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3-deoxyglucosone and skin

A deoxyglucosone, skin technology, applied in the direction of peptides, etc., can solve the problems of no effective therapeutic agent and/or diagnostic agent, increased concentration, harmful activity, etc.

Inactive Publication Date: 2007-12-05
DYNAMIS THERAPEUTICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

3DG evades detoxification through the glyoxalase pathway and is converted by aldehyde reductase to 3-deoxyfructose, an inert metabolite; however, 3DG can also compromise the activity of this enzyme
[0009] 3DG has numerous toxic effects on cells and is present in elevated concentrations in several disease states
[0063] The skin is a vital organ and there are still no effective therapeutic and / or diagnostic agents for many disorders, diseases and conditions related to the skin

Method used

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preparation example Construction

[0449] The present invention includes methods for the preparation and use of pharmaceutical compositions comprising compounds for the treatment of various skin-related diseases, disorders or conditions described herein, including skin aging, Photoaging and wrinkling of the skin. The invention also includes non-skin diseases and disorders associated with 3DG, including, but not limited to, gum diseases and disorders. Such pharmaceutical compositions may consist of a single active ingredient in a form suitable for administration to a subject; or the pharmaceutical composition may comprise at least one active ingredient and one or more pharmaceutically acceptable carriers , one or more other components, or some combination thereof. The active ingredient may be present in the pharmaceutical composition in the form of a physiologically acceptable ester or salt, such as in combination with a physiologically acceptable cation or anion, as is well known in the art.

[0450] The barr...

Embodiment 1

[0509] Isolation and identification of FL3P:

[0510] The following experiments were performed to verify that fructose-lysine (FL), such as FL3P, could be identified in its phosphorylation state. Perchloric acid extracts of diabetic rat kidney 31 P NMR analysis at 6.24 ppm revealed a new sugar-monophosphate resonance not observed in non-kidney tissues and significantly reduced in non-diabetic kidney. The compound responsible for the observed resonance was isolated by chromatography of the extract on a microcrystalline cellulose column using 1-butanol-acetic acid-water (5:2:3) as eluent. The structure was determined to be fructose-lysine 3-phosphate by proton 2D COZY. This result was confirmed hereinafter by injecting animals with FL prepared as described above (Finot and Mauson, 1969, Helv. Chim. Acta, 52:1488) and showing direct phosphorylation to FL3P.

[0511] Phosphoric acid was confirmed to be at the carbon-3 position using FL deuterated specifically at the 3-positio...

Embodiment 2

[0513] Synthesis of FL3P:

[0514] 1 mmol of dibenzyl-glucose 3-phosphate and 0.25 mmol of α-carbocarboxy-lysine were refluxed in 50 ml of MeOH for 3 hours. The solution was diluted with 100 ml of water and chromatographed in the pyridinium form on a Dow-50 column (2.5 x 20 cm), eluting first with water (200 ml) and then with 600 ml of buffer (0.1M pyridine and 0.3M acetic acid). Compounds of interest were eluted at the end of the water wash and at the beginning of the buffer wash. The results confirmed that FL3P was obtained in 6% yield after removal of cbz and benzyl blocking group using 5% Pd / C under 20 psi hydrogen.

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PUM

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Abstract

The invention relates to the discovery that 3-deoxyglucosone (3DG) and other alpha-dicarbonyl sugars associated diseases and disorders are present and produced in the skin. Further, the invention relates to the discovery that amadorase, an enzyme that mediates 3DG synthesis, is also present in the skin. Thus, the invention further relates to methods of inhibiting production and function of 3-deoxyglucosone and other alpha-dicarbonyl sugars in skin thereby treating or prevention various diseases, disorders or conditions. Additionally, the invention relates to treatment of various diseases, disorders or conditions associated with or mediated by oxidative stress since 3DG induces ROS and AGEs, which are associated with the inflammatory response caused by oxidative stress.

Description

Background of the invention [0001] Two of the most dangerous substances for biological macromolecules are the same as those necessary for life - oxygen and glucose. [0002] Various harmful forms of oxygen are produced in the body; singlet oxygen, superoxide radicals, hydrogen peroxide, and hydroxyl groups can all cause tissue damage. The collective term for these and similar oxygen-related species is "reactive oxygen species" (ROS). ROS damage tissue proteins, lipids and nucleic acid (DNA) and are the endpoint of many chronic and acute diseases such as cancer, atherosclerosis, diabetes, aging, rheumatoid arthritis, dementia, trauma, stroke and infection . [0003] ROS can also be generated from glucose. One mechanism is through the formation of cytotoxic carbonyls, such as methylglyoxal (MG) and 3-deoxyglucosone (3-deoxyglucosone, 3DG), which are responsible for the formation of advanced glycation end products (Advanced Glycation End Products, AGEs ) precursor. [0004] ...

Claims

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Application Information

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IPC IPC(8): C07K2/00
Inventor A・托拜厄F・卡普勒
Owner DYNAMIS THERAPEUTICS
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