Amphiphilic or lipophilic polar functionalized fullerenes and their uses

• US 8,241,648 B2
• Filed: 03/03/2008
• Issued: 08/14/2012
• Est. Priority Date: 03/02/2007
• Status: Active Grant

• Current Assignee: Luna Labs USA LLC
• Original Assignee: Luna Innovations, Inc.
• Inventors: Zhou, Zhiguo, Lenk, Robert P., Macfarland, Darren, Walker, Kenneth L., Zhang, Jing, Wilson, Stephen R.
• Primary Examiner(s): Padmanabhan, Sreeni
• Assistant Examiner(s): Betton, Timothy E
• Application Number:
  US12/073,230
• Publication Number:
  US 20080213324A1
• Time in Patent Office: 1,625 Days
• Field of Search: 424/401
• US Class Current: 424/401
• CPC Class Codes: A61K 2300/00 Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
• CPC Class Codes: A61K 31/661 Phosphorus acids or esters thereof not having P—C bonds, e.g. fosfosal, dichlorvos, malathion or mevinphos
• CPC Class Codes: A61K 38/28 Insulins
• CPC Class Codes: A61K 8/0208 Tissues; Wipes; Patches
• CPC Class Codes: A61K 8/19 containing inorganic ingredients
• CPC Class Codes: A61K 9/0014 Skin, i.e. galenical aspects of topical compositions non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00
• CPC Class Codes: A61K 9/1271 Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers liposome as conjugate A61K47/6911
• CPC Class Codes: A61P 27/14 Decongestants or antiallergics
• CPC Class Codes: A61Q 1/02 Preparations containing skin colorants, e.g. pigments preparations in powder form A61Q1/12
• CPC Class Codes: A61Q 13/00 Formulations or additives for perfume preparations essential oils or perfumes per se C11B9/00
• CPC Class Codes: A61Q 19/007 Preparations for dry skin
• CPC Class Codes: A61Q 5/02 Preparations for cleaning the hair
• CPC Class Codes: A61Q 9/00 Preparations for removing hair or for aiding hair removal

Abstract

Described herein are synthetically modified fullerene molecules, wherein the fullerene is preferably ellipsoid in shape with an equatorial band and two opposing poles, comprising an adduct at one or both poles, at least one adduct being a hydrophobic chemical moiety capable of anchoring the fullerene on or in a lipid membrane.

Claims

1. A synthetically modified fullerene molecule having the formula

Z_m—

F—

Y_n;

wherein F is fullerene of formula C_p, the fullerene having two opposing poles and an equatorial region;

Z and Y are positioned near respective opposite poles of C_p;

m=1-5 and Z is a hydrophilic chemical moiety;

n=1-5 and Y is a lipophilic chemical moiety;

p=60-120 and p is an even number.

2. The synthetically modified fullerene of claim 1, wherein each chemical moiety Z is composed of formula A_rB in which A is a hydrophilic chemical moiety, r=1-4, and B is a chemical linker connecting said A to the fullerene, and each chemical moiety Y is composed of formula DE_v in which E is a lipophilic chemical moiety and, v=1-4, and D is a chemical linker connecting the lipophilic chemical moiety to the fullerene.

3. The synthetically modified fullerene of claim 1, wherein F is a prolate ellipsoid shaped fullerene having a major axis and said poles are located at opposing ends of the major axis of the prolate ellipsoid fullerene.

4. The synthetically modified fullerene of claim 1, wherein Z and Y are configured such that when the molecule is contacted with a lipid bilayer in an aqueous medium, the equatorial region of F is selectively located within or in close proximity to the bilayer.

5. The synthetically modified fullerene of claim 2, wherein Z and Y are configured such that when the molecule is contacted with a lipid bilayer in an aqueous medium, the equatorial region of F is selectively located within or in close proximity to the bilayer.

6. The synthetically modified fullerene of claim 1, wherein the molecule in an extended configuration has an aspect ratio of about 2.1 to 15, and a diameter less than about 2 nm.

7. The synthetically modified fullerene of claim 2, wherein the molecule in an extended configuration has an aspect ratio of about 2.1 to 15, and a diameter less than about 2 nm.

8. The synthetically modified fullerene of claim 1, wherein p=60.

9. The synthetically modified fullerene of claim 1, wherein p=70.

10. A therapeutic or cosmetic composition comprising the synthetically modified fullerene of claim 1 uniformly dispersed within phospholipid bilayers.

11. A composition of claim 10, in which the molar ratio of fullerene to phospholipid is from about 1:

10 to 1;

2.

12. A topical composition in the form of a ointment, cream, lotion, moisturized patch or moisture-free patch, shampoo, gel, rinse, face lotion, milky lotion, paste, shaving cream, foundation, cologne, or pack comprising a synthetically modified fullerene according to claim 1.

13. A synthetic fullerene molecule having the formula Z(C₇₀)Y;

wherein Y is a lipophilic moiety covalently connected to C₇₀, optionally through a linking group, near a pole thereof, and wherein Z is a hydrophilic moiety covalently connected to C₇₀, optionally through a linking group, at or near a pole opposite to said Y; and

, wherein said lipophilic moiety Y is capable of anchoring the synthetic fullerene molecule to a lipid membrane.

14. A composition comprising a plurality of synthetic fullerene molecules according to claim 13 uniformly dispersed in phospholipids.

15. A topical composition in the form of a ointment, cream, lotion, moisturized patch or moisture-free patch, shampoo, gel, rinse, face lotion, milky lotion, paste, shaving cream, foundation, cologne, or pack comprising a synthetic fullerene molecule according to claim 13.

16. A composition comprising in a pharmaceutically acceptable medium, a synthetic fullerene molecule according to claim 13 and another pharmaceutical molecule.

17. The composition of claim 16, wherein the pharmaceutical molecule is insulin.