Lipid-based nitric oxide donors
Abstract
Novel nitric-oxide releasing lipid molecules are provided which comprise a lipid molecule selected from (a) phosphoglycerides, (b) lipids having a sphingosine base as a backbone, (c) monoacylglyerols, (d) diacylglycerols, (e) glycosylacylglycerols, and (f) sterol compounds of the formula: where R is a branched aliphatic chain of eight or more carbon atoms, wherein the lipid molecule is provided with a nitric-oxide containing group which comprises (a) a —S—N═O moiety, (b) a —O—N═O moiety, or (c) a moiety. Also provided are methods of forming such nitric oxide releasing lipid molecules. Various pharmaceutical compositions, topical liquids and drug delivery systems comprising the nitric-oxide releasing lipid molecules are also described. Further provided are methods for therapeutically administering nitric oxide to patients, methods of treating or preventing various conditions, methods for promoting wound healing and methods of reducing the cells present in an atherosclerotic lesion, which methods utilize the nitric-oxide releasing lipid molecules.
Claims
exact text as granted — not AI-modified1 . A nitric oxide releasing compound comprising:
a lipid molecule selected from (a) lipids having a sphingosine base as a backbone, (b) monoacylglyerols, (c) diacylglycerols, (d) glycosylacylglycerols, and (e) sterol compounds of the formula:
where R is a branched aliphatic chain of eight or more carbon atoms,
said lipid molecule provided with a nitric-oxide containing group which comprises (a) a —S—N═O moiety, (b) a —O—N═O moiety, or (c) a
moiety.
2 . The compound of claim 1 , wherein the lipid molecule is said lipid having a sphingosine base as a backbone.
3 . The compound of claim 2 , wherein the lipid having a sphingosine base as a backbone is N,N,N-trimethylsphingosine.
4 . The compound of claim 2 , wherein the lipid having a sphingosine base as a backbone is a sphingolipid.
5 . The compound of claim 4 , wherein the sphingolipid is a ganglioside.
6 . The compound of claim 1 , wherein the lipid molecule is said sterol compound.
7 . The compound of claim 6 , wherein said sterol compound is cholesterol.
8 . The compound of claim 1 , wherein said nitric-oxide containing group comprises a —S—N═O moiety.
9 . The compound of claim 1 , wherein said nitric-oxide containing group comprises a —O—N═O moiety.
10 . The compound of claim 1 , wherein said nitric-oxide containing group comprises a
moiety.
11 . The compound of claim 10 , wherein said nitric-oxide containing group comprises a
moiety.
12 . The compound of claim 11 , wherein said nitric-oxide containing group comprises a
moiety.
13 . A pharmaceutical composition comprising at least 0.001 wt % of the compound of claim 1 .
14 . A pharmaceutical composition comprising at least 0.01 wt % of the compound of claim 1 .
15 . A pharmaceutical composition comprising at least 0.1 wt % of the compound of claim 1 .
16 . A pharmaceutical composition comprising at least 1 wt % of the compound of claim 1 .
17 . A pharmaceutical composition comprising at least 10 wt % of the compound of claim 1 .
18 . A pharmaceutical composition comprising at least 90 wt % of the compound of claim 1 .
19 . A method of forming a nitric oxide releasing lipid molecule comprising:
providing a lipid molecule having a nucleophilic moiety selected from a thiol moiety, an amine moiety and an alcohol moiety, said lipid molecule selected from (a) lipids having a sphingosine base as a backbone, (b) monoacylglyerols, (c) diacylglycerols, (d) glycosylacylglycerols, and (e) sterol compounds of the formula:
where R is a branched aliphatic chain of eight or more carbon atoms; and supplying said lipid molecule with a nitric-oxide containing group at a position corresponding to said nucleophilic moiety, said nitric-oxide containing group comprising a —S—N═O moiety, a —O—N═O moiety, or a
moiety.
20 . The method of claim 19 , wherein the lipid molecule is said lipid having a sphingosine base as a backbone.
21 . The method of claim 19 , wherein the lipid molecule is said sterol compound.
22 . The method of claim 19 , wherein said nitric-oxide containing group comprises a —S—N═O moiety.
23 . The method of claim 19 , wherein said nitric-oxide containing group comprises a —O—N═O moiety.
24 . The method of claim 19 , wherein said nitric-oxide containing group comprises a
moiety.
25 . The method of claim 19 , wherein said nitric-oxide containing group comprises a
moiety.
26 . The method of claim 19 , wherein an alcohol moiety on said lipid molecule is converted to a group comprising a thiol moiety prior to supplying said lipid molecule with said nitric-oxide containing group.
27 . The method of claim 26 , wherein an —S—N═O moiety is formed on said lipid molecule at a position corresponding to said thiol moiety.
28 . A topical liquid comprising the compound of claim 1 .
29 . A topical liquid selected from the group consisting of a solution, a dispersion, a spray, a lotion, a gel, a cream and an ointment, said topical liquid comprising the compound of claim 1 .
30 . A method for therapeutically administering nitric oxide to a patient comprising
administering the compound of claim 1 to said patient, wherein the compound is administered within the body, and wherein the compound is administered by direct injection.
31 . A liposome comprising the compound of claim 1 .Join the waitlist — get patent alerts
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