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Pharmaceuticals 2018, 11(1), 8; https://doi.org/10.3390/ph11010008

In Silico Study, Synthesis, and Cytotoxic Activities of Porphyrin Derivatives

1
School of Pharmacy, Bandung Institute of Technology, Jalan Ganesha 10, Bandung 40132, Indonesia
2
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan
3
Center for Radioisotope and Radiopharmaceutical Technology, National Nuclear Energy Agency (BATAN), Serpong, Tangerang 15310, Indonesia
*
Author to whom correspondence should be addressed.
Received: 28 December 2017 / Revised: 14 January 2018 / Accepted: 19 January 2018 / Published: 20 January 2018
(This article belongs to the Special Issue Chemoinformatics and Drug Design)
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Abstract

Five known porphyrins, 5,10,15,20-tetrakis(p-tolyl)porphyrin (TTP), 5,10,15,20-tetrakis(p-bromophenyl)porphyrin (TBrPP), 5,10,15,20-tetrakis(p-aminophenyl)porphyrin (TAPP), 5,10,15-tris(tolyl)-20-mono(p-nitrophenyl)porphyrin (TrTMNP), 5,10,15-tris(tolyl)-20-mono(p-aminophenyl)porphyrin (TrTMAP), and three novel porphyrin derivatives, 5,15-di-[bis(3,4-ethylcarboxymethylenoxy)phenyl]-10,20-di(p-tolyl)porphyrin (DBECPDTP), 5,10-di-[bis(3,4-ethylcarboxymethylenoxy)phenyl]-15,20-di-(methylpyrazole-4-yl)porphyrin (cDBECPDPzP), 5,15-di-[bis(3,4-ethylcarboxymethylenoxy)phenyl]-10,20-di-(methylpyrazole-4-yl)porphyrin (DBECPDPzP), were used to study their interaction with protein targets (in silico study), and were synthesized. Their cytotoxic activities against cancer cell lines were tested using 3-(4,5-dimetiltiazol-2-il)-2,5-difeniltetrazolium bromide (MTT) assay. The interaction of porphyrin derivatives with carbonic anhydrase IX (CAIX) and REV-ERBβ proteins were studied by molecular docking and molecular dynamic simulation. In silico study results reveal that DBECPDPzP and TrTMNP showed the highest binding interaction with REV- ERBβ and CAIX, respectively, and both complexes of DBECPDPzP-REV-ERBβ and TrTMNP-CAIX showed good and comparable stability during molecular dynamic simulation. The studied porphyrins have selective growth inhibition activities against tested cancer cells and are categorized as marginally active compounds based on their IC50. View Full-Text
Keywords: porphyrin derivative; molecular dynamics; synthesis; cytotoxicity; cancer cell lines porphyrin derivative; molecular dynamics; synthesis; cytotoxicity; cancer cell lines
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Kurniawan, F.; Miura, Y.; Kartasasmita, R.E.; Yoshioka, N.; Mutalib, A.; Tjahjono, D.H. In Silico Study, Synthesis, and Cytotoxic Activities of Porphyrin Derivatives. Pharmaceuticals 2018, 11, 8.

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