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Novel triphenyltin() compounds with carboxylato -functionalized 2-quinolones as promising potential anticancer drug candidates: and evaluation
Three newly synthesized triphenyltin( iv ) compounds, Ph 3 SnL1 ( L1 − = 3-(4-methyl-2-oxoquinolin-1(2 H )-yl)propanoato), Ph 3 SnL2 ( L2 − = 2-(4-methyl-2-oxoquinolin-1(2 H )-yl)ethanoato), and Ph 3 SnL3 ( L3 − = 2-(4-hydroxy-2-oxoquinolin-1(2 H )-yl)ethanoato), were characterized by elemental micr...
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| Published in: | Dalton transactions : an international journal of inorganic chemistry 2024-05, Vol.53 (19), p.8298-8314 |
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| Main Authors: | , , , , , , , , , , , , |
| Format: | Article |
| Language: | |
| Online Access: | Get full text |
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| Summary: | Three newly synthesized triphenyltin(
iv
) compounds,
Ph
3
SnL1
(
L1
−
= 3-(4-methyl-2-oxoquinolin-1(2
H
)-yl)propanoato),
Ph
3
SnL2
(
L2
−
= 2-(4-methyl-2-oxoquinolin-1(2
H
)-yl)ethanoato), and
Ph
3
SnL3
(
L3
−
= 2-(4-hydroxy-2-oxoquinolin-1(2
H
)-yl)ethanoato), were characterized by elemental microanalysis, FT-IR spectroscopy and multinuclear (
1
H,
13
C and
119
Sn) NMR spectroscopy. A single X-ray diffraction study indicates that compounds
Ph
3
SnL1
and
Ph
3
SnL2
exhibit a 1D zig-zag chain polymeric structure, which in the case of
Ph
3
SnL2
is additionally stabilized by π-interactions. In addition, the synthesized compounds were further examined using density functional theory and natural bond orbital analysis. The compounds have been evaluated for their
in vitro
anticancer activity against three human cell lines: MCF-7 (breast adenocarcinoma), A375 (melanoma), HCT116 (colorectal carcinoma), and three murine cell lines: 4T1 (breast carcinoma), B16 (melanoma), CT26 (colon carcinoma) using MTT and CV assays. The IC
50
values fall in the nanomolar range, indicating that these compounds possess better anticancer activity than cisplatin. The study of the effect of the newly developed drug
Ph
3
SnL1
showed its plasticity in achieving an antitumor effect
in vitro
, which depends on the specificity of the phenotype and the redox status of the malignant cell line and ranges from the initiation of apoptotic cell death to the induction of differentiation to a more mature cell form. In the syngeneic model of murine melanoma,
Ph
3
SnL1
showed the potential to reduce the tumor volume similar to cisplatin, but in a well-tolerated form and with low systemic toxicity, representing a significant advantage over the conventional drug.
Three triphenyltin(
iv
) compounds with carboxylato
N
-functionalized 2-quinolones are reported. The compounds showed remarkable anticancer activity in lower micromolar concentrations. The most active compound exhibited a better
in vivo
profile than cisplatin. |
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| ISSN: | 1477-9226 1477-9234 |
| DOI: | 10.1039/d4dt00182f |