M. Sollner et al., THE INFLUENCE OF THE LIPOPHILICITY OF 7-OXOACYL-L-ALANYL-D-ISOGLUTAMINES ON THEIR IMMUNORESTORATION ACTIVITY IN-VIVO, European journal of medicinal chemistry, 31(11), 1996, pp. 927-933
In search for immunologically active dipeptides, a series of new N-(7-
oxoacyl)-L-alanyl-D-isoglutamines has been synthesized where lipophili
city was varied by changing the 7-oxoacyl residue from 7-oxooctanoyl t
o 7-oxotetradecanoyl. The immunological properties of the compounds we
re examined in an in vivo immunorestoration test. It was found that li
pophilicity had a significant influence on the potency of the compound
s tested. Compounds between N-(7-oxodecanoyl)-L-alanyl-D-isoglutamine
and N-(7-oxotetradecanoyl)-L-alanyl-D-isoglutamine showed biphasic inf
luence on efficacy. The most active compound found was 7-oxododecanoyl
-L-alanyl-D-isoglutamine, which also has an activity comparable to tha
t of azimexone.