Sialic carbohydrates

• US 20050070464A1
• Filed: 01/31/2003
• Published: 03/31/2005
• Est. Priority Date: 02/01/2002
• Status: Abandoned Application

• Current Assignee: nv nutricia
• Original Assignee: nv nutricia
• Inventors: Schmitt, Joachim, Stahl, Bernd, Finke, Berndt, Boehm, Gunther, Kelm, Sorge
• Application Number:
  US10/502,049
• Publication Number:
  US 20050070464A1
• Time in Patent Office: Days
• US Class Current: 424/278.100
• CPC Class Codes: A23C 9/20 Dietetic milk products not covered by groups A23C9/12 - A23C9/18
• CPC Class Codes: A23F 3/30 Further treatment of dried tea extract; Preparations produced thereby, e.g. instant tea A23F3/166 takes precedence; flavouring A23F3/40
• CPC Class Codes: A23L 29/30 containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin products from apiculture A23L21/20; artificial sweetening agents A23L27/30
• CPC Class Codes: A23L 33/125 containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates indigestible substances A23L33/21
• CPC Class Codes: A23L 33/40 Complete food formulations for specific consumer groups or specific purposes, e.g. infant formula
• CPC Class Codes: A23V 2002/00 Food compositions, function of food ingredients or processes for food or foodstuffs
• CPC Class Codes: A23V 2250/0644 Taurine
• CPC Class Codes: A23V 2250/156 Mineral combination undefined extract A23V2250/1638
• CPC Class Codes: A23V 2250/5438 Sialic acid, glycomacroprotein
• CPC Class Codes: A23V 2250/70 Vitamins
• CPC Class Codes: A61P 37/00 Drugs for immunological or allergic disorders
• CPC Class Codes: C07H 17/04 Heterocyclic radicals containing only oxygen as ring hetero atoms
• CPC Class Codes: C07H 7/027 Keto-aldonic acids

Abstract

The invention relates to the use of sialic carbohydrates of general formula (I), containing at least one carbohydrate unit of general formula (II) for the immune modulation, immune suppression and in the prevention and treatment of infections in humans and animals. In said formula (II), Sia represents a sialic acid or a sialic acid derivative in an α2-3 bond, Gal represents a galactose-monosaccharide-unit, HexNac represents an N-acetylated galactosamine or glucosamine-monosaccharide-unit (GalNAc or GlcNAc), Hex represents a galactose- or glucose-monosaccharide-unit (Gal or Glc), C represents HexNac or Hex or is absent, n represents 1-50, V represents OH, a carbohydrate radical or a connecting point on a support T, with the proviso that if V represents OH, n represents 1, and if V represents a carbohydrate radical or a support T, n represents the number of carbohydrate unites of general formula (II) directly connected to said carbohydrate radical or support, X represents a sialic acid or a sialic acid derivative, wherein a second sialic acid or a sialic acid derivative or more sialic acid or sialic acid derivatives can be connected to an α2-8 bond, a phosphate, a sulphate, or carboxyl-group or a monosaccharide having a phosphate, sulphate, or carboxyl group and only one of the radicals X is present.

Claims

1. Use of sialyzed carbohydrates of the following general formula I having at least one carbohydrate unit of the following general formula II:

2. Use according to claim 1, characterized in that one, two, three, four, or all of the following criteria i) through iv) are met:

i) Sia represents acetyl neuraminic acid (NeuAc) or N-glycolyl neuraminic acid (NeuGc),

ii) the sialic acid derivative or the sialic acid derivatives of the residues Sia and X is/are an O-acyl derivative and in particular an O-acetyl derivative,

iii) the carrier T is a peptide, a protein, a polymer or a biopolymer, with the linkage with said peptide or protein in particular being N-glycosidic or O-glycosidic, and

iv) the carbohydrate residue constituting the residue V is a monosaccharide residue, an oligosaccharide residue or a polysaccharide residue.

3. Use according to claim 1, characterized in that the carbohydrates of general formula I are selected from disialyl-lacto-N-tetraose (DS-LNT, V=OH, HexNac=GlcNAc, Hex=galactose (Gal), C=glucose, Sia=α

2-3 NeuAc, X=α

2-6 NeuAc on HexNac), disialyl-lacto-N-neo-tetraose (DS-LNnT), glycomacropeptide (GMP), ganglioside G_D1a, ganglioside G_T1b and ganglioside G_T1c.

4. Use according to claim 1 any one of claims 1, characterized in that T represents lipophilic compounds, and the carbohydrate unit or carbohydrate units of general formula II represents or represent the head group(s) thereof.

5. Use according to claim 4, characterized in that said lipophilic compounds are glycolipids and in particular gangliosides.

6. Use according to claim 1, characterized in that the carbohydrate or carbohydrates of general formula I is/are used in an amount of at least 1 mg per kg of body weight.

7. Use according to claim 1, for the prevention and treatment of infections of the gastrointestinal tract, blood system, respiratory passages, urogenital tract, as well as the nasopharynx.

8. Use according to claim 1, characterized in that the carbohydrate or carbohydrates of general formula I are incorporated into a fluid or solid food composition (with the exception of human milk), dietetic composition or pharmaceutical composition for administration to a human or an animal, or serve for the preparation of such a composition for the immunomodulation, immunosuppression and treatment of infections in humans and animals.

9. Use according to claim 8, characterized in that the pharmaceutical composition serves for an oral, lingual, nasal, bronchial, vaginal, topical (skin and mucosa) and per os administration, for an administration by means of a probe into the stomach of a human or an animal, or for an administration as an infusion.

10. Food composition, dietetic composition or pharmaceutical composition containing at least one carbohydrate of general formula I as described in claim 1.

11. Composition according to claim 10, characterized in that the composition may contain a further carbohydrate or several further carbohydrates, which are different from the carbohydrates of claim 1, a further active agent or several further active agents and/or a further ingredient, which is known and suited for the corresponding composition, or more of such ingredients, wherein in the case of a pharmaceutical composition a usual auxiliary agent or several usual auxiliary agents, including diluents, moisturizing agents, thickening agents, flavoring agents, sweetening agents and carriers, may be present, and in the case of a food composition or a dietetic composition, at least one further food component may be present.

12. Method of immunomodulation, immunosuppression and treatment of infections in humans and animals, characterized in that at least one carbohydrate of general formula I or a composition according to claim 10 is administered to a human or an animal, but not in the form of human milk, in particular in such an amount that at least 1 mg of carbohydrate of general formula I is administered per kg of body weight to the human or the animal once daily.

13. Sialyzed carbohydrates of the following general formula I having at least one carbohydrate unit of the following general formula II: