SYNTHESIS AND BIOLOGICAL ACTIVITY OF SPERGUALIN ANALOGUES. I

Stable spergualin analogues were synthesized by substitutions of the α-hydroxyglycine residue of spergualin with various α- or ω-amino acids. The antitumor activity of these analogues against L1210 and their immunosuppressive effects on delayed-type hypersensitivity and antibody formation was then e...

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Bibliographic Details
Published in:Journal of antibiotics 1988/11/25, Vol.41(11), pp.1629-1643
Main Authors: NISHIZAWA, RINZO, TAKEI, YUKIO, YOSHIDA, MASAO, TOMIYOSHI, TSUGIO, SAINO, TETSUSHI, NISHIKAWA, KIYOHIRO, NEMOTO, KYUICHI, TAKAHASHI, KATSUTOSHI, FUJII, AKIO, NAKAMURA, TERUYA, TAKITA, TOMOHISA, TAKEUCHI, TOMIO
Format: Article
Language:English
Subjects:
Animals
Antibiotics, Antineoplastic - chemical synthesis
Antibiotics, Antineoplastic - pharmacology
Biological and medical sciences
General pharmacology
Guanidines - chemical synthesis
Guanidines - pharmacology
Immunosuppressive Agents - pharmacology
Leukemia L1210 - drug therapy
Medical sciences
Mice
Pharmacology. Drug treatments
Physicochemical properties. Structure-activity relationships
Stereoisomerism
Structure-Activity Relationship
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Summary:Stable spergualin analogues were synthesized by substitutions of the α-hydroxyglycine residue of spergualin with various α- or ω-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.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.41.1629