University of Oulu

Asmaa Ahmed, Walaa A.E. Omar, Hala A. El-Asmy, Laila Abou-Zeid, Ahmed A. Fadda, Docking studies, antitumor and antioxidant evaluation of newly synthesized porphyrin and metalloporphyrin derivatives, Dyes and Pigments, Volume 183, 2020, 108728, ISSN 0143-7208, https://doi.org/10.1016/j.dyepig.2020.10872

Docking studies, antitumor and antioxidant evaluation of newly synthesized porphyrin and metalloporphyrin derivatives

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Author: Ahmed, Asmaa1,2; Omar, Walaa A.E.3,4; El-Asmy, Hala A.2;
Organizations: 1Research Unit of Sustainable Chemistry, Faculty of Technology, P.O. Box 8000, FI-90014, University of Oulu, Finland
2Chemistry Department, Faculty of Science, Mansoura University, 35516, Mansoura, Egypt
3Department of Basic Sciences, Faculty of Energy & Environmental Engineering, The British University in Egypt, El Sherouk City, P.O.Box 43, 11837, Cairo, Egypt
4Department of Engineering Sciences and Mathematics, Faculty of Petroleum and Mining Engineering, Suez University, Egypt
5Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Mansoura University, 35516, Mansoura, Egypt
6Pharmaceutical Chemistry Department, Faculty of Pharmacy, Delta University, 35516, Gamassa, Egypt
Format: article
Version: accepted version
Access: embargoed
Persistent link: http://urn.fi/urn:nbn:fi-fe2020083165467
Language: English
Published: Elsevier, 2020
Publish Date: 2022-08-05
Description:

Abstract

In this work, we have synthesized a series of novel porphyrin derivatives, 1–5, in high yields. The metal complexes of two of the newly synthesized porphyrin derivatives, 1a–d and 2a–d, have also been synthesized in high yields and characterized. In the synthesis of the new porphyrins and metalloporphrins, we employed our reported strategy in which we utilized N,N-dimethylformamide (DMF) as a capping agent in the reaction of pyrrole with different hetero-aryl aldehydes. The new porphyrin derivatives are equipped with different aromatic substituents and hetero-cycles at the peripheral position. The structures of the new compounds were confirmed by elemental and spectral analyses. The geometry and magnetic properties of the new metalloporphyrins 1a–d and 2a–d have also been studied. Antioxidant and cytotoxic activities of the new compounds were evaluated and structure-activity relationships were performed. Porphyrin derivatives 2a and 4 showed exceptional antioxidant activity compared to ascorbic acid as a reference. While the derivatives 2, 3, and 5 exhibited very strong cytotoxic activity against two human cell lines, HePG-2 and MCF-7. Docking for the most promising antioxidant porphyrins, 2a and 4, into the binding active site of antioxidant protein Human Peroxiredoxin (code: 1HD2) has been carried out to detect the degree of recognition antioxidant activity. Molecular docking of the most cytotoxic active porphyrins, 3 and 5, into the biding site of telomerase inhibitor enzyme has been carried out to assess the degree of recognition cytotoxic activity.

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Series: Dyes and pigments
ISSN: 0143-7208
ISSN-E: 1873-3743
ISSN-L: 0143-7208
Volume: 183
Article number: 108728
DOI: 10.1016/j.dyepig.2020.108728
OADOI: https://oadoi.org/10.1016/j.dyepig.2020.108728
Type of Publication: A1 Journal article – refereed
Field of Science: 115 Astronomy and space science
Subjects:
Copyright information: © 2020. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/.
  https://creativecommons.org/licenses/by-nc-nd/4.0/