Design, synthesis, cytotoxic activity, and apoptosis inducing effects of
4- and N-substituted benzoyltaurinamide derivatives

Birim, Dervis; ARMAGAN, GÜLİZ; Akgul, Ozlem; Kayabasi, Cagla; Gunduz, Cumhur; Erdogan, Mumin

doi:10.3906/kim-2009-1

Design, synthesis, cytotoxic activity, and apoptosis inducing effects of 4- and N-substituted benzoyltaurinamide derivatives

Özlem AKGÜL, (Ege Üniversitesi, Eczacılık Fakültesi, Farmasötik Kimya Anabilim Dalı, İzmir, Türkiye)

Mümin Alper ERDOĞAN, (İzmir Katip Çelebi Üniversitesi, Tıp Fakültesi, Fizyoloji Anabilim Dalı, İzmir, Türkiye)

Derviş BİRİM, (Ege Üniversitesi, Eczacılık Fakültesi, Biyokimya Anabilim Dalı, İzmir, Türkiye)

Çağla KAYABAŞI, (Ege Üniversitesi, Tıp Fakültesi, Tıbbi Biyoloji Anabilim Dalı, İzmir, Türkiye)

Cumhur GÜNDÜZ, (Ege Üniversitesi, Tıp Fakültesi, Tıbbi Biyoloji Anabilim Dalı, İzmir, Türkiye)

Güliz ARMAGAN (Ege Üniversitesi, Eczacılık Fakültesi, Biyokimya Anabilim Dalı, İzmir, Türkiye)

Turkish Journal of Chemistry

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Yıl: 2020 Cilt: 44 Sayı: 6 Sayfa Aralığı: 1674 - 1693 Metin Dili: İngilizce DOI: 10.3906/kim-2009-1 İndeks Tarihi: 24-06-2022

Design, synthesis, cytotoxic activity, and apoptosis inducing effects of 4- and N-substituted benzoyltaurinamide derivatives

Öz:

In this study, a group of 4-substituted benzoyltaurinamide derivatives were designed, synthesized, and investigated for their anticancer activity against three cancer cell lines and one nontumorigenic cell line by MTT assay. Among the final compounds, methoxyphenyl derivatives 14, 15, 16 were found to be effective against all the tested cancerous cell lines with promising selectivity. The most active compounds were further evaluated to determine the molecular mechanism of their anticancer activity by using western blot assay and the Annexin V-FITC/PI test. Compound 14 (in SH-SY5Y and MDA-MB-231 cell lines) and 15 (in SH-SY5Y cell line) were found to induce intrinsic apoptotic pathway by upregulating BAX, caspase-3, and caspase-9, while downregulating Bcl-2 and Bcl-xL expression levels. According to mechanistic studies, compounds displayed their anticancer activity via three different mechanisms: a. caspase-dependent, b. caspase-independent, and c. caspase-dependent pathway that excluded caspase-9 activation. As a result, this study provides interesting data which can be used to design new taurine-based anticancer derivatives.

Anahtar Kelime:

