Sulfoglycolipid antigens, their process of preparation, and their use against tuberculosis

A compound of general formula (I):

• wherein:
• R2′, R3′, identical or different, are independently chosen from H, SO3H or SO3−/M+, provided that at least one of R2′, R3′ is SO3H or SO3−/M+;
• M+ is the cation of a metal, such as Na+, K+;
• R2, R3, identical or different, are independently chosen from:
• a) fatty acyl groups
• b)
• where X is an unsaturated linear or ramified hydrocarbon chain optionally substituted with one or more substituents;
• where at least one of R2, R3 is b);
• and its enantiomers, diastereoisomers, mixtures thereof and pharmaceutically acceptable salts or esters.

An in vitro method for diagnosing tuberculosis comprising the following steps:

• providing a biological sample from a PPD positive individual;
• contacting said sample with a compound of formula (X):
• where
• R2′, R3′, identical or different, are independently chosen from H, SO3H or SO3−/M+, provided that at least one of R2′, R3′ is SO3H or SO3−/M+;
• M+ is the cation of a metal, such as Na+, K+.
• R2, R3, identical or different, are independently chosen from:
• a) fatty acyl groups
• b)
• where X is an unsaturated linear or ramified hydrocarbon chain optionally substituted with one or more substituents;
• and its enantiomers, diastereoisomers, mixtures thereof and pharmaceutically acceptable salts or esters,
• assessing T lymphocytes activation;
• and comparing T lymphocytes activation after and before administration of the compound.

A kit for diagnosing tuberculosis comprising:

• a compound of formula (X):
• where
• R2, R3, identical or different, are independently chosen from H, SO3H or SO3−/M+, provided that at least one of R2′, R3′ is SO3H or SO3−/M+;
• M+ is the cation of a metal, such as Na+, K+.
• R2, R3, identical or different, are independently chosen from:
• a) fatty acyl groups
• b)
• where X is an unsaturated linear or ramified hydrocarbon chain optionally substituted with one or more substituents;
• and its enantiomers, diastereoisomers, mixtures thereof and pharmaceutically acceptable salts or esters,
• dendritic cells;
• and
• means for detecting T lymphocytes activation.

Ligands to the compounds of formula (X):

• where
• R2′, R3′, identical or different, are independently chosen from H, SO3H or SO3−/M+, provided that at least one of R2′, R3′ is SO3H or SO3−/M+;
• M+ is the cation of a metal, such as Na+, K+.
• R2, R3, identical or different, are independently chosen from:
• a) fatty acyl groups
• b)
• where X is an unsaturated linear or ramified hydrocarbon chain optionally substituted with one or more substituents;
• and its enantiomers, diastereoisomers, mixtures thereof and pharmaceutically acceptable salts or esters.