Antineoplastic agents. 168. Isolation and structure of axinohydantoin

Pettit, George R.; Herald, Cherry L.; Leet, John E.; Gupta, Ramji; Schaufelberger, Daniel; Bates, Robert B.; Clewlow, Paul J.; Doubek, Dennis L.; Manfredi, Kirk P.; Rützler, Klaus; Schmidt, Jean M.; Tackett, Larry P.; Ward, Franklin B.; Bruck, Michael A.; Camou, Fernando A.

doi:10.1139/v90-250

Cited by 47 publications

(30 citation statements)

References 5 publications

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“…Also the 1 H-NMR spectrum showed one aromatic proton [δ H 6.60 (s)] attached to C-4 (δ C 114.4) while no signals for the NH 2 between 7 to 8 ppm were observed as found in the known congeners 8 and 13. Both 1 H and 13 C-NMR values of C-4 were similar to those observed in related compounds as in hymenialdisine [2], axinohydantoin [20], and spongiacidin D [21]. The HMBC spectrum (Figure 1) exhibited correlations between H-4 to carbons C-2 (δ C 129.6) and C-5 (δ C 103.3).…”

supporting

confidence: 76%

Dibromopyrrole Alkaloids from the Marine Sponge Acanthostylotella sp

Ebada

Edrada-Ebel

Voogd

et al. 2009

Natural Product Communications

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Fourteen dibromopyrrole alkaloids were isolated from the marine sponge Acanthostylotella sp. collected in Indonesia. In addition to the known compounds 4,5-dibromo-N-(methoxy-methyl)-1H-pyrrole-2-carboxamide (7), 4,5-dibromo-1H-pyrrole-2-carboxamide (8), mukanadin D (9), (±)-longamide B methyl ester (10), (±)-longamide B (11), (±)-longamide (12), 3,4-dibromo-1H-pyrrole-2-carboxamide (13), 2-cyano-4,5-dibromo-1H-pyrrole (14), six compounds were isolated that proved to be new natural products including acanthamides AD (1-4), methyl 3,4-dibromo-1H-pyrrole-2-carboxylate (5) and 3,5-dibromo-1H-pyrrole-2-carboxylic acid (6). The structures of the new compounds were unequivocally identified based on one and two dimensional NMR and on HRFTMS as well as by comparison with the literature.

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supporting

confidence: 76%

Dibromopyrrole Alkaloids from the Marine Sponge Acanthostylotella sp

Ebada

Edrada-Ebel

Voogd

et al. 2009

Natural Product Communications

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“…Olomoucine and roscovitine were from Alexis corporation; purvalanol was a gift of N. Gray. HD was purified as described previously [40]. The following proteins and antibodies were generously donated: cdk4/cyclin D1, GST–p16 INK4 , GST–p21 CIP1 , high mobility group protein (HMG)I, monoclonal antibodies against H 2 N‐EGVPSTAIRESLLKEGGC‐COOH (‘anti‐PSTAIRE’ antibodies) [8].…”

Section: Methodsmentioning

confidence: 99%

Characterization of a novel cdk1‐related kinase

Détivaud

Pettit

Meijer

1999

European Journal of Biochemistry

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The p13 suc1 /p9 CKShs proteins bind tightly to the cyclin-dependent kinases cdk1 and cdk2. The distantly related protein, p15 cdk-BP , binds cdk4/6, cdk5 and cdk8. We now show that immobilized p15 cdk-BP binds both an HMG-I kinase and a 35-kDa protein that cross-reacts with anti-PSTAIRE antibodies (PSTAIRE is a totally conserved motif located in subdomain III of cdk). This`cdkX' and the HMG-I kinase also bind to an immobilized inhibitor of cdks (HD). Several properties clearly distinguish cdkX, and its associated HMG-I kinase, from known anti-PSTAIRE cross-reactive cdks: (a) cdkX migrates, in SDS/PAGE, in a position intermediate between prophase phosphorylated cdk1 and metaphase dephosphorylated cdk1; (b) in contrast with cdk1, cdkX and associated HMG-I kinase activity do not decrease following successive depletions on p9 CKShs1 ±sepharose; (c) cdkX and associated HMG-I kinase activity, but not cdk1, decrease following depletions on immobilized inhibitor; (d) cdkX is expressed during the early development of sea urchin embryos; in contrast with cdk1/cyclin B kinase, the p15 cdk-BP -bound HMG-I kinase is active throughout the cell cycle; compared with cdk1 it is active later in development; (e) p15 cdk-BP -bound HMG-I kinase is essentially insensitive to powerful inhibitors of cdk such as purvalanol, roscovitine, olomoucine, p21 cip1 and p16 INK4A ; HD is only moderately inhibitory. Altogether these results suggest the existence of a new cdk1-related kinase, possibly involved in the regulation of early development. The presence of this kinase in all organisms investigated so far, from plants to mammals, calls for its definitive identification.Keywords: cdc2; cdk-BP; CKS; CKShs1; cyclin-dependent kinases; HMG-I; cell cycle; PSTAIRE; suc1.The cyclin-dependent kinases (cdk), regulate the cell division cycle (for reviews, see [1,2]). Cdc2 was the first cdk to be described, as a gene essential for G 1 /S and G 2 /M transitions in Schizosaccharomyces pombe [3]. In addition to cdc2 and CDC28, its homologue in Saccharomyces cerevisiae [4], the yeast genomes contain several related kinases: Mop1 (Sc. pombe), PHO85, KIN28, CTK1, SVG1 and SRB10 in S. cerevisiae (for a review see [5]). A human cdc2 homologue, cdk1, was identified by complementation [6], followed by homologues in all species from yeast and plants to mammals [2,7]. They all share a totally conserved motif, known as the PSTAIRE motif, located in subdomain III of the kinase. Antibodies directed against the PSTAIRE motif are widely used in the immunodetection of cdk1 and cdk2 [8]; this domain is involved in the binding of cyclins and has been used to design oligonucleotides by which to identify and name new cdk1-related kinases [9]. So far, nine mammalian cdks have been described: cdk1, 2, 3, 4, 6 and 7 regulate the cell cycle, cdk5 is involved in neural tissue and cdk7, 8 and 9 regulate transcription (for a review see [2,10] whereas PCTAIRE-2 is expressed in postmitotic neurones [18]. The PITSLRE kinase family appears to play an important role in apoptosis [19,...

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“…Hymenialdisine (361) was identified by analysis of spectral data and X-ray diffraction, as well as. 2-Debromohymenialdisine (357) and hymenialdisine (361) were subsequently isolated from Palau (Caroline Islands), Truk (Caroline Islands) and Papua New Guinea Axinella and Hymeniacidon sponge specimens (630). (361) A biogenetic pathway was proposed for monobromophakellin (4), dibromophakellin (5), 2-debromohymenialdisine (357) and hymenialdisine (361), with proline and cx-guanidinoornithine as their precursors.…”

Section: Marine Spongesmentioning

confidence: 99%

Some Aspects of Guanidine Secondary Metabolites

Berlinck

1995

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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Antineoplastic agents. 168. Isolation and structure of axinohydantoin

Cited by 47 publications

References 5 publications

Dibromopyrrole Alkaloids from the Marine Sponge Acanthostylotella sp

Dibromopyrrole Alkaloids from the Marine Sponge Acanthostylotella sp

Characterization of a novel cdk1‐related kinase

Some Aspects of Guanidine Secondary Metabolites

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