In Silico Study, Synthesis, and Cytotoxic Activities of Porphyrin Derivatives
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...
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| Format: | Article |
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MDPI AG
2018-01-01
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| Series: | Pharmaceuticals |
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| Online Access: | http://www.mdpi.com/1424-8247/11/1/8 |
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| author | Fransiska Kurniawan Youhei Miura Rahmana Emran Kartasasmita Naoki Yoshioka Abdul Mutalib Daryono Hadi Tjahjono |
| author_facet | Fransiska Kurniawan Youhei Miura Rahmana Emran Kartasasmita Naoki Yoshioka Abdul Mutalib Daryono Hadi Tjahjono |
| author_sort | Fransiska Kurniawan |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-10T23:36:38Z |
| format | Article |
| id | doaj.art-a0ed2e1d4f0e40f4b5e4bf27861ae746 |
| institution | Directory Open Access Journal |
| issn | 1424-8247 |
| language | English |
| last_indexed | 2024-12-10T23:36:38Z |
| publishDate | 2018-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceuticals |
| spelling | doaj.art-a0ed2e1d4f0e40f4b5e4bf27861ae7462022-12-22T01:29:10ZengMDPI AGPharmaceuticals1424-82472018-01-01111810.3390/ph11010008ph11010008In Silico Study, Synthesis, and Cytotoxic Activities of Porphyrin DerivativesFransiska Kurniawan0Youhei Miura1Rahmana Emran Kartasasmita2Naoki Yoshioka3Abdul Mutalib4Daryono Hadi Tjahjono5School of Pharmacy, Bandung Institute of Technology, Jalan Ganesha 10, Bandung 40132, IndonesiaDepartment of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, JapanSchool of Pharmacy, Bandung Institute of Technology, Jalan Ganesha 10, Bandung 40132, IndonesiaDepartment of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, JapanCenter for Radioisotope and Radiopharmaceutical Technology, National Nuclear Energy Agency (BATAN), Serpong, Tangerang 15310, IndonesiaSchool of Pharmacy, Bandung Institute of Technology, Jalan Ganesha 10, Bandung 40132, IndonesiaFive 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.http://www.mdpi.com/1424-8247/11/1/8porphyrin derivativemolecular dynamicssynthesiscytotoxicitycancer cell lines |
| spellingShingle | Fransiska Kurniawan Youhei Miura Rahmana Emran Kartasasmita Naoki Yoshioka Abdul Mutalib Daryono Hadi Tjahjono In Silico Study, Synthesis, and Cytotoxic Activities of Porphyrin Derivatives Pharmaceuticals porphyrin derivative molecular dynamics synthesis cytotoxicity cancer cell lines |
| title | In Silico Study, Synthesis, and Cytotoxic Activities of Porphyrin Derivatives |
| title_full | In Silico Study, Synthesis, and Cytotoxic Activities of Porphyrin Derivatives |
| title_fullStr | In Silico Study, Synthesis, and Cytotoxic Activities of Porphyrin Derivatives |
| title_full_unstemmed | In Silico Study, Synthesis, and Cytotoxic Activities of Porphyrin Derivatives |
| title_short | In Silico Study, Synthesis, and Cytotoxic Activities of Porphyrin Derivatives |
| title_sort | in silico study synthesis and cytotoxic activities of porphyrin derivatives |
| topic | porphyrin derivative molecular dynamics synthesis cytotoxicity cancer cell lines |
| url | http://www.mdpi.com/1424-8247/11/1/8 |
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