11-Deoxylandomycinone and landomycins X-Z, new cytotoxic angucyclin(on)es from a streptomyces cyanogenus K62 mutant strain

Khaled A. Shaaban; Chris Stamatkin; Chendil Damodaran; Jürgen Rohr

doi:10.1038/ja.2010.121

11-Deoxylandomycinone and landomycins X-Z, new cytotoxic angucyclin(on)es from a streptomyces cyanogenus K62 mutant strain

Khaled A. Shaaban, Chris Stamatkin, Chendil Damodaran, Jürgen Rohr

Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

37 Scopus citations

Abstract

Four new angucyclin(on)es, 11-deoxylandomycinone (1) and landomycins X-Z (2-4) were isolated from the crude extract of Streptomyces cyanogenus K62 mutant strain, along with the recently reported landomycins S, T and V (5-7) and five other known compounds. The structures of the new compounds 1-4 were elucidated by 1D and 2D NMR studies along with HR-MS analyses. Unique about the structures is that the fourth sugar moiety (sugar D) in landomycins X-Z (2-4) was β-D-amicetose instead of β-D-olivose, usually found in this position. The new angucyclin(on)es were biologically evaluated in comparison with previously known congeners against a small panel of MCF-7 (estrogen responsive) and MDA 231 (estrogen refractory) breast cancer cell lines. 11- deoxylandomycinone (IC₅₀ 2.1±0.3 and 1.2±0.4 μM) and landomycin Y (IC₅₀ 1.0±0.1 and 2.0±0.1 μM) showed the highest cytotoxic potencies against both the cell lines.

Original language	English
Pages (from-to)	141-150
Number of pages	10
Journal	Journal of Antibiotics
Volume	64
Issue number	1
DOIs	https://doi.org/10.1038/ja.2010.121
State	Published - Jan 2011

Bibliographical note

Funding Information:
The mass spectrometry department, University of Wisconsin Biotechnology Centre is acknowledged for the HR-MS data. This work was supported by grant CA 102102 from the US National Institutes of Health to JR.

Keywords

angucyclines
anticancer agents
cytotoxicity
landomycins
polyketides
structureactivity relationships

ASJC Scopus subject areas

Pharmacology
Drug Discovery

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1038/ja.2010.121

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title = "11-Deoxylandomycinone and landomycins X-Z, new cytotoxic angucyclin(on)es from a streptomyces cyanogenus K62 mutant strain",

abstract = "Four new angucyclin(on)es, 11-deoxylandomycinone (1) and landomycins X-Z (2-4) were isolated from the crude extract of Streptomyces cyanogenus K62 mutant strain, along with the recently reported landomycins S, T and V (5-7) and five other known compounds. The structures of the new compounds 1-4 were elucidated by 1D and 2D NMR studies along with HR-MS analyses. Unique about the structures is that the fourth sugar moiety (sugar D) in landomycins X-Z (2-4) was β-D-amicetose instead of β-D-olivose, usually found in this position. The new angucyclin(on)es were biologically evaluated in comparison with previously known congeners against a small panel of MCF-7 (estrogen responsive) and MDA 231 (estrogen refractory) breast cancer cell lines. 11- deoxylandomycinone (IC50 2.1±0.3 and 1.2±0.4 μM) and landomycin Y (IC50 1.0±0.1 and 2.0±0.1 μM) showed the highest cytotoxic potencies against both the cell lines.",

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AU - Stamatkin, Chris

AU - Damodaran, Chendil

AU - Rohr, Jürgen

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11-Deoxylandomycinone and landomycins X-Z, new cytotoxic angucyclin(on)es from a streptomyces cyanogenus K62 mutant strain

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

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