Drug – bio-affecting and body treating compositions – Immune response affecting drug
Patent
1994-10-24
1998-03-03
Kunz, Gary L.
Drug, bio-affecting and body treating compositions
Immune response affecting drug
514 2, 514 23, 514 42, 536 172, 536 174, 536 187, 5361231, 53612313, 530300, A61K 3173, A61K 3939, A61K 900, C12P 2100
Patent
active
057235040
DESCRIPTION:
BRIEF SUMMARY
This application was filed under 35 USC 371 as a national stage of International case PCT/EP93/00327 filed Feb. 11, 1993.
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention related to novel Amadori reaction compounds and products, to the production thereof and to a new use of these compounds and products, having at least partly entered an Amadori rearrangement as per the following reaction scheme and/or a Maillard reaction: ##STR1## Amadori reaction products are known; they are reaction products, for example, of an aminoacid or a peptide with a sugar, oligo- or polysaccharide having entered an Amadori rearrangement (J. Biol. Soc. 215 (1955), Henri Borsock et al.). Thus, in DE-C-3914354, a water-soluble glycoprotein of an aminoacid and a sugar is described which is isolated from an extract of Avena sativa seeds. Further, EP-A-406087 describes water-soluble polysaccharide-glycopeptide complexes which are derived from the cell wall of Gram positive bacterium, and J. Biol. Chem. 1985, 260/9 states that NMR-spectroscopy has been used to characterize Amadori reaction products formed by reaction of glucose with free amino groups of protein.
2. Description of the Related Art
The invention now describes specific novel Amadori rearrangement compounds.
These compounds reduce potassium ferricyanide, a test reaction for biological active substances formed in a reaction of sugar and aminoacid.
The invention further relates to a novel use of such compounds and simultaneously a novel use of Amadori reaction products of sugars and aminoacids in general. In the past, nobody has tested the various steps of purification of the extract of an Amadori reaction product (in order to get ride of ballast substances and impurities) for biological activity.
Immunostimulating drugs are indeed known from natural sources such as mistletoe extracts, peat extracts etc. with the drawback of expensive treatment of large quantities of raw material to obtain a few grams of active substance. Uncontrolable impurities might lead to toxicity and side effects and therefore, further, to problems with administration during practical use due to the complex nature and the hardly reproducible composition.
Comparable products or product mixes from artificial sources, such as interferon or other genetic engineering methods are even more expensive to make furthermore, the molecules of human interferon are very often too big to penetrate the human cell wall so that only a fraction of the administered dose is effectively becoming active. Also, genetic engineering products usually have side effects and some are even toxic furthermore, some of them act effectively on one day and not on the next day, for reasons unknown so far.
Surprisingly, it has now been found that nearly any simple amino-acid/sugar complex after having at least partly entered an Amadori rearrangement does not show any of the above-mentioned disadvantages but on the contrary has a surprisingly high immuno-logical activity. They can therefore be used in pharmaceutical formulations and in cosmetics. These small molecules easily penetrate the cell wall and virtually act as a nutrient. They induce the formation of natural interferon and other cytokines, including tumor necrosis factor. Even three days after the administration, they still show this stimulating effect on biological activity. This effect increases with increasing completion of the Amadori rearrangement and decreases again with increasing decomposition of the complex.
Instead of simple sugars also--preferably low molecular weight, especially of less than 1000 daltons--polysaccharides may be used, for instance dextran, which react similarly. Polysaccharides show biological activity and may retain some of this activity after they become oligosaccharides.
Very little has been known heretofore about the biological activity of these compounds. It was now found that combinations of these substances in contact with human leukocytes produce interferon and other cytokines. This is called polyclonal activation of t
REFERENCES:
patent: 4022920 (1977-05-01), Doornbus et al.
Analysis of the 220-MHz, P.M.R. spectra of some products of the Amadori and Heyns rearrangements Altena H. J. et al. Carbohydrate Research, vol. 92, 1981, pp. 37-49.
Glycoproteins-Their Composition, Structure and Function-Part A Alfred Gottschalk, B.B.A. Library, vol. 5, 1972 pp. 146-157.
Quantitative Untersuchungen der Reaktion von Hexosen mit Aminsauren Heyns K. et al. Justus Liebigs Annalen der Chemie, vol. 703, 1967, pp. 202-214.
Gottschalk, Alfred, B.B.A. Library vol. 5, Part A, Glycoproteins, Elsevier Publishing Co., New York, 1972, pp. 141-156.
Inglot Anna
Mioduszewski Jan Zbigniew
Witkiewicz Krystyna
Kunz Gary L.
Torf Establishment
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