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Journal articles on the topic 'Etoposide – Synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 5 February 2022

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1

Saulnier, Mark G., David R. Langley, John F. Kadow, et al. "Synthesis of etoposide phosphate, BMY-40481: A water-soluble clinically active prodrug of etoposide." Bioorganic & Medicinal Chemistry Letters 4, no. 21 (1994): 2567–72. http://dx.doi.org/10.1016/s0960-894x(01)80285-7.

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2

Bertounesque, Emmanuel, Philippe Meresse, Claude Monneret, and Jean-Claude Florent. "Synthetic approach to condensed heterocyclic analogues from etoposide revisited. Synthesis of A-ring pyridazine etoposide." Tetrahedron Letters 48, no. 33 (2007): 5781–84. http://dx.doi.org/10.1016/j.tetlet.2007.06.105.

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3

Wrasidlo, Wolf, Ulrike Schröder, Kathrin Bernt, et al. "Synthesis, Hydrolytic Activation and Cytotoxicity of Etoposide Prodrugs." Bioorganic & Medicinal Chemistry Letters 12, no. 4 (2002): 557–60. http://dx.doi.org/10.1016/s0960-894x(01)00801-0.

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4

Kasperek, Cynthia, and Curtis D. Black. "Two Cases of Suspected Immunologic-Based Hypersensitivity Reactions to Etoposide Therapy." Annals of Pharmacotherapy 26, no. 10 (1992): 1227–30. http://dx.doi.org/10.1177/106002809202601005.

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OBJECTIVE: To report two cases of suspected immunologic-based hypersensitivity reactions to etoposide therapy. DATA SYNTHESIS: Two cases are presented that differ from the majority of reported hypersensitivity reactions to etoposide. One patient, who tolerated etoposide during his first three-day chemotherapeutic dosage regimen, developed a hypersensitivity reaction to etoposide upon re-exposure to the drug during the first day of a subsequent three-day cycle. Another patient experienced a hypotensive episode on the first day of an initial three-day regimen, which did not recur on the two subs

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5

STEFANELLI, Claudio, Francesca BONAVITA, Ivana STANIC, et al. "Inhibition of etoposide-induced apoptosis with peptide aldehyde inhibitors of proteasome." Biochemical Journal 332, no. 3 (1998): 661–65. http://dx.doi.org/10.1042/bj3320661.

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Recent investigations have indicated the involvement of proteasome in programmed cell death. The present studies show that although peptide aldehyde inhibitors of proteasome are by themselves weak inducers of apoptosis, they inhibit the apoptotic effect of the anticancer drug etoposide in rat thymocytes. Acetyl-Leu-Leu-norvalinal (LLnV-al) and other related peptide aldehydes inhibited the increase in caspase activity and DNA fragmentation that followed treatment with etoposide and their effect was related to their potency as proteasome inhibitors. To inhibit etoposide-induced apoptosis, LLnV-a

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6

Kandemiş, Emine, Sara Alkhatib, Barış Sergi, and Gülay Bulut. "Effect of Etoposide Treatment on ERG Transfected H358 Cell Line." Proceedings 2, no. 25 (2018): 1589. http://dx.doi.org/10.3390/proceedings2251589.

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Lung cancer is listed as the most fatal type of cancer around the world. ERG, a transcription factor, is an ETS family member protein. It is involved in Epithelial Mesenchymal Transition (EMT), metastasis and DNA repair defects. Etoposide is a chemotherapeutic agent used in treatment of a variety of different cancer types, including lung cancer. Moreover, Etoposide has been tested alone and in combination with other drugs in order to inhibit DNA synthesis and exhibit antitumor activity. The purpose of this study is to examine the effect of Etoposide treatment on ERG transfected non-small cell

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7

Kadow, John F., Min Min Tun, Alfred R. Crosswell, William C. Rose, Dolatrai M. Vyas, and Terrence W. Doyle. "Synthesis and antileukemic activity of etoposide a-ring analogs." Bioorganic & Medicinal Chemistry Letters 2, no. 1 (1992): 17–22. http://dx.doi.org/10.1016/s0960-894x(00)80646-0.

