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Inorganics 2017, 5(3), 56; https://doi.org/10.3390/inorganics5030056

(18-Crown-6)potassium(I) Trichlorido[28-acetyl-3-(tris-(hydroxylmethyl)amino-ethane)betulinic ester-κN]platinum(II): Synthesis and In Vitro Antitumor Activity

1
Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle (Saale), Germany
2
Institute for Biological Research “Siniša Stanković” University of Belgrade, Bulevar despota Stefana 142, 11060 Belgrade, Serbia
3
Biozentrum, Martin-Luther-Universität Halle-Wittenberg, Weinbergweg 22, D-06120 Halle, Germany
4
Department of Chemistry, Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Studentski trg 14, 11000 Belgrade, Serbia
*
Authors to whom correspondence should be addressed.
Received: 28 June 2017 / Revised: 16 August 2017 / Accepted: 16 August 2017 / Published: 19 August 2017
(This article belongs to the Special Issue Tumor Inhibiting Metal Complexes)
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Abstract

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 as elemental analysis were used for characterization of BATRISPt. Cytotoxicity (3-(4,5-dimethythiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), crystal violet (CV), and sulforhodamine B (SRB) assays) of BA, BATRIS, BATRISPt, and cisplatin were assessed on seven different tumor cell lines: melanoma B16, colon HCT116 and DLD-1, adenocarcinoma HeLa, breast MCF-7, and anaplastic thyroid tumor 8505C and SW1736; as well as normal MRC-5 fibroblasts. Furthermore, the effect of the mentioned compounds on the apoptosis (Annexin V/PI assay) and autophagy induction (acridine orange (AO) assay) as well as caspase 3, 8, and 9 activation were investigated on the selected B16 melanoma cell line. BATRISPt showed lower activity than BA, BATRIS, or cisplatin. All tested compounds triggered apoptosis in B16 cells. Induction of autophagy was observed in B16 cells exposed only to BATRIS. On the other hand, new conjugate activates caspases 8 and 9 in B16 cells with higher impact than BATRIS or cisplatin alone. View Full-Text
Keywords: betulinic acid; cisplatin; drug conjugate; apoptosis; autophagy betulinic acid; cisplatin; drug conjugate; apoptosis; autophagy
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Kaluđerović, G.N.; Bulatović, M.; Krajnović, T.; Paschke, R.; B. Zmejkovski, B.; Maksimović-Ivanić, D.; Mijatović, S. (18-Crown-6)potassium(I) Trichlorido[28-acetyl-3-(tris-(hydroxylmethyl)amino-ethane)betulinic ester-κN]platinum(II): Synthesis and In Vitro Antitumor Activity. Inorganics 2017, 5, 56.

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