Design and total synthesis of a fluorescent phorboxazole a analog for cellular studies

Jiehao Chen; Lu Ying; T. Matthew Hansen; Mary M. Engler; Chi Sing Lee; James J. La Clair; Craig J. Forsyth

doi:10.1016/j.bmcl.2005.10.109

Design and total synthesis of a fluorescent phorboxazole a analog for cellular studies

Jiehao Chen
, Lu Ying
, T. Matthew Hansen
, Mary M. Engler
, Chi Sing Lee
, James J. La Clair
, Craig J. Forsyth^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

17 Citations (Scopus)

Abstract

To enable studies to elucidate the intracellular processing and targeting of the potent cytostatic/apoptotic anticancer natural products phorboxazoles A and B, a fluorescent derivative has been developed. This involved the total syntheses of the terminal alkyne 33-O-Me-45,46-dehydrobromophorboxazole A (MDHBPA) and a terminal vinyl iodide derivative of the blue fluorescent dye N,N,-dimethyl-7-aminocoumarin (DMC). Sonogashira coupling of these partners provided enyne DMC-MDHBPA in high yield.

Original language	English
Pages (from-to)	901-904
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	16
Issue number	4
Early online date	21 Nov 2005
DOIs	https://doi.org/10.1016/j.bmcl.2005.10.109
Publication status	Published - 15 Feb 2006

User-Defined Keywords

Anticancer
Coumarin
Phorboxazole
Probe
Total synthesis

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmcl.2005.10.109

Cite this

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title = "Design and total synthesis of a fluorescent phorboxazole a analog for cellular studies",

abstract = "To enable studies to elucidate the intracellular processing and targeting of the potent cytostatic/apoptotic anticancer natural products phorboxazoles A and B, a fluorescent derivative has been developed. This involved the total syntheses of the terminal alkyne 33-O-Me-45,46-dehydrobromophorboxazole A (MDHBPA) and a terminal vinyl iodide derivative of the blue fluorescent dye N,N,-dimethyl-7-aminocoumarin (DMC). Sonogashira coupling of these partners provided enyne DMC-MDHBPA in high yield.",

keywords = "Anticancer, Coumarin, Phorboxazole, Probe, Total synthesis",

author = "Jiehao Chen and Lu Ying and Hansen, \{T. Matthew\} and Engler, \{Mary M.\} and Lee, \{Chi Sing\} and \{La Clair\}, \{James J.\} and Forsyth, \{Craig J.\}",

year = "2006",

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doi = "10.1016/j.bmcl.2005.10.109",

language = "English",

volume = "16",

pages = "901--904",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

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}

TY - JOUR

T1 - Design and total synthesis of a fluorescent phorboxazole a analog for cellular studies

AU - Chen, Jiehao

AU - Ying, Lu

AU - Hansen, T. Matthew

AU - Engler, Mary M.

AU - Lee, Chi Sing

AU - La Clair, James J.

AU - Forsyth, Craig J.

PY - 2006/2/15

Y1 - 2006/2/15

N2 - To enable studies to elucidate the intracellular processing and targeting of the potent cytostatic/apoptotic anticancer natural products phorboxazoles A and B, a fluorescent derivative has been developed. This involved the total syntheses of the terminal alkyne 33-O-Me-45,46-dehydrobromophorboxazole A (MDHBPA) and a terminal vinyl iodide derivative of the blue fluorescent dye N,N,-dimethyl-7-aminocoumarin (DMC). Sonogashira coupling of these partners provided enyne DMC-MDHBPA in high yield.

AB - To enable studies to elucidate the intracellular processing and targeting of the potent cytostatic/apoptotic anticancer natural products phorboxazoles A and B, a fluorescent derivative has been developed. This involved the total syntheses of the terminal alkyne 33-O-Me-45,46-dehydrobromophorboxazole A (MDHBPA) and a terminal vinyl iodide derivative of the blue fluorescent dye N,N,-dimethyl-7-aminocoumarin (DMC). Sonogashira coupling of these partners provided enyne DMC-MDHBPA in high yield.

KW - Anticancer

KW - Coumarin

KW - Phorboxazole

KW - Probe

KW - Total synthesis

UR - https://www.scopus.com/pages/publications/30344442147

UR - https://www.sciencedirect.com/science/article/pii/S0960894X05014186?via%3Dihub

U2 - 10.1016/j.bmcl.2005.10.109

DO - 10.1016/j.bmcl.2005.10.109

M3 - Journal article

C2 - 16300946

AN - SCOPUS:30344442147

SN - 0960-894X

VL - 16

SP - 901

EP - 904

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 4

ER -

Design and total synthesis of a fluorescent phorboxazole a analog for cellular studies

Abstract

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