Redox behavior and biological properties of ferrocene bearing porphyrins
Само за регистроване кориснике
2017
Аутори
Lippert, RainerShubina, Tatyana E.
Vojnović, Sandra
Pavić, Aleksandar
Veselinović, Jovana
Nikodinović-Runić, Jasmina
Stanković, Nada
Ivanović-Burmazović, Ivana
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
In order to improve antimicrobial effects of previously studied meso-tetrakis(4-ferrocenylphenyl)porphyrin 1, we have modified its structure by replacing two trans-positioned ferrocenylphenyl moieties with methoxy methylene substituted tert-butylphenyl moieties. Newly synthesized 5(4),15(4)-bis-(ferrocenyl)-10(4),20(4)-bis-(tert-butyl)10(2),10(6),20(2),20(6)-tetrakis-(methoxy-methylene)-5,10,15,20-tetraphenylporphyrin 4 was chemically characterized in detail (by NMR, UV/Vis, IR, MALDI-TOF and ESI MS spectrometry, cyclic voltammetry, prediction of the relative lipophilicity as well as computational methods) and its biological effects were studied in terms of its antibacterial and antifungal activity (both with and without photoactivation), cytotoxicity, hemolysis and DNA cleavage. New ferrocene bearing porphyrin 4 has demonstrated a broader antimicrobial spectrum and modified effects on eukaryotic cells compared to 1. This was discussed in terms of its i) increased lipophilicity, while ...exhibiting.lower toxicity, and ii) the redox potential of a two-electron process that is shifted to lower values, in comparison to ferrocene, thus, entering the physiologically available range and being activated towards redox interactions with biomolecules.
Кључне речи:
Porphyrin / Ferrocene / Antimicrobial / Cytotoxicity / Redox propertiesИзвор:
Journal of Inorganic Biochemistry, 2017, 171, 76-89Издавач:
- Elsevier Science Inc, New York
Финансирање / пројекти:
- Изучавање микробиолошког диверзитета и карактеризација корисних срединских микроорганизама (RS-MESTD-Basic Research (BR or ON)-173048)
Напомена:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3078
DOI: 10.1016/j.jinorgbio.2017.03.002
ISSN: 0162-0134
PubMed: 28371681
WoS: 000402581000009
Scopus: 2-s2.0-85016402721
Колекције
Институција/група
Inovacioni centar / Innovation CentreTY - JOUR AU - Lippert, Rainer AU - Shubina, Tatyana E. AU - Vojnović, Sandra AU - Pavić, Aleksandar AU - Veselinović, Jovana AU - Nikodinović-Runić, Jasmina AU - Stanković, Nada AU - Ivanović-Burmazović, Ivana PY - 2017 UR - https://cherry.chem.bg.ac.rs/handle/123456789/2467 AB - In order to improve antimicrobial effects of previously studied meso-tetrakis(4-ferrocenylphenyl)porphyrin 1, we have modified its structure by replacing two trans-positioned ferrocenylphenyl moieties with methoxy methylene substituted tert-butylphenyl moieties. Newly synthesized 5(4),15(4)-bis-(ferrocenyl)-10(4),20(4)-bis-(tert-butyl)10(2),10(6),20(2),20(6)-tetrakis-(methoxy-methylene)-5,10,15,20-tetraphenylporphyrin 4 was chemically characterized in detail (by NMR, UV/Vis, IR, MALDI-TOF and ESI MS spectrometry, cyclic voltammetry, prediction of the relative lipophilicity as well as computational methods) and its biological effects were studied in terms of its antibacterial and antifungal activity (both with and without photoactivation), cytotoxicity, hemolysis and DNA cleavage. New ferrocene bearing porphyrin 4 has demonstrated a broader antimicrobial spectrum and modified effects on eukaryotic cells compared to 1. This was discussed in terms of its i) increased lipophilicity, while exhibiting.lower toxicity, and ii) the redox potential of a two-electron process that is shifted to lower values, in comparison to ferrocene, thus, entering the physiologically available range and being activated towards redox interactions with biomolecules. PB - Elsevier Science Inc, New York T2 - Journal of Inorganic Biochemistry T1 - Redox behavior and biological properties of ferrocene bearing porphyrins VL - 171 SP - 76 EP - 89 DO - 10.1016/j.jinorgbio.2017.03.002 ER -
@article{ author = "Lippert, Rainer and Shubina, Tatyana E. and Vojnović, Sandra and Pavić, Aleksandar and Veselinović, Jovana and Nikodinović-Runić, Jasmina and Stanković, Nada and Ivanović-Burmazović, Ivana", year = "2017", abstract = "In order to improve antimicrobial effects of previously studied meso-tetrakis(4-ferrocenylphenyl)porphyrin 1, we have modified its structure by replacing two trans-positioned ferrocenylphenyl moieties with methoxy methylene substituted tert-butylphenyl moieties. Newly synthesized 5(4),15(4)-bis-(ferrocenyl)-10(4),20(4)-bis-(tert-butyl)10(2),10(6),20(2),20(6)-tetrakis-(methoxy-methylene)-5,10,15,20-tetraphenylporphyrin 4 was chemically characterized in detail (by NMR, UV/Vis, IR, MALDI-TOF and ESI MS spectrometry, cyclic voltammetry, prediction of the relative lipophilicity as well as computational methods) and its biological effects were studied in terms of its antibacterial and antifungal activity (both with and without photoactivation), cytotoxicity, hemolysis and DNA cleavage. New ferrocene bearing porphyrin 4 has demonstrated a broader antimicrobial spectrum and modified effects on eukaryotic cells compared to 1. This was discussed in terms of its i) increased lipophilicity, while exhibiting.lower toxicity, and ii) the redox potential of a two-electron process that is shifted to lower values, in comparison to ferrocene, thus, entering the physiologically available range and being activated towards redox interactions with biomolecules.", publisher = "Elsevier Science Inc, New York", journal = "Journal of Inorganic Biochemistry", title = "Redox behavior and biological properties of ferrocene bearing porphyrins", volume = "171", pages = "76-89", doi = "10.1016/j.jinorgbio.2017.03.002" }
Lippert, R., Shubina, T. E., Vojnović, S., Pavić, A., Veselinović, J., Nikodinović-Runić, J., Stanković, N.,& Ivanović-Burmazović, I.. (2017). Redox behavior and biological properties of ferrocene bearing porphyrins. in Journal of Inorganic Biochemistry Elsevier Science Inc, New York., 171, 76-89. https://doi.org/10.1016/j.jinorgbio.2017.03.002
Lippert R, Shubina TE, Vojnović S, Pavić A, Veselinović J, Nikodinović-Runić J, Stanković N, Ivanović-Burmazović I. Redox behavior and biological properties of ferrocene bearing porphyrins. in Journal of Inorganic Biochemistry. 2017;171:76-89. doi:10.1016/j.jinorgbio.2017.03.002 .
Lippert, Rainer, Shubina, Tatyana E., Vojnović, Sandra, Pavić, Aleksandar, Veselinović, Jovana, Nikodinović-Runić, Jasmina, Stanković, Nada, Ivanović-Burmazović, Ivana, "Redox behavior and biological properties of ferrocene bearing porphyrins" in Journal of Inorganic Biochemistry, 171 (2017):76-89, https://doi.org/10.1016/j.jinorgbio.2017.03.002 . .