Absolute configuration and antitumor activity of myxochelin A produced by Nonomuraea pusilla TP-A0861

Satoshi Miyanaga; Takamasa Obata; Hiroyasu Onaka; Tsuyoshi Fujita; Noriko Saito; Hiroaki Sakurai; Ikuo Saiki; Tamotsu Furumai; Yasuhiro Igarashi

doi:10.1038/ja.2006.93

Absolute configuration and antitumor activity of myxochelin A produced by Nonomuraea pusilla TP-A0861

J Antibiot (Tokyo). 2006 Nov;59(11):698-703. doi: 10.1038/ja.2006.93.

Authors

Satoshi Miyanaga¹, Takamasa Obata, Hiroyasu Onaka, Tsuyoshi Fujita, Noriko Saito, Hiroaki Sakurai, Ikuo Saiki, Tamotsu Furumai, Yasuhiro Igarashi

Affiliation

¹ Department of Engineering, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan.

PMID: 17256468
DOI: 10.1038/ja.2006.93

Abstract

In the screening of antitumor compounds from microbial secondary metabolites, myxochelin A was isolated from a culture broth of Nonomuraea pusilla TP-A0861. The absolute configuration was determined to be S by synthesizing both enantiomers from an L- or D-lysine derivative and comparing their specific rotations. Both enantiomers of myxochelin A showed remarkable inhibitory effects on the invasion of murine colon 26-L5 carcinoma cells at non-cytotoxic concentrations.

MeSH terms

Actinobacteria / chemistry*
Actinobacteria / metabolism
Actinobacteria / ultrastructure
Animals
Antineoplastic Agents / chemical synthesis
Antineoplastic Agents / chemistry*
Antineoplastic Agents / isolation & purification
Antineoplastic Agents / pharmacology*
Cell Adhesion / drug effects
Cell Line, Tumor
Cell Movement / drug effects
Colonic Neoplasms / drug therapy
Colonic Neoplasms / pathology
Lysine / analogs & derivatives*
Lysine / chemical synthesis
Lysine / chemistry
Lysine / isolation & purification
Lysine / pharmacology
Mice
Microscopy, Electron, Scanning
Nuclear Magnetic Resonance, Biomolecular
Spectrometry, Mass, Fast Atom Bombardment
Stereoisomerism

Substances

Antineoplastic Agents
myxochelin A
Lysine