title: Synthesis and biological activity of spergualin analogues. I.
abstract: Stable spergualin analogues were synthesized by substitutions of the alpha-hydroxyglycine residue of spergualin with various alpha- or omega-amino acids. The antitumor activity of these analogues against L1210 and their immunosuppressive effects on delayed-type hypersensitivity and antibody formation was then examined. Analogues substituted with glycine and L-serine showed significant biological activity but were less potent than 15-deoxyspergualin. Among the analogues synthesized so far, 10-[N-4-(4-guanidinophenyl)butyryl-L-seryl]-1,5,10-triazadecane has possessed the strongest antitumor and immunosuppressive activities.
authors.affiliation: Research Laboratories, Nippon Kayaku Co., Ltd., Tokyo, Japan.
authors.forename: R
authors.initials: R
authors.lastname: Nishizawa
authors.forename: Y
authors.initials: Y
authors.lastname: Takei
authors.forename: M
authors.initials: M
authors.lastname: Yoshida
authors.forename: T
authors.initials: T
authors.lastname: Tomiyoshi
authors.forename: T
authors.initials: T
authors.lastname: Saino
authors.forename: K
authors.initials: K
authors.lastname: Nishikawa
authors.forename: K
authors.initials: K
authors.lastname: Nemoto
authors.forename: K
authors.initials: K
authors.lastname: Takahashi
authors.forename: A
authors.initials: A
authors.lastname: Fujii
authors.forename: T
authors.initials: T
authors.lastname: Nakamura
mesh_terms: D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000494:pharmacology; D006146:Guanidines / Q000138:chemical synthesis / Q000494:pharmacology; D007166:Immunosuppressive Agents / Q000494:pharmacology; D007939:Leukemia L1210 / Q000188:drug therapy; D051379:Mice; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000903:Antibiotics, Antineoplastic; D006146:Guanidines; D007166:Immunosuppressive Agents; C033797:spergualin