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.
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Kohn EC, Liotta LA . Molecular insights into cancer invasion: strategies for prevention and intervention. Cancer Res 51: 1856–1862 ( 1995)
Latreille J, Batist G, Laberge F, Champagne P, Croteau D, Falardeau P, Levinton C, Hariton C, Evans WK, Dupont E . Phase I/II trial of the safety and efficacy of AE-941 (Neovastat) in the treatment of non-small-cell lung cancer. Clin Lung Cancer 4: 231–236 ( 2003)
Rosenbaum E, Zahurak M, Sinibaldi V, Carducci MA, Pili R, Laufer M, DeWeese TL, Eisenberger MA . Marimastat in the treatment of patients with biochemically relapsed prostate cancer: a prospective randomized, double-blind, phase I/II trial. Clin Cancer Res 11: 4437–4443 ( 2005)
Saito KI, Oku T, Ata N, Miyashiro H, Hattori M, Saiki I . A modified and convenient method for assessing tumor cell invasion and migration and its application to screening for inhibitors. Biol Pharm Bull 20: 345–348 ( 1997)
Kunze B, Bedorf N, Kohl W, Höfle G, Reichenbach H . Myxochelin A, a new iron-chelating compound from Angiococcus disciformis (Myxobacterales). Production, isolation, physico-chemical and biological properties. J Antibiot 42: 14–17 ( 1989)
Silakowski B, Kunze B, Nordsiek G, Blocker H, Höfle G, Muller R . The myxochelin ion transport regulon of the myxobacerium Stigmatella aurantiaca Sg a15. Eur J Biochem 267: 6476–6485 ( 2000)
Soai K, Yokoyama S, Mochida K . Reduction of symmetric and mixed anhydrides of carboxylic acids by sodium borohydride with dropwise addition of methanol. Synthesis 647–648 ( 1987)
Kanai F, Isshiki K, Umezawa Y, Morishima H, Naganawa H, Takita T, Takeuchi T, Umezawa H . Vanoxonin, a new inhibitor of thymidylate synthetase. II. Structure determination and total syntheses. J Antibiot 38: 31–38 ( 1985)
Castro B, Dormoy JR, Dourtoglou B, Evin G, Selve C, Ziegler JC . Peptide coupling reagents VI. A novel, cheaper preparation of benzotrizaolyloxytris[dimethylamino]phosphonium hexafluorophosphate (BOP reagent). Synthesis 751–752 ( 1976)
Lee HH, Ahn JW, Lee J, Kim YC, Chung SK, Kwon JH . Antioxidative and free radical scavenging activities of myxochelin A isolated from Angiococcus sp. (Myxobacteria). Food Sci Biotechnol 11: 184–187 ( 2002)
Bergeron RJ, Cavanaugh PF Jr, Kline SJ, Hughes RG Jr, Elliott GT, Porter CW . Antineoplastic and antiherpetic activity of spermidine catecholamide iron chelators. Biochem Biophys Res Commun 121: 848–854 ( 1984)
Wells JS, Trejo WH, Principe PA, Sykes RB . Obafluorin, a novel beta-lactone produced by Pseudomonas fluorescens. Taxonomy, fermentation and biological properties. J Antibiot 37: 802–803 ( 1984)
Igarashi Y, Iida T, Sasaki T, Saito N, Yoshida R, Furumai T . Isolation of actinomycetes from live plants and evaluation of antiphytopathogenic activity of their metabolites. Actinomycetology 16: 9–13 ( 2002)
Igarashi Y, Iida T, Yoshida R, Furumai T . Pteridic acids A and B, novel plant growth promoters with auxin-like activity from Streptomyces hygroscopicus TP-A0451. J Antibiot 55: 764–767 ( 2002)
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†Bioactive microbial metabolites Part 30. Part 29: Y. Igarashi, S. Miura, T. Fujita, T. Furumai. Pterocidin, a cytotoxic compound from the endophytic Streptomyces hygroscopicus. J Antibiot 59: 193-195 (2006)
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Miyanaga, S., Obata, T., Onaka, H. et al. Absolute Configuration and Antitumor Activity of Myxochelin A Produced by Nonomuraea pusilla TP-A0861†. J Antibiot 59, 698–703 (2006). https://doi.org/10.1038/ja.2006.93
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DOI: https://doi.org/10.1038/ja.2006.93
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