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      Novel Triazole Hybrids of Betulin: Synthesis and Biological Activity Profile

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          Abstract

          Betulin derivatives containing a 1,2,3-triazole ring possess a wide spectrum of biological activities, including antiviral, anticancer, and antibacterial activity. A series of novel triazoles were prepared by the 1,3-dipolar cycloaddition reaction between the alkyne derivatives of betulin and organic azides. The chemical structures of the obtained compounds were defined by 1H and 13C NMR, IR, and high-resolution mass spectrometry (HR-MS) analysis. The target triazoles were screened for their antiviral activity against DNA and RNA viruses. The cytotoxic activity of the obtained compounds 5ak and 6ah was determined using five human cancer cell lines (T47D, MCF-7, SNB-19, Colo-829, and C-32) by a WST-1 assay. The bistriazole 6b displayed a promising IC 50 value (0.05 μM) against the human ductal carcinoma T47D (500-fold higher potency than cisplatin). The microdilution method was applied for an evaluation of the antimicrobial activity of all of the compounds. The triazole 5e containing a 3′-deoxythymidine-5′-yl moiety exhibited antibacterial activity against two gram-negative bacteria vz. Klebsiella pneumoniae and Escherichia coli (minimal inhibitory concentration (MIC) range of 0.95–1.95 μM).

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          Most cited references 35

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          An improved colorimetric assay for interleukin 2.

          Mosmann's method for measuring the number of viable cells with a tetrazolium salt, 3-(4,5-dimethylthiazol-2-yl)-2,5-di-phenyltetrazolium bromide (MTT), was modified to make it possible to measure a large number of interleukin 2 (IL-2) samples at one time with less labor and more accuracy. Each step of the method was examined in detail and modified (the modified MTT method). An IL-2-dependent mouse natural killer cell line, NKC3, was used as an indicator cell line. The incubation period before adding MTT was reduced to 24 h, A solution of 10% sodium dodecyl sulfate-0.01 N HCl was used to dissolve the MTT formazan produced. We have compared the values obtained by the modified MTT method and the conventional [3H]thymidine method (3H-TdR method), and confirmed that the estimates of IL-2 content were almost equal. The variation of IL-2 content measured by both methods was within 5% in terms of the standard error.
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            Medicinal attributes of 1,2,3-triazoles: Current developments.

            1,2,3-Triazoles are important five-membered heterocyclic scaffold due to their extensive biological activities. This framework can be readily obtained in good to excellent yields on the multigram scale through click chemistry via reaction of aryl/alkyl halides, alkynes and NaN3 under ambient conditions. It has been an emerging area of interest for many researchers throughout the globe owing to its immense pharmacological scope. The present work aims to summarize the current approaches adopted for the synthesis of the 1,2,3-triazole and medicinal significance of these architectures as a lead structure for the discovery of drug molecules such as COX-1/COX-2 inhibitors (celecoxib, pyrazofurin), HIV protease inhibitors, CB1 cannabinoid receptor antagonist and much more which are in the pipeline of clinical trials. The emphasis has been given on the major advancements in the medicinal prospectus of this pharmacophore for the period during 2008-2016.
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              Apoptotic mechanisms in T47D and MCF-7 human breast cancer cells

              To investigate the mechanisms underlying apoptosis in breast cancer cells, staurosporine was used as an apoptotic stimulus in the human breast cancer cell lines MCF-7 and T47D. Staurosporine induced dose and time dependent increases in DNA fragmentation which was abrogated by z-VAD-fmk. MCF-7 cells did not express caspase-3, suggesting that DNA fragmentation occurred in the absence of caspase-3 and that other caspases may be involved. Staurosporine induced DEVDase activity in T47D cells suggesting the involvement of caspase-3 and/or caspase-7, yet there was no DEVDase activity in MCF-7 cells, probably ruling out the involvement caspase-7. However, staurosporine induced the cleavage of pro-caspase-6 in MCF-7 cells, but not in T47D cells. Caspase dependent PARP cleavage was detected in MCF-7 cells at 3 h, whereas only partial PARP cleavage was detected in T47D cells and then only after 24 h. Moreover, staurosporine led to cytochrome c release at 2 h in MCF-7 cells and 6 h in T47D cells. In addition, a time dependent and caspase-independent reduction of the mitochondrial transmembrane potential was observed; which appeared to occur after the release of cytochrome c. Translocation of Bax from the cytosol to mitochondria was observed in both cell types, and this preceded cytochrome c release in both T47D and MCF-7 cells. Apoptotic events in both cell types differ temporally, involving activation of different caspases and mitochondrial changes. British Journal of Cancer (2002) 87, 909–917. doi:10.1038/sj.bjc.6600541 www.bjcancer.com © 2002 Cancer Research UK
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                Author and article information

                Journal
                Molecules
                Molecules
                molecules
                Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry
                MDPI
                1420-3049
                01 November 2017
                November 2017
                : 22
                : 11
                Affiliations
                [1 ]Department of Organic Chemistry, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia in Katowice, 4 Jagiellońska Str., 41-200 Sosnowiec, Poland; mkadela@ 123456sum.edu.pl (M.K.-T.); echrobak@ 123456sum.edu.pl (E.C.); boryczka@ 123456sum.edu.pl (S.B.)
                [2 ]Department of Solid State Physics, Institute of Physics, University of Silesia, 4 Uniwersytecka Str., 40-007 Katowice, Poland; maria.jastrzebska@ 123456us.edu.pl
                [3 ]Silesian Center for Education and Interdisciplinary Research, University of Silesia, 75 Pułku Piechoty 1, 41-500 Chorzów, Poland
                [4 ]Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Laboratory of Virology, 12 Rudolfa Weigla Str., 53-114 Wrocław, Poland; orzechow@ 123456iitd.pan.wroc.pl (B.O.); kjzwolinska@ 123456iitd.pan.wroc.pl (K.Z.)
                [5 ]Department of Cell Biology, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia in Katowice, 8 Jedności Str., 41-200 Sosnowiec; Poland; mlatocha@ 123456sum.edu.pl
                [6 ]Department of Microbiology and Immunology, School of Medicine with the Division of Dentistry in Zabrze, Medical University of Silesia in Katowice, 19 Jordana Str., 41-808 Zabrze, Poland; amertas@ 123456sum.edu.pl (A.M.); zczuba@ 123456sum.edu.pl (Z.C.)
                Author notes
                [* ]Correspondence: ebebenek@ 123456sum.edu.pl ; Tel.: +48-323-641-666
                Article
                molecules-22-01876
                10.3390/molecules22111876
                6150379
                29104263
                © 2017 by the authors.

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

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