Mass spectrometric determination of amino acid sequence in Cyl-2, a novel cyclotetrapeptide from Cylindrocladium scoparium

Hirota, Akira; Suzuki, Akira; Aizawa, K.; Tamura, Saburo

doi:10.1002/bms.1200010106

Cited by 22 publications

(3 citation statements)

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“…Our research group is focused on investigating the chemical diversity of fungi to generate new and therapeutically useful bioactive compounds. − In our investigation of fungal natural products that are active against human pancreatic carcinoma cell lines, a potent HDAC inhibitor, 1-alaninechlamydocin ( 1 ), was obtained from a Great Lakes-derived fungal isolate identified as a Tolypocladium sp. Structurally, 1-alaninechlamydocin ( 1 ) belongs to the cyclic epoxytetrapeptide family of HDAC inhibitors that include the trapoxins, , HC toxin, Cyl-1 and Cyl-2, and WF-3161 . Although the planar structure of compound 1 was reported by Kim et al in 1992, details of its absolute configuration and assessment of its biological activities had not been described.…”

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confidence: 99%

A Potent HDAC Inhibitor, 1-Alaninechlamydocin, from a Tolypocladium sp. Induces G2/M Cell Cycle Arrest and Apoptosis in MIA PaCa-2 Cells

Risinger

King

et al. 2014

J. Nat. Prod.

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The cyclic tetrapeptide 1-alaninechlamydocin was purified from a Great Lakes-derived fungal isolate identified as a Tolypocladium sp. Although the planar structure was previously described, a detailed analysis of its spectroscopic data and biological activity are reported here for the first time. Its absolute configuration was determined using a combination of spectroscopic (1H–1H ROESY, ECD, and X-ray diffraction) and chemical (Marfey’s analysis) methods. 1-Alaninechlamydocin showed potent antiproliferative/cytotoxic activities in a human pancreatic cancer cell line (MIA PaCa-2) at low-nanomolar concentrations (GI50 5.3 nM, TGI 8.8 nM, LC50 22 nM). Further analysis revealed that 1-alaninechlamydocin induced G2/M cell cycle arrest and apoptosis. Similar to other cyclic epoxytetrapeptides, the inhibitory effects of 1-alaninechlamydocin are proposed to be produced primarily via inhibition of histone deacetylase (HDAC) activity.

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confidence: 99%

A Potent HDAC Inhibitor, 1-Alaninechlamydocin, from a Tolypocladium sp. Induces G2/M Cell Cycle Arrest and Apoptosis in MIA PaCa-2 Cells

Risinger

King

et al. 2014

J. Nat. Prod.

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“…Several of these HDAC inhibitors inhibit tumor growth, and many of these are under clinical trials. Trichostatin A (TSA), a cyclic tetrapeptide family, including trapoxin (TPX), chlamydocin, HC toxin, Cyl-1, Cyl-2, WF-3161, apicidin, and the recent depsipeptide FK228 (formerly FR901228) are naturally occurring HDAC inhibitors (Figure ). Inhibitors such as butyrate, valproate, suberoyl anilide hydroxamic acid, analogues of TSA, and benzamide derivatives of MS-275 14 were prepared through synthetic methods.…”

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confidence: 99%

Cyclic Tetrapeptides Bearing a Sulfhydryl Group Potently Inhibit Histone Deacetylases

et al. 2003

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“…(II) Cyclic tetrapeptides with the epoxyketone-containing amino acid (2S,9S)-2-amino-8-oxo-9,10-epoxydecanoyl (Aoe) (such as trapoxin A and B [44], Cyl-1 and Cyl-2 [45], HC-toxin [46], WF-3161 [47], chlamydocin [48]);…”

Section: Chromatin Remodelling and Histone Deacetylases (Hdacs)mentioning

confidence: 99%

Histone Deacetylase Inhibitors: Recent Insights from Basic to Clinical Knowledge & Patenting of Anti-Cancer Actions

Carafa

Nebbioso²,

Altucci³

2011

PRA

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Epigenetic modiﬁcations have been causally linked to cancer development and progression, and are potentially reversible by drug treatments. The N-terminal tails of histones contain amino acid residues modiﬁable by post-translational modifications such as acetylation. Given that HDAC inhibitors induce cancer cell differentiation and death, an increasing number of these compounds has been synthesized in the last ten years. Many HDAC inhibitors are in clinical trials for the treatment of cancer. Two of them, the hydroxamic acid (SAHA) and Romidepsin (FK 228), are approved in the second line treatment of refractory, persistent or relapsed Cutaneous T Cell Lymphoma (CTCL). The growing evidence of the potential benefits of an anti-cancer treatment based on the use of HDAC inhibitors have led to a large number of patent applications all over the world. The aim of this review is to give an overview of the basic current knowledge and molecular mechanisms of HDAC inhibitors and their clinical trials as well as to focus on the recent patent applications existing in the field of HDAC inhibitors and cancer treatment between 2008 and 2010 in USA.

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Mass spectrometric determination of amino acid sequence in Cyl-2, a novel cyclotetrapeptide from Cylindrocladium scoparium

Cited by 22 publications

References 5 publications

A Potent HDAC Inhibitor, 1-Alaninechlamydocin, from a Tolypocladium sp. Induces G2/M Cell Cycle Arrest and Apoptosis in MIA PaCa-2 Cells

A Potent HDAC Inhibitor, 1-Alaninechlamydocin, from a Tolypocladium sp. Induces G2/M Cell Cycle Arrest and Apoptosis in MIA PaCa-2 Cells

Cyclic Tetrapeptides Bearing a Sulfhydryl Group Potently Inhibit Histone Deacetylases

Histone Deacetylase Inhibitors: Recent Insights from Basic to Clinical Knowledge & Patenting of Anti-Cancer Actions

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