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


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-ERB? 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- ERB? and CAIX, respectively, and both complexes of DBECPDPzP-REV-ERB? 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.

SUBMITTER: Kurniawan F 

PROVIDER: S-EPMC5874704 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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

Kurniawan Fransiska F   Miura Youhei Y   Kartasasmita Rahmana Emran RE   Yoshioka Naoki N   Mutalib Abdul A   Tjahjono Daryono Hadi DH  

Pharmaceuticals (Basel, Switzerland) 20180120 1


Five known porphyrins, 5,10,15,20-<i>tetrakis</i>(<i>p</i>-tolyl)porphyrin (TTP), 5,10,15,20-<i>tetrakis</i>(<i>p</i>-bromophenyl)porphyrin (TBrPP), 5,10,15,20-<i>tetrakis</i>(<i>p</i>-aminophenyl)porphyrin (TAPP), 5,10,15-<i>tris</i>(tolyl)-20-mono(<i>p</i>-nitrophenyl)porphyrin (TrTMNP), 5,10,15-<i>tris</i>(tolyl)-20-mono(<i>p</i>-aminophenyl)porphyrin (TrTMAP), and three novel porphyrin derivatives, 5,15-di-[<i>bis</i>(3,4-ethylcarboxymethylenoxy)phenyl]-10,20-di(<i>p</i>-tolyl)porphyrin (DBE  ...[more]

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