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8

Hasinoff, Brian B., Gaik-Lean Chee, Billy W. Day, et al. "Synthesis and Biological Activity of a Photoaffinity Etoposide Probe." Bioorganic & Medicinal Chemistry 9, no. 7 (2001): 1765–71. http://dx.doi.org/10.1016/s0968-0896(01)00102-x.

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9

Kadow, J. F., D. M. Vyas, and T. W. Doyle. "Synthesis of etoposide lactam via a mitsunobu reaction sequence." Tetrahedron Letters 30, no. 25 (1989): 3299–302. http://dx.doi.org/10.1016/s0040-4039(00)99226-8.

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10

Saulnier, Mark G., Karen L. LeBoulluec, Danny P. C. McGee, Byron H. Long, Alfred R. Crosswell, and Dolatrai M. Vyas. "Synthesis and biological activity of 3′,4′,5′-trihydroxy etoposide." Bioorganic & Medicinal Chemistry Letters 3, no. 8 (1993): 1619–24. http://dx.doi.org/10.1016/s0960-894x(00)80029-3.

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11

Allevi, Pietro, Mario Anastasia, Pierangela Ciuffreda, Anna Maria Sanvito, and Peter Macdonald. "A short and simple synthesis of the antitumor agent etoposide." Tetrahedron Letters 33, no. 33 (1992): 4831–34. http://dx.doi.org/10.1016/s0040-4039(00)61297-2.

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12

Kolar, Cenek, Hans Moldenhauer, and Günther Kneißl. "A New Approach to the Synthesis of Etoposide (VP 16)." Journal of Carbohydrate Chemistry 9, no. 5 (1990): 571–83. http://dx.doi.org/10.1080/07328309008543854.

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13

Hollis Showalterk, H. D., R. Thomas Winters, Anthony D. Sercel, and Andrè Michel. "Facile synthesis of thioglucose analogs of the anticancer agent etoposide." Tetrahedron Letters 32, no. 25 (1991): 2849–52. http://dx.doi.org/10.1016/0040-4039(91)80629-k.

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14

Maschera, B., E. Ferrazzi, M. Rassu, M. Toni, and G. Palù. "Evaluation of Topoisomerase Inhibitors as Potential Antiviral Agents." Antiviral Chemistry and Chemotherapy 4, no. 2 (1993): 85–91. http://dx.doi.org/10.1177/095632029300400202.

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Anti-eukaryotic topoisomerase drugs, Camptothecin and Etoposide, were tested for their ability of selectively interfering with the replication of simian virus 40 (SV40) DNA. Nalidixic acid was also assayed for a comparison, since the compound has been previously reported to affect papoyavirus growth. Our results indicate that anti-eukaryotic topoisomerase drugs significantly inhibit viral DNA replication but at concentrations that are also toxic for uninfected cells. Etoposide treatment produced a relatively higher number of DNA-protein cross-links in virus-infected cells as compared to uninfe

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15

Lazo, John S., Tianhu Li, Elizabeth S. Woo, Catherine E. Settineri, William P. Allan, and Jack C. Yalowich. "Chemical synthesis and biological activity of a novel fluorescent etoposide derivative." Biochemical Pharmacology 53, no. 5 (1997): 715–22. http://dx.doi.org/10.1016/s0006-2952(96)00906-9.

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16

Allevi, Pietro, Mario Anastasia, Pierangela Ciuffreda, and Antonio Scala. "A Simple Synthesis ofC-Glucosides Related to the Antitumor Agent Etoposide." Journal of Carbohydrate Chemistry 12, no. 2 (1993): 209–22. http://dx.doi.org/10.1080/07328309308021271.

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17

Allevi, Pietro, Mario Anastasia, Pierangela Ciuffreda, Ettore Bigatti, and Peter Macdonald. "Stereoselective glucosidation of podophyllum lignans. A new simple synthesis of etoposide." Journal of Organic Chemistry 58, no. 15 (1993): 4175–78. http://dx.doi.org/10.1021/jo00067a071.

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18

Hakovirta, H., M. Parvinen, and J. Lähdetie. "Effects of etoposide on stage-specific DNA synthesis during rat spermatogenesis." Mutation Research Letters 301, no. 3 (1993): 189–93. http://dx.doi.org/10.1016/0165-7992(93)90077-9.

