(18-Crown-6)potassium(I) Trichlorido[28-acetyl-3-(tris-(hydroxylmethyl)amino-ethane)betulinic ester-κN]platinum(II): Synthesis and In Vitro Antitumor Activity
作者： Goran Kaluđerović , Mirna Bulatović , Tamara Krajnović , Reinhard Paschke , Bojana B. Zmejkovski
DOI: 10.3390/INORGANICS5030056
关键词:
摘要: Synthesis of platinum(II) conjugate with acetylated betulinic acid tris(hydroxymethyl)aminomethane ester (BATRIS) is presented (BATRISPt). HR-ESI-MS and multinuclear NMR spectroscopy, as well elemental analysis were used for characterization BATRISPt. Cytotoxicity (3-(4,5-dimethythiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), crystal violet (CV), sulforhodamine B (SRB) assays) BA, BATRIS, BATRISPt, cisplatin assessed on seven different tumor cell lines: melanoma B16, colon HCT116 DLD-1, adenocarcinoma HeLa, breast MCF-7, anaplastic thyroid 8505C SW1736; normal MRC-5 fibroblasts. Furthermore, the effect mentioned compounds apoptosis (Annexin V/PI assay) autophagy induction (acridine orange (AO) caspase 3, 8, 9 activation investigated selected B16 line. BATRISPt showed lower activity than or cisplatin. All tested triggered in cells. Induction was observed cells exposed only to BATRIS. On other hand, new activates caspases 8 higher impact BATRIS alone.
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sci-hub.se 参考文章(49)
Mohamed Ali‐Seyed, Ibrahim Jantan, Kavitha Vijayaraghavan, Syed Nasir Abbas Bukhari, None, Betulinic Acid: Recent Advances in Chemical Modifications, Effective Delivery, and Molecular Mechanisms of a Promising Anticancer Therapy Chemical Biology & Drug Design. ,vol. 87, pp. 517- 536 ,(2016) , 10.1111/CBDD.12682
Andrea Dietrich, Thomas Mueller, Reinhard Paschke, Bernd Kalinowski, Timo Behlendorf, Franziska Reipsch, Angelika Fruehauf, Hans-Joachim Schmoll, Charlotte Kloft, Wieland Voigt, 2-(4-(Tetrahydro-2H-pyran-2-yloxy)-undecyl)-propane-1,3-diamminedichloroplatinum(II): a novel platinum compound that overcomes cisplatin resistance and induces apoptosis by mechanisms different from that of cisplatin. Journal of Medicinal Chemistry. ,vol. 51, pp. 5413- 5422 ,(2008) , 10.1021/JM800334Z
G Kroemer, L Galluzzi, P Vandenabeele, J Abrams, E S Alnemri, E H Baehrecke, M V Blagosklonny, W S El-Deiry, P Golstein, D R Green, M Hengartner, R A Knight, S Kumar, S A Lipton, W Malorni, G Nuñez, M E Peter, J Tschopp, J Yuan, M Piacentini, B Zhivotovsky, G Melino, Classification of cell death: recommendations of the Nomenclature Committee on Cell Death 2009 Cell Death & Differentiation. ,vol. 16, pp. 3- 11 ,(2005) , 10.1038/CDD.2008.150
R. Adam Smith, Hushan Yuan, Ralph Weissleder, Lewis C. Cantley, Lee Josephson, A Wortmannin-Cetuximab As A Double Drug Bioconjugate Chemistry. ,vol. 20, pp. 2185- 2189 ,(2009) , 10.1021/BC900176A
Abdelouahid El-Khattouti, Denis Selimovic, Youssef Haikel, Mohamed Hassan, Crosstalk Between Apoptosis and Autophagy: Molecular Mechanisms and Therapeutic Strategies in Cancer Journal of Cell Death. ,vol. 6, pp. 37- 55 ,(2013) , 10.4137/JCD.S11034
N. Mizushima, Autophagy: process and function Genes & Development. ,vol. 21, pp. 2861- 2873 ,(2007) , 10.1101/GAD.1599207
Harish Kommera, Goran N. Kaluđerović, Jutta Kalbitz, Reinhard Paschke, Synthesis and Anticancer Activity of Novel Betulinic acid and Betulin Derivatives Archiv Der Pharmazie. ,vol. 343, pp. 449- 457 ,(2010) , 10.1002/ARDP.201000011
Harish Kommera, Goran N. Kaluđerović, Sebastian Dittrich, Jutta Kalbitz, Birgit Dräger, Thomas Mueller, Reinhard Paschke, Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity Bioorganic & Medicinal Chemistry Letters. ,vol. 20, pp. 3409- 3412 ,(2010) , 10.1016/J.BMCL.2010.04.004
Emily Pisha, Heebyung Chai, Ik-Soo Lee, Tangai E. Chagwedera, Norman R. Farnsworth, Geoffrey A. Cordell, Christopher W.W. Beecher, Harry H.S. Fong, A. Douglas Kinghorn, Daniel M. Brown, Mansukh C. Wani, Monroe E. Wall, Tina J. Hieken, Tapas K. Das Gupta, John M. Pezzuto, Discovery of betulinic acid as a selective inhibitor of human melanoma that functions by induction of apoptosis Nature Medicine. ,vol. 1, pp. 1046- 1051 ,(1995) , 10.1038/NM1095-1046
Harish Kommera, Goran N. Kaluđerović, Jutta Kalbitz, Reinhard Paschke, Lupane triterpenoids--betulin and betulinic acid derivatives induce apoptosis in tumor cells. Investigational New Drugs. ,vol. 29, pp. 266- 272 ,(2011) , 10.1007/S10637-009-9358-X