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Journal articles on the topic 'ELLIPTICINE'

Author: Grafiati

Published: 4 June 2021

Last updated: 18 February 2022

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1

Poljaková, Jitka, Martin Dračínský, Eva Frei, Jiří Hudeček, and Marie Stiborová. "The Effect of pH on Peroxidase-Mediated Oxidation of and DNA Adduct Formation by Ellipticine." Collection of Czechoslovak Chemical Communications 71, no. 8 (2006): 1169–85. http://dx.doi.org/10.1135/cccc20061169.

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In order to understand the mechanism of enzymatic activation of an antineoplastic agent ellipticine, we investigated the effect of pH on the efficiency of three model peroxidases (bovine lactoperoxidase, human myeloperoxidase and horseradish peroxidase) in oxidation of ellipticine and in formation ellipticine-DNA adducts. The formation of the major ellipticine metabolite, ellipticine dimer, in which two ellipticine residues are connected through nitrogenN6in the pyrrole ring of one of the ellipticine moieties and carbon C9 of the other ellipticine, and formation of four ellipticine-DNA adducts

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2

Lin, Jingjing, Mei Tang, Ru Zhao, et al. "Synthetic Optimization of Ellipticine and Antitumor Activity of Novel Hexacyclic Derivatives of Ellipticine." Current Pharmaceutical Design 25, no. 33 (2019): 3578–89. http://dx.doi.org/10.2174/1381612825666190404122650.

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Background: For decades, a great deal of research work has been done to synthesize ellipticine and its derivatives because of their potential antitumor properties and anti-HIV activities. However, the resonance structures in different media, a low level of solubility at physiological pH and systemic toxicity have prevented the use of ellipticine as a therapeutic agent. Besides, the low yield and complex steps of ellipticine synthesis limit its application. Methods: A high-yield synthetic procedure of ellipticine has been optimized, and the total yield was up to 50% without silica gel column ch

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3

Poljaková, Jitka, Tomáš Eckschlager, Jana Hřebačková, Jan Hraběta, and Marie Stiborová. "The comparison of cytotoxicity of the anticancer drugs doxorubicin and ellipticine to human neuroblastoma cells." Interdisciplinary Toxicology 1, no. 2 (2008): 186–89. http://dx.doi.org/10.2478/v10102-010-0036-9.

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The comparison of cytotoxicity of the anticancer drugs doxorubicin and ellipticine to human neuroblastoma cellsEllipticine is an antineoplastic agent, whose mode of action is based mainly on DNA intercalation, inhibition of topoisomerase II and formation of covalent DNA adducts mediated by cytochromes P450 and peroxidases. Here, the cytotoxicity of ellipticine to human neuroblastoma derived cell lines IMR-32 and UKF-NB-4 was investigated. Treatment of neuroblastoma cells with ellipticine was compared with that of these cancer cells with doxorubicin. The toxicity of ellipticine was essentially

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4

Bořek-Dohalská, Lucie, Eva Frei, and Marie Stiborová. "DNA Adduct Formation by the Anticancer Drug Ellipticine and Its Hydroxy Derivatives in Human Breast Adenocarcinoma MCF-7 Cells." Collection of Czechoslovak Chemical Communications 69, no. 3 (2004): 603–15. http://dx.doi.org/10.1135/cccc20040603.

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The cytotoxicity of the antineoplastic agent ellipticine and its 9- and 7-hydroxylated metabolites to human breast adenocarcinoma MCF-7 cells and their ability to generate DNA adducts in these cancer cells were investigated. Ellipticine and its 9-hydroxylated metabolite were found to be toxic to MCF-7 cells with IC50 values of 1.25 and 3.25 μmol l-1 for ellipticine and 9-hydroxyellipticine, respectively. In contrast, no toxicity to these cancer cells was detectable for 7-hydroxyellipticine. The nuclease P1 version of the 32P-postlabeling assay yielded a pattern of ellipticine-DNA adducts with

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5

Pohlit, A. M., L. F. Rocha e Silva, M. C. Henrique, et al. "Antimalarial activity of ellipticine." Phytomedicine 19, no. 11 (2012): 1049. http://dx.doi.org/10.1016/j.phymed.2012.06.005.

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6

Ho, Tse-Lok, and Sheng-Ying Hsieh. "Regioselective Synthesis of Ellipticine." Helvetica Chimica Acta 89, no. 1 (2006): 111–16. http://dx.doi.org/10.1002/hlca.200690001.

