Design of Engineered Cyclodextrin Derivatives for Spontaneous Coating of Highly Porous Metal-Organic Framework Nanoparticles in Aqueous Media
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials
2.2. Synthesis of 1-O-propargyl-13-O-acetyl-1,4,7,10,13-pentaoxatridecane (3)
2.3. Synthesis of Heptakis{6-deoxy-6-[4′-(2″,3″,4″,6″-tetra-O-acetyl-α-d-mannopyranosyloxymethyl)-1H- 1,2,3-triazol-1′-yl]}cyclomaltoheptaose (5)
2.4. Synthesis of Heptakis(6-deoxy-6-{4′-[14″-O-acetyl-(2″,5″,8″,11″,14″-pentaoxatetradecyl)]-1H-1,2,3-tri- azol-1′-yl})cyclomaltoheptose (6)
2.5. Synthesis of Heptakis(6-deoxy-6-{4′-[14″-O-(2‴,3‴,4‴,6‴-tetra-O-acetyl-α-d-mannopyranosyl)-2″, 5″,8″,11″,14″-pentaoxatetradecyl]-1H-1,2,3-triazol-1′-yl})cyclomaltoheptose (7)
2.6. Synthesis of Heptakis{6-deoxy-6-[4′-(α-d-mannopyranosyloxymethyl)-1H-1,2,3-triazol-1′-yl]}cyclomal- toheptaose Phosphate Sodium Salt (8)
2.7. Synthesis of Heptakis{6-deoxy-6-[4′-(13″-hydroxy-2″,5″,8″,11″-tetraoxatridecyl)-1H-1,2,3-triazol-1′- yl]}cyclomaltoheptose Phosphate Sodium Salt (9)
2.8. Synthesis of Heptakis{6-desoxi-6-{4′-[14″-O-(α-d-mannopyranosyl)-2″,5″,8″,11″,14″-pentaoxatetrade- cyl]-1H-1,2,3-triazol-1′-yl}}ciclomaltoheptose Phosphate Sodium Salt (10)
2.9. Synthesis of Heptakis(6-O-tert-butyldimethylsilyl)cyclomaltoheptaose (11)
2.10. Synthesis of 1-azido-1-deoxy-ω-O-methoxypentatetraconta(ethylene glycol) (14)
2.11. Synthesis of Heptakis{2,3-di-O-{1′-[methoxypentatetraconta(ethylene glycol)yl-1H-1,2,3-triazol-4′-yl]- methyl}}cyclomaltoheptaose (15)
2.12. Synthesis of Heptakis{2,3-di-O-{1′-[methoxypentatetraconta(ethylene glycol)yl-1H-1,2,3-triazol-4′-yl]- methyl}}cyclomaltoheptaose Phosphate Sodium Salt (16)
2.13. Synthesis and Characterization of MIL-100(Fe) nanoMOFs
2.14. Surface Modification of MIL-100(Fe) nanoMOFs and Their Characterization
2.15. Quantification of nanoMOFs Uptake by Macrophage Cells
2.16. Surface Modification of Doxorubicin (DOX)-Loaded MIL-100(Fe) Nanomofs with 9
2.17. Isothermal Titration Calorimetry (ITC) Measurements
3. Results and Discussion
3.1. Synthesis of Phosphate β-CD Derivatives (PCDs)
3.2. MIL-100(Fe) nanoMOFs Synthesis and Surface Modification
3.3. ITC Experiments on ConA Biorecognition
3.4. Interactions of Surface-Modified nanoMOFs with a Macrophage Cell Line
3.5. DOX-Loaded MIL-100(Fe) nanoMOFs Surface Modification
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Abbreviations
β-CD | β-cyclodextrin |
CD-P | β-cyclodextrin phosphate sodium salt |
ConA | concanavalin A |
DMAP | 4-dimethylaminopyridine |
DMEM | Dulbecco’s modified Eagle’s medium |
DMF | dimethylformamide |
DOX | doxorubicin |
EtOAc | ethyl acetate |
FBS | fetal bovine serum |
HR-ICP-MS | high resolution inductively couples plasma mass spectrometry |
ITC | isothermal titration calorimetry |
MALDI-TOF-MS | matrix-assisted laser desorption/ionization time-of-flight mass spectrometry |
MWCO | molecular weight cut-off |
NaAsc | (+)-sodium l-ascorbate |
nanoMOFs | nanosized metal-organic frameworks |
PCDs | phosphorylated β-CD derivatives |
PEG | polyethylene glycol |
TEG | tetraethylene glycol |
TEM | transmission electron microscopy |
TLC | thin-layer chromatography |
XRDP | X-ray diffraction patterns |
ZP | zeta potential |
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Conjugate | N a | K × 10−5 (M−1) | ΔG0 (kcal mol−1) | ΔH (kcal mol−1) | TΔS0 (kcal mol−1) |
---|---|---|---|---|---|
8b | 2.44 ± 0.01 | 2.25 ± 0.08 | −7.30 ± 0.02 | −14.49 ± 0.06 | −7.19 |
10b | 2.79 ± 0.01 | 5.12 ± 0.25 | −7.79 ± 0.03 | −13.96 ± 0.07 | −6.17 |
nanoMOFs@8 c | 0.90 ± 0.01 | 14.20 ± 1.64 | −8.39 ± 0.07 | −334.20 ± 6.91 | −325.81 |
nanoMOFs@10 c | 1.06 ± 0.01 | 24.50 ± 1.17 | −8.72 ± 0.03 | −314.10 ± 3.37 | −305.38 |
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Cutrone, G.; Li, X.; Casas-Solvas, J.M.; Menendez-Miranda, M.; Qiu, J.; Benkovics, G.; Constantin, D.; Malanga, M.; Moreira-Alvarez, B.; Costa-Fernandez, J.M.; et al. Design of Engineered Cyclodextrin Derivatives for Spontaneous Coating of Highly Porous Metal-Organic Framework Nanoparticles in Aqueous Media. Nanomaterials 2019, 9, 1103. https://doi.org/10.3390/nano9081103
Cutrone G, Li X, Casas-Solvas JM, Menendez-Miranda M, Qiu J, Benkovics G, Constantin D, Malanga M, Moreira-Alvarez B, Costa-Fernandez JM, et al. Design of Engineered Cyclodextrin Derivatives for Spontaneous Coating of Highly Porous Metal-Organic Framework Nanoparticles in Aqueous Media. Nanomaterials. 2019; 9(8):1103. https://doi.org/10.3390/nano9081103
Chicago/Turabian StyleCutrone, Giovanna, Xue Li, Juan M. Casas-Solvas, Mario Menendez-Miranda, Jingwen Qiu, Gábor Benkovics, Doru Constantin, Milo Malanga, Borja Moreira-Alvarez, José M. Costa-Fernandez, and et al. 2019. "Design of Engineered Cyclodextrin Derivatives for Spontaneous Coating of Highly Porous Metal-Organic Framework Nanoparticles in Aqueous Media" Nanomaterials 9, no. 8: 1103. https://doi.org/10.3390/nano9081103