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19

Chow, K. C., and W. E. Ross. "Topoisomerase-specific drug sensitivity in relation to cell cycle progression." Molecular and Cellular Biology 7, no. 9 (1987): 3119–23. http://dx.doi.org/10.1128/mcb.7.9.3119.

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The nuclear enzyme DNA topoisomerase II catalyzes the breakage and resealing of duplex DNA and plays an important role in several genetic processes. It also mediates the DNA cleavage activity and cytotoxicity of clinically important anticancer agents such as etoposide. We have examined the activity of topoisomerase II during the first cell cycle of quiescent BALB/c 3T3 cells following serum stimulation. Etoposide-mediated DNA break frequency in vivo was used as a parameter of topoisomerase II activity, and enzyme content was assayed by immunoblotting. Density-arrested A31 cells exhibited a muc

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20

Chow, K. C., and W. E. Ross. "Topoisomerase-specific drug sensitivity in relation to cell cycle progression." Molecular and Cellular Biology 7, no. 9 (1987): 3119–23. http://dx.doi.org/10.1128/mcb.7.9.3119-3123.1987.

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The nuclear enzyme DNA topoisomerase II catalyzes the breakage and resealing of duplex DNA and plays an important role in several genetic processes. It also mediates the DNA cleavage activity and cytotoxicity of clinically important anticancer agents such as etoposide. We have examined the activity of topoisomerase II during the first cell cycle of quiescent BALB/c 3T3 cells following serum stimulation. Etoposide-mediated DNA break frequency in vivo was used as a parameter of topoisomerase II activity, and enzyme content was assayed by immunoblotting. Density-arrested A31 cells exhibited a muc

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21

Gielen, Marcel, Karel Handlir, Martin Hollein, and Dick de Vos. "Synthesis, Characterization and Antitumour Activity of Some Butyltin(IV) Cysteaminates and N,N-Dimethylcysteaminates." Metal-Based Drugs 7, no. 5 (2000): 233–36. http://dx.doi.org/10.1155/mbd.2000.233.

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The synthesis and characterization of four di- and tri-n-butyltin cysteaminates and N,N-dimethylcysteaminates and three protonated / quaternized derivatives are reported. They all exhibit moderate or high in vitro cytotoxic activity. Six of seven compounds presented in this work are more active than cisplatin, etoposide and 5-fluorouracil, but less active than methotrexate and doxorubicin.

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22

Schmidt, Frédéric, and Claude Monneret. "Prodrug Mono therapy: synthesis and biological evaluation of an etoposide glucuronide-prodrug." Bioorganic & Medicinal Chemistry 11, no. 10 (2003): 2277–83. http://dx.doi.org/10.1016/s0968-0896(03)00108-1.

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23

SHOWALTER, H. D. H., R. T. WINTERS, A. D. SERCEL, and A. MICHEL. "ChemInform Abstract: Facile Synthesis of Thioglucose Analogs of the Anticancer Agent Etoposide." ChemInform 23, no. 13 (2010): no. http://dx.doi.org/10.1002/chin.199213314.

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24

Liu, Ying-Qian, Hua Yang, and Xuan Tian. "Design, Synthesis and Biological Evaluation of Novel Etoposide Analogues as Cytotoxic Agents." Chinese Journal of Chemistry 24, no. 6 (2006): 785–90. http://dx.doi.org/10.1002/cjoc.200690149.

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25

KIKUTA, HIDKAKI, and YUKIO SAKIYAMA. "ETOPOSIDE (VP-16) INHIBITS EPSTEIN-BARR VIRUS DETERMINED NUCLEAR ANTIGEN (EBNA) SYNTHESIS." British Journal of Haematology 90, no. 4 (1995): 971–72. http://dx.doi.org/10.1111/j.1365-2141.1995.tb05232.x.

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26

SU, IH-JEN. "ETOPOSIDE (VP-16) INHIBITS EPSTEIN-BARR VIRUS DETERMINED NUCLEAR ANTIGEN (EBNA) SYNTHESIS." British Journal of Haematology 90, no. 4 (1995): 971–72. http://dx.doi.org/10.1111/j.1365-2141.1995.tb05233.x.

