Shubina, Tatyana E.

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Redox behavior and biological properties of ferrocene bearing porphyrins

Lippert, Rainer; Shubina, Tatyana E.; Vojnović, Sandra; Pavić, Aleksandar; Veselinović, Jovana; Nikodinović-Runić, Jasmina; Stanković, Nada; Ivanović-Burmazović, Ivana

(Elsevier Science Inc, New York, 2017)

TY  - 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 . .
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