Per-N-methylated analogues of an antitumor bicyclic hexapeptide RA-VII.

Abstract

Penta-N-methyl and hexa-N-methyl analogues of RA-VII, an antitumor bicyclic hexapeptide of plant origin, were prepared. In the former, the nitrogens of d-Ala-1 and Ala-4 and in the latter, those of d-Ala-1, Ala-2, and Ala-4 were methylated under the phase-transfer catalysis conditions. Their solution structures were established by NOESY experiments and the crystal structures by X-ray crystallography. Those two methylated analogues showed much weaker cytotoxicity against P-388 leukemia cells than the parent RA-VII.

• Authors: Yukio Hitotsuyanagi, Ji-Ean Lee, Saori Kato, Ik-Hwi Kim, Hideyuki Kohashi, Haruhiko Fukaya, Koichi Takeya
• Journal: Bioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 19 Issue 7 Pg. 2458-63 (Apr 01 2011) ISSN: 1464-3391 [Electronic] England
• PMID: 21382716 (Publication Type: Journal Article)
• Copyright: Copyright © 2011 Elsevier Ltd. All rights reserved.

Chemical References

• Antineoplastic Agents, Phytogenic
• Oligopeptides
• Peptides, Cyclic
• RA VII

Topics

• Animals
• Antineoplastic Agents, Phytogenic (chemistry, pharmacology)
• Crystallography, X-Ray
• Humans
• Leukemia P388 (drug therapy)
• Mice
• Molecular Conformation
• Oligopeptides (chemistry, pharmacology)
• Peptides, Cyclic (chemistry, pharmacology)
• Rubia (chemistry)