Revised structure and structure–activity relationship of bisebromoamide and structure of norbisebromoamide from the marine cyanobacterium Lyngbya sp.

Sasaki, Hiroaki; Teruya, Toshiaki; Fukazawa, Hidesuke; Suenaga, Kiyotake

doi:10.1016/j.tet.2010.11.106

Cited by 34 publications

(25 citation statements)

References 25 publications

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“…Based on the total synthesis of bisebromoamide, reported by Gao and co-workers [65], the stereochemistry of the molecule has been revised to compound 32. The revised structure of bisebromoamide was also confirmed through synthesis by Sasaki and co-workers [66]. In addition, a highly convergent method of synthesizing bisebromoamide and other simplified analogues was recently reported by Li and co-workers [67].…”

Section: Bisebromoamidementioning

confidence: 74%

Molecular Targets of Anticancer Agents from Filamentous Marine Cyanobacteria

Tan

Gupta

2014

Handbook of Anticancer Drugs From Marine Origin

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The prokaryotic marine cyanobacteria, especially the filamentous forms, are known to produce a plethora of structurally unique natural products. A majority of these molecules are nitrogen-containing, belonging to the hybrid polyketide-polypeptide structural class. Various activities of clinical significance have been attributed to these molecules, ranging from anticancer, neuromodulating to antiprotozoal properties. Particularly in the area of cancer therapy, a number of potent marine cyanobacterial compounds, including dolastatins 10, 15, and largazole, have been identified as anticancer drug leads and are being further developed synthetically for clinical usage. The high potencies of these compounds are due to their exquisite interactions or interference with cellular pathways, specific macromolecules, or enzymes, such as the JAK-STAT signaling pathway, histone deacetylase, proteasome, protein kinase C, actin and microtubule filaments. This mini review covers more than 90 references and features more than 40 anticancer compounds, consisting of marine cyanobacterial natural products and their synthetic analogues. Biological data of these compounds are discussed based on their molecular targets.

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Section: Bisebromoamidementioning

confidence: 74%

Molecular Targets of Anticancer Agents from Filamentous Marine Cyanobacteria

Tan

Gupta

2014

Handbook of Anticancer Drugs From Marine Origin

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“…8.23; 190, 191) [159], thioester containing "quorum sensing" cyclopeptides in autoinducing peptides 1-3 (192-194) [160,161], MS-271 or siamycin I (195) [162,163], and alkylamine chains in MS-681 A-D (Fig. SAR studies clearly suggested that 3-bromo-4-hydroxy unit and ketone group are essential for activity [168]. Bisebromoamide (200) and norbisebromoamide (201) are very unusual peptides containing a methyl thiazoline unit, an oxo propyl pyrrolidine unit, N-methyl-3 bromo tyrosine, and N-pivalamide moieties [166,167].…”

Section: )mentioning

confidence: 99%

Protein Kinase Inhibitors from Microorganisms

Radhika

Kumar

Nagasree

2015

Studies in Natural Products Chemistry

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“…2) and norbisebromoamide originally isolated from an Okinawan collection of Lyngbya spp. [40] are currently produced by total synthesis [41]. Their antitumour activity is in the nanomolar range with a mechanism of action that implies inhibition of ERK phosphorylation by PDGF stimulation [40,41].…”

Section: E-dehydroapratoxin Amentioning

confidence: 99%

“…[40] are currently produced by total synthesis [41]. Their antitumour activity is in the nanomolar range with a mechanism of action that implies inhibition of ERK phosphorylation by PDGF stimulation [40,41]. However, a recent investigation identified bisebromoamide as an actin filament stabilizer [42].…”

Section: E-dehydroapratoxin Amentioning

confidence: 99%