Three Pt( ii ) complexes based on thiosemicarbazone: synthesis, HSA interaction, cytotoxicity, apoptosis and cell cycle arrest
Three thiosemicarbazone-based platinum(ii) complexes [Pt(MH-TSC)Cl] (1), [Pt(ME-TSC)Cl] (2) and [Pt(NH-TSC)2]Cl (3) (MH-TSC = (E)-2-(1-(pyridin-2-yl)ethylidene)hydrazinecarbothioamide, ME-TSC = (E)-N-ethyl-2-(1-(pyridin-2-yl)ethylidene) hydrazinecarbothioamide, NH-TSC = (Z)-2-(amino(pyridin-2-yl)met...
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Published in | RSC advances Vol. 7; no. 42; pp. 26478 - 26486 |
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Format | Journal Article |
Language | English |
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Abstract | Three thiosemicarbazone-based platinum(ii) complexes [Pt(MH-TSC)Cl] (1), [Pt(ME-TSC)Cl] (2) and [Pt(NH-TSC)2]Cl (3) (MH-TSC = (E)-2-(1-(pyridin-2-yl)ethylidene)hydrazinecarbothioamide, ME-TSC = (E)-N-ethyl-2-(1-(pyridin-2-yl)ethylidene) hydrazinecarbothioamide, NH-TSC = (Z)-2-(amino(pyridin-2-yl)methylene)hydrazinecarbothioamide) were synthesized and structurally characterized. X-ray analyses revealed that 1 and 2 possessed similar a neutral mononuclear unit in which one tridentate TSC ligand and one leaving group (Cl-) coordinated to Pt(ii) ion, while 3 was cationic and formed by two NH-TSC ligands surrounding one Pt atom in a meridional arrangement. UV-visible and fluorescence spectra of human serum albumin (HSA) with the complexes displayed that the quenching mechanism of HSA by 1-3 might be a static binding mode. Moreover, synchronous fluorescence experiments proved that 1-3 affected the microenvironment of tryptophan residues of HSA. In addition, the antiproliferative activities against MCF-7 (human breast cancer lines), HepG-2 (human liver hepatocellular carcinoma cell line), NCI-H460 (non-small cell lung cancer lines) and HeLa (human epithelial cervical cancer cell line) were screened for 1-3. Inspiringly, their cytotoxic activity (IC50 = 1.7-9.6 mu M) appeared much better than that of cisplatin (IC50 = 5.2-13.5 mu M) against different cell lines, respectively. Among them, complex 3 exhibited the strongest inhibition on the viability of all tested cell lines with IC50 values of 1.7-2.2 mu M. Inductively-coupled plasma mass spectrometry (ICP-MS) showed that 3 accumulated rapidly in cells and reached intracellular levels of up to 10-fold higher than those determined for 1 and 2. Furthermore, fluorescence microscopic observation and flow cytometric analysis revealed that 1-3 could effectively induce apoptosis of HeLa cells, which were arrested in the S phase after treatment with 1 (30.31%) and 3 (46.96%), and in G2 phase with 2 (20.2%). All the results mentioned above suggest that complexes 1-3 might be efficient antitumor agents. |
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AbstractList | Three thiosemicarbazone-based platinum(
ii
) complexes [Pt(MH-TSC)Cl] (
1
), [Pt(ME-TSC)Cl] (
2
) and [Pt(NH-TSC)
2
]Cl (
3
) (MH-TSC = (
E
)-2-(1-(pyridin-2-yl)ethylidene)hydrazinecarbothioamide, ME-TSC = (
E
)-
N
-ethyl-2-(1-(pyridin-2-yl)ethylidene) hydrazinecarbothioamide, NH-TSC = (
Z
)-2-(amino(pyridin-2-yl)methylene)hydrazinecarbothioamide) were synthesized and structurally characterized. X-ray analyses revealed that
1
and
2
possessed similar a neutral mononuclear unit in which one tridentate TSC ligand and one leaving group (Cl
−
) coordinated to Pt(
ii
) ion, while
3
was cationic and formed by two NH-TSC ligands surrounding one Pt atom in a meridional arrangement. UV-visible and fluorescence spectra of human serum albumin (HSA) with the complexes displayed that the quenching mechanism of HSA by
1–3
might be a static binding mode. Moreover, synchronous fluorescence experiments proved that
1–3
affected the microenvironment of tryptophan residues of HSA. In addition, the antiproliferative activities against MCF-7 (human breast cancer lines), HepG-2 (human liver hepatocellular carcinoma cell line), NCI-H460 (non-small cell lung cancer lines) and HeLa (human epithelial cervical cancer cell line) were screened for
1–3
. Inspiringly, their cytotoxic activity (IC
50
= 1.7–9.6 μM) appeared much better than that of cisplatin (IC
50
= 5.2–13.5 μM) against different cell lines, respectively. Among them, complex
3
exhibited the strongest inhibition on the viability of all tested cell lines with IC