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7

Aimová, Dagmar, Jitka Poljaková, Věra Kotrbová, et al. "Ellipticine and benzo(a)pyrene increase their own metabolic activation via modulation of expression and enzymatic activity of cytochromes P450 1A1 and 1A2." Interdisciplinary Toxicology 1, no. 2 (2008): 160–68. http://dx.doi.org/10.2478/v10102-010-0033-z.

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Ellipticine and benzo(a)pyrene increase their own metabolic activation via modulation of expression and enzymatic activity of cytochromes P450 1A1 and 1A2Two compounds known to covalently bind to DNA after their activation with cytochromes P450 (CYPs), carcinogenic benzo(a)pyrene (BaP) and an antineoplastic agent ellipticine, were investigated for their potential to induce CYP and NADPH:CYP reductase (POR) enzymes in rodent livers, the main target organ for DNA adduct formation. Two animal models were used in the study: (i) rats as animals mimicking the fate of ellipticine in humans and (ii) m

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8

Alunni-Bistocchi, Giovanni, Pierluigi Orvietani, Olivier Mauffret, et al. "Isomeric ellipticines. Part 1. Synthesis of two linear isomers of the antitumour alkaloid ellipticine." Journal of the Chemical Society, Perkin Transactions 1, no. 21 (1992): 2935. http://dx.doi.org/10.1039/p19920002935.

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9

McKee, Mary L., Limian Zheng, Elaine C. O’Sullivan, et al. "Synthesis and Evaluation of Novel Ellipticines and Derivatives as Inhibitors of Phytophthora infestans." Pathogens 9, no. 7 (2020): 558. http://dx.doi.org/10.3390/pathogens9070558.

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The pathogen Phytophthora infestans is responsible for worldwide catastrophic crop damage and discovery of new inhibitors of this organism is of paramount agricultural and industrial importance. Current strategies for crop treatment are inadequate with limitations of efficacy and market alternatives. Ellipticines have recently been reported to have fungicidal properties and have been assessed against P. infestans growth with promising results. We hereby report a probe of the ellipticine framework to investigate the alkyl subunit and screen a set ellipticines and derivatives to identify new lea

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10

Stiborová, Marie, Helena Dračínská, Dagmar Aimová, et al. "The Anticancer Drug Ellipticine is an Inducer of Rat NAD(P)H:Quinone Oxidoreductase." Collection of Czechoslovak Chemical Communications 72, no. 10 (2007): 1350–64. http://dx.doi.org/10.1135/cccc20071350.

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The antineoplastic agent ellipticine was investigated for its ability to induce the biotransformation enzyme NAD(P)H:quinone oxidoreductase (DT-diaphorase, EC 1.6.99.2) in male Wistar rats. Using the real-time polymerase chain reaction, the levels of NAD(P)H:quinone oxidoreductase mRNA were determined in livers, kidneys and lungs of rats treated intraperitoneally with ellipticine (40 mg/kg body weight) and of control (untreated) rats. Cytosolic fractions were isolated from the same tissues of control and ellipticine-treated rats and tested for NAD(P)H:quinone oxidoreductase protein expression

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11

Mustafin, A. G., I. N. Khalilov, V. M. Sharafutdinov, D. I. D'yachenko, I. B. Abdrakhmanov, and G. A. Tolstikov. "A modified synthesis of ellipticine." Russian Chemical Bulletin 46, no. 3 (1997): 608–9. http://dx.doi.org/10.1007/bf02495431.

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12

Boogaard, Adrian T., Upendra K. Pandit, and Gerrit-Jan Koome. "Ring D modifications of ellipticine. Part 1. New ellipticine derivatives from 1-cyano-6-methylellipticine." Tetrahedron 50, no. 8 (1994): 2551–60. http://dx.doi.org/10.1016/s0040-4020(01)86971-4.

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13

Oh, Jisu, Hyeon Hae Lee, Yunhui Jeong, et al. "Paradoxical Pro-angiogenic Effect of Low-Dose Ellipticine Identified by In Silico Drug Repurposing." International Journal of Molecular Sciences 22, no. 16 (2021): 9067. http://dx.doi.org/10.3390/ijms22169067.

