Biological Activity of Some Newly Synthesized Hydrazone Derivatives Derived From (Dicyclopropylmethylene)hydrazone

Abdel‐Motaal, Marwa; Nabil, Ahmed

doi:10.17628/ecb.2018.7.280-287

Cited by 10 publications

(5 citation statements)

References 22 publications

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“…Firstly, p ‐aminoacetophenone was chosen as a precursor for the preparation of linkers to N ‐position (Scheme 1). Hence, p ‐aminoacetophenone was condensed with (dicyclopropylmethylene)hydrazine (Abdel‐Motaal & Nabil, 2018) in refluxing ethanol affording the hydrazone derivative 2 in excellent yield. Next, compound 2 was reacted with tetrabomophthalic anhydride to give the N ‐substituted tetrabromophtalimide derivative 3 .…”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of novel tetrabromophthalimide derivatives as potential tubulin inhibitors endowed with apoptotic induction for cancer treatment

Abdel‐Motaal,

Aldakhili,

Abo Elmaaty

et al. 2024

Drug Development Research

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Although various approaches exist for treating cancer, chemotherapy continues to hold a prominent role in the management of this disease. Besides, microtubules serve as a vital component of the cellular skeleton, playing a pivotal role in the process of cell division making it an attractive target for cancer treatment. Hence, the scope of this work was adapted to design and synthesize new anti‐tubulin tetrabromophthalimide hybrids (3‐17) with colchicine binding site (CBS) inhibitory potential. The conducted in vitro studies showed that compound 16 displayed the lowest IC50 values (11.46 µM) at the FaDu cancer cell lines, whereas compound 17 exhibited the lowest IC50 value (13.62 µM) at the PC3 cancer cell line. However, compound 7b exhibited the lowest IC50 value (11.45 µM) at the MDA‐MB‐468 cancer cell line. Moreover, compound 17 was observed to be the superior antitumor candidate against all three tested cancer cell lines (MDA‐MB‐468, PC3, and FaDu) with IC50 values of 17.22, 13.15, and 13.62 µM, respectively. In addition, compound 17 showed a well‐established upregulation of apoptotic markers (Caspases 3, 7, 8, and 9, Bax, and P53). Moreover, compound 17 induced downregulation of the antiapoptotic markers (MMP2, MMP9, and BCL‐2). Furthermore, the colchicine binding site inhibition assay showed that compounds 15a and 17 exhibited particularly significant inhibitory potentials, with IC50 values of 23.07 and 4.25 µM, respectively, compared to colchicine, which had an IC50 value of 3.89 µM. Additionally, cell cycle analysis was conducted, showing that compound 17 could prompt cell cycle arrest at both the G0‐G1 and G2‐M phases. On the other hand, a molecular docking approach was applied to investigate the binding interactions of the examined candidates compared to colchicine towards CBS of the β‐tubulin subunit. Thus, the synthesized tetrabromophthalimide hybrids can be regarded as outstanding anticancer candidates with significant apoptotic activity.

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Section: Resultsmentioning

confidence: 99%

Design and synthesis of novel tetrabromophthalimide derivatives as potential tubulin inhibitors endowed with apoptotic induction for cancer treatment

Abdel‐Motaal,

Aldakhili,

Abo Elmaaty

et al. 2024

Drug Development Research

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“…Biological experiments were conducted at the Faculty of Pharmacy, Mansoura University. Compound numbers 2 , 3 , and 6 , 7 were synthesised according to previously documented procedures [ 5 , 42 , 43 , 44 , 45 , 46 ].…”

Section: Methodsmentioning

confidence: 99%

“…The products’ anticancer activity was examined using the MTT assay against breast (MCF-7) carcinoma cells, liver (HepG2), and normal WI-38 cells, following the previously reported method [ 38 , 44 , 45 , 46 ]. Experimental details can be found in the Supplementary Materials .…”

Section: Methodsmentioning

confidence: 99%

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Design, Synthesis, and Biological Evaluation of Novel Hydroxamic Acid-Based Organoselenium Hybrids

