Exploring the Influence of Spacers in EDTA–β-Cyclodextrin Dendrimers: Physicochemical Properties and In Vitro Biological Behavior
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis
2.2. Characterization
2.3. Availability of the βCD Cavities in EDTA di-βCD (A–C) and EDTA G0-βCD Dendrimers (D–F)
2.4. Determination of Quantitative Water Solubility for EDTA di-βCD (A–C) and EDTA G0-βCD Dendrimers (D–F)
2.5. Dynamic Light Scattering Size Analysis of the EDTA di-βCD (A–C) and EDTA-βCD Dendrimers (D–F)
2.6. Viability Studies
3. Materials and Methods
3.1. General Notes
3.2. Synthetic Procedures
3.2.1. Mono-tosyl-βCD (mOTsβCD)
3.2.2. Mono-azide-βCD (mN3βCD)
3.2.3. General Procedure for the Synthesis of Tert-butyl Carbamate Intermediates (4–6)
Tert-butyl(4-hydroxyphenyl)carbamate (4)
Tert-butyl(4-hydroxybenzyl)carbamate (5)
Tert-butyl(4-hydroxyphenetyl)carbamate (6)
3.2.4. General Procedure for the Synthesis of tert-butyl 4-(Prop-2-yn-1-yloxy)carbamates Intermediaries (7–9)
Tert-butyl (4-(Prop-2-yn-1-yloxy)phenyl)carbamate (7)
Tert-butyl (4-(Prop-2-yn-1-yloxy)benzyl)carbamate (8)
Tert-butyl (4-(Prop-2-yn-1-yloxy)phenetyl)carbamate (9)
3.2.5. General Procedure for the Synthesis of 4-(Prop-2-yn-1-yloxy)amines Intermediaries (10–12)
4-(Prop-2-yn-1-yloxy)aniline (10)
[4-(Prop-2-yn-1-yloxy)phenyl]methanamine (11)
2-(4-(Prop-2-yn-1-yloxy)phenyl)ethan-1-amine (12)
3.2.6. General Procedure for the Synthesis of Disubstituted EDTA Alkynes (13–15)
Disubstituted EDTA Alkyne (13)
Disubstituted EDTA Alkyne (14)
Disubstituted EDTA Alkyne (15)
3.2.7. General Procedure for the Synthesis of Tetrasubstituted EDTA G0-alkyne (16–18)
Tetrasubstituted EDTA G0-Alkyne (16)
Tetrasubstituted EDTA G0-Alkyne (17)
Tetrasubstituted EDTA G0-Alkyne (18)
3.2.8. General Procedure for the Synthesis of Dendritic Compounds EDTA di-βCD (A, B, C)
EDTA2PhCD (A)
EDTA2BenCD (B)
EDTA2TyrCD (C)
3.2.9. General Procedure for the Synthesis of EDTA-βCD Dendrimers (D–F)
EDTA4PhCD Dendrimer (D)
EDTA4BenCD Dendrimer (E)
EDTA4TyrCD Dendrimer (F)
3.3. Job Plot Method
3.4. Determination of Water Solubility for EDTA di-βCD (A–C) and EDTA-βCD Dendrimers (D–F)
3.5. DLS Measurements
3.6. Biological Procedures
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Compound | Solubility (g/mL) | Compound | Solubility (g/mL) |
---|---|---|---|
EDTA2PhCD (A) | 1.582 ± 0.002 | EDTA4PhCD (D) | 1.594 ± 0.003 |
EDTA2BenCD (B) | 1.594 ± 0.001 | EDTA4BenCD (E) | 1.601 ± 0.002 |
EDTA2TyrCD (C) | 1.591 ± 0.003 | EDTA4TyrCD (F) | 1.623 ± 0.002 |
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González-Méndez, I.; Sorroza-Martínez, K.; González-Sánchez, I.; Gracia-Mora, J.; Bernad-Bernad, M.J.; Cerbón, M.; Rivera, E.; Yatsimirsky, A.K. Exploring the Influence of Spacers in EDTA–β-Cyclodextrin Dendrimers: Physicochemical Properties and In Vitro Biological Behavior. Int. J. Mol. Sci. 2023, 24, 14422. https://doi.org/10.3390/ijms241914422
González-Méndez I, Sorroza-Martínez K, González-Sánchez I, Gracia-Mora J, Bernad-Bernad MJ, Cerbón M, Rivera E, Yatsimirsky AK. Exploring the Influence of Spacers in EDTA–β-Cyclodextrin Dendrimers: Physicochemical Properties and In Vitro Biological Behavior. International Journal of Molecular Sciences. 2023; 24(19):14422. https://doi.org/10.3390/ijms241914422
Chicago/Turabian StyleGonzález-Méndez, Israel, Kendra Sorroza-Martínez, Ignacio González-Sánchez, Jesús Gracia-Mora, María Josefa Bernad-Bernad, Marco Cerbón, Ernesto Rivera, and Anatoly K. Yatsimirsky. 2023. "Exploring the Influence of Spacers in EDTA–β-Cyclodextrin Dendrimers: Physicochemical Properties and In Vitro Biological Behavior" International Journal of Molecular Sciences 24, no. 19: 14422. https://doi.org/10.3390/ijms241914422