Structural modifications of anguidin and antitumor activities of its analogs

Kaneko, Toshihiko; Schmitz, H; Essery, J. M.; Rose, William C.; Howell, H. G.; O'herron, F. A.; Nachfolger, S.; Huftalen, James B.; Bradner, William T.

doi:10.1021/jm00347a018

Cited by 31 publications

(11 citation statements)

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“…13 To calibrate our findings, it is first necessary to briefly review literature data dealing with the cytotoxicity and antitumor and anticancer evaluation of trichothecenes. Highlights of this SAR appear in Chart S2 and reflect substantial in vivo data collected in the early 1980s from the P388 leukemia mouse model on 61 anguidoid (I′) 33 analogues and on 37 type III and IV macrocycles. 21 The positive in vivo activity in the mouse for anguidin (17) 34 prompted, in the late 1970s, five distinct series of Phase II studies that involved a total of 484 patients.…”

Section: Resultsmentioning

confidence: 74%

Structures and Cytotoxic Properties of Trichoverroids and Their Macrolide Analogues Produced by Saltwater Culture of Myrothecium verrucaria

et al. 2003

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Saltwater culture of Myrothecium verrucaria, separated from a Spongia sp. collected in Hawaii, was a source of three new trichothecenes, 3-hydroxyroridin E (1a), 13′-acetyltrichoverrin B (2), and miophytocen C (3) and nine known related compounds (1b, 4, 5, 6, 7a, 7b, 8, 9a, and 9b). The stereostructures of the new compounds were established on the basis of 1D and 2D NMR spectral analyses and a chemical transformation. At the same time, the stereostructures of known compounds, 1b, 4, and 5 reported previously were also elucidated. All the compounds except 3 showed significant cytotoxicity against murine and human tumor cell lines. Moreover, the structure-activity relationships (SARs) were established from the results of the bioassay data.

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Section: Resultsmentioning

confidence: 74%

Structures and Cytotoxic Properties of Trichoverroids and Their Macrolide Analogues Produced by Saltwater Culture of Myrothecium verrucaria

et al. 2003

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“…Both of these fungal species have been isolated from maize and wheat kernels, but in comparison with E graminearum, their pathogenicity is regarded as weak [30]. DAS is highly toxic to humans and animals [64], and has reported antibiotic and anti-tumour properties [65].…”

Section: Diacetyoxyscirpenol (Das)mentioning

confidence: 99%

The phytotoxicity ofFusarium metabolites: An update since 1989

McLean

1996

Mycopathologia

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The present article summarises the published phytotoxic effects of severalFusarium metabolites (mycotoxins, phytotoxins, antibiotics and pigments) since 1989. The phytotoxicity of many of the commonly isolated metabolites cannot be disputed, but their role in pathogenesis ofFusarium-induced plant diseases is uncertain. Plant species/varieties differ in their susceptibililty resistance to these toxinsin vitro, as well as toFusarium pathogens under field conditions. Such variations in plant response may reflect resistance mechanisms that operate at several levels, including an initial ability to prevent fungal invasion; prevention of fungal spread and toxin tolerance or degradation. Little is known about the mode of action of most of these metabolites on either animal or plant cells. Several novelFusarium metabolites have been isolated in the past few years. Many are toxic to animals and cell lines, but assessment of their phytotoxicity has largely been neglected. Since many plant pathogenic Fusaria produce a plethora of metabolites, the additive or synergistic actions of toxins in combination must be considered in plant pathology.

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“…and is phytotoxic and cytotoxic. Because of its antibiotic and antitumor effects, DAS and structurally modified related trichothecenes have undergone extensive studies for their antitumor properties (1, 7,11). Clinically, DAS is sometimes called anguidine (11).…”

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confidence: 99%

Production and characterization of antibody against diacetoxyscirpenol

Chu¹,

Liang²,

Zhang³

1984

Appl Environ Microbiol

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Antibodies against diacetoxyscirpenol (DAS) were obtained from rabbits after immunizing them with hemisuccinate or hemiglutarate derivatives of DAS conjugated to bovine serum albumin (BSA). DAShemiglutarate-BSA was found to be a much better immunogen than DAS-hemisuccinate-BSA. Competitive radioimmunoassay revealed that the antisera obtained from rabbits after immunization with DAS-hemiglutarate-BSA showed high specificity toward DAS. The concentrations causing 50% displacement of radioactive DAS by unlabeled DAS, 4-monoacetoxyscirpenol (MAS), and 15-MAS were found to be 1.5, 130, and 300 ng per assay, respectively. Thus, the cross-reactivities for 4-MAS and 15-MAS are ca. 87 and 300 times weaker than that of DAS. Practically no cross-reaction (less than 5% displacement) was observed when deoxynivalenol, T-2 toxin, deoxyverrucarol, and scirpentriol were tested at a concentration of 2,000 ng/ml.

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Structural modifications of anguidin and antitumor activities of its analogs

Cited by 31 publications

References 0 publications

Structures and Cytotoxic Properties of Trichoverroids and Their Macrolide Analogues Produced by Saltwater Culture of Myrothecium verrucaria

Structures and Cytotoxic Properties of Trichoverroids and Their Macrolide Analogues Produced by Saltwater Culture of Myrothecium verrucaria

The phytotoxicity ofFusarium metabolites: An update since 1989

Production and characterization of antibody against diacetoxyscirpenol

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