Nitric oxide-releasing S-nitrosothiol-modified silica particles and methods of making the same
View Patent ↗Provided according to some embodiments of the invention are methods of forming co-condensed silica particles. In some embodiments, the methods include reacting a thiol-containing silane and a backbone alkoxysilane in a reaction solution that comprises water to form thiol-functionalized co-condensed silica particles, wherein the thiol-functionalized co-condensed silica particles include a polysiloxane matrix and at least some of thiol groups are present within the polysiloxane matrix; and reacting the thiol-functionalized co-condensed silica particles with a nitrosating agent to provide the S-nitrosothiol-functionalized co-condensed silica particles. In some embodiments, provided are S-nitrosothiol-functionalized co-condensed silica particles.
1. S-nitrosothiol-functionalized co-condensed silica particles having an NO storage in a range of about 0.01 μmol to about 10 μmol NO per mg particle.
2. The S-nitrosothiol-functionalized co-condensed silica particles of claim 1 , wherein the particles have an NO storage in a range of about 0.09 μmol to about 4.40 μmol NO per mg particle.
3. The S-nitrosothiol-functionalized co-condensed silica particles of claim 1 , wherein the particles comprise a polysiloxane matrix and have at least some nitrosothiol functional groups distributed within the polysiloxane matrix.
4. The S-nitrosothiol-functionalized co-condensed silica particles of claim 1 , wherein the S-nitrosothiol functional groups comprise primary nitrosothiol functional groups.
5. The S-nitrosothiol-functionalized co-condensed silica particles of claim 1 , wherein the S-nitrosothiol functional groups comprise tertiary nitrosothiol functional groups.
6. S-nitrosothiol-functionalized monodisperse co-condensed silica particles having an average particle diameter in a range of about 200 nm to about 700 nm.
7. The S-nitrosothiol-functionalized co-condensed silica particles of claim 6 , wherein the particles comprise a polysiloxane matrix and have at least some nitrosothiol functional groups distributed within the polysiloxane matrix.
8. The S-nitrosothiol-functionalized co-condensed silica particles of claim 6 , wherein the S-nitrosothiol functional groups comprise primary nitrosothiol functional groups.
9. The S-nitrosothiol-functionalized co-condensed silica particles of claim 6 , wherein the S-nitrosothiol functional groups comprise tertiary nitrosothiol functional groups.
10. The S-nitrosothiol-functionalized co-condensed silica particles of claim 6 , wherein the particles are formed from the condensation of a thiol-containing silane and a backbone alkoxysilane.
11. The S-nitrosothiol-functionalized co-condensed silica particles of claim 10 , wherein the thiol-containing silane is a tertiary thiol-containing silane.
12. A method of forming the S-nitrosothiol-functionalized monodisperse co-condensed silica particles of claim 6 , the method comprising:
reacting a thiol-containing silane and a backbone alkoxysilane in a sol precursor solution that comprises water to form thiol-functionalized co-condensed silica particles, wherein the thiol-functionalized co-condensed silica particles comprise a polysiloxane matrix and at least some of thiol groups are present within the polysiloxane matrix; and
reacting the thiol-functionalized co-condensed silica particles with a nitrosating agent to provide the S-nitrosothiol-functionalized monodisperse co-condensed silica particles.
13. The method of claim 12 , wherein the thiol-containing silane comprises a primary thiol-containing silane.
14. The method of claim 13 , wherein the primary thiol-containing silane is mercaptopropyltrimethoxysilane and the backbone alkoxysilane is tetraethoxysilane.
15. The method of claim 13 , wherein the primary thiol-containing silane comprises mercaptopropyltrimethoxysilane and the backbone alkoxysilane comprises tetramethoxysilane.
16. The method of claim 15 , wherein the sol precursor solution comprises an ammonia catalyst at a concentration in a range of about 1.9 to about 5.5 M;
wherein the total silane monomer concentration in the sol precursor solution is in a range of about 0.1 M to about 0.4 M;
wherein the total silane monomer concentration comprises about 25 to about 85 mol % mercaptopropyltrimethoxysilane; and
wherein the water is present in the sol precursor solution at a concentration in a range of about 8.0 to about 32.5 M.
17. The method of claim 12 , wherein the thiol-containing silane comprises a tertiary thiol-containing silane.
18. The method of claim 17 , wherein the tertiary thiol-containing silane comprises a tertiary thiol having the following structure:
wherein R, R′ and R″ are each independently alkyl and n is in a range of 0 to 10.
19. The method of claim 18 , wherein the tertiary thiol-containing silane has the following structure:
20. The method of claim 18 , wherein the backbone alkoxysilane comprises tetraethoxysilane.
21. The method of claim 12 , wherein the thiol-functionalized co-condensed silica particles are sonicated prior to reacting the thiol-functionalized co-condensed silica particles with a nitrosating agent.