Sulfur-containing phospholipid derivatives
The present invention provides a lipid compound comprising at least one non-polar moiety and a polar moiety, wherein each or at least one non-polar moiety is of the formula X—Y—Z—, wherein X is a hydrocarbyl chain, Y is selected from at least one of S, Se, SO 2 , SO, and O, and Z is an optional hydrocarbyl group, wherein the polar moiety is of the formula —[C(O)] m PHG, wherein PHG is a polar head group, and wherein m is the number of non-polar moieties.
1. A compound chosen from
2. A method for the production of a lipid compound according to claim 1 , wherein said compound is chosen from
the method comprising:
(a) combining an unsaturated analogue of tetradecylthioacetic acid (TTA 3) chosen from dTTA 4 or tTTA 5 with N,N′-carbonyldiimidazolide (CDI) to form an imidazolide;
(b) combining the imidazolide of step (a) with sn-Glycero-3-phosphocholine (GPC) cadmium (II) adduct (GPC.CdC 2 ) to form a phosphatidylcholine derivative; and
(c) subjecting the phosphatidylcholine derivative of step (b) to enzymatic transphosphatidylation to form said compound.
3. A method for the production of a lipid compound according to claim 1 , wherein said compound is chosen from
the method comprising combining an unsaturated analogue of tetradecylthioacetic acid (TTA 3) chosen from dTTA 4 or tTTA 5 with glycerol.
4. A combination comprising a liposome and a compound according to claim 1 .
5. A method for the production of a lipid compound according to claim 1 , wherein said compound is chosen from
the method comprising:
(a) combining an unsaturated analogue of tetradecylthioacetic acid (TTA 3) chosen from dTTA 4 or tTTA 5 with N,N′-carbonyldiimidazolide (CDI) to form an imidazolide; and
(b) combining the imidazolide of step (a) with sn-Glycero-3-phosphocholine (GPC) cadmium (II) adduct (GPC.CdCl 2 ) to form said compound.
6. A cosmetic formulation comprising a lipid compound according to claim 1 .
7. A pharmaceutical composition comprising a compound according to claim 1 .
8. A method of treating a condition chosen from syndrome X, obesity or an overweight condition, hypertension, fatty liver, diabetes, hyperglycaemia, hyperinsulinemia, insulin resistance, hyperlipidemia, hypercholesterolemia, hypertriglyceridemia (HTG), and stenosis, comprising administering to a subject in need thereof an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
9. The method according to claim 8 , for producing weight loss or a reduction of fat mass in a human or non-human animal in need thereof.
10. A method for the treatment of inflammatory disorders, comprising administering to a subject in need thereof an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
11. A method of lowering concentration of cholesterol and triglycerides in the blood of mammals and/or inhibiting the oxidative modification of low density lipoprotein, comprising administering to a subject in need thereof an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
12. A method for producing weight loss or a reduction of the fat mass in a human or non-human animal in need thereof, comprising administering thereto an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
13. A method for the modification of the fat distribution and content of animals, comprising administering to a subject in need thereof an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
14. A method of inhibiting the growth of tumours, comprising administering to a subject in need thereof an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
15. A method for the treatment or inhibition of primary and secondary metastatic neoplasms, comprising administering to a subject in need thereof an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
16. A method for the treatment of proliferative skin disorders, comprising administering to a subject in need thereof an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
17. A method for the inhibition of proliferation or induction of differentiation of keratinocytes, comprising administering to a subject in need thereof an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
18. A method for the treatment of inflammatory disorders, comprising administering to a subject in need thereof an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
19. A method for enhancing the endogenous production of interleukin-10 (IL-10) in mammalian cells or tissues, comprising administering to a subject in need thereof an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
20. A method for suppression of the endogenous production of interleukin-2 (IL-2) in mammalian cells or tissues, comprising administering to a subject in need thereof an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
21. A method for the inhibition of proliferation of stimulated peripheral mononuclear cells (PBMC), comprising administering to a subject in need thereof an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
22. The pharmaceutical composition according to claim 7 , admixed with at least one of a pharmaceutically acceptable carrier, diluent, excipient, or adjuvant.
23. A topically administrable pharmaceutical composition according to claim 22 .
24. A parenterally administrable pharmaceutical composition according to claim 22 .
25. An intravenously administrable pharmaceutical composition according to claim 22 .