Design, Synthesis, Anticancer Activity and Molecular Docking of New 1,2,3-Triazole-Based Glycosides Bearing 1,3,4-Thiadiazolyl, Indolyl and Arylacetamide Scaffolds
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Biological Evaluation
2.2.1. Cytotoxic Screening
2.2.2. Structure–Activity Relationship
2.2.3. In Vitro Inhibitory Assessment of EGFRWT, EGFRT790M and HER-2
2.2.4. Detection of Apoptosis and Cell Cycle Analysis
2.3. Molecular Docking Study
3. Experimental Section
3.1. General
3.2. Synthesis of Bromoethyl-1,3,4-Thidiazole Derivative 2 and Azide Derivative 3
3.3. Synthesis of Acetylated O-Glycosides (5,6)
3.4. Synthesis of Deacetylated O-Glycosides (7,8)
3.5. Synthesis of Acetylated O-Glycosides 11–14
3.6. Synthesis of Deacetylated O-Glycosides 15–18
4. Materials and Methods
4.1. In Vitro Cytotoxic Activity
4.2. MTT Cytotoxicity Assay
4.3. Statistical Analysis
4.4. EGFRWT, EGFRT790M and HER-2 Inhibition Assessment
4.5. Detection of Apoptosis and Cell Cycle Analysis
5. Molecular Docking Study
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Compound No. | IC50 (µM) ± SD | |
---|---|---|
HCT-116 | MCF-7 | |
1 | 46.9 ± 0.5 | 18.1 ± 0.2 |
2 | 52.7 ± 0.6 | 14.1 ± 0.3 |
3 | 30.8 ± 0.4 | 1.1 ± 0.1 |
5 | 22.6 ± 0.2 | 13.9 ± 0.2 |
6 | 20.8 ± 0.2 | 10.8 ± 1.5 |
7 | 15.5 ± 0.2 | 0.5 ± 0.0 |
8 | 4.6 ± 0.1 | 4.2 ± 0.1 |
9a | 42.3 ± 0.6 | 24.1 ± 0.3 |
9b | 33.3 ± 0.4 | 26.4 ± 0.3 |
11 | 15.4 ± 0.2 | 0.8 ± 0.0 |
12 | 2.2 ± 0.1 | 5.7 ± 0.1 |
13 | 38.2 ± 0.5 | 34.4 ± 0.4 |
14 | 33.8 ± 0.3 | 35.3 ± 0.3 |
15 | 11.4 ± 0.3 | 0.6 ±0.0 |
16 | 35.7 ± 0.4 | 20.3 ± 0.9 |
17 | 26.5 ± 0.3 | 30.1 ± 0.4 |
18 | 28.8 ± 0.1 | 31.6 ± 0.5 |
Doxorubicin | 12.1 ± 0.2 | 9.4 ± 0.1 |
Compounds | IC50 (Mean ± SEM) (µM) | ||
---|---|---|---|
EGFRWT | EGFRT790M | HER-2 | |
7 | 0.30 ± 0.01 | 1.12 ± 0.55 | 2.25 ± 0.30 |
8 | 0.38 ± 0.05 | 1.95 ± 0.02 | 2.77 ± 0.13 |
11 | 6.45 ± 0.10 | 11.80 ± 0.05 | 8.60 ± 0.20 |
12 | 12.70 ± 0.15 | 15.22 ± 0.20 | 18. 40 ± 0.12 |
15 | 0.21 ± 0.05 | 1.50 ± 0.11 | 2.18 ± 0.42 |
Erlotinib | 0.13 ± 0.01 | 0.62 ± 0.10 | 1.40 ± 0.05 |
Compd. | Apoptosis | Necrosis | ||
---|---|---|---|---|
Total | Early | Late | ||
7/MCF-7 | 34.61 | 4.39 | 18.81 | 11.41 |
15/MCF-7 | 42.45 | 2.69 | 25.48 | 14.28 |
Cont./MCF-7 | 1.99 | 0.46 | 0.28 | 1.25 |
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Elganzory, H.H.; Alminderej, F.M.; El-Bayaa, M.N.; Awad, H.M.; Nossier, E.S.; El-Sayed, W.A. Design, Synthesis, Anticancer Activity and Molecular Docking of New 1,2,3-Triazole-Based Glycosides Bearing 1,3,4-Thiadiazolyl, Indolyl and Arylacetamide Scaffolds. Molecules 2022, 27, 6960. https://doi.org/10.3390/molecules27206960
Elganzory HH, Alminderej FM, El-Bayaa MN, Awad HM, Nossier ES, El-Sayed WA. Design, Synthesis, Anticancer Activity and Molecular Docking of New 1,2,3-Triazole-Based Glycosides Bearing 1,3,4-Thiadiazolyl, Indolyl and Arylacetamide Scaffolds. Molecules. 2022; 27(20):6960. https://doi.org/10.3390/molecules27206960
Chicago/Turabian StyleElganzory, Hussein H., Fahad M. Alminderej, Mohamed N. El-Bayaa, Hanem M. Awad, Eman S. Nossier, and Wael A. El-Sayed. 2022. "Design, Synthesis, Anticancer Activity and Molecular Docking of New 1,2,3-Triazole-Based Glycosides Bearing 1,3,4-Thiadiazolyl, Indolyl and Arylacetamide Scaffolds" Molecules 27, no. 20: 6960. https://doi.org/10.3390/molecules27206960