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27

Gielen, Marcel, Abdelaziz El Khloufi, Monique Biesemans, et al. "Synthesis, Characterization and High In Vitro Antitumour Activity of Novel Triphenyltin Carboxylates." Metal-Based Drugs 1, no. 4 (1994): 305–9. http://dx.doi.org/10.1155/mbd.1994.305.

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The synthesis and spectral characterization of six novel triphenyltin compounds are described. The in vitro antitumour activity of three of these compounds against two human tumour cell lines, MCF-7, a mammary tumour, and WiDr, a colon carcinoma, was determined. All three compounds are more active than cis-platin, etoposide and doxorubicin against both tumour cell lines. They are as active as mitomycin C against WiDr, but less active against MCF-7.

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28

Kutney, James P., G. M. Hewitt, Terence C. Jarvis, Jan Palaty, and Steven J. Rettig. "Studies with plant cell cultures of Catharanthusroseus. Oxidative coupling of dibenzylbutanolides catalyzed by plant cell culture extracts." Canadian Journal of Chemistry 70, no. 7 (1992): 2115–33. http://dx.doi.org/10.1139/v92-267.

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Utilizing appropriate dibenzylbutanolides, for example 7, obtained via an efficient synthetic route from readily available aldehydes, and cell-free extracts obtained from Catharanthusroseus cell cultures, it was possible to achieve enzyme-catalyzed oxidative coupling of 7 to picropodophyllotoxin analogues. Studies are presently underway to convert such compounds to intermediates employed in the synthesis of the commercially important anti-cancer drug, etoposide.

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29

Chen, Jing, and Wenting Du. "Synthesis and Evaluation of Water-Soluble Etoposide Esters of Malic Acid as Prodrugs." Medicinal Chemistry 9, no. 5 (2013): 740–47. http://dx.doi.org/10.2174/1573406411309050014.

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30

Allevi, Pietro, Mario Anastasia, and Pierangela Ciuffreda. "The first synthesis of the N-glucosyl analogue of the antitumor agent etoposide." Tetrahedron Letters 34, no. 45 (1993): 7313–16. http://dx.doi.org/10.1016/s0040-4039(00)79317-8.

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31

Saulnier, Mark G., Karen L. LeBoulleuc, Byron H. Long, Dolatrai M. Vyas, Alfred R. Crosswell, and Terrence W. Doyle. "Synthesis of biological evaluation of 4′-deshydroxy-4′-methyl etoposide and teniposide analogs." Bioorganic & Medicinal Chemistry Letters 2, no. 10 (1992): 1213–18. http://dx.doi.org/10.1016/s0960-894x(00)80216-4.

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32

ALLEVI, P., M. ANASTASIA, P. CIUFFREDA, A. M. SANVITO, and P. MACDONALD. "ChemInform Abstract: A Short and Simple Synthesis of the Antitumor Agent Etoposide (I)." ChemInform 24, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.199301275.

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33

Kubota, Masaru, Akihiko Tanizawa, Hisako Hashimoto, et al. "Cell type dependent activation of poly(ADP-ribose) synthesis following treatment with etoposide." Leukemia Research 14, no. 4 (1990): 371–75. http://dx.doi.org/10.1016/0145-2126(90)90165-6.

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34

Hu, Jie-li, Ge Xu, Ling Lei, Wen-lu Zhang, Ai-long Huang, and Xue-fei Cai. "Etoposide Phosphate Enhances the Acetylation Level of Translation Elongation Factor 1A in PLC5 Cells." Zeitschrift für Naturforschung C 67, no. 5-6 (2012): 327–30. http://dx.doi.org/10.1515/znc-2012-5-613.

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Translation elongation factor 1A (eEF1A) is a factor critically involved in the process of protein synthesis. The activity of eEF1A has been shown by several studies to be regulated by post-translational modifi cations such as phosphorylation and dephosphorylation. However, until now less research has focused on other post-translational modifi cations of eEF1A, especially acetylation. In this report, we provide new evidence for the existence of eEF1A acetylation in PLC5 cells by immunoprecipitation and Western blotting. Using the histone deacetylase (HDAC) inhibitor trichostatin A (TSA), we fo

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35

Ravinaik, Bhukya, Dittakavi Ramachandran, and Mandava Venkata Basaveswara Rao. "Design, Synthesis and Anticancer Evaluation of 1,2,4-Oxadiazole Bearing Isoxazole-Pyrazole Derivatives." Letters in Organic Chemistry 17, no. 5 (2020): 352–59. http://dx.doi.org/10.2174/1570178616666190725090906.

