v17i8.20

Abstract

Purpose: To synthesise derivatives of N-allylthiourea and evaluate their anticancer activities against epidermal growth factor receptor (EGFR) using in silico and in vitro methods. Methods: Four compounds were synthesized using the Schotten-Baumann reaction. The structures of the synthesized compounds were confirmed using infrared (IR), proton nuclear magnetic resonance (1H-NMR), carbon nuclear magnetic resonence (13C-NMR) and electrospray ionization mass spectrometry (ESI-MS) methods. Molecular modeling was carried out with Molegro Virtual Docker version 5.5 through docking of the compounds onto the protein binding site of EGFR, with protein data bank (PBD) codes 1M17, 1XKK, and 3POZ. In vitro cytotoxicity was evaluated in MCF-7 cell lines using MTT assay. Results: The synthesized compounds showed lower Rerank Scores, relative to N-allylthiourea and hydroxyurea. The low Rerank Score values implied stable molecular bonds, and hence higher biological activities. In addition, the derivatives showed cytotoxicities against MCF-7 cell line (IC50: 0.21 – 0.38 mM) which were superior to those of N-allylthiourea (IC50: 5.22 mM) and hydroxyurea (IC50: 2.89 mM). Conclusion: The predicted anticancer activities of the synthesized compounds are consistent with results from in silico studies and assays of cytotoxicity against MCF-7 cell lines. Thus, N-allylthiourea derivatives can potentially be developed as anticancer drugs.

Item Type: Article
Uncontrolled Keywords: N-allylthiourea derivatives, In silico, Synthesis, Cytotoxicity, MCF-7, EGFR
Subjects: R Medicine
R Medicine > RS Pharmacy and materia medica
R Medicine > RS Pharmacy and materia medica > RS1-441 Pharmacy and materia medica
R Medicine > RS Pharmacy and materia medica > RS200-201 Pharmaceutical dosage forms
Divisions: 05. Fakultas Farmasi
Creators:
CreatorsEmail
Widiandani, Tritri-w@ff.unair.ac.id
Siswandono, Siswandono1siswandono@ff.unair.ac.id
Meiyanto, EdyUNSPECIFIED
Sulistyowaty, Melanny IkaUNSPECIFIED
Purwanto, Bambang Tribambang-t-p@ff.unair.ac.id
Hardjono, Sukosuko-h@ff.unair.ac.id
Depositing User: Mr M. Fuad Sofyan
Date Deposited: 06 Jan 2019 03:43
Last Modified: 09 Jan 2019 02:03
URI: http://repository.unair.ac.id/id/eprint/77450
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