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Inadequate vessel maintenance or growth causes ischemia in diseases such as myocardial infarction, stroke, and neurodegenerative disorders. Therefore, developing an effective strategy to salvage ischemic tissues using a novel compound is urgent. Drug repurposing has become a widely used method that can make drug discovery more efficient and less expensive. Additionally, computational virtual screening tools make drug discovery faster and more accurate. This study found a novel drug candidate for pro-angiogenesis by in silico virtual screening. Using Gene Expression Omnibus (GEO) microarray dat

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14

ALUNNI-BISTOCCHI, G., P. ORVIETANI, O. MAUFFRET, et al. "ChemInform Abstract: Isomeric Ellipticines. Part 1. Synthesis of Two Linear Isomers of the Antitumor Alkaloid Ellipticine." ChemInform 24, no. 11 (2010): no. http://dx.doi.org/10.1002/chin.199311279.

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15

Ishikura, Minoru, Ayako Hino, and Nobuya Katagiri. "An Efficient Total Synthesis of Ellipticine." HETEROCYCLES 53, no. 1 (2000): 11. http://dx.doi.org/10.3987/com-99-8759.

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16

Indra, R., T. Cerna, Z. Heger, et al. "Apoferritine-encapsulated ellipticine – construction and properties." Toxicology Letters 295 (October 2018): S91. http://dx.doi.org/10.1016/j.toxlet.2018.06.578.

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17

Moody, Terry W., Gregory Czerwinski, Nadia I. Tarasova, Deborah L. Moody, and Christopher J. Michejda. "The development of VIP–ellipticine conjugates." Regulatory Peptides 123, no. 1-3 (2004): 187–92. http://dx.doi.org/10.1016/j.regpep.2004.03.021.

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18

Langendoen, Albert, Gerrit-Jan Koomen, and Upendra K. Pandit. "An approach to novel ellipticine glycosides." Tetrahedron 44, no. 12 (1988): 3627–31. http://dx.doi.org/10.1016/s0040-4020(01)85992-5.

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19

Etemad-Moghadam, Guita, Li Ding, Fatemeh Tadj, and Bernard Meunier. "Synthesis of hybrid “metalloporphyrin-ellipticine” molecules." Tetrahedron 45, no. 9 (1989): 2641–48. http://dx.doi.org/10.1016/s0040-4020(01)80094-6.

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20

Dormoy, Jean-Robert, and Alain Heymes. "Synthese industrielle en serie ellipticine. I." Tetrahedron 49, no. 14 (1993): 2885–914. http://dx.doi.org/10.1016/s0040-4020(01)80387-2.

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21

Dormoy, Jean-Robert, and Alain Heymes. "Synthese industrielle en serie ellipticine. II." Tetrahedron 49, no. 14 (1993): 2915–38. http://dx.doi.org/10.1016/s0040-4020(01)80388-4.

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22

Alberici, Gilles F., Jean-Michel Bidart, Philippe Moingeon, et al. "Ellipticine derivatives interact with muscarinic receptors." Biochemical Pharmacology 34, no. 10 (1985): 1701–4. http://dx.doi.org/10.1016/0006-2952(85)90637-9.

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23

BOOGAARD, A. T., U. K. PANDIT, and G. J. KOOMEN. "ChemInform Abstract: Ring D Modifications of Ellipticine. Part 1. New Ellipticine Derivatives from 1-Cyano-6-methylellipticine." ChemInform 25, no. 26 (2010): no. http://dx.doi.org/10.1002/chin.199426251.

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24

Formisyn, P., C. Tran-Minh, and J. Bourgois. "Biotransformation by fungi: oxidation of ellipticine into 9-hydroxy-ellipticine by an Aspergillus alliaceus strain CBS 536.65." Letters in Applied Microbiology 19, no. 4 (1994): 244–46. http://dx.doi.org/10.1111/j.1472-765x.1994.tb00954.x.

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25

Garbett, Nichola, and David Graves. "Extending Natures Leads: The Anticancer Agent Ellipticine." Current Medicinal Chemistry-Anti-Cancer Agents 4, no. 2 (2004): 149–72. http://dx.doi.org/10.2174/1568011043482070.

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26

Ibrahim-Ouali, Malika, and Frederic Dumur. "Recent synthesis of ellipticine and its derivatives." Arkivoc 2018, no. 1 (2018): 216–43. http://dx.doi.org/10.24820/ark.5550190.p010.445.

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27

Davis, Deborah A., and Gordon W. Gribble. "A regioselective diels-alder synthesis of ellipticine." Tetrahedron Letters 31, no. 8 (1990): 1081–84. http://dx.doi.org/10.1016/s0040-4039(00)88731-6.

