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

Hiroaki Sasaki, Toshiaki Teruya, Hidesuke Fukazawa, Kiyotake Suenaga

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Novel potent cytotoxic peptides bisebromoamide (1) and norbisebromoamide (2) have been isolated from the marine cyanobacterium Lyngbya sp. The planar structure of these peptides was elucidated through the extensive application of 1D and 2D NMR techniques. The absolute stereostructure of 1 was determined by chemical degradation followed by chiral HPLC analysis. Recently, Tao and co-workers achieved synthesis of bisebromoamide, and the configuration of thiazoline moiety was revised. We re-investigated the stereochemistry of thiazoline moiety of 1. The structure-activity relationships of bisebromoamide (1) were investigated with the use of natural and synthetic analogs. Furthermore, bisebromoamide (1) potently inhibited protein kinase: the phosphorylation of ERK in NRK cells by PDGF-stimulation was selectively inhibited by treatment with 10-0.1 μM of 1.

Original languageEnglish
Pages (from-to)990-994
Number of pages5
JournalTetrahedron
Volume67
Issue number5
DOIs
Publication statusPublished - 2011 Feb 4

Fingerprint

Cyanobacteria
Structure-Activity Relationship
Peptides
Stereochemistry
Phosphorylation
Protein Kinases
High Pressure Liquid Chromatography
Nuclear magnetic resonance
Degradation
bisebromoamide

Keywords

  • Cyanobacteria
  • Cytotoxicity
  • Kinase inhibitor
  • Natural products
  • Peptide

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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.

In: Tetrahedron, Vol. 67, No. 5, 04.02.2011, p. 990-994.

Research output: Contribution to journalArticle

@article{0883eafa00f6435fb2f89fc42eb95933,
title = "Revised structure and structure-activity relationship of bisebromoamide and structure of norbisebromoamide from the marine cyanobacterium Lyngbya sp.",
abstract = "Novel potent cytotoxic peptides bisebromoamide (1) and norbisebromoamide (2) have been isolated from the marine cyanobacterium Lyngbya sp. The planar structure of these peptides was elucidated through the extensive application of 1D and 2D NMR techniques. The absolute stereostructure of 1 was determined by chemical degradation followed by chiral HPLC analysis. Recently, Tao and co-workers achieved synthesis of bisebromoamide, and the configuration of thiazoline moiety was revised. We re-investigated the stereochemistry of thiazoline moiety of 1. The structure-activity relationships of bisebromoamide (1) were investigated with the use of natural and synthetic analogs. Furthermore, bisebromoamide (1) potently inhibited protein kinase: the phosphorylation of ERK in NRK cells by PDGF-stimulation was selectively inhibited by treatment with 10-0.1 μM of 1.",
keywords = "Cyanobacteria, Cytotoxicity, Kinase inhibitor, Natural products, Peptide",
author = "Hiroaki Sasaki and Toshiaki Teruya and Hidesuke Fukazawa and Kiyotake Suenaga",
year = "2011",
month = "2",
day = "4",
doi = "10.1016/j.tet.2010.11.106",
language = "English",
volume = "67",
pages = "990--994",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "5",

}

TY - JOUR

T1 - Revised structure and structure-activity relationship of bisebromoamide and structure of norbisebromoamide from the marine cyanobacterium Lyngbya sp.

AU - Sasaki, Hiroaki

AU - Teruya, Toshiaki

AU - Fukazawa, Hidesuke

AU - Suenaga, Kiyotake

PY - 2011/2/4

Y1 - 2011/2/4

N2 - Novel potent cytotoxic peptides bisebromoamide (1) and norbisebromoamide (2) have been isolated from the marine cyanobacterium Lyngbya sp. The planar structure of these peptides was elucidated through the extensive application of 1D and 2D NMR techniques. The absolute stereostructure of 1 was determined by chemical degradation followed by chiral HPLC analysis. Recently, Tao and co-workers achieved synthesis of bisebromoamide, and the configuration of thiazoline moiety was revised. We re-investigated the stereochemistry of thiazoline moiety of 1. The structure-activity relationships of bisebromoamide (1) were investigated with the use of natural and synthetic analogs. Furthermore, bisebromoamide (1) potently inhibited protein kinase: the phosphorylation of ERK in NRK cells by PDGF-stimulation was selectively inhibited by treatment with 10-0.1 μM of 1.

AB - Novel potent cytotoxic peptides bisebromoamide (1) and norbisebromoamide (2) have been isolated from the marine cyanobacterium Lyngbya sp. The planar structure of these peptides was elucidated through the extensive application of 1D and 2D NMR techniques. The absolute stereostructure of 1 was determined by chemical degradation followed by chiral HPLC analysis. Recently, Tao and co-workers achieved synthesis of bisebromoamide, and the configuration of thiazoline moiety was revised. We re-investigated the stereochemistry of thiazoline moiety of 1. The structure-activity relationships of bisebromoamide (1) were investigated with the use of natural and synthetic analogs. Furthermore, bisebromoamide (1) potently inhibited protein kinase: the phosphorylation of ERK in NRK cells by PDGF-stimulation was selectively inhibited by treatment with 10-0.1 μM of 1.

KW - Cyanobacteria

KW - Cytotoxicity

KW - Kinase inhibitor

KW - Natural products

KW - Peptide

UR - http://www.scopus.com/inward/record.url?scp=78651367196&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=78651367196&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2010.11.106

DO - 10.1016/j.tet.2010.11.106

M3 - Article

VL - 67

SP - 990

EP - 994

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 5

ER -