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A novel library of 1,2,4-oxadiazole bearing isoxazole-pyrazole derivatives (13a-j) were designed, synthesized and evaluated for their anticancer activity towards MCF-7 (breast cancer), A549 (lung cancer), DU-145 (prostate cancer) and MDA MB-231 (breast cancer) human cancer cell lines by MTT assay. Here etoposide used as standard drug. Among them, five compounds (13b, 13c, 13d, 13h and 13i) were exhibited more potent activity. In which compound 13h was the most promising compound against all cell lines MCF-7, A549, DU-145 and MDA MB-231.

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36

Alfei, Silvana, Barbara Marengo, Giulia Valenti, and Cinzia Domenicotti. "Synthesis of Polystyrene-Based Cationic Nanomaterials with Pro-Oxidant Cytotoxic Activity on Etoposide-Resistant Neuroblastoma Cells." Nanomaterials 11, no. 4 (2021): 977. http://dx.doi.org/10.3390/nano11040977.

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Drug resistance is a multifactorial phenomenon that limits the action of antibiotics and chemotherapeutics. Therefore, it is essential to develop new therapeutic strategies capable of inducing cytotoxic effects circumventing chemoresistance. In this regard, the employment of natural and synthetic cationic peptides and polymers has given satisfactory results both in microbiology, as antibacterial agents, but also in the oncological field, resulting in effective treatment against several tumors, including neuroblastoma (NB). To this end, two polystyrene-based copolymers (P5, P7), containing prim

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37

Meresse, Philippe, Emmanuel Bertounesque, Thierry Imbert, and Claude Monneret. "Synthetic approaches to condensed aromatic analogues from etoposide. Synthesis of A-ring pyridazine picroetoposide." Tetrahedron 55, no. 44 (1999): 12805–18. http://dx.doi.org/10.1016/s0040-4020(99)00756-5.

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38

ALLEVI, P., M. ANASTASIA, P. CIUFFREDA, and A. SCALA. "ChemInform Abstract: A Simple Synthesis of C-Glucosides Related to the Antitumor Agent Etoposide." ChemInform 25, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.199431226.

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39

Silverberg, Lee J., Sean Kelly, Purushotham Vemishetti, et al. "A Crystallization-Induced Stereoselective Glycosidation Reaction in the Synthesis of the Anticancer Drug Etoposide†." Organic Letters 2, no. 21 (2000): 3281–83. http://dx.doi.org/10.1021/ol006262n.

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40

Silverberg, Lee J., Sean Kelly, Purushotham Vemishetti, et al. "A Crystallization-Induced Stereoselective Glycosidation Reaction in the Synthesis of the Anticancer Drug Etoposide." Organic Letters 2, no. 24 (2000): 3953. http://dx.doi.org/10.1021/ol006709s.

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41

Allevi, Pietro, Mario Anastasia, and Pierangela Ciuffreda. "A short and simple synthesis of the thioglucose analog of the antitumor agent etoposide." Tetrahedron Letters 32, no. 47 (1991): 6927–30. http://dx.doi.org/10.1016/0040-4039(91)80446-d.

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42

Yadav, Arun A., Gaik-Lean Chee, Xing Wu, Daywin Patel, Jack C. Yalowich, and Brian B. Hasinoff. "Structure-based design, synthesis and biological testing of piperazine-linked bis-epipodophyllotoxin etoposide analogs." Bioorganic & Medicinal Chemistry 23, no. 13 (2015): 3542–51. http://dx.doi.org/10.1016/j.bmc.2015.04.022.

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43

STEFANELLI, Claudio, Carla PIGNATTI, Benedetta TANTINI, et al. "Effect of polyamine depletion on caspase activation: a study with spermine synthase-deficient cells." Biochemical Journal 355, no. 1 (2001): 199–206. http://dx.doi.org/10.1042/bj3550199.

