The structure of the toxin from helminthosporium carbonum

Gross, Michael L.; McCrery, David A.; Crow, Frank W.; Tomer, Kenneth B.; Pope, Mark R.; Ciuffetti, Lynda M.; Knoche, H. W.; Daly, J.M.; Dunkle, Larry D.

doi:10.1016/0040-4039(82)80135-4

Cited by 88 publications

(37 citation statements)

References 6 publications

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“…For instance, HC-toxin I (35, commonly referred to as HC-toxin), a fungal metabolite produced at low levels by Helminthosporium carbonum, was one of the first cyclotetrapeptides in this structural class identified. Its structure, initially characterized by Liesch et al [62], later was revised by Knoche and co-workers [63,64]. Further investigations led to the identification of additional fermentation congeners present in this broth, including HC-toxin III (36) [65], bearing a trans-3-hydroxyproline.…”

Section: Inhibitory Efficacy Of Benzamide-derived Trichostatin Mimicsmentioning

confidence: 96%

Histone Deacetylase: A Target for Antiproliferative and Antiprotozoal Agents

Meinke¹,

Liberator²

2001

CMC

108

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Histone deacetylase (HDAC) and histone acetyltransferase (HAT) are enzymes that influence transcription by selectively deacetylating or acetylating the eta-amino groups of lysines located near the amino termini of core histone proteins. It is well-established that in transcriptionally active chromatin, histones generally are hyperacetylated and, conversely, hypoacetylated histones are coincident with silenced chromatin. Revived interest in these enzymatic pathways and how they modulate eukaryotic transcription has led to the identification of multiple cofactors whose complex interplay with HDAC affects gene expression. Concurrent with these discoveries, screening of natural product sources yielded new small molecules that were subsequently identified as potent inhibitors of HDAC. While predominantly identified using antiproliferative assays, the biological activity of these new HDAC inhibitors also encompasses significant antiprotozoal, antifungal, phytotoxic and antiviral applications. These newly discovered HDAC inhibitors served as lead structures for the development of improved derivatives including related reagents with considerable potential as tools to further elucidate the mechanism of transcriptional regulation.

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Section: Inhibitory Efficacy Of Benzamide-derived Trichostatin Mimicsmentioning

confidence: 96%

Histone Deacetylase: A Target for Antiproliferative and Antiprotozoal Agents

Meinke¹,

Liberator²

2001

CMC

108

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“…The first collisionally activated dissociation (CAD) studies of protonated cyclic peptides were published in the early 1980s by Gross et al [16] and Aubagnac et al [17], and the work up to 1994 has been reviewed by Eckart [18]. Since then, groups have reported CAD and MS n results for protonated synthetic and naturally occurring cyclic peptides [19 -30].…”

mentioning

confidence: 98%

MSⁿcharacterization of protonated cyclic peptides and metal complexes

Williams

Brodbelt

2004

J. Am. Soc. Mass Spectrom.

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MS(n) experiments involving low energy collisionally activated dissociation (CAD) in a quadrupole ion trap were used to characterize the fragmentation of alkali, alkaline earth and transition metal complexes of five cyclic peptides, and the results were compared with those obtained for protonated cyclic peptides. Complexes with metal ions produced enhanced abundances of the most diagnostic fragments for elucidating the primary structures. For cyclosporin A, nickel and lithium complexes gave additional sequence information compared with the protonated peptide. For depsipeptides, sodium and lead complexes were superior to the protonated peptide or other metal complexes for sequencing residues, and CAD of the lead complexes led to preferential cleavage of two residues at a time. For cyclic lipopeptides, complexes with silver, nickel and strontium ions provided enhanced abundances of key fragment ions.

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“…Since then many other natural products, closely related to chlamydocin (33), [103] such as HC-toxin (34), [104] and WF-3161 (35), [105] were described.…”

Section: Cyclic Peptidesmentioning

confidence: 99%

Chemistry and Biology of Chromatin Remodeling Agents: State of Art and Future Perspectives of HDAC Inhibitors

Rodriquez¹,

Aquino²,

Bruno³

et al. 2006

CMC

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Chromatin remodeling is a fundamental phenomenon in the life of eukaryotic cells, bearing implications to numerous physiological and pathological phenomena. This review outlines the chemistry of natural and synthetic agents endowed with the ability to interfere with such biological function, with a particular emphasis on histone deacetylase (HDAC) inhibitors. Other aspects covered in this article comprise structure activity relationships (SAR) and modes of action at molecular level, including the description of crystal structures of enzyme-inhibitor complexes.

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The structure of the toxin from helminthosporium carbonum

Cited by 88 publications

References 6 publications

Histone Deacetylase: A Target for Antiproliferative and Antiprotozoal Agents

Histone Deacetylase: A Target for Antiproliferative and Antiprotozoal Agents

MSⁿcharacterization of protonated cyclic peptides and metal complexes

Chemistry and Biology of Chromatin Remodeling Agents: State of Art and Future Perspectives of HDAC Inhibitors

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The structure of the toxin from helminthosporium carbonum

Cited by 88 publications

References 6 publications

Histone Deacetylase: A Target for Antiproliferative and Antiprotozoal Agents

Histone Deacetylase: A Target for Antiproliferative and Antiprotozoal Agents

MSncharacterization of protonated cyclic peptides and metal complexes

Chemistry and Biology of Chromatin Remodeling Agents: State of Art and Future Perspectives of HDAC Inhibitors

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MSⁿcharacterization of protonated cyclic peptides and metal complexes