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 inDalton transactions : an international journal of inorganic chemistry Vol. 49; no. 14; pp. 4404 - 4415
Main Authors Meng, Ting, Liu, Tong, Qin, Qi-Pin, Chen, Zi-Lu, Zou, Hua-Hong, Wang, Kai, Liang, Fu-Pei
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 07.04.2020
Subjects
Anticancer properties
Apoptosis
Cancer
Crystallography
Fluorescence
Ligands
Mitochondria
Structural analysis
Toxicity
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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.
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
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SSID ssj0022052
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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
URI https://www.ncbi.nlm.nih.gov/pubmed/32175553
https://www.proquest.com/docview/2386721260
https://search.proquest.com/docview/2377682886
Volume 49
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