Trigonometric Bundling Disulfide Unit Starship Synergizes More Effectively to Promote Cellular Uptake
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Biological Activity
2.2.1. CCK-8 Assay
2.2.2. Time-Dependent Cellular Uptake of SS1/3-FITC Probe
2.2.3. Concentration-Dependent Cellular Uptake of SS1/3-FITC Probe
2.2.4. Cellular Uptake of SS3-FITC Probe with Thiols Inhibitors
2.2.5. Molecular Dynamics Simulations Analysis
3. Materials and Methods
3.1. General Method
3.2. General Method for Preparation of Probe SS1/3-FITC
3.2.1. Synthesis of 3-(Tert-butyldisulfaneyl)propyl-4-methylbenzenesulfonate (2)
3.2.2. Synthesis of Ethyl 4-(3-(Tert-butyldisulfaneyl)propoxy)benzoate (5a)
3.2.3. Synthesis of Methyl 3,4,5-tris(3-(Tert-butyldisulfaneyl)propoxy)benzoate (5b)
3.2.4. Synthesis of Methyl 6-(4-(3-(Tert-butyldisulfaneyl)propoxy)benzamido) Hexanoate (6a)
3.2.5. Synthesis of Methyl 6-(3,4,5-tris(3-(Tert-butyldisulfaneyl)propoxy)benzamido) Hexanoate (6b)
3.2.6. Synthesis of Tert-butyl (2-(6-(4-(3-(tert-butyldisulfaneyl)propoxy)benzamido)hexan-amido)ethyl)carbamate (7a)
3.2.7. Synthesis of Tert-butyl (2-(6-(3,4,5-tris(3-(tert-butyldisulfaneyl)propoxy)benzamido)hexan-amido)ethyl)carbamate (7b)
3.2.8. Synthesis of SS1-FITC (8a)
3.2.9. Synthesis of SS3-FITC (8b)
3.3. Cell Culture
3.4. Time-Dependent Fluorescence Microscopy Measurement of the Cancer Cells Treated with the SS1-FITC and SS3-FITC Probe
3.5. Concentration-Dependent Fluorescence Microscopy Measurement of the Cancer Cells Treated with the SS1-FITC and SS3-FITC Probe
3.6. CCK-8 Assay
3.7. Fluorescence Microscopy Measurement of the Cancer Cells Pretreated with Thiols Inhibitors
3.8. Molecular Dynamics Simulations
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Wang, L.; Wang, D.; Lei, W.; Sun, T.; Gu, B.; Dong, H.; Taniguchi, Y.; Liu, Y.; Ling, Y. Trigonometric Bundling Disulfide Unit Starship Synergizes More Effectively to Promote Cellular Uptake. Int. J. Mol. Sci. 2024, 25, 7518. https://doi.org/10.3390/ijms25147518
Wang L, Wang D, Lei W, Sun T, Gu B, Dong H, Taniguchi Y, Liu Y, Ling Y. Trigonometric Bundling Disulfide Unit Starship Synergizes More Effectively to Promote Cellular Uptake. International Journal of Molecular Sciences. 2024; 25(14):7518. https://doi.org/10.3390/ijms25147518
Chicago/Turabian StyleWang, Lei, Dezhi Wang, Wenzhuo Lei, Tiantian Sun, Bei Gu, Han Dong, Yosuke Taniguchi, Yichang Liu, and Yong Ling. 2024. "Trigonometric Bundling Disulfide Unit Starship Synergizes More Effectively to Promote Cellular Uptake" International Journal of Molecular Sciences 25, no. 14: 7518. https://doi.org/10.3390/ijms25147518