Mitochondria-localizing dicarbohydrazide Ln complexes and their mechanism of in vitro anticancer activity
In this study, two novel organic ligands, bis(salicylaldehyde)pyrazino-1,10-phenanthroline-7,10-dicarbohydrazide (L) and bis(salicylaldehyde)-1,10-phenanthroline-7,10-dicarbohydrazide (L1), were synthesized. These ligands were used to react with lanthanide(iii) acetate to obtain complexes 1-6, namel...
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Published in | Dalton transactions : an international journal of inorganic chemistry Vol. 49; no. 14; pp. 4404 - 4415 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
England
Royal Society of Chemistry
07.04.2020
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Abstract | In this study, two novel organic ligands, bis(salicylaldehyde)pyrazino-1,10-phenanthroline-7,10-dicarbohydrazide (L) and bis(salicylaldehyde)-1,10-phenanthroline-7,10-dicarbohydrazide (L1), were synthesized. These ligands were used to react with lanthanide(iii) acetate to obtain complexes 1-6, namely, [Dy5(L)2(CH3COO)5(CH3OH)(μ3-OH)(μ2-OH)(H2O)]·2CH3OH (1), [Tb5(L)2(CH3COO)5(CH3OH)(μ3-OH)(μ2-OH)(H2O)]·3CH3OH (2), [Gd5(L)2(CH3COO)5(CH3OH)(μ3-OH)(μ2-OH)(H2O)]·3CH3OH (3), [Dy5(L1)2(μ2-OH)(μ3-OH)(CH3COO)5(CH3OH)(H2O)2]·2H2O (4), [Dy5(L1)2(μ3-OH)(CH3COO)6(CH3OH)3]·CH3OH (5), and [Dy5(L1)2(μ2-OH)2(μ3-OH)(CH3COO)4(CH3OH)(H2O)2]·CH3OH (6). Fluorescence studies demonstrated that complexes 1-6 show appreciable fluorescence in the yellow-green region. In vitro antitumor screening revealed that complex 1 exhibits better inhibitory activities than the commercial anticancer drug cisplatin against SK-OV-3 and A549 tumor cell lines, with IC50 values of 8.09 ± 1.25 and 13.26 ± 0.39 μM, respectively. All six complexes showed low cytotoxicity toward normal human liver HL-7702 cells compared with cisplatin. Complexes 1 and 3 induced the highest apoptosis rate of SK-OV-3/DDP cells. They also bind to DNA via an intercalative mode with the binding constant Kq values of 1.6 × 104 and 1.19 × 104 L mol-1, respectively. Confocal fluorescence imaging ascertained that complexes 1 and 3 are primarily localized in the mitochondria. Further studies revealed that these complexes trigger SK-OV-3/DDP cell apoptosis via a mitochondrial dysfunction pathway, which is probably caused by the reduction of the mitochondrial membrane potential and the induction of reactive oxygen species production. |
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AbstractList | In this study, two novel organic ligands, bis(salicylaldehyde)pyrazino-1,10-phenanthroline-7,10-dicarbohydrazide (L) and bis(salicylaldehyde)-1,10-phenanthroline-7,10-dicarbohydrazide (L
1
), were synthesized. These ligands were used to react with lanthanide(
iii
) acetate to obtain complexes
1–6
, namely, [Dy
5
(L)
2
(CH
3
COO)
5
(CH
3
OH)(μ
3
-OH)(μ
2
-OH)(H
2
O)]·2CH
3
OH (
1
), [Tb
5
(L)
2
(CH
3
COO)
5
(CH
3
OH)(μ
3
-OH)(μ
2
-OH)(H
2
O)]·3CH
3
OH (
2
), [Gd
5
(L)
2
(CH
3
COO)
5
(CH
3
OH)(μ
3
-OH)(μ
2
-OH)(H
2
O)]·3CH
3
OH (
3
), [Dy
5
(L
1
)
2
(μ
2
-OH)(μ
3
-OH)(CH
3
COO)
5
(CH
3
OH)(H
2
O)
2
]·2H
2
O (
4
), [Dy
5
(L
1
)
2
(μ
3
-OH)(CH
3
COO)
6
(CH
3
OH)
3
]·CH
3
OH (
5
), and [Dy
5
(L
1
)
2
(μ
2
-OH)
2
(μ
3
-OH)(CH
3
COO)
4
(CH
3
OH)(H
2
O)
2
]·CH
3
OH (
6
). Fluorescence studies demonstrated that complexes
1–6
show appreciable fluorescence in the yellow-green region.
