Yatakemycin, a Novel Antifungal Antibiotic Produced by Streptomyces sp. TP-A0356.

Igarashi, Yasuhiro; Futamata, Katsuyuki; Fujita, Tsuyoshi; Sekine, Akira; Senda, Hisato; Naoki, Hideo; Furumai, Tamotsu

doi:10.7164/antibiotics.56.107

Cited by 106 publications

(73 citation statements)

References 6 publications

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“…More recently, (+)-yatakemycin (10) has been isolated from Streptomyces sp. and represents the most potent member of this class of natural products [4]. The biological activity of these natural products is related to a characteristic sequence-selective alkylation of adenine N3 in AT-rich sites by the least substituted carbon of the activated cyclopropane ( Fig.…”

Section: Investigations Of Cc-1065 the Duocarmycins And Synthetic Anmentioning

confidence: 99%

Chemical and Biological Explorations of the Family of CC-1065 and the Duocarmycin Natural Products

Ghosh¹,

Sheldrake²,

Searcey³

et al. 2009

CTMC

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CC-1065, the duocarmycins and yatakemycin are members of a family of ultrapotent antitumour antibiotics that have been the subject of extensive investigations due to their mode of action and potential in the design of new anticancer therapeutics. The natural products and their analogues exert their effects through a sequence selective alkylation of duplex DNA in the minor groove at the N3 of adenine. An understanding of their structure and its effect on biological activity has been derived through chemical synthesis and has also generated new potential lead compounds. These studies form the first section of the review. The desire to progress these compounds to clinic has also led to studies of bioconjugation and prodrug formation and this is discussed in the second section of the review. The combination of synthesis with key biological experiments is a powerful tool to define the requirements for the development of natural products as potential therapeutic agents. The studies described herein form an excellent paradigm for the study and development of other natural products

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Section: Investigations Of Cc-1065 the Duocarmycins And Synthetic Anmentioning

confidence: 99%

Chemical and Biological Explorations of the Family of CC-1065 and the Duocarmycin Natural Products

Ghosh¹,

Sheldrake²,

Searcey³

et al. 2009

CTMC

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“…TP-A0356, [89] represents the newest and most potent member of a class of natural antitumor compounds. [84][85][86][87][88] Its biological activity is derived from the ability of alkylating specific adenine residues in the minor groove of AT-rich tracts.…”

Section: Quantum Mechanical Calculation Of Nmr Parameters As a Tool Fmentioning

confidence: 99%

Quantum Mechanical Calculation of NMR Parameters in the Stereostructural Determination of Natural Products

et al. 2010

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The present microreview highlights the recent goals reached by the application of a combined approach of NMR spectroscopy and quantum chemical methods in the structural studies of natural products. In particular, different case studies are reported, showing the comparison of calculated NMR parameters at the quantum mechanical (QM) theory level with experimental data for the configurational assignment of organic compounds. Moreover, it is shown that the QM-NMR

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“…17 Since the three diketopiperazines we isolated proved uninhibitory in our cancer cell line evaluations, we did not determine their chirality. Separation was continued to yield the PS cell-line-active 3-(hydroxyacetyl)indole (8). 18 The diazaanthraquinone 1 and 3-(hydroxyacetyl)indole (8) exhibited significant growth inhibitory activity when evaluated against the murine P388 lymphocytic leukemia cell line and a minipanel of six human tumor cell lines (Table 1).…”

mentioning

confidence: 99%

Antineoplastic Agents. 554. The Manitoba Bacterium Streptomyces sp.^,1

Pettit

et al. 2006

J. Nat. Prod.

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A Streptomyces sp. isolated from riverbank soil in Manitoba, Canada, was found to contain two cancer cell growth inhibitories: diazaanthraquinone 1 and 3-(hydroxyacetyl)indole (8). The structures were determined by interpretation of data from HRMS, UV, and high-field (400 MHz) NMR experiments. The red-colored diazaanthraquinone 1 and 3-(hydroxyacetyl)indole (8) were found to inhibit (0.1-3 microg/mL) growth of a minipanel of human cancer cell lines and P388 lymphocytic leukemia cells. Diazaanthraquinone 1 was also found to inhibit growth of the bacteria Streptococcus pneumoniae and Neisseria gonorrheae. However, three companion constituents, cyclo-Pro-Leu (5), cyclo-Pro-Phe (6), and cyclo-Pro-Val (7), did not inhibit cancer cell growth.

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Yatakemycin, a Novel Antifungal Antibiotic Produced by Streptomyces sp. TP-A0356.

Cited by 106 publications

References 6 publications

Chemical and Biological Explorations of the Family of CC-1065 and the Duocarmycin Natural Products

Chemical and Biological Explorations of the Family of CC-1065 and the Duocarmycin Natural Products

Quantum Mechanical Calculation of NMR Parameters in the Stereostructural Determination of Natural Products

Antineoplastic Agents. 554. The Manitoba Bacterium Streptomyces sp.^,1

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Yatakemycin, a Novel Antifungal Antibiotic Produced by Streptomyces sp. TP-A0356.

Cited by 106 publications

References 6 publications

Chemical and Biological Explorations of the Family of CC-1065 and the Duocarmycin Natural Products

Chemical and Biological Explorations of the Family of CC-1065 and the Duocarmycin Natural Products

Quantum Mechanical Calculation of NMR Parameters in the Stereostructural Determination of Natural Products

Antineoplastic Agents. 554. The Manitoba Bacterium Streptomyces sp.,1

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Product

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Antineoplastic Agents. 554. The Manitoba Bacterium Streptomyces sp.^,1