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Activation of the caspase proteases represents a central point in apoptosis. The requirement for spermine for the processes leading to caspase activation has been studied in transformed embryonic fibroblasts obtained from gyro (Gy) mutant male mice. These cells lack spermine synthase activity and thus provide a valuable model to study the role of spermine in cell processes. Gy fibroblasts do not contain spermine and have a higher spermidine content. However, when compared with fibroblasts obtained from normal male littermates (N cells), Gy fibroblasts were observed to grow normally. The lack o

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44

ALLEVI, P., M. ANASTASIA, and P. CIUFFREDA. "ChemInform Abstract: The First Synthesis of the N-Glucosyl Analogue of the Antitumor Agent Etoposide." ChemInform 25, no. 19 (2010): no. http://dx.doi.org/10.1002/chin.199419260.

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45

Daley, Laurent, Yves Guminski, Pierre Demerseman, et al. "Synthesis and Antitumor Activity of New Glycosides of Epipodophyllotoxin, Analogues of Etoposide, and NK 611." Journal of Medicinal Chemistry 41, no. 23 (1998): 4475–85. http://dx.doi.org/10.1021/jm9800752.

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46

Murphy, Matthew B., Priyanka Kumar, Amber M. Bradley, Christopher E. Barton, Joseph E. Deweese та Susan L. Mercer. "Synthesis and evaluation of etoposide and podophyllotoxin analogs against topoisomerase IIα and HCT-116 cells". Bioorganic & Medicinal Chemistry 28, № 22 (2020): 115773. http://dx.doi.org/10.1016/j.bmc.2020.115773.

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47

Ploegmakers, H. H. J. L., and W. J. van Oort. "Post-column coulometric generation and cyclic voltammetric identification of the free radical of the antineoplastic agent etoposide (VP 16-213)." Journal of Automatic Chemistry 10, no. 3 (1988): 135–39. http://dx.doi.org/10.1155/s1463924688000252.

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It has been suggested that etoposide can be transformed ‘in vivo’ into a radical intermediate, which may be involved in the irreversible binding of etoposide to microsomal proteins and in DNA damage. To investigate some physico-chemical properties, the on-line coulometric production of this free radical and its subsequent cyclic voltammetric detection is described. For the synthesis, a coulometric ESA Coulochem 5100A module, equipped with an ESA 5010 analytical cell, has been used. For its detection the computerized cyclic voltammetric detection system after HPLC controlled by an Apple IIe com

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48

Abzianidze, Victoria, Petr Beltyukov, Sofya Zakharenkova, et al. "Synthesis and Biological Evaluation of Phaeosphaeride A Derivatives as Antitumor Agents." Molecules 23, no. 11 (2018): 3043. http://dx.doi.org/10.3390/molecules23113043.

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New derivatives of phaeosphaeride A (PPA) were synthesized and characterized. Anti-tumor activity studies were carried out on the HCT-116, PC3, MCF-7, A549, К562, NCI-Н929, Jurkat, THP-1, RPMI8228 tumor cell lines, and on the HEF cell line. All of the compounds synthesized were found to have better efficacy than PPA towards the tumor cell lines mentioned. Compound 6 was potent against six cancer cell lines, HCT-116, PC-3, K562, NCI-H929, Jurkat, and RPMI8226, showing a 47, 13.5, 16, 4, 1.5, and 7-fold increase in anticancer activity comparative to those of etoposide, respectively. Compound 1 p

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49

Silverberg, Lee J., Sean Kelly, Purushotham Vemishetti, et al. "ChemInform Abstract: A Crystallization-Induced Stereoselective Glycosidation Reaction in the Synthesis of the Anticancer Drug Etoposide." ChemInform 32, no. 4 (2001): no. http://dx.doi.org/10.1002/chin.200104081.

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50

Meresse, Philippe, Emmanuel Bertounesque, Thierry Imbert, and Claude Monneret. "ChemInform Abstract: Synthetic Approaches to Condensed Aromatic Analogues from Etoposide. Synthesis of A-Ring Pyridazine Picroetoposide." ChemInform 31, no. 6 (2010): no. http://dx.doi.org/10.1002/chin.200006234.

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