In vitro
antitumor screening revealed that complex
1
exhibits better inhibitory activities than the commercial anticancer drug cisplatin against SK-OV-3 and A549 tumor cell lines, with IC
50
values of 8.09 ± 1.25 and 13.26 ± 0.39 μM, respectively. All six complexes showed low cytotoxicity toward normal human liver HL-7702 cells compared with cisplatin. Complexes
1
and
3
induced the highest apoptosis rate of SK-OV-3/DDP cells. They also bind to DNA
via
an intercalative mode with the binding constant
K
q
values of 1.6 × 10
4
and 1.19 × 10
4
L mol
−1
, respectively. Confocal fluorescence imaging ascertained that complexes
1
and
3
are primarily localized in the mitochondria. Further studies revealed that these complexes trigger SK-OV-3/DDP cell apoptosis
via
a mitochondrial dysfunction pathway, which is probably caused by the reduction of the mitochondrial membrane potential and the induction of reactive oxygen species production. In this study, two novel organic ligands, bis(salicylaldehyde)pyrazino-1,10-phenanthroline-7,10-dicarbohydrazide (L) and bis(salicylaldehyde)-1,10-phenanthroline-7,10-dicarbohydrazide (L1), were synthesized. These ligands were used to react with lanthanide(iii) acetate to obtain complexes 1–6, namely, [Dy5(L)2(CH3COO)5(CH3OH)(μ3-OH)(μ2-OH)(H2O)]·2CH3OH (1), [Tb5(L)2(CH3COO)5(CH3OH)(μ3-OH)(μ2-OH)(H2O)]·3CH3OH (2), [Gd5(L)2(CH3COO)5(CH3OH)(μ3-OH)(μ2-OH)(H2O)]·3CH3OH (3), [Dy5(L1)2(μ2-OH)(μ3-OH)(CH3COO)5(CH3OH)(H2O)2]·2H2O (4), [Dy5(L1)2(μ3-OH)(CH3COO)6(CH3OH)3]·CH3OH (5), and [Dy5(L1)2(μ2-OH)2(μ3-OH)(CH3COO)4(CH3OH)(H2O)2]·CH3OH (6). Fluorescence studies demonstrated that complexes 1–6 show appreciable fluorescence in the yellow-green region. In vitro antitumor screening revealed that complex 1 exhibits better inhibitory activities than the commercial anticancer drug cisplatin against SK-OV-3 and A549 tumor cell lines, with IC50 values of 8.09 ± 1.25 and 13.26 ± 0.39 μM, respectively. All six complexes showed low cytotoxicity toward normal human liver HL-7702 cells compared with cisplatin. Complexes 1 and 3 induced the highest apoptosis rate of SK-OV-3/DDP cells. They also bind to DNA via an intercalative mode with the binding constant Kq values of 1.6 × 104 and 1.19 × 104 L mol−1, respectively. Confocal fluorescence imaging ascertained that complexes 1 and 3 are primarily localized in the mitochondria. Further studies revealed that these complexes trigger SK-OV-3/DDP cell apoptosis via a mitochondrial dysfunction pathway, which is probably caused by the reduction of the mitochondrial membrane potential and the induction of reactive oxygen species production. In this study, two novel organic ligands, bis(salicylaldehyde)pyrazino-1,10-phenanthroline-7,10-dicarbohydrazide (L) and bis(salicylaldehyde)-1,10-phenanthroline-7,10-dicarbohydrazide (L1), were synthesized. These ligands were used to react with lanthanide(iii) acetate to obtain complexes 1-6, namely, [Dy5(L)2(CH3COO)5(CH3OH)(μ3-OH)(μ2-OH)(H2O)]·2CH3OH (1), [Tb5(L)2(CH3COO)5(CH3OH)(μ3-OH)(μ2-OH)(H2O)]·3CH3OH (2), [Gd5(L)2(CH3COO)5(CH3OH)(μ3-OH)(μ2-OH)(H2O)]·3CH3OH (3), [Dy5(L1)2(μ2-OH)(μ3-OH)(CH3COO)5(CH3OH)(H2O)2]·2H2O (4), [Dy5(L1)2(μ3-OH)(CH3COO)6(CH3OH)3]·CH3OH (5), and [Dy5(L1)2(μ2-OH)2(μ3-OH)(CH3COO)4(CH3OH)(H2O)2]·CH3OH (6). Fluorescence studies demonstrated that complexes 1-6 show appreciable fluorescence in the yellow-green region. In vitro antitumor screening revealed that complex 1 exhibits better inhibitory activities than the commercial anticancer drug cisplatin against SK-OV-3 and A549 tumor cell lines, with IC50 values of 8.09 ± 1.25 and 13.26 ± 0.39 μM, respectively. All six complexes showed low cytotoxicity toward normal human liver HL-7702 cells compared with cisplatin. Complexes 1 and 3 induced the highest apoptosis rate of SK-OV-3/DDP cells. They also bind to DNA via an intercalative mode with the binding constant Kq values of 1.6 × 104 and 1.19 × 104 L mol-1, respectively. Confocal fluorescence imaging ascertained that complexes 1 and 3 are primarily localized in the mitochondria. Further studies revealed that these complexes trigger SK-OV-3/DDP cell apoptosis via a mitochondrial dysfunction pathway, which is probably caused by the reduction of the mitochondrial membrane potential and the induction of reactive oxygen species production. |
Author | Liang, Fu-Pei Liu, Tong Chen, Zi-Lu Zou, Hua-Hong Meng, Ting Wang, Kai Qin, Qi-Pin |
Author_xml | – sequence: 1 givenname: Ting surname: Meng fullname: Meng, Ting email: gxnuchem@foxmail.com, fliangoffce@yahoo.com organization: State Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmacy, Guangxi Normal University, 15 Yucai Road, Guilin 541004, PR China. gxnuchem@foxmail.com fliangoffce@yahoo.com – sequence: 2 givenname: Tong surname: Liu fullname: Liu, Tong email: gxnuchem@foxmail.com, fliangoffce@yahoo.com organization: State Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmacy, Guangxi Normal University, 15 Yucai Road, Guilin 541004, PR China. gxnuchem@foxmail.com fliangoffce@yahoo.com – sequence: 3 givenname: Qi-Pin orcidid: 0000-0001-9596-4512 surname: Qin fullname: Qin, Qi-Pin email: gxnuchem@foxmail.com, fliangoffce@yahoo.com, qpqin2018@126.com organization: State Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmacy, Guangxi Normal University, 15 Yucai Road, Guilin 541004, PR China. gxnuchem@foxmail.com fliangoffce@yahoo.com and Guangxi Key Lab of Agricultural Resources Chemistry and Biotechnology, College of Chemistry and Food Science, Yulin Normal University, 1303 Jiaoyudong Road, Yulin 537000, PR China. qpqin2018@126.com – sequence: 4 givenname: Zi-Lu orcidid: 0000-0003-1341-2330 surname: Chen fullname: Chen, Zi-Lu email: gxnuchem@foxmail.com, fliangoffce@yahoo.com organization: State Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmacy, Guangxi Normal University, 15 Yucai Road, Guilin 541004, PR China. gxnuchem@foxmail.com fliangoffce@yahoo.com – sequence: 5 givenname: Hua-Hong orcidid: 0000-0003-1759-3714 surname: Zou fullname: Zou, Hua-Hong email: gxnuchem@foxmail.com, fliangoffce@yahoo.com organization: State Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmacy, Guangxi Normal University, 15 Yucai Road, Guilin 541004, PR China. gxnuchem@foxmail.com fliangoffce@yahoo.com – sequence: 6 givenname: Kai surname: Wang fullname: Wang, Kai email: gxnuchem@foxmail.com, fliangoffce@yahoo.com organization: State Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmacy, Guangxi Normal University, 15 Yucai Road, Guilin 541004, PR China. gxnuchem@foxmail.com fliangoffce@yahoo.com and Guangxi Key Laboratory of Electrochemical and Magnetochemical Functional Materials, College of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, China – sequence: 7 givenname: Fu-Pei orcidid: 0000-0001-7435-0140 surname: Liang fullname: Liang, Fu-Pei email: gxnuchem@foxmail.com, fliangoffce@yahoo.com organization: State Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmacy, Guangxi Normal University, 15 Yucai Road, Guilin 541004, PR China. gxnuchem@foxmail.com fliangoffce@yahoo.com and Guangxi Key Laboratory of Electrochemical and Magnetochemical Functional Materials, College of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, China |
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Snippet | In this study, two novel organic ligands, bis(salicylaldehyde)pyrazino-1,10-phenanthroline-7,10-dicarbohydrazide (L) and... |
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SubjectTerms | Anticancer properties Apoptosis Cancer Crystallography Fluorescence Ligands Mitochondria Structural analysis Toxicity |
Title | Mitochondria-localizing dicarbohydrazide Ln complexes and their mechanism of in vitro anticancer activity |
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