# US 2022/0146516 A1 · Methods for labeling eukaryotic cells from a multicellular organism as well as for treating and/or diagnosing a cancer using modified monosaccharide compounds

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- Number: US 2022/0146516 A1
- Document ID: US20220146516A1
- Status: Published application
- Kind: A1
- Application number: 17/432,331
- Filed: 2020-02-20
- Published: 2022-05-12
- Earliest claimed: 2019-02-20
- Assignees: Diamidex
- Applicants: Diamidex
- Inventors: Sam DUKAN
- Web page: https://patentgrep.com/patent/US20220146516A1

## CPC

- A61K 31/70: Carbohydrates; Sugars; Derivatives thereof (sorbitol A61K31/047)
- G01N 33/57585: {involving compounds identifiable in body fluids}
- C07H 3/02: Monosaccharides
- G01N 33/532: Production of labelled immunochemicals
- G01N 33/575: for cancer
- G01N 33/58: involving labelled substances (G01N33/53 takes precedence)
- G01N 33/84: involving inorganic compounds or pH
- 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)
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

The present invention relates to modified monosaccharide compounds implemented in methods for labeling and/or detecting an eukaryotic cell from a multicellular organism. It also relates to such modified monosaccharide compounds implemented in methods for identifying or isolating cancer cells, diagnosing a cancer or for cell therapy.

## Claims

### Claim 1

An in vitro method for labeling or detecting or targeting an eukaryotic cell from a multicellular organism, the method comprising the steps of:
a) contacting a sample comprising eukaryotic cells with at least one modified monosaccharide compound or a precursor thereof;
b) contacting the sample of step (a) with a compound bearing a first reactive group, optionally in presence of copper; and
c) optionally detecting the compound of step (b) bond to the monosaccharide of step (a), as to detect eukaryotic cells;
wherein said at least one modified monosaccharide compound has the following formula (I):
in which X is a second reactive group, the first and the second reactive groups being able to react together in a click chemistry reaction.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the second reactive group X is an azido group (—N3) and the first reactive group is an alkyne group.

### Claim 3 (depends on 1)

The method according to claim 1, wherein said at least one modified monosaccharide compound of formula (I) is selected in the group consisting of the following formulae:

### Claim 4 (depends on 1)

The method according to claim 1, wherein said at least one modified monosaccharide compound of formula (I) is 5-azido-5-deoxy-D-arabinofuranose having the following formula:

### Claim 5 (depends on 1)

An in vitro or ex vivo method for identifying or isolating cancer cells, wherein said method comprises implementing a method according to claim 1.

### Claim 6 (depends on 1)

An in vitro or ex vivo method for diagnosing a cancer in a subject, wherein said method comprises implementing a method according to claim 1.

### Claim 7 (depends on 5)

The method according to claim 5, wherein the method further comprises the step of detecting the labeling, and optionally comparing the labeling to a reference level; and then identifying cancer cells or diagnosing a cancer based on the measuring of the label.

### Claim 8 (depends on 5)

The method according to claim 5, wherein the sample of step (a) is a biological sample from a subject, said subject having or being suspected to have cancer.

### Claim 9 (depends on 1)

A kit for implementing the method for labeling or detecting or targeting an eukaryotic cell of claim 1 comprising:
a modified monosaccharide compound of formula (I) or a precursor thereof, preferably of formula (I′), and
a compound bearing a first reactive group.

### Claim 10 (depends on 1)

A pharmaceutical composition comprising an eukaryotic cell presenting on its surface at least one modified monosaccharide compound of formula (I) or a precursor thereof, as defined in claim 1, optionally linked operably or not to an anti-cancer drug or to particles comprising an anti-cancer drug.

### Claim 11 (depends on 10)

The composition according to claim 10, wherein the anti-cancer drug is an antitumoral drug, preferably selected from the group consisting of chemotherapeutics, anti-cancer antibodies, hormonal therapy, immunotherapy, and kinase inhibitors.

### Claim 12 (depends on 10)

The composition according to claim 10, wherein the cell is an isolated non-cancer cell, and preferably MSC.

### Claim 13 (depends on 12)

A method for treating a cancer in a subject in need thereof, comprising administering to said subject an efficient amount of a pharmaceutical composition according to claim 12.

### Claim 14

(canceled)

### Claim 15 (depends on 5)

The method according to claim 5 for diagnosing a cancer, wherein the cancer is chosen among rectal cancer, colorectal cancer, stomach cancer, head and neck cancer, thyroid cancer, cervical cancer, uterine cancer, breast cancer, ovarian cancer, brain cancer, lung cancer, skin cancer, bladder cancer, blood cancer, renal cancer, liver cancer, prostate cancer, multiple myeloma, and endometrial cancer.

### Claim 16

(canceled)

### Claim 17 (depends on 13)

The method for treating a cancer according to claim 13, wherein the cancer is chosen among rectal cancer, colorectal cancer, stomach cancer, head and neck cancer, thyroid cancer, cervical cancer, uterine cancer, breast cancer, ovarian cancer, brain cancer, lung cancer, skin cancer, bladder cancer, blood cancer, renal cancer, liver cancer, prostate cancer, multiple myeloma, and endometrial cancer.

### Claim 18 (depends on 12)

A method for medical imaging or diagnosing in a subject, preferably for medical imaging or diagnosing a cancer, comprising administering to said subject a pharmaceutical composition according to claim 12.

### Claim 19 (depends on 1)

A method for medical imaging or diagnosing in a subject, preferably for medical imaging or diagnosing a cancer, comprising administering to said subject a modified monosaccharide compound or a precursor thereof as defined in claim 1.

### Claim 20 (depends on 6)

The method according to claim 6, wherein the sample of step (a) is a biological sample from a subject, said subject having or being suspected to have cancer.