Biological potential of carbazole derivatives

Głuszyńska, Agata

doi:10.1016/j.ejmech.2015.02.059

Cited by 235 publications

(120 citation statements)

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“…Of particular interest is the interaction with DNA or its metabolizing enzymes that induce programmed cell death, namely apoptosis . Several carbazole analogues structurally derived from ellipticine, an alkaloid from Ochrosia elliptica labill, introduced for the treatment of metastatic breast cancer, but later dismissed because of poor aqueous solubility and severe side effects, were synthesized …”

Section: Introductionmentioning

confidence: 99%

“…[7][8][9][10][11][12][13] Of particular interesti st he interaction with DNA or its metabolizing enzymes that induce programmedc ell death, namely apoptosis. [14][15][16][17][18] Several carbazole analogues structurally derived from ellipticine, an alkaloid from Ochrosia elliptica Chemotherapyi su sed for the treatment of all stages of breast cancer,i ncluding the metastatic stage of the disease. Treatment regimens are generally tailored for each patient'sparticular situation.…”

Section: Introductionmentioning

confidence: 99%

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Inhibition of Human Topoisomerase II by N,N,N‐Trimethylethanammonium Iodide Alkylcarbazole Derivatives

et al. 2018

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Chemotherapy is used for the treatment of all stages of breast cancer, including the metastatic stage of the disease. Treatment regimens are generally tailored for each patient′s particular situation. However, chemotherapeutic agents are the leading cause of serious drug‐related adverse effects; moreover, drug resistance often occurs. In this study, we designed and synthesized a new series of N‐alkylcarbazoles derived from ellipticine, an alkaloid with a carbazole skeleton initially used in the treatment of metastatic breast cancer and later dismissed because of poor aqueous solubility and severe side effects. After evaluating the binding modes of our class of newly synthesized compounds with human topoisomerase II (hTopo II), we performed hTopo II decatenation assays, identifying compound 4 f (2‐(4‐((3‐chloro‐9H‐carbazol‐9‐yl)pentyl)piperazin‐1‐yl)‐N,N,N‐trimethylethanammonium iodide) as a good inhibitor. Moreover, 4 f and 4 g (2‐(4‐((3‐chloro‐9H‐carbazol‐9‐yl)hexyl)piperazin‐1‐yl)‐N,N,N‐trimethylethanammonium iodide) showed a good anti‐proliferative activity toward breast cancer cells, causing apoptosis by activation of the caspase pathway. Interestingly, the activity of these two compounds on triple‐negative MDA‐MB‐231 cells, which tend to be highly metastatic and aggressive, is strictly connected to the observed inhibition of hTopo II.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Inhibition of Human Topoisomerase II by N,N,N‐Trimethylethanammonium Iodide Alkylcarbazole Derivatives

et al. 2018

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“…The carbazole skeleton is the key structural motif of many synthetic and naturally occurring biologically active compounds34. In recent years, promising compounds for the design of disease-modifying drugs for the therapy of AD have been found among carbazole derivatives.…”

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confidence: 99%

Novel conjugates of aminoadamantanes with carbazole derivatives as potential multitarget agents for AD treatment

Бачурин¹,

Shevtsova²,

Махаева³

et al. 2017

Sci Rep

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A new group of compounds, promising for the design of original multitarget therapeutic agents for treating neurodegenerative diseases, based on conjugates of aminoadamantane and carbazole derivatives was synthesized and investigated. Compounds of these series were found to interact with a group of targets that play an important role in the development of this type of diseases. First of all, these compounds selectively inhibit butyrylcholinesterase, block NMDA receptors containing NR2B subunits while maintaining the properties of MK-801 binding site blockers, exert microtubules stabilizing properties, and possess the ability to protect nerve cells from death at the calcium overload conditions. The leading compound C-2h has been shown the most promising effects on all analyzed parameters. Thus, these compounds can be regarded as promising candidates for the design of multi-target disease-modifying drugs for treatment of AD and/or similar neuropathologies.

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“…Carbazole is a prominent core structure found in numerous natural and synthetic compounds with a wide range of biological activities, including antimalarial, antineoplastic, and neuroprotective effects . In view of anticancer agents, many carbazole derivatives have been shown to exhibit antitumor activity by targeting diverse enzymes or kinases .…”

Section: Introductionmentioning

confidence: 99%

Carbazole Aminoalcohols Induce Antiproliferation and Apoptosis of Human Tumor Cells by Inhibiting Topoisomerase I

Wang

Sun

et al. 2016

ChemMedChem

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Novel carbazole aminoalcohols were designed and synthesized as anticancer agents. Among them, alkylamine-chain-substituted compounds showed the most promising antiproliferative activity, with IC values in the single-digit micromolar range against two human tumor cell lines. Topoisomerase I (topo I) is likely to be one of the targets of these compounds. Results of comet assays and molecular docking indicate that the representative compounds may act as topo I poisons, causing single-strand DNA damage by stabilizing the topo I-DNA cleavage complex. In particular, the most potent compound, 1-(butylamino)-3-(3,6-dichloro-9H-carbazol-9-yl)propan-2-ol (6), was shown to be able to induce G -phase cell-cycle arrest and apoptosis in HeLa cells.

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Biological potential of carbazole derivatives

Cited by 235 publications

References 151 publications

Inhibition of Human Topoisomerase II by N,N,N‐Trimethylethanammonium Iodide Alkylcarbazole Derivatives

Inhibition of Human Topoisomerase II by N,N,N‐Trimethylethanammonium Iodide Alkylcarbazole Derivatives

Novel conjugates of aminoadamantanes with carbazole derivatives as potential multitarget agents for AD treatment

Carbazole Aminoalcohols Induce Antiproliferation and Apoptosis of Human Tumor Cells by Inhibiting Topoisomerase I

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