In silico study, synthesis, and cytotoxic activities of porphyrin derivatives

Fransiska Kurniawan, Youhei Miura, Rahmana Emran Kartasasmita, Abdul Mutalib, Naoki Yoshioka, Daryono Hadi Tjahjono

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Abstract

Five known porphyrins, 5,10,15,20-tetrakis(p-tolyl)porphyrin (TTP), 5,10,15,20-tetrakis(pbromophenyl) 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(paminophenyl) 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 DBECPDPzPREV- 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.

Original languageEnglish
Article number8
JournalPharmaceuticals
Volume11
Issue number1
DOIs
Publication statusPublished - 2018 Mar 1

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Porphyrins
Computer Simulation
Molecular Dynamics Simulation
Bromides
Inhibitory Concentration 50
Neoplasms
Proteins

Keywords

  • Cancer cell lines
  • Cytotoxicity
  • Molecular dynamics
  • Porphyrin derivative
  • Synthesis

ASJC Scopus subject areas

  • Molecular Medicine
  • Pharmaceutical Science

Cite this

In silico study, synthesis, and cytotoxic activities of porphyrin derivatives. / Kurniawan, Fransiska; Miura, Youhei; Kartasasmita, Rahmana Emran; Mutalib, Abdul; Yoshioka, Naoki; Tjahjono, Daryono Hadi.

In: Pharmaceuticals, Vol. 11, No. 1, 8, 01.03.2018.

Research output: Contribution to journalArticle

Kurniawan, Fransiska ; Miura, Youhei ; Kartasasmita, Rahmana Emran ; Mutalib, Abdul ; Yoshioka, Naoki ; Tjahjono, Daryono Hadi. / In silico study, synthesis, and cytotoxic activities of porphyrin derivatives. In: Pharmaceuticals. 2018 ; Vol. 11, No. 1.
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AU - Kartasasmita, Rahmana Emran

AU - Mutalib, Abdul

AU - Yoshioka, Naoki

AU - Tjahjono, Daryono Hadi

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