Lipid-amino acid conjugates and methods of use

A technology of amino acids and fatty acids, applied in the field of treatment of diseases, can solve problems such as lack of affinity

Inactive Publication Date: 2007-11-07
UNIV OF MASSACHUSETTS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

NAGly is a structural analog of the endogenous cannabinoid anandamide, but it has been reported to be deficient in the cannabinoid receptors CB1 and CB2, the vanilloid ...

Method used

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  • Lipid-amino acid conjugates and methods of use

Examples

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preparation example Construction

[0145] Starch microspheres can be prepared by adding a warm water-soluble starch solution such as potato starch to a hot aqueous polyethylene glycol solution and stirring to form an emulsion. After the formation of the two-phase system (starch solution as the internal phase), the mixture is cooled to room temperature with continuous stirring, whereupon the internal phase transforms into gel particles. The particles are then filtered off at room temperature and slurried in a solvent such as ethanol, after which the particles are filtered off again and left to air dry.

[0146] Microspheres can be hardened by well known crosslinking methods such as heat treatment or use of chemical crosslinking agents. Suitable reagents include dialdehydes, including glyoxal, malondialdehyde, succinaldehyde, adipaldehyde, glutaraldehyde and o-phthalaldehyde, diketones such as diacetyl, epichlorohydrin, polyphosphates, and borates. Dialdehydes are used to cross-link proteins such as albumin by ...

Embodiment 1

[0153] Embodiment 1. the synthesis of arachidonoyl-D-alanine

[0154] N-Fatty acid-D-alanine conjugates were prepared from chirally pure D-amino acid methyl esters (Aldrich Chemicals). Arachidonic acid chloride (Nucheck) in dichloromethane was reacted with alanine methyl ester in dichloromethane containing 5% triethylamine for 4 hours at room temperature. The mixture was partitioned between ethyl acetate and dilute HCl, washed, dried and evaporated to an oily residue. The residue was dissolved in THF, then stirred with 1N LiOH under nitrogen, and saponified at room temperature for 5 hours. The product was extracted as above and subjected to thin-layer chromatography. The main product was identified as N-arachidonic acid-D-alanine by mass spectrometry, and the mass spectrometry showed an MH of 376.1 + . Circular dichroism measurements showed a mirror image corresponding spectrum between 220 and 240 nm when compared to the L isomer. The [α] value of the D isomer is -16.6×10...

Embodiment 2

[0155] Embodiment 2. Synthesis of other Elmiric acid

[0156]The synthetic method of Example 1 was used to prepare the conjugates of arachidonyl and palmityl and 1-aminocyclohexanecarboxylic acid, 1-aminocyclopentanecarboxylic acid, and 2-aminoisobutyric acid. The synthesized compounds are N-palmitoyl-1-aminocyclohexane-COOH, N-palmitoyl-1-aminocyclopentane-COOH, N-palmitoyl-2-aminoisobutyric acid, N-arachidonoyl -1-aminocyclohexane-COOH, N-arachidonoyl-1-aminocyclopentane-COOH and N-arachidonoyl-2-aminoisobutyric acid.

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Abstract

N-fatty acid-amino acid conjugates and J2 prostanoid-amino acid conjugates are disclosed along with methods for making such conjugates and methods of using these conjugates in the treatment of conditions that involved dysfunctional lipid metabolism, insulin sensitivity, glucose homeostasis, and/or inflammation.

Description

[0001] Cross-references with related applications [0002] This application claims the benefit of U.S. Provisional Patent Application 60 / 588,697, filed July 16, 2004. This prior application is hereby incorporated by reference in its entirety. [0003] Statement Regarding Federally Sponsored Research [0004] This invention was made with NIH grants DA12178 and DA017969; therefore, the Government has specific rights in this invention. technical field [0005] The present invention relates to lipid-amino acid conjugates, methods of making the conjugates and methods of using the conjugates in the treatment of diseases involving, for example, abnormal lipid metabolism, insulin sensitivity, glucose homeostasis, and / or Inflammation etc. The present invention relates to the fields of molecular biology, medicinal chemistry, pharmacy and medicine. Background technique [0006] Lipoaminoacids are a class of molecules initially identified in bacteria, consisting of fatty acid moieti...

Claims

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Application Information

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IPC IPC(8): A61K31/19C07C62/00
CPCC07C233/49A61K31/202C07C233/47A61K31/401A61P17/06A61P19/02A61P29/00A61P31/18A61P37/06A61P3/10
Inventor 萨姆纳·H·伯斯坦罗伯特·B·祖里尔
Owner UNIV OF MASSACHUSETTS
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