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28

Langendoen, Albert, Johannes P. M. Plug, Gerrit-Jan Koomen, and Upendra K. Pandit. "Regiospecific C-9 substitution of ellipticine derivatives." Tetrahedron 45, no. 6 (1989): 1759–62. http://dx.doi.org/10.1016/s0040-4020(01)80040-5.

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29

Meesala, Ramu, Mohammed Ezzat, Mohd Mordi, and Sharif Mansor. "Synthesis of Novel Pyridocarbazoles Analogues of Ellipticine." Synlett 25, no. 15 (2014): 2176–78. http://dx.doi.org/10.1055/s-0034-1378518.

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30

MUSTAFIN, A. G., I. N. KHALILOV, V. M. SHARAFUTDINOV, D. I. D'YACHENKO, I. B. ABDRAKHMANOV, and G. A. TOLSTIKOV. "ChemInform Abstract: A Modified Synthesis of Ellipticine." ChemInform 28, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.199738259.

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31

Kibal'nyi, A. V., O. I. Kharaneko, and V. I. Dulenko. "ChemInform Abstract: New Approach to Ellipticine Analogues." ChemInform 33, no. 32 (2010): no. http://dx.doi.org/10.1002/chin.200232145.

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32

Michel, Sylvie, Fran�ois Tillequin, and Michel Koch. "Strellidimine: the first natural bis-ellipticine alkaloid." Journal of the Chemical Society, Chemical Communications, no. 4 (1987): 229. http://dx.doi.org/10.1039/c39870000229.

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33

Calabrò, Salvatrice, Kousi Alzoubi, Rosi Bissinger, Caterina Faggio, and Florian Lang. "Stimulation of Suicidal Erythrocyte Death by Ellipticine." Basic & Clinical Pharmacology & Toxicology 116, no. 6 (2014): 485–92. http://dx.doi.org/10.1111/bcpt.12350.

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34

Zsila, Ferenc. "The anticancer agent ellipticine binds to glycosaminoglycans at mildly acidic pH characteristic of the extracellular matrix of tumor tissues." RSC Advances 6, no. 1 (2016): 810–14. http://dx.doi.org/10.1039/c5ra23437a.

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35

Thakur, Raina, Anupam Das, Chandan Adhikari, and Anjan Chakraborty. "Partitioning of prototropic species of an anticancer drug ellipticine in bile salt aggregates of different head groups and hydrophobic skeletons: a photophysical study to probe bile salts as multisite drug carriers." Phys. Chem. Chem. Phys. 16, no. 29 (2014): 15681–91. http://dx.doi.org/10.1039/c4cp01308e.

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36

Márquez, Edgar, José R. Mora, Virginia Flores-Morales, Daniel Insuasty, and Luis Calle. "Modeling the Antileukemia Activity of Ellipticine-Related Compounds: QSAR and Molecular Docking Study." Molecules 25, no. 1 (2019): 24. http://dx.doi.org/10.3390/molecules25010024.

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The antileukemia cancer activity of organic compounds analogous to ellipticine representes a critical endpoint in the understanding of this dramatic disease. A molecular modeling simulation on a dataset of 23 compounds, all of which comply with Lipinski’s rules and have a structure analogous to ellipticine, was performed using the quantitative structure activity relationship (QSAR) technique, followed by a detailed docking study on three different proteins significantly involved in this disease (PDB IDs: SYK, PI3K and BTK). As a result, a model with only four descriptors (HOMO, softness, AC1RA

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37

Tian, Erming, Owen Stephens, Susan Holbeck, Bart Barlogie, and John Shaughnessy. "The Ellipticine Derivative NSC 338258 Has Anti-Myeloma Activity." Blood 106, no. 11 (2005): 3379. http://dx.doi.org/10.1182/blood.v106.11.3379.3379.

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Abstract We recently discovered that amplification and overexpression of the CKS1B gene, which regulates the ubiquitination and proteasomal degradation of the cyclin-dependent kinase inhibitor p27Kip1, is linked to a poor prognosis in myeloma. We used the COMPARE algorithm (NCI, Developmental Therapeutics Program) to identify correlations between the expression of CKS1B in the NCI 60 cell line panel and the GI50 of nearly 50,000 anticancer compounds. This analysis revealed a strong correlation between CKS1B expression and the anticancer activity of Ellipticine and multiple derivatives of it. E

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38

Poljakova, Jitka, Kristina Forsterova, Miroslav Sulc, Eva Frei, and Marie Stiborova. "OXIDATION OF AN ANTITUMOR DRUG ELLIPTICINE BY PEROXIDASES." Biomedical Papers 149, no. 2 (2005): 449–53. http://dx.doi.org/10.5507/bp.2005.078.

