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US 12,460,050 B2Granted
Nitric oxide-releasing hyperbranched compounds as antibacterial scaffolds and methods pertaining thereto
AssigneeThe University of North Carolina at Chapel Hill
InventorsMark H. Schoenfisch, Lei Yang, Haibao Jin
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Abstract
Several embodiments of hyperbranched structures are disclosed. In some embodiments, the hyperbranched structures are covalently modified to store and release nitric oxide. Some embodiments pertain to methods of making and also to the use of hyperbranched structures. The covalently modified hyperbranched structures may be tailored to release nitric oxide in a controlled manner and are useful for eradication of both gram positive and gram negative bacteria as well as other microbes.
Claims13
A hyperbranched nitric oxide (NO) donating compound, comprising:
- a linking group comprising any one or more of Formulas A, B, C, or D:
- wherein,
- indicates an attachment to another portion of the hyperbranched NO donating compound;
- X1, X2, X3, and X4 are independently selected from the group consisting of —NH—, —N(Ra)—, —O—, and —S—;
- wherein, at least one instance of X1, X2, X3, and X4 is —N(Ra)—;
- wherein each instance of Ra is selected from a NO donating moiety, —H, an optionally substituted C1-C6 alkyl group, or an optionally substituted polyether having 1 to 6 to repeat units;
- wherein, in at least one instance of Formula A, the secondary amine of Formula A is directly bound to a NO donating moiety or at least one instance of Ra is a NO donating moiety, wherein the NO donating moiety is selected from the group consisting of:
- R1, R2, and R3 are independently selected from the group consisting of —RbN(Rc)Rd—(N(Rc))n—Rb—, —Rb(ORd—)nO—Rb—, and C1-C6 alkyl;
- wherein each instance of Rc is independently selected from a NO donating moiety, —H, an optionally substituted C1-C6 alkyl group, or an optionally substituted poly ether having 1 to 6 repeat units;
- wherein Rb is a single bond or an optionally substituted C1-C6 alkylene group;
- wherein Ra is an optionally substituted C1-C6 alkylene group;
- wherein n is an integer selected from 0, 1, 2, 3, 4, 5, or 6;
- wherein, where R2 is present, at least one instance of Rd comprises the —C(O)—(CH2)2—X3— group;
- wherein, where R3 is present, at least one instance of Rd comprises the —C(O)—(CH2)2—X3— group and at least one instance of Rd comprises the —C(O)—(CH2)2—X4— group;
- and,
- wherein the hyperbranched compound does not comprise an aminoglycoside or glycoside unit.
13 more elements
Dependencies are inferred from the claim text.