Journal of Inorganic Biochemistry, volume 203, pages 110868

Synthesis, DNA binding studies, and antiproliferative activity of novel Pt(II)-complexes with an L-alanyl-based ligand

C. Riccardi 1
Giovanna M Rozza 1
Chiara Platella 1
Daniela Montesarchio 1
Tiziano Marzo 4
Alessandro Pratesi 5, 6
L. Messori 7
Giovanni N Roviello 8
Domenica Musumeci 8, 9
Publication typeJournal Article
Publication date2020-02-01
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor3.9
ISSN01620134, 18733344
Biochemistry
Inorganic Chemistry
Abstract
An artificial alanine-based amino acid {(S)-2-amino-3-[4-propyl-3-(thiophen-2-yl)-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]propanoic acid, here named TioxAla}, bearing a substituted triazolyl-thione group on the side chain and able to bind RNA biomedical targets, was here chosen as a valuable scaffold for the synthesis of new platinum complexes with potential dual action owing to the concomitant presence of the metal centre and the amino acid moiety. Three new platinum complexes, obtained from the reaction of TioxAla with K2PtCl4, were characterized by mass spectrometry, nuclear magnetic resonance and UV-vis spectroscopy: one compound (Pt1, bis-{(S)-2-amino-3-[4-propyl-3-(thiophen-2-yl)-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]propanoate-O,S} platinum(II)) consisted of two amino acid units coordinating the Pt(II) ion; the other two, Pt2 [potassium dichloro-{(S)-2-amino-3-[4-propyl-3-(thiophen-2-yl)-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]propanoate (O,S)} platinum(II)] and Pt3 [potassium dichloro-{(S)-2-amino-3-[4-propyl-3-(thiophen-2-yl)-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]propanoate (O,N)} platinum(II)], were isomers bearing one TioxAla unit, and two chlorides as Pt-ligands. Pt coordination involved preferentially the amino, carboxylic and thione functions of TioxAla. By preliminary antiproliferative assays, a moderate cytotoxic activity on cancer cells was observed only for Pt2 and Pt3, while no anticancer activity was found for both the chloride-free complex (Pt1) and TioxAla. This cytotoxicity, however lower than that of cisplatin, well correlated with the marked ability, here found only for Pt2 and Pt3 complexes, to bind DNA sequences either in random coil or in structured forms (duplex and G-quadruplex), as verified by spectroscopic and spectrometric analysis.

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Riccardi C. et al. Synthesis, DNA binding studies, and antiproliferative activity of novel Pt(II)-complexes with an L-alanyl-based ligand // Journal of Inorganic Biochemistry. 2020. Vol. 203. p. 110868.
GOST all authors (up to 50) Copy
Riccardi C., Capasso D., Rozza G. M., Platella C., Montesarchio D., Di Gaetano S., Marzo T., Pratesi A., Messori L., Roviello G. N., Musumeci D. Synthesis, DNA binding studies, and antiproliferative activity of novel Pt(II)-complexes with an L-alanyl-based ligand // Journal of Inorganic Biochemistry. 2020. Vol. 203. p. 110868.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1016/j.jinorgbio.2019.110868
UR - https://doi.org/10.1016/j.jinorgbio.2019.110868
TI - Synthesis, DNA binding studies, and antiproliferative activity of novel Pt(II)-complexes with an L-alanyl-based ligand
T2 - Journal of Inorganic Biochemistry
AU - Riccardi, C.
AU - Capasso, Domenica
AU - Rozza, Giovanna M
AU - Platella, Chiara
AU - Montesarchio, Daniela
AU - Di Gaetano, Sonia
AU - Marzo, Tiziano
AU - Pratesi, Alessandro
AU - Messori, L.
AU - Roviello, Giovanni N
AU - Musumeci, Domenica
PY - 2020
DA - 2020/02/01
PB - Elsevier
SP - 110868
VL - 203
SN - 0162-0134
SN - 1873-3344
ER -
BibTex
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BibTex Copy
@article{2020_Riccardi,
author = {C. Riccardi and Domenica Capasso and Giovanna M Rozza and Chiara Platella and Daniela Montesarchio and Sonia Di Gaetano and Tiziano Marzo and Alessandro Pratesi and L. Messori and Giovanni N Roviello and Domenica Musumeci},
title = {Synthesis, DNA binding studies, and antiproliferative activity of novel Pt(II)-complexes with an L-alanyl-based ligand},
journal = {Journal of Inorganic Biochemistry},
year = {2020},
volume = {203},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016/j.jinorgbio.2019.110868},
pages = {110868},
doi = {10.1016/j.jinorgbio.2019.110868}
}
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