Mesoporous nitric oxide-releasing silica particles, methods of making, and uses thereof
Nitric oxide-releasing materials, methods of making nitric oxide-releasing materials, and uses of nitric oxide-releasing materials are provided. The nitric oxide-releasing materials include a mesoporous silica core and an outer surface having a plurality of nitric oxide donors. In an exemplary aspects, the nitric oxide-releasing material includes a mesoporous diatomaceous earth core, and an outer surface having a plurality of S-nitroso-N-acetyl-penicillamine groups covalently attached thereto. Uses of the nitric oxide-releasing materials can include coatings for medical devices such as catheters, grafts, and stents; wound gauzes; acne medications; and antiseptic mouthwashes; among others.
1. A nitric oxide-releasing material comprising:
a mesoporous diatomaceous earth core having an outer surface with an aminosilane covalently bonded to the outer surface, wherein the aminosilane is covalently bonded to the outer surface of the mesoporous diatomaceous earth core by a silicon atom of the aminosilane; and
a S-nitroso-N-acetyl-penicillamine group covalently bonded to the amino group of the aminosilane,
wherein the S-nitroso-N-acetyl-penicillamine group covalently bonded to the amino group of the aminosilane has the following formula
where A is the S-nitroso-N-acetyl-penicillamine group;
where R 1 is a substituted or unsubstituted C 1 -C 20 alkyl, a substituted or unsubstituted C 1 -C 20 heteroalkyl, a substituted or unsubstituted C 2 -C 20 alkenyl, a substituted or unsubstituted C 2 -C 20 herteroalkenyl, a substituted or unsubstituted C 1 -C 20 alkoxy, or a substituted or unsubstituted C 1 -C 20 heteroalkoxy;
where each occurrence of R 2 is independently a substituted or unsubstituted C 1 -C 20 alkyl, a substituted or unsubstituted C 1 -C 20 heteroalkyl, a substituted or unsubstituted C 2 -C 20 alkenyl, a substituted or unsubstituted C 2 -C 20 herteroalkenyl, a substituted or unsubstituted C 1 -C 20 alkoxy, a substituted or unsubstituted C 1 -C 20 heteroalkoxy, or a bond to an oxygen atom on the outer surface of the mesoporous diatomaceous earth core wherein at least one occurrence of R 2 is a bond to an oxygen atom on the outer surface of the mesoporous diatomaceous earth core.
2. The nitric oxide-releasing material according to claim 1 , wherein the nitric oxide-releasing material has a nitric oxide content of about 0.025 μmol to about 0.05 μmol per mg of the nitric oxide-releasing material.
3. The nitric oxide-releasing material according to claim 1 , wherein the nitric oxide-releasing material has a half-life for nitric oxide release of about 20 hours to about 40 hours.
4. The nitric oxide-releasing material according to claim 1 , wherein the nitric oxide-releasing material has an average pore size of about 300 nm to about 600 nm.
5. The nitric oxide-releasing material according to claim 1 , wherein the nitric oxide-releasing material is a particle having a longest dimension of about 10 μm to about 20 μm.
6. The nitric oxide-releasing material according claim 1 , wherein R 1 is a substituted or unsubstituted C 1 -C 12 alkyl.
7. The nitric oxide-releasing material according claim 1 , wherein the aminosilane is 3-aminopropyl)triethoxysilane (APTES), N-(6-aminohexyl)aminomethyltriethoxysilane (AHAMTES), or 3-aminopropyldimethylethoxysilane (APDMES).
8. The nitric oxide-releasing material according claim 1 , wherein the aminosilane is 3-aminopropyl)triethoxysilane (APTES).
9. A medical device having at least one surface, wherein the surface comprises the nitric oxide-releasing material having a structure according to claim 1 .
10. The medical device according to claim 9 , wherein the medical device is a urinary catheter, a vascular catheter, a graft, a stent, or a hydrogel strip.