Supporting information for
Drug-eluting conformal coatings on individual cells
Yu Zhang,† Duo An,† Wei Song,† Yehudah Pardo, †† Minglin Ma†,*
†Department
of Biological and Environmental Engineering, Cornell University, Ithaca,
New York 14853, United States
††Department
of Biomedical Engineering, Cornell University, Ithaca, New York 14853,
United States
* Correspondence and requests for materials should be addressed to M.M. (email:
[email protected])
Synthesis and characterization of 3-maleimidopropionyl chloride
3-maleimidopropionyl chloride was synthesized with a modified method published by
Figueiredo et al and Mantovani et al.1, 2 Typically, beta-alanine (9.27 g) was completely
dissolved in 50 mL acetic acid. Then, maleic anhydride (10.09 g) was dissolved in 50
mL acetic acid and then added drop-wise into beta-alanine solution. The mixture was
stirred at room temperature for one hour (After the addition of maleic anhydride
solution, the colorless transparent solution turned into white suspension). Then, the
mixture was heated at 115 °C for 3 hours (The white suspension dissolved again and
the solution became yellow). Acetic acid was removed by azeotroping with toluene at
66 °C. Then the yellowish solid was dissolved in 50 mL water and the solution was
extracted with ethyl acetate. After rotate evaporation of most of the solvent, the result
solution was left to recrystallization overnight. After the second time of
recrystallization with water and ethyl acetate, 3-maleimidopropionic acid was obtained
as white powder. The
1
H NMR spectrum is shown in Figure S1. Then, 3-
maleimidopropionic acid (0.5 g) was added into thionyl chloride (5 mL), heated to
60 °C to get completely dissolved and left to react overnight. The redundant thionyl
chloride was eliminated by vacuum at 60 °C. 3-maleimidopropionyl chloride was
obtained. The 1H NMR spectrum is shown in Figure S2.
Figure S1. 1H NMR spectrum of 3-maleimidopropionic acid in CDCl3.
Figure S2. 1H NMR spectrum of 3-maleimidopropionyl chloride in CDCl3.
Figure S3. Calibration curve of curcumin absorbance versus concentration.
Figure S4. DLS result of the NPs after the addition of DMSO.
Figure S5. CLSM images of HEK293 cells after being incubated with free FITC or free
rhodamine B.
Figure S6. Bright-field and fluorescent images of the 3T3 fibroblast cells with the
MTM coating of Dex-Chol-Mal-FITC, Dex-SH and Dex-Chol-Mal-Rho.
Figure S7. CLSM images of rat islets after the “MTM” coating with Dex-Chol-MalFITC, Dex-SH and Dex-Chol-Mal-Rho.
Figure S8. Calibration curve of curcumin fluorescence versus concentration.
Figure S9. Stability of the DECC on HEK293 cells after different incubation time
intervals.
1
De Figueiredo, R. M., P. Oczipka, R. Fröhlich, M. Christmann. Synthesis of 4-maleimidobutyric acid
and related maleimides. Synthesis 8:1316-1318, 2008.
2
Mantovani, G., F. Lecolley, L. Tao, L, D. M. Haddleton, J. Clerx, J. J. Cornelissen, K. Velonia. Design
and synthesis of N-maleimido-functionalized hydrophilic polymers via copper-mediated living radical
polymerization: a suitable alternative to PEGylation chemistry. J. Am. Chem. Soc. 127:2996-2973, 2005.