Biomaterial Database

Stereospecificity in allergic contact dermatitis to simple substituted methylene lactone derivatives. 1987

H Mattes, and K Hamada, and C Benezra

Laboratoire de Dermato-Chimie, Université Louis Pasteur, CHU, Strasbourg, France.

The enantiomers of beta,gamma-dimethyl- and beta-methyl-alpha-methylene-gamma-butyrolactones have been synthesized stereospecifically from glutamic acid and beta-hydroxy isobutyric acid, respectively. Guinea pigs have been sensitized (Freund complete adjuvant technique) and tested to them. Both enantiomers of beta-methyl lactone as well as (+)-beta,gamma-dimethyl lactone induced enantiospecific allergic contact dermatitis (ACD); in turn, (-)-beta,gamma-dimethyl lactone showed no specificity. An interpretation is proposed.

UI	MeSH Term	Description	Entries
D003877	Dermatitis, Contact	A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.	Contact Dermatitis,Dermatitis Venenata,Eczema, Contact,Hypersensitivity, Contact,Sensitivity, Contact,Contact Dermatitides,Contact Eczema,Contact Hypersensitivities,Contact Hypersensitivity,Contact Sensitivities,Contact Sensitivity,Dermatitides, Contact,Hypersensitivities, Contact,Sensitivities, Contact
D005260	Female		Females
D005663	Furans	Compounds with a 5-membered ring of four carbons and an oxygen. They are aromatic heterocycles. The reduced form is tetrahydrofuran.	Tetrahydrofurans
D006168	Guinea Pigs	A common name used for the genus Cavia. The most common species is Cavia porcellus which is the domesticated guinea pig used for pets and biomedical research.	Cavia,Cavia porcellus,Guinea Pig,Pig, Guinea,Pigs, Guinea
D000485	Allergens	Antigen-type substances that produce immediate hypersensitivity (HYPERSENSITIVITY, IMMEDIATE).	Allergen
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia
D012882	Skin Tests	Epicutaneous or intradermal application of a sensitizer for demonstration of either delayed or immediate hypersensitivity. Used in diagnosis of hypersensitivity or as a test for cellular immunity.	Skin Test,Test, Skin,Tests, Skin
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D013329	Structure-Activity Relationship	The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups.	Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D015107	4-Butyrolactone	One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.	1,4-Butanolide,4-Hydroxybutyric Acid Lactone,Furanone, tetrahydro-2-,gamma-Butyrolactone,Dihydro-2(3H)-furanone,1,4 Butanolide,4 Butyrolactone,4 Hydroxybutyric Acid Lactone,Furanone, tetrahydro 2,Lactone, 4-Hydroxybutyric Acid,gamma Butyrolactone