New potential immunoenhancing compounds. Synthesis and pharmacological evaluation of new long-chain 2-amido-2-deoxy-D-glucose derivatives.
A series of long-chain fatty acids and the corresponding 2-hydroxy, 2-oxo, 3-hydroxy acid glucosamides were evaluated as immunomodulating compounds. In a preliminary screening, 2-[(2-ethoxycarbonyloxy)tetradecanoylamino]-2-deoxy-D-glucos e (2b) and 2-(3-hydroxydodecanoylamino)-2-deoxy-D-glucose (5a) resulted to be the most effective in enhancing the glucosamine activity. The findings of in vitro-ex vivo tests (unidirectional mixed lymphocyte culture reaction and primary antibody production) and in vivo tests (delayed type hypersensitivity, protection against bacterial or fungal infection and against Sarcoma 180 or Lewis lung carcinoma transplants) were very encouraging and allowed to assume for the two substances a protective activity, presumably through the ability of activating phagocytic and NK cells.
Valcavi
U
U
Dipartimento di Chimica Organica ed Industriale, Facoltà di Scienze, Università di Milano, Italy.
Albertoni
C
C
Brandt
A
A
Corsi
G B
GB
Farina
P
P
Foresta
P
P
Pascucci
G
G
Ramacci
M T
MT
D000276:Adjuvants, Immunologic / Q000138:chemical synthesis / Q000494:pharmacology*; D000818:Animals; D000917:Antibody Formation / Q000187:drug effects; D055598:Chemical Phenomena; D002621:Chemistry; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology / Q000633:toxicity; D006801:Humans; D006968:Hypersensitivity, Delayed / Q000276:immunology; D007075:Immunoglobulin M / Q000276:immunology; D066298:In Vitro Techniques; D008175:Lung Neoplasms / Q000188:drug therapy; D008214:Lymphocytes / Q000187:drug effects; D008297:Male; D051379:Mice; D051381:Rats; D011919:Rats, Inbred Strains; D012510:Sarcoma 180 / Q000188:drug therapy
D000276:Adjuvants, Immunologic; D007075:Immunoglobulin M; C062486:2-((2-ethoxycarbonyloxy)tetradecanoylamino)-2-deoxyglucose; C062487:2-(3-hydroxydodecanoylamino)-2-deoxyglucose; D005944:Glucosamine