# US 2019/0169315 A1 · Antibodies Targeted to Fungal Cell Wall Polysaccharides

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- Number: US 2019/0169315 A1
- Document ID: US20190169315A1
- Status: Published application
- Kind: A1
- Application number: 16/267,430
- Filed: 2019-02-05
- Published: 2019-06-06
- Earliest claimed: 2013-03-12
- Assignees: Wellstat Vaccines, LLC
- Applicants: Wellstat Vaccines, LLC
- Inventors: Francis MICHON; Samuel J. WOHLSTADTER; Frank COMER; Kuishu REN
- Web page: https://patentgrep.com/patent/US20190169315A1

## CPC

- C08B 37/003: {Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof}
- A61K 39/0002: {Fungal antigens, e.g. Trichophyton, Aspergillus, Candida}
- A61K 39/385: Haptens or antigens, bound to carriers
- A61K 47/6415: {Toxins or lectins, e.g. clostridial toxins or Pseudomonas exotoxins}
- A61K 47/646: {the entire peptide or protein drug conjugate elicits an immune response, e.g. conjugate vaccines}
- A61P 31/10: Antimycotics
- C07K 16/14: against material from fungi, algea or lichens
- A61K 2039/6031: {Proteins}
- A61K 2039/6037: {Bacterial toxins, e.g. diphteria toxoid [DT], tetanus toxoid [TT]}
- A61K 2039/627: {characterised by the linker}
- C08B: POLYSACCHARIDES; DERIVATIVES THEREOF (polysaccharides containing less than six saccharide radicals attached to each other by glycosidic linkages C07H; fermentation or enzyme-using processes C12P19/00; sugar industry C13; production of cellulose D21)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)

## Abstract

A compound comprising one or more polysaccharide moieties each independently represented by the formula β(1→4)-[GlcNH-R]n-2,5-anhydromannose, wherein n is a positive integer from 3 to 500, and R is H or an acyl group, is described. The compound can be manufactured by (a) reacting chitosan with an acylating agent sufficient to partially N-acylate the chitosan, yielding a modified chitin/chitosan mixed polymer; and (b) reacting the modified chitin/chitosan mixed polymer with a deaminating agent to cleave the mixed polymer at the unacylated chitosan moieties. The compound can be used to immunize against fungal infection. Antibodies specific to the compound, and the use of such antibodies to protect against fungal infection are also described.

## Claims

### Claim 1

A compound comprising one or more polysaccharide moieties each independently represented by the formula β(1→4)-[GlcNH-R]n-2,5-anhydromannose, wherein n is a positive integer from 3 to 500, R is H or an acyl group, and the one or more polysaccharide moieties are chitin/chitosan mied polymers;
and an immunogenic carrier protein covalently linked to the one or more polysaccharide moieties at the anhydromannose group of the polysaccharide moieties.

### Claim 2 (depends on 1)

The compound of claim 1, wherein n is a positive integer from 3 to 100.

### Claim 3 (depends on 2)

The compound of claim 2, wherein n is a positive integer from 6 to 50.

### Claim 4 (depends on 1)

The compound of claim 1, wherein the acyl group R is an acetyl group.

### Claim 5 (depends on 1)

The compound of claim 1, wherein at least 30% of the acyl groups in the compound are acetyl.

### Claim 6 (depends on 1)

The compound of claim 1, wherein the carrier protein is tetanus toxoid.

### Claim 7 (depends on 1)

The compound of claim 1, wherein the carrier protein is diphtheria toxoid.

### Claim 8 (depends on 1)

The compound of claim 1, wherein the carrier protein is a fungal protein virulence factor.

### Claim 9 (depends on 1)

The compound of claim 1, further comprising one or more linear β-mannan or glucan epitopes covalently linked to the carrier protein.

### Claim 10 (depends on 9)

The compound of claim 9, wherein the β-mannan is a β-1,2-mannose tetrasaccharide.

### Claim 11 (depends on 9)

The compound of claim 9, wherein one of the one or more glucan epitopes is a linear α-1,3-glucan epitope.

### Claim 12 (depends on 9)

The compound of claim 9, wherein one of the one or more glucan epitopes is a linear β-1,3-glucan epitope.

### Claim 13 (depends on 1)

The compound of claim 1, wherein the carrier protein is covalently linked to the one or more polysaccharide moieties via one or more immunogenic scaffold moieties.

### Claim 14 (depends on 13)

The compound of claim 13, wherein each of the scaffold moieties is selected from the group consisting of a polysaccharide, a peptidoglycan, a polypeptide, and a polyglycerol.

### Claim 15 (depends on 13)

The compound of claim 13, wherein the scaffold is linear.

### Claim 16 (depends on 13)

The compound of claim 13, wherein the scaffold is dendrimeric.

### Claim 17 (depends on 13)

The compound of claim 13, further comprising one or more linear β-mannan or glucan epitopes covalently linked to the carrier protein or the scaffold.

### Claim 18 (depends on 17)

The compound of claim 17, wherein the β-mannan is a β-1,2-mannose tetrasaccharide.

### Claim 19 (depends on 17)

The compound of claim 17, wherein one of the one or more glucan epitopes is a linear α-1,3-glucan epitope.

### Claim 20 (depends on 17)

The compound of claim 17, wherein one of the one or more glucan epitopes is a linear β-1,3-glucan epitope.

### Claim 21 (depends on 1)

A composition comprising the compound of claim 1, wherein for at least 80% of molecules of the compound in the composition n has a value from 6 to 50.

### Claim 22 (depends on 1)

A composition comprising the compound of claim 1, wherein the mean value of n is from 10 to 50.
