Copper Complexes as Anticancer Agents Targeting Topoisomerases I and II
Abstract
:Simple Summary
Abstract
1. Introduction
2. Copper Complexes as Topoisomerases Inhibitors
2.1. CuC Top1 Inhibitors
2.2. CuC Top2α Inhibitors
2.3. CuC Dual Top1/Top2α Inhibitors
3. Cell Cycle Regulation by Copper Complexes and Top Inhibitors
4. Programmed Cell Death Engaged by Copper Complexes and Top Inhibitors
5. Future Strategies for Copper Complexes as Top Inhibitors in Cancer Cell Treatments
6. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Ligand Class of Cu-C | Compound Number | Targeted Top(s) | Inhibition of DNA Relaxation Total (µM) (minimal (µM)) | Inhibition Mecanism | Cancer Cell Lines | IC50 (µM) | Cell Cycle Arrest | Cell Death Type | Other Specificity | Reference Number |
---|---|---|---|---|---|---|---|---|---|---|
Oxindolimine | 1 | Top1 | 50 (25) | Fixation in the DNA Top1 binding site | Neuroblastoma SH-SY5Y Promonocytic U937 | G2/M arrest | Apoptosis | ROS induction | [70,71,72,73] | |
Hydrazone with triphenylphosphonium | 2 | Top1 | 40 | DNA Binding | Lung A549 | 4.2 ± 0.8 | [74] | |||
Enzyme complex formation | Prostatic PC-3 | 3.2 ± 0.2 | ||||||||
Plumbagin | 3 | Top1 | 1.56 | DNA intercalation | Breast MCF-7 | 3.2 ± 1.1 | [75] | |||
Colon HCT116 | 5.9 ± 1.4 | |||||||||
Hepatoma BEL7404 | 12.9 ± 3.6 | |||||||||
Hepatoma HepG2 | 9.0 ± 0.7 | |||||||||
Kidney 786-O | 2.5 ± 0.9 | |||||||||
Lung NCI-H460 | 2.0 ± 1.2 | |||||||||
Nasopharyngeal cancer CNE2 | 11.8 ± 5.9 | |||||||||
Phenanthroline with amino acids | 4 | Top1 | 50 | DNA intercalation | Nasopharyngeal cancer HK1 | 2.2–5.2 | Apoptosis | [76] | ||
(10) | ||||||||||
Pyrophosphate | 5 | Top1 | 500 | DNA interaction | Ovarian A2780/AD | 0.64 ± 0.12 | [77] | |||
Heterobimetallic Cu(II)-Sn2(IV) phenanthroline | 6 | Top1 | 20 | DNA intercalation | Breast Zr-75–1 | [78] | ||||
cleavage | Cervix SiHa | |||||||||
Colon HCT15, SW620 | <10 (GI50) | |||||||||
Kidney 786-O, A498 | ||||||||||
Lung Hop-62, A569 | ||||||||||
Pancreatic MIA PaCa-2 | ||||||||||
Neuroblastoma SH-SY5Y | 2–8 | Apoptosis | [79] | |||||||
Analogs | [80] | |||||||||
Tridentate chiral Schiff base | 7, 8 | Top1 | 25 | DNA binding | Hepatoma HuH7 | 25 | ROS | [81,82] | ||
(15) | major groove | Hepatoma HepG2 | 6.2 ± 10 | Cytokine TGFb | ||||||
mRNA upregulation | ||||||||||
Salicylidene | 9 | Top1 | (E. coli) * | DNA binding | Prostatic PC-3 | 7.3 ± 0.2 | antimetastasis | [83] | ||
DNA cleavage | Breast MCF7 | 51.1 ± 1.6 | [84] | |||||||
Colon HT29 | 16.6 ± 0.6 | |||||||||
Hepatoma HepG2 | 2.3 ± 0.1 | |||||||||
Lung A549 | 16.8 ± 1.0 | |||||||||
Ovary A2780 | 14.6 ± 0.2 | |||||||||
Prostatic LNCaP | 25.4 ± 0.8 | |||||||||
Chalcone-derived Thiosemicarbazone | 10 | Top1 | 3 | DNA binding | Breast MCF-7 | 0.16 ± 0.06 | [85] | |||
(0.75) | DNA cleavage | Leukemia THP-1 | 0.20 ± 0.06 | |||||||
Religation inhibition | ||||||||||
Pyridyl-substituted tetrazolopyrimidie | 11 | Top1 | (Molecular docking) * | DNA binding | Cervix HeLa | 0.565 ± 0.01 | Apoptosis | CDK receptor | [86] | |
groove mode | Colon HCT-15 | 0.358 | binding | |||||||
Lung A549 | 0.733 | |||||||||
Tetrazolopyrimidine Diimine | Top1 | 102 ± 1.1 | DNA binding | Cervical HeLa | 0.620 ± 0.0013 | Apoptosis | vEGF receptor | [87] | ||
groove mode | Colon HCT-15 | 0.540 ± 0.00015 | binding | |||||||
Lung A549 | 0.120 ± 0.002 | |||||||||
Piperazine | 12 | Top1 | 12.5 | DNA binding | SOD mimic | [88] | ||||
(5) | minor groove | |||||||||
Elesclomol | 13 | Top1 | 50 | Poison | Erythroleukemic K562 | 0.0075 | Apoptosis | Copper chelator | [89] | |
Necrosis | Not a substrat for | |||||||||
Oxidative stress | ABC transporters | |||||||||
Cu(SBCM)2 | 14 | Top1 | * (Molecular | DNA intercalation | Breast MCF7 | 27 | G2/M arrest | Apoptosis | p53 increase | [90] |
docking) | DNA binding | Breast MDA-MB-231 | 18.7 ± 3.1 | No ROS | [91] | |||||
TSC and TSC CuC | [92,93,94,95,96,97] | |||||||||
Pyridine-TSC | 15 | Top2a | 50 | Breast MDA-MB-231 | 1.01 | [98] | ||||
(10) | Breast MCF7 | 0.0558 | ||||||||
50 | ATP hydrolysis inhibition | [99] | ||||||||
Top2β | (5) | ATP hydrolysis inhibition | [100] | |||||||
Piperazine-TSC | 16 | Top2a | 0.9 ± 0.7 | Potentially catalytic | Breast MCF7 | 4.7 ± 0.3 | [101,102] | |||
Breast SK-BR-3 | 1.3 ± 0.3 | [99] | ||||||||
Thiazole-TSC | 17 | Top2a | 4 | Breast MDA-MB-231 | 1.41 (EC50) | [103] | ||||
(2) | Breast MCF7 | 0.13 (EC50) | ||||||||
17–18 | Top2a | 25 | ATP hydrolysis inhibition | Breast | [104,105] | |||||
(10) | + Poison | HCC 70, HCC 1395, | 1 to 20 | |||||||
HCC 1500, and HCC 1806 | ||||||||||
Colon | 0.83 to 41.2 | |||||||||
Caco-2, HCT-116 and HT-29 | ||||||||||
L- and D-Proline-TSC | 19 | Top2a | 300 | Ovarian carcinoma CH1 | 113 ± 16 | [106] | ||||
Quinoline-TSC | 20 | Top2a | 0.48 | Potentially catalytic | Lymphoma U937 | 0.48-16.2 | [107] | |||
Naphthoquinone-TSC | 21 | Top2α | 1 mM | Breast MCF7 | 3.98 ± 1.01 | No apoptosis | [108] | |||
Bis-TSC | 22 | Top2a | 100 | Poison | Breast MDA-MB-231 | 1.45 ± 0.07 | G2/M arrest | Apoptosis | DNA synthesis | [109] |
(5) | Colon HCT116 | 1.23 ± 0.27 | inhibition | |||||||
Keratinocyte HaCaT | 0.65 ± 0.07 | No ROS | ||||||||
Colon HCT116 | Delayed mice xenograft | |||||||||
Carbohydrazone | 23 | Top2α | 250 | DNA binding | Breast MCF7 | 9.916 | Apoptosis | [110] | ||
(25) | major groove | Breast MDA-MB-231 | 7.557 | |||||||
Breast HCC 1937 | 3.278 | |||||||||
Breast MX1 | 4.534 | |||||||||
Breast MDA-MB-436 | 5.249 | |||||||||
Breast MX-1 | Reducted mice xenograft (83%) | |||||||||
Chromone | 24 | Top2a | 25 | DNA binding | Breast MCF7 | 18.6 (GI 50) | [111] | |||
(15) | major groove | Breast Zr-75-1 | 25.2 (GI 50) | |||||||
Colon HT29 | >80 (GI 50) | |||||||||
Cervix SiHa | 34.6 (GI 50) | |||||||||
Kidney A498 | 73.3 (GI 50) | |||||||||
Lung A549 | 31.7 (GI 50) | |||||||||
Ovary A2780 | 17.4 (GI 50) | |||||||||
Quinolinone Shiff Base | 25 | Top2α | 9 | No intercalation | Hepatic HepG2 | 17.9 ± 3.8 | DNA synthesis | [112] | ||
inhibition | ||||||||||
Slight substrate | ||||||||||
for ABC transporter | ||||||||||
Bis-pyrazolyl Carboxylate | 26 | Dual Top1/Top2 | (Molecular docking) * | ATP entry (potentially) | Hepatic HepG2 | 3.3 ± 0.02 | Apoptosis | DNA replication | [113] | |
DNA religation inhibition (potentially) | ROS |
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Molinaro, C.; Martoriati, A.; Pelinski, L.; Cailliau, K. Copper Complexes as Anticancer Agents Targeting Topoisomerases I and II. Cancers 2020, 12, 2863. https://doi.org/10.3390/cancers12102863
Molinaro C, Martoriati A, Pelinski L, Cailliau K. Copper Complexes as Anticancer Agents Targeting Topoisomerases I and II. Cancers. 2020; 12(10):2863. https://doi.org/10.3390/cancers12102863
Chicago/Turabian StyleMolinaro, Caroline, Alain Martoriati, Lydie Pelinski, and Katia Cailliau. 2020. "Copper Complexes as Anticancer Agents Targeting Topoisomerases I and II" Cancers 12, no. 10: 2863. https://doi.org/10.3390/cancers12102863