Total synthesis and chemical biology of the sarcodictyins

K. C. Nicolaou, Jeffrey Pfefferkorn, Jinyou Xu, Nicolas Winssinger, Takashi Ohshima, Sanghee Kim, Seijiro Hosokawa, Dionisios Vourloumis, Floris Van Delft, Tianhu Li

Research output: Contribution to journalArticle

54 Citations (Scopus)

Abstract

The sarcodictyins A - F and eleutherobin comprise a family of marine- derived diterpenoids with potent cytotoxicities against various tumor cell lines. Investigations have revealed that several of these compounds exert their cytotoxic effects through tubulin binding in a mechanism analogous to that of the clinical anticancer drug Taxol(TM). The biological importance, challenging molecular architecture, and relative scarcity of these natural products have prompted several groups to undertake their total chemical synthesis. In this review, we summarize the current synthetic efforts and examine the preliminary structure-activity relationships which have emerged from early combinatorial libraries.

Original languageEnglish
Pages (from-to)1199-1213
Number of pages15
JournalChemical and Pharmaceutical Bulletin
Volume47
Issue number9
Publication statusPublished - 1999 Sep
Externally publishedYes

Fingerprint

Diterpenes
Structure-Activity Relationship
Tubulin
Cytotoxicity
Paclitaxel
Tumor Cell Line
Biological Products
Tumors
Cells
Pharmaceutical Preparations
eleutherobin

Keywords

  • Anticancer
  • Combinatorial library
  • Eleutherobin
  • Sarcodictyin
  • Synthesis
  • Tubulin

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Pharmacology

Cite this

Nicolaou, K. C., Pfefferkorn, J., Xu, J., Winssinger, N., Ohshima, T., Kim, S., ... Li, T. (1999). Total synthesis and chemical biology of the sarcodictyins. Chemical and Pharmaceutical Bulletin, 47(9), 1199-1213.

Total synthesis and chemical biology of the sarcodictyins. / Nicolaou, K. C.; Pfefferkorn, Jeffrey; Xu, Jinyou; Winssinger, Nicolas; Ohshima, Takashi; Kim, Sanghee; Hosokawa, Seijiro; Vourloumis, Dionisios; Van Delft, Floris; Li, Tianhu.

In: Chemical and Pharmaceutical Bulletin, Vol. 47, No. 9, 09.1999, p. 1199-1213.

Research output: Contribution to journalArticle

Nicolaou, KC, Pfefferkorn, J, Xu, J, Winssinger, N, Ohshima, T, Kim, S, Hosokawa, S, Vourloumis, D, Van Delft, F & Li, T 1999, 'Total synthesis and chemical biology of the sarcodictyins', Chemical and Pharmaceutical Bulletin, vol. 47, no. 9, pp. 1199-1213.
Nicolaou KC, Pfefferkorn J, Xu J, Winssinger N, Ohshima T, Kim S et al. Total synthesis and chemical biology of the sarcodictyins. Chemical and Pharmaceutical Bulletin. 1999 Sep;47(9):1199-1213.
Nicolaou, K. C. ; Pfefferkorn, Jeffrey ; Xu, Jinyou ; Winssinger, Nicolas ; Ohshima, Takashi ; Kim, Sanghee ; Hosokawa, Seijiro ; Vourloumis, Dionisios ; Van Delft, Floris ; Li, Tianhu. / Total synthesis and chemical biology of the sarcodictyins. In: Chemical and Pharmaceutical Bulletin. 1999 ; Vol. 47, No. 9. pp. 1199-1213.
@article{2418898a4d8a48aaa2f6f4e9de530ad9,
title = "Total synthesis and chemical biology of the sarcodictyins",
abstract = "The sarcodictyins A - F and eleutherobin comprise a family of marine- derived diterpenoids with potent cytotoxicities against various tumor cell lines. Investigations have revealed that several of these compounds exert their cytotoxic effects through tubulin binding in a mechanism analogous to that of the clinical anticancer drug Taxol(TM). The biological importance, challenging molecular architecture, and relative scarcity of these natural products have prompted several groups to undertake their total chemical synthesis. In this review, we summarize the current synthetic efforts and examine the preliminary structure-activity relationships which have emerged from early combinatorial libraries.",
keywords = "Anticancer, Combinatorial library, Eleutherobin, Sarcodictyin, Synthesis, Tubulin",
author = "Nicolaou, {K. C.} and Jeffrey Pfefferkorn and Jinyou Xu and Nicolas Winssinger and Takashi Ohshima and Sanghee Kim and Seijiro Hosokawa and Dionisios Vourloumis and {Van Delft}, Floris and Tianhu Li",
year = "1999",
month = "9",
language = "English",
volume = "47",
pages = "1199--1213",
journal = "Chemical and Pharmaceutical Bulletin",
issn = "0009-2363",
publisher = "Pharmaceutical Society of Japan",
number = "9",

}

TY - JOUR

T1 - Total synthesis and chemical biology of the sarcodictyins

AU - Nicolaou, K. C.

AU - Pfefferkorn, Jeffrey

AU - Xu, Jinyou

AU - Winssinger, Nicolas

AU - Ohshima, Takashi

AU - Kim, Sanghee

AU - Hosokawa, Seijiro

AU - Vourloumis, Dionisios

AU - Van Delft, Floris

AU - Li, Tianhu

PY - 1999/9

Y1 - 1999/9

N2 - The sarcodictyins A - F and eleutherobin comprise a family of marine- derived diterpenoids with potent cytotoxicities against various tumor cell lines. Investigations have revealed that several of these compounds exert their cytotoxic effects through tubulin binding in a mechanism analogous to that of the clinical anticancer drug Taxol(TM). The biological importance, challenging molecular architecture, and relative scarcity of these natural products have prompted several groups to undertake their total chemical synthesis. In this review, we summarize the current synthetic efforts and examine the preliminary structure-activity relationships which have emerged from early combinatorial libraries.

AB - The sarcodictyins A - F and eleutherobin comprise a family of marine- derived diterpenoids with potent cytotoxicities against various tumor cell lines. Investigations have revealed that several of these compounds exert their cytotoxic effects through tubulin binding in a mechanism analogous to that of the clinical anticancer drug Taxol(TM). The biological importance, challenging molecular architecture, and relative scarcity of these natural products have prompted several groups to undertake their total chemical synthesis. In this review, we summarize the current synthetic efforts and examine the preliminary structure-activity relationships which have emerged from early combinatorial libraries.

KW - Anticancer

KW - Combinatorial library

KW - Eleutherobin

KW - Sarcodictyin

KW - Synthesis

KW - Tubulin

UR - http://www.scopus.com/inward/record.url?scp=0032862624&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032862624&partnerID=8YFLogxK

M3 - Article

C2 - 10517002

AN - SCOPUS:0032862624

VL - 47

SP - 1199

EP - 1213

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

SN - 0009-2363

IS - 9

ER -