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

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APA	Akgul O, Erdogan M, Birim D, Kayabasi C, Gunduz C, ARMAGAN G (2020). Design, synthesis, cytotoxic activity, and apoptosis inducing effects of 4- and N-substituted benzoyltaurinamide derivatives. , 1674 - 1693. 10.3906/kim-2009-1
Chicago	Akgul Ozlem,Erdogan Mumin,Birim Dervis,Kayabasi Cagla,Gunduz Cumhur,ARMAGAN GÜLİZ Design, synthesis, cytotoxic activity, and apoptosis inducing effects of 4- and N-substituted benzoyltaurinamide derivatives. (2020): 1674 - 1693. 10.3906/kim-2009-1
MLA	Akgul Ozlem,Erdogan Mumin,Birim Dervis,Kayabasi Cagla,Gunduz Cumhur,ARMAGAN GÜLİZ Design, synthesis, cytotoxic activity, and apoptosis inducing effects of 4- and N-substituted benzoyltaurinamide derivatives. , 2020, ss.1674 - 1693. 10.3906/kim-2009-1
AMA	Akgul O,Erdogan M,Birim D,Kayabasi C,Gunduz C,ARMAGAN G Design, synthesis, cytotoxic activity, and apoptosis inducing effects of 4- and N-substituted benzoyltaurinamide derivatives. . 2020; 1674 - 1693. 10.3906/kim-2009-1
Vancouver	Akgul O,Erdogan M,Birim D,Kayabasi C,Gunduz C,ARMAGAN G Design, synthesis, cytotoxic activity, and apoptosis inducing effects of 4- and N-substituted benzoyltaurinamide derivatives. . 2020; 1674 - 1693. 10.3906/kim-2009-1
IEEE	Akgul O,Erdogan M,Birim D,Kayabasi C,Gunduz C,ARMAGAN G "Design, synthesis, cytotoxic activity, and apoptosis inducing effects of 4- and N-substituted benzoyltaurinamide derivatives." , ss.1674 - 1693, 2020. 10.3906/kim-2009-1
ISNAD	Akgul, Ozlem vd. "Design, synthesis, cytotoxic activity, and apoptosis inducing effects of 4- and N-substituted benzoyltaurinamide derivatives". (2020), 1674-1693. https://doi.org/10.3906/kim-2009-1

APA	Akgul O, Erdogan M, Birim D, Kayabasi C, Gunduz C, ARMAGAN G (2020). Design, synthesis, cytotoxic activity, and apoptosis inducing effects of 4- and N-substituted benzoyltaurinamide derivatives. Turkish Journal of Chemistry, 44(6), 1674 - 1693. 10.3906/kim-2009-1
Chicago	Akgul Ozlem,Erdogan Mumin,Birim Dervis,Kayabasi Cagla,Gunduz Cumhur,ARMAGAN GÜLİZ Design, synthesis, cytotoxic activity, and apoptosis inducing effects of 4- and N-substituted benzoyltaurinamide derivatives. Turkish Journal of Chemistry 44, no.6 (2020): 1674 - 1693. 10.3906/kim-2009-1
MLA	Akgul Ozlem,Erdogan Mumin,Birim Dervis,Kayabasi Cagla,Gunduz Cumhur,ARMAGAN GÜLİZ Design, synthesis, cytotoxic activity, and apoptosis inducing effects of 4- and N-substituted benzoyltaurinamide derivatives. Turkish Journal of Chemistry, vol.44, no.6, 2020, ss.1674 - 1693. 10.3906/kim-2009-1
AMA	Akgul O,Erdogan M,Birim D,Kayabasi C,Gunduz C,ARMAGAN G Design, synthesis, cytotoxic activity, and apoptosis inducing effects of 4- and N-substituted benzoyltaurinamide derivatives. Turkish Journal of Chemistry. 2020; 44(6): 1674 - 1693. 10.3906/kim-2009-1
Vancouver	Akgul O,Erdogan M,Birim D,Kayabasi C,Gunduz C,ARMAGAN G Design, synthesis, cytotoxic activity, and apoptosis inducing effects of 4- and N-substituted benzoyltaurinamide derivatives. Turkish Journal of Chemistry. 2020; 44(6): 1674 - 1693. 10.3906/kim-2009-1
IEEE	Akgul O,Erdogan M,Birim D,Kayabasi C,Gunduz C,ARMAGAN G "Design, synthesis, cytotoxic activity, and apoptosis inducing effects of 4- and N-substituted benzoyltaurinamide derivatives." Turkish Journal of Chemistry, 44, ss.1674 - 1693, 2020. 10.3906/kim-2009-1
ISNAD	Akgul, Ozlem vd. "Design, synthesis, cytotoxic activity, and apoptosis inducing effects of 4- and N-substituted benzoyltaurinamide derivatives". Turkish Journal of Chemistry 44/6 (2020), 1674-1693. https://doi.org/10.3906/kim-2009-1