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39

K. Pandit, Upendra, Willem F. A. Wijsmuller, Martin J. Wanner, and Gerrit-Jan Koomen. "Pyridocarbazole Alkaloids. Synthesis of Olivacine and Ellipticine Analogues." HETEROCYCLES 24, no. 7 (1986): 1795. http://dx.doi.org/10.3987/r-1986-07-1795.

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40

Chabane, Hadjila, Christelle Lamazzi, Valérie Thiéry, Gérald Guillaumet, and Thierry Besson. "Synthesis of novel 2-cyanothiazolocarbazoles analogues of ellipticine." Tetrahedron Letters 43, no. 14 (2002): 2483–86. http://dx.doi.org/10.1016/s0040-4039(02)00353-2.

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41

Zee, Sheng-Hsu, and Hsiao-Ping Su. "A Convenient Method for the Preparation of Ellipticine." Journal of the Chinese Chemical Society 34, no. 2 (1987): 135–39. http://dx.doi.org/10.1002/jccs.198700020.

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42

Pautet, Felix, Pascal Formisyn, and Jacques Bourgois. "Oxidation of Ellipticine withFremy's Salt under Sonochemical Conditions." Archiv der Pharmazie 326, no. 8 (1993): 499–500. http://dx.doi.org/10.1002/ardp.19933260815.

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43

Ishikura, Minoru, Ayako Hino, and Nobuya Katagiri. "ChemInform Abstract: An Efficient Total Synthesis of Ellipticine." ChemInform 31, no. 16 (2010): no. http://dx.doi.org/10.1002/chin.200016232.

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44

Alvarez, Mercedes, and John Arthur Joule. "ChemInform Abstract: Ellipticine, Uleine, Apparicine, and Related Alkaloids." ChemInform 33, no. 13 (2010): no. http://dx.doi.org/10.1002/chin.200213275.

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45

Peng, Yanhua, Changgong Li, Lihong Chen, Said Sebti, and Jiandong Chen. "Rescue of mutant p53 transcription function by ellipticine." Oncogene 22, no. 29 (2003): 4478–87. http://dx.doi.org/10.1038/sj.onc.1206777.

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46

Werbel, Leslie M., Mario Angelo, David W. Fry, and Donald F. Worth. "Basically substituted ellipticine analogs as potential antitumor agents." Journal of Medicinal Chemistry 29, no. 7 (1986): 1321–22. http://dx.doi.org/10.1021/jm00157a040.

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47

Gavvala, Krishna, Raj Kumar Koninti, Abhigyan Sengupta, and Partha Hazra. "Excited state proton transfer dynamics of an eminent anticancer drug, ellipticine, in octyl glucoside micelle." Phys. Chem. Chem. Phys. 16, no. 28 (2014): 14953–60. http://dx.doi.org/10.1039/c4cp01783h.

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Prototropical and photophysical properties of an anticancer drug, ellipticine, are explored inside the octyl-β-d-glucoside micelles using steady state and time-resolved fluorescence spectroscopic techniques.

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48

Thakur, Raina, Anupam Das, Vandna Sharma, Chandan Adhikari, Kalyan Sundar Ghosh, and Anjan Chakraborty. "Interaction of different prototropic species of an anticancer drug ellipticine with HSA and IgG proteins: multispectroscopic and molecular modeling studies." Physical Chemistry Chemical Physics 17, no. 26 (2015): 16937–46. http://dx.doi.org/10.1039/c4cp05734a.

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Studies on interactions between an anticancer alkaloid, ellipticine, and various carrier proteins in blood serum show tangible results to gain insight into the solubility and transport of the drug under physiological conditions.

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49

Zsila, Ferenc, and Tamás Beke-Somfai. "Dimeric binding of plant alkaloid ellipticine to human serum proteins." RSC Advances 6, no. 50 (2016): 44096–105. http://dx.doi.org/10.1039/c6ra06078a.

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50

W. Gribble, Gordon, and Mark G. Saulnier. "Syntheses of Ellipticine and Related Pyridocarbazole Alkaloids — A Review." HETEROCYCLES 23, no. 5 (1985): 1277. http://dx.doi.org/10.3987/r-1985-05-1277.

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