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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Publication Number
US-12517131-B2
Publication Date
2026-01-06
Expiration Date
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.
Core Innovation
The invention relates to modified monosaccharide compounds having a formula (I) in which X is a second reactive group. The first and second reactive groups are able to react together in a click chemistry reaction to form a covalent linkage between the modified monosaccharide and a compound bearing a first reactive group.
The modified monosaccharide compounds and precursors are used to label, detect, or target an eukaryotic cell from a multicellular organism. A sample comprising eukaryotic cells is contacted with at least one modified monosaccharide compound or a precursor thereof, and then contacted with a compound bearing a first reactive group, optionally in presence of copper, to enable click chemistry bonding to the monosaccharide.
The disclosed compounds are presented for use in cancer probing, including identifying or isolating cancer cells and diagnosing cancer from subject samples. The disclosed example focus includes Ara-N3 (5-azido-5-deoxy-D-arabinofuranose) with detectable conjugation, and evidence is described for higher signal in tumor cells versus matched non-tumor cells across multiple cancer types/lines, including in vivo xenograft imaging contrast readout.
Claims Coverage
The independent claim covers an in vitro or ex vivo method with multiple inventive features centered on a modified monosaccharide of formula (I) having click-reactive groups and a subsequent click chemistry reaction, optionally with detection of the bonded product. The claim specifies that the click chemistry is selected from several click chemistry types, and dependent claims narrow the reactive group pairing and the selected monosaccharide identity to specific structural options and a specific example.
Modified monosaccharide formula with click-reactive groups
A method comprising contacting a sample comprising eukaryotic cells with at least one modified monosaccharide compound having formula (I), in which X is a second reactive group, wherein the first and second reactive groups are able to react together in click chemistry.
Click chemistry reaction with optional copper
Contacting the sample with a compound bearing a first reactive group, optionally in presence of copper, such that click chemistry bonding occurs between the compound and the monosaccharide.
Labeling, detecting, or targeting with optional detection of bonded product
Optionally detecting the compound of step (b) bond to the monosaccharide of step (a), as to detect eukaryotic cells, wherein the click chemistry is selected from azide-alkyne cycloaddition click chemistry, copper-free click-chemistry, thiol-ene click chemistry, nitrile-oxide-ene click chemistry, nitrile imine-ene click chemistry and isonitrile-tetrazine click chemistry.
Azido/alkyne reactive group pairing
The second reactive group X is an azido group (N3) and the first reactive group is an alkyne group.
Selection of modified monosaccharide from structural formula options
Selecting at least one modified monosaccharide compound of formula (I) from structural formulae shown in the claim, including N3- and OH-substituted monosaccharide structures with variants bearing an additional “CH4” substituent.
Use of 5-azido-5-deoxy-D-arabinofuranose
Using at least one modified monosaccharide compound of formula (I) defined as 5-azido-5-deoxy-D-arabinofuranose.
Across the independent claim and dependents, coverage is directed to eukaryotic cell labeling, detecting, or targeting by contacting cells with a modified monosaccharide of formula (I) bearing click-reactive groups, performing a selected click chemistry reaction (optionally with copper), and optionally detecting the bonded product. Dependent claims further narrow the reactive group pairing to azide/alkyne, constrain the monosaccharide selection to specified structural options, and include a specific named example: 5-azido-5-deoxy-D-arabinofuranose.
Stated Advantages
Enables detection of eukaryotic cells by click chemistry bonding and optional detection of the bonded product.
Provides a basis for labeling, detecting, or targeting eukaryotic cells from a multicellular organism.
Allows cancer probing, including identifying or isolating cancer cells and diagnosing cancer from subject samples.
Described example indicates higher fluorescence in tumor versus matched non-tumor cells and provides tumor/muscle contrast in vivo.
Documented Applications
In vitro or ex vivo labeling, detecting, or targeting of eukaryotic cells from a multicellular organism using modified monosaccharide compounds with click chemistry.
Cancer probing for identifying or isolating cancer cells and diagnosing cancer from subject samples.
Cell-based therapy using drug/particle conjugates [procedural detail omitted for safety].
In vivo xenograft imaging design using Ara-N3 followed by DBCO-IRDye800CW with a tumor/muscle contrast readout.
Use of Ara-N3 (5-azido-5-deoxy-D-arabinofuranose) with detectable conjugation (e.g., sulfo-DBCO-biotin and Alexa Fluor anti-biotin) to show tumor versus non-tumor fluorescence differences.
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