STRUCTURAL STUDIES ON STREPTONIVICIN,<sup>1</sup> A NEW ANTIBIOTIC

Hoeksema, Herman; Johnson, Jerry; Hinman, J. W.

doi:10.1021/ja01629a129

Cited by 67 publications

(28 citation statements)

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“…The coumarin antibiotic, novobiocin [75], was the first small-molecule observed to bind the HSP90 C-terminus, as assessed by the ability of an immobilized derivative to selectively interact with this domain [76–79]. These observations elicited efforts to identify other C-terminal HSP90 interactors, many of which are based upon the novobiocin scaffold (Fig.…”

Section: Hsp90mentioning

confidence: 99%

The Chemical Biology of Molecular Chaperones—Implications for Modulation of Proteostasis

Brandvold

Morimoto

2015

Journal of Molecular Biology

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Protein homeostasis (proteostasis) is inextricably tied to cellular health and organismal lifespan. Aging, exposure to physiological and environmental stress, and expression of mutant and metastable proteins can cause an imbalance in the protein folding landscape, resulting in the formation of non-native protein aggregates that challenge the capacity of the proteostasis network (PN), increasing the risk for diseases associated with misfolding, aggregation and aberrant regulation of cell stress responses. Molecular chaperones have central roles in each of the arms of the PN (protein synthesis, folding, disaggregation, and degradation), leading to the proposal that modulation of chaperone function could have therapeutic benefits for the large and growing family of diseases of protein conformation including neurodegeneration, metabolic diseases, and cancer. In this review, we will discuss the current strategies used to tune the PN through targeting molecular chaperones and assess the potential of the chemical biology of proteostasis.

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Section: Hsp90mentioning

confidence: 99%

The Chemical Biology of Molecular Chaperones—Implications for Modulation of Proteostasis

Brandvold

Morimoto

2015

Journal of Molecular Biology

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“…Novobiocin (albamycin, cathomycin), first reported in 1955 under the name streptonivicin (Hoeksema 1955), is an aminocoumarin antibiotic that is produced by the actinomycetes Streptomyces niveus and Streptomyces spheroides, members of the order Actinobacteria. The HSP90 inhibitor engages a C-terminal motif 16 .…”

Section: Hsp90 Inhibitorsmentioning

confidence: 99%

Molecular Inhibitors of Growth Signals

Weber

2015

Molecular Therapies of Cancer

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“…4-Hydroxy-3-prenylbenzoic acid (Ring B) is a known compound, and is part of the antibiotic novobiocin. [9][10][11][12][13] The structure of Ring B was elucidated by comparing the spectroscopic data of PF1223 with those of 4-hydroxy-3-prenylbenzoic acid. The structure of Ring A was determined mainly from two-dimensional NMR spectra (Fig.…”

Section: Isolation and Structural Determinationmentioning

confidence: 99%

Isocoumarin Derivative as a Novel GABA Receptor Ligand from Neosartorya quadricincta

et al. 2004

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The receptor for the inhibitory neurotransmitter GABA is known as a target for such insecticides and acaricides as fipronil and avermectins.1) These insecticides selectively act on the insect GABA receptor, and thus are toxic to insects but not mammals. We previously reported that naturally occurring terpenoids such as picrodendrins and anisatin exhibit insecticidal activity by binding to the antagonist site of the GABA receptor. [2][3][4][5] Several terpene lactones such as picrodendrin O exhibited selective affinity for the insect versus mammalian GABA receptors. We have also isolated insecticidal alkaloid GABA antagonists from the culture of Aspergillus terreus by binding assay-guided screening.6) This earlier screening convinced us that our fungal cultures are a rich source of GABAergic or anti-GABAergic compounds.We report here on the subsequent isolation and structural elucidation of a novel ligand for the insect GABA receptor. MATERIALS AND METHODS InstrumentsThe NMR spectra were recorded on a JEOL GSX400 instrument. Mass spectra were obtained on a JEOL JMS-700 spectrometer. The UV and IR spectra were measured on Shimadzu UV-260 and FTIR-8100 spectrophotometers, respectively. Optical rotations were obtained on a JASCO DIP-370 polarimeter. Observations by electron microscopy were performed with a JEOL JSM-6300F electron microscope. Taxonomic StudiesTaxonomic studies of strain PF1223 were performed according to the method of Horie et al.7) The fungal strain PF1223 was deposited at the National Institute of Bioscience and Human-Technology Agency of Industrial Science and Technology, Japan, under the accession number FERM P-17658. FermentationStrain PF1223 was inoculated from an agar slant into a 100-ml Erlenmeyer flask containing 20 ml of a seed medium made up of 1.0% starch, 1.0% glucose, 0.6% wheat germ, 0.2% soybean meal, 0.3% yeast extract, 0.5% polypeptone, 0.2% CaCO 3 , and tap water (pH 7.0 before sterilization). The inoculated flask was shaken on a rotary shaker (200 rpm) at 25°C Matsue, Shimane 690-8504, Japan † Pharmaceutical Research Center, Meiji Seika Kaisha, Ltd., Yokohama, Kanagawa 222-8567, Japan (Received April 27, 2004; Accepted June 2, 2004) For the purpose of discovering GABA receptor-directed insecticides in natural products, fungal culture extracts were screened for their ability to inhibit the specific binding of the noncompetitive antagonist [ 3 H]EBOB to housefly head membranes. The screening efforts led to the isolation of a derivative of dihydroisocoumarin (PF1223) from the culture of Neosartorya quadricincta. This compound at 2.2 mM inhibited [3 H]EBOB binding by 65%. This ligand might prove to be a lead compound for the identification of novel insecticides acting at the insect GABA receptor.

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STRUCTURAL STUDIES ON STREPTONIVICIN,¹ A NEW ANTIBIOTIC

Cited by 67 publications

References 0 publications

The Chemical Biology of Molecular Chaperones—Implications for Modulation of Proteostasis

The Chemical Biology of Molecular Chaperones—Implications for Modulation of Proteostasis

Molecular Inhibitors of Growth Signals

Isocoumarin Derivative as a Novel GABA Receptor Ligand from Neosartorya quadricincta

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STRUCTURAL STUDIES ON STREPTONIVICIN,1 A NEW ANTIBIOTIC

Cited by 67 publications

References 0 publications

The Chemical Biology of Molecular Chaperones—Implications for Modulation of Proteostasis

The Chemical Biology of Molecular Chaperones—Implications for Modulation of Proteostasis

Molecular Inhibitors of Growth Signals

Isocoumarin Derivative as a Novel GABA Receptor Ligand from Neosartorya quadricincta

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Product

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STRUCTURAL STUDIES ON STREPTONIVICIN,¹ A NEW ANTIBIOTIC