2023

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We report the design and synthesis of novel hydroxamic acid-tethered organoselenium (OSe) hybrids. Their antimicrobial and anticancer activities were assessed against different microbes (e.g., Candida albicans (C. albicans), Escherichia coli (E. coli), and Staphylococcus aureus (S. aureus)), as well as liver and breast carcinomas. OSe hybrid 8 showed promising anticancer activity, with IC50 = 7.57 ± 0.5 µM against HepG2 and IC50 = 9.86 ± 0.7 µM against MCF-7 cells. Additionally, OSe compounds 8 and 15 exhibited promising antimicrobial activities, particularly against C. albicans (IA% = 91.7 and 83.3) and S. aureus (IA% = 90.5 and 71.4). The minimum inhibitory concentration (MIC) assay confirmed the potential antimicrobial activity of OSe compound 8. OSe compounds 8 and 16 displayed good antioxidant activities compared to vitamin C in the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and the 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid (ABTS) assays. These results indicate that hydroxamic acid-based organoselenium hybrids have promising biological activities such as anticancer, antimicrobial, and antioxidant properties, especially compounds 8, 13, 15, and 16, which warrant further studies.

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“…The DPPH and ABTS in vitro bioassays were used to assess the OSe antioxidant activities following the reported method [ 16 , 19 , 20 , 21 ]. Experimental details can be found in the Supplementary Materials Section S1 .…”

Section: Methodsmentioning

confidence: 99%

Anticancer, Antimicrobial, and Antioxidant Activities of Organodiselenide-Tethered Methyl Anthranilates

2022

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Novel methyl anthranilate-based organodiselenide hybrids were synthesized, and their chemical structures were confirmed by state-of-the-art spectroscopic techniques. Their antimicrobial properties were assessed against Staphylococcus aureus, Escherichia coli, and Candida albicans microbial strains. Moreover, the antitumor potential was estimated against liver and breast carcinomas, as well as primary fibroblast cell lines. The Staphylococcus aureus and Candida albicans strains were more sensitive than Escherichia coli toward the OSe compounds. Interestingly, methyl 2-amino-5-(methylselanyl) benzoate (14) showed similar antifungal activity to the standard drug clotrimazole (IA% = 100%) and manifested promising antibacterial activity against E. coli (IA% = 91.3%) and S. aureus (IA% = 90.5%). Furthermore, the minimum inhibitory concentration experiments confirmed the antimicrobial activity of the OSe 14, which in turn was comparable to clotrimazole and ampicillin drugs. Interestingly, the anticancer properties were more pronounced in the HepG2 cells. The OSe 14 was the most cytotoxic (IC50 = 3.57 ± 0.1 µM), even more than the Adriamycin drug (IC50 = 4.50 ± 0.2 µM), and with therapeutic index (TI) 17 proposing its potential selectivity and safety. Additionally, OSe compounds 14 and dimethyl 5,5′-diselanediylbis(2-aminobenzoate) (5) exhibited promising antioxidants in the 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) in vitro assays with 96%, 92%, 91%, and 86% radical scavenging activities compared to 95% by vitamin C in the DPPH and ABTS assays, respectively. These results point to promising antimicrobial, anticancer, and antioxidant activities of OSe 14 and 5 and warrant further studies.

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Biological Activity of Some Newly Synthesized Hydrazone Derivatives Derived From (Dicyclopropylmethylene)hydrazone

Cited by 10 publications

References 22 publications

Design and synthesis of novel tetrabromophthalimide derivatives as potential tubulin inhibitors endowed with apoptotic induction for cancer treatment

Design and synthesis of novel tetrabromophthalimide derivatives as potential tubulin inhibitors endowed with apoptotic induction for cancer treatment

Design, Synthesis, and Biological Evaluation of Novel Hydroxamic Acid-Based Organoselenium Hybrids

Anticancer, Antimicrobial, and Antioxidant Activities of Organodiselenide-Tethered Methyl Anthranilates

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