Targeting Carbohydrate Mimetics of Tetrahydrofuran-Containing Acetogenins to Prostate Cancer
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis
2.2. Cytotoxicity Data
3. Materials and Methods
3.1. Chemical Synthesis
3.1.1. 6-aminohexyl 4-methylbenzenesulfonate Hydrochloride (7)
3.1.2. Di-tert-butyl(((S)-1-(tert-butoxy)-5-((6-chlorohexyl)amino)-1,5-dioxopentan-2-yl)carbamoyl)-L-glutamate (8)
3.1.3. Tri-tert-butyl (14S,18S)-2,11,16-trioxo-3-thia-10,15,17-triazaicosane-14,18,20-tricarboxylate (9)
3.1.4. (14. S,18S)-2,11,16-trioxo-3-thia-10,15,17-triazaicosane-14,18,20-tricarboxylic Acid (10)
3.1.5. Mannose-thiophene-SS-DUPA (3)
3.1.6. 1-((S)-5-methyl-2-oxo-2,5-dihydro-1H-1λ3-furan-3-yl)-15-(((2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-((undecyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)pentadecan-8-yl (2-(pyridin-2-yldisulfaneyl)ethyl) Carbonate (15)
3.1.7. Mannose-butenolide-SS-DUPA (5)
3.2. Cytotoxicity Measurements
3.2.1. Cell Lines and Cell Number Optimization
3.2.2. IC50 Determination
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Test Compound | LNCaP | PC3 | Selectivity LNCaP/PC-3 |
---|---|---|---|
2 | 0.48 | 0.06 | 0.125 |
3 | 0.81 | 2.1 | 2.6 |
4 | 3.4 | 4.5 | 1.3 |
5 | 4.8 | 58 | 12 |
Doxorubicin | 0.71 | 2.3 | 3.2 |
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Periche, P.G.; Lin, J.; Bhupathiraju, N.V.S.D.K.; Kalidindi, T.; Johnson, D.S.; Pillarsetty, N.; Mootoo, D.R. Targeting Carbohydrate Mimetics of Tetrahydrofuran-Containing Acetogenins to Prostate Cancer. Molecules 2023, 28, 2884. https://doi.org/10.3390/molecules28072884
Periche PG, Lin J, Bhupathiraju NVSDK, Kalidindi T, Johnson DS, Pillarsetty N, Mootoo DR. Targeting Carbohydrate Mimetics of Tetrahydrofuran-Containing Acetogenins to Prostate Cancer. Molecules. 2023; 28(7):2884. https://doi.org/10.3390/molecules28072884
Chicago/Turabian StylePeriche, Patricia Gonzalez, Jacky Lin, Naga V. S. D. K. Bhupathiraju, Teja Kalidindi, Delissa S. Johnson, Nagavarakishore Pillarsetty, and David R. Mootoo. 2023. "Targeting Carbohydrate Mimetics of Tetrahydrofuran-Containing Acetogenins to Prostate Cancer" Molecules 28, no. 7: 2884. https://doi.org/10.3390/molecules28072884