Literature DB >> 12715869

Yatakemycin, a novel antifungal antibiotic produced by Streptomyces sp. TP-A0356.

Yasuhiro Igarashi1, Katsuyuki Futamata, Tsuyoshi Fujita, Akira Sekine, Hisato Senda, Hideo Naoki, Tamotsu Furumai.   

Abstract

In the screening of novel antifungal compounds, yatakemycin was found in the culture broth of Streptomyces sp. TP-A0356. Yatakemycin was obtained by solvent extraction of the fermentation broth and chromatographic purification using ODS column and preparative HPLC. The structure of yatakemycin was elucidated by NMR and CID-MS/MS experiments as a novel antibiotic belonging to a family of CC-1065 and duocarmycins known to be DNA alkylating agents. Yatakemycin inhibited the growth of pathogenic fungi such as Aspergillus fumigatus and Candida albicans with the MIC values of 0.01-0.03 microg/ml, more potent than amphotericin B (MIC: 0.1-0.5 microg/ml) or itraconazole (MIC: 0.03-0.2 microg/ml). It also showed potent cytotoxicity against cancer cell lines with the IC50 of 0.01-0.3 microg/ml.

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Year:  2003        PMID: 12715869     DOI: 10.7164/antibiotics.56.107

Source DB:  PubMed          Journal:  J Antibiot (Tokyo)        ISSN: 0021-8820            Impact factor:   2.649


  34 in total

1.  Synthesis and evaluation of duocarmycin SA analogs incorporating the methyl 1,2,8,8a-tetrahydrocyclopropa[c]oxazolo[2,3-e]indol-4-one-6-carboxylate (COI) alkylation subunit.

Authors:  Kristopher E Boyle; Karen S MacMillan; David A Ellis; James P Lajiness; William M Robertson; Dale L Boger
Journal:  Bioorg Med Chem Lett       Date:  2010-02-02       Impact factor: 2.823

2.  Systematic exploration of the structural features of yatakemycin impacting DNA alkylation and biological activity.

Authors:  Mark S Tichenor; Karen S MacMillan; John D Trzupek; Thomas J Rayl; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2007-08-11       Impact factor: 15.419

3.  A five-membered lactone prodrug of CBI-based analogs of the duocarmycins.

Authors:  Mika Uematsu; Daniel M Brody; Dale L Boger
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

4.  Synthesis and evaluation of a series of C5'-substituted duocarmycin SA analogs.

Authors:  William M Robertson; David B Kastrinsky; Inkyu Hwang; Dale L Boger
Journal:  Bioorg Med Chem Lett       Date:  2010-03-25       Impact factor: 2.823

5.  Asymmetric total synthesis of (+)- and ent-(-)-yatakemycin and duocarmycin SA: evaluation of yatakemycin key partial structures and its unnatural enantiomer.

Authors:  Mark S Tichenor; John D Trzupek; David B Kastrinsky; Futoshi Shiga; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2006-12-13       Impact factor: 15.419

6.  Efficacious cyclic N-acyl O-amino phenol duocarmycin prodrugs.

Authors:  Amanda L Wolfe; Katharine K Duncan; Nikhil K Parelkar; Douglas Brown; George A Vielhauer; Dale L Boger
Journal:  J Med Chem       Date:  2013-05-10       Impact factor: 7.446

7.  Insights into conformational changes in AlkD bound to DNA with a yatakemycin adduct from computational simulations.

Authors:  Pavel Silvestrov; G Andrés Cisneros
Journal:  Theor Chem Acc       Date:  2018-05-12       Impact factor: 1.702

8.  A unique class of duocarmycin and CC-1065 analogues subject to reductive activation.

Authors:  Wei Jin; John D Trzupek; Thomas J Rayl; Melinda A Broward; George A Vielhauer; Scott J Weir; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2007-11-17       Impact factor: 15.419

9.  Synthesis and evaluation of a thio analogue of duocarmycin SA.

Authors:  Karen S MacMillan; James P Lajiness; Carlota Lopez Cara; Romeo Romagnoli; William M Robertson; Inkyu Hwang; Pier Giovanni Baraldi; Dale L Boger
Journal:  Bioorg Med Chem Lett       Date:  2009-10-17       Impact factor: 2.823

Review 10.  Fundamental relationships between structure, reactivity, and biological activity for the duocarmycins and CC-1065.

Authors:  Karen S MacMillan; Dale L Boger
Journal:  J Med Chem       Date:  2009-10-08       Impact factor: 7.446

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