50
values of 1.7–2.2 μM. Inductively-coupled plasma mass spectrometry (ICP-MS) showed that
3
accumulated rapidly in cells and reached intracellular levels of up to 10-fold higher than those determined for
1
and
2
. Furthermore, fluorescence microscopic observation and flow cytometric analysis revealed that
1–3
could effectively induce apoptosis of HeLa cells, which were arrested in the S phase after treatment with
1
(30.31%) and
3
(46.96%), and in G2 phase with
2
(20.2%). All the results mentioned above suggest that complexes
1–3
might be efficient antitumor agents. Three thiosemicarbazone-based platinum(ii) complexes [Pt(MH-TSC)Cl] (1), [Pt(ME-TSC)Cl] (2) and [Pt(NH-TSC)2]Cl (3) (MH-TSC = (E)-2-(1-(pyridin-2-yl)ethylidene)hydrazinecarbothioamide, ME-TSC = (E)-N-ethyl-2-(1-(pyridin-2-yl)ethylidene) hydrazinecarbothioamide, NH-TSC = (Z)-2-(amino(pyridin-2-yl)methylene)hydrazinecarbothioamide) were synthesized and structurally characterized. X-ray analyses revealed that 1 and 2 possessed similar a neutral mononuclear unit in which one tridentate TSC ligand and one leaving group (Cl-) coordinated to Pt(ii) ion, while 3 was cationic and formed by two NH-TSC ligands surrounding one Pt atom in a meridional arrangement. UV-visible and fluorescence spectra of human serum albumin (HSA) with the complexes displayed that the quenching mechanism of HSA by 1-3 might be a static binding mode. Moreover, synchronous fluorescence experiments proved that 1-3 affected the microenvironment of tryptophan residues of HSA. In addition, the antiproliferative activities against MCF-7 (human breast cancer lines), HepG-2 (human liver hepatocellular carcinoma cell line), NCI-H460 (non-small cell lung cancer lines) and HeLa (human epithelial cervical cancer cell line) were screened for 1-3. Inspiringly, their cytotoxic activity (IC50 = 1.7-9.6 mu M) appeared much better than that of cisplatin (IC50 = 5.2-13.5 mu M) against different cell lines, respectively. Among them, complex 3 exhibited the strongest inhibition on the viability of all tested cell lines with IC50 values of 1.7-2.2 mu M. Inductively-coupled plasma mass spectrometry (ICP-MS) showed that 3 accumulated rapidly in cells and reached intracellular levels of up to 10-fold higher than those determined for 1 and 2. Furthermore, fluorescence microscopic observation and flow cytometric analysis revealed that 1-3 could effectively induce apoptosis of HeLa cells, which were arrested in the S phase after treatment with 1 (30.31%) and 3 (46.96%), and in G2 phase with 2 (20.2%). All the results mentioned above suggest that complexes 1-3 might be efficient antitumor agents. |
Author | Lin, Xu-Dong Liu, Ya-Hong Shen, Jun Xie, Cheng-Zhi Bao, Wei-Guo Xu, Jing-Yuan |
Author_xml | – sequence: 1 givenname: Xu-Dong surname: Lin fullname: Lin, Xu-Dong – sequence: 2 givenname: Ya-Hong surname: Liu fullname: Liu, Ya-Hong – sequence: 3 givenname: Cheng-Zhi surname: Xie fullname: Xie, Cheng-Zhi – sequence: 4 givenname: Wei-Guo surname: Bao fullname: Bao, Wei-Guo – sequence: 5 givenname: Jun surname: Shen fullname: Shen, Jun – sequence: 6 givenname: Jing-Yuan surname: Xu fullname: Xu, Jing-Yuan |
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CitedBy_id | crossref_primary_10_1039_D3NJ02067C crossref_primary_10_1039_D2DT02455A crossref_primary_10_1007_s10534_019_00172_w crossref_primary_10_1007_s00775_023_02001_5 crossref_primary_10_1016_j_molliq_2023_122187 crossref_primary_10_1002_aoc_7459 crossref_primary_10_1007_s10812_022_01306_8 crossref_primary_10_3389_fphar_2022_1018951 crossref_primary_10_1016_j_jinorgbio_2020_111001 crossref_primary_10_1080_00958972_2018_1525488 |
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Snippet | Three thiosemicarbazone-based platinum(
ii
) complexes [Pt(MH-TSC)Cl] (
1
), [Pt(ME-TSC)Cl] (
2
) and [Pt(NH-TSC)
2
]Cl (
3
) (MH-TSC = (
E... Three thiosemicarbazone-based platinum(ii) complexes [Pt(MH-TSC)Cl] (1), [Pt(ME-TSC)Cl] (2) and [Pt(NH-TSC)2]Cl (3) (MH-TSC =... |
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SubjectTerms | Apoptosis Biotechnology Cancer Fluorescence Ligands Synthesis Toxicity Tryptophan |
Title | Three Pt( ii ) complexes based on thiosemicarbazone: synthesis, HSA interaction, cytotoxicity, apoptosis and cell cycle arrest |
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