Angiogenic factors: syntheses of 12(R)- and 12(S)-hydroxyeicosa-5(Z),8(Z),14(Z)-trienoic acid and their 14,15-dehydro analogs

Kamlesh Chauhan; Dhamjewar Ravi; J R Falck; Robert A. Stoltz; Michal Laniado-Schwartzman

doi:10.1016/S0960-894X(01)80697-1

Angiogenic factors: syntheses of 12(R)- and 12(S)-hydroxyeicosa-5(Z),8(Z),14(Z)-trienoic acid and their 14,15-dehydro analogs

Kamlesh Chauhan, Dhamjewar Ravi, J R Falck, Robert A. Stoltz, Michal Laniado-Schwartzman

Biochemistry

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

The title autacoids and acetylenic analogs were conveniently prepared from 2-deoxy-D-ribose via Barton deoxygenation, cuprate coupling, and Wittig homologation. 12(R)-HETrE, but not the 12(S)-isomer, significantly stimulated microvessel endothelial cell proliferation and proto-oncogene mRNA levels at sub-nano to picomolar concentrations. A high affinity binding site for 12(R)-HETrE was detected on microvessle endothelial cells.

Original language	English (US)
Pages (from-to)	2689-2692
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	4
Issue number	22
DOIs	https://doi.org/10.1016/S0960-894X(01)80697-1
State	Published - Nov 1994

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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title = "Angiogenic factors: syntheses of 12(R)- and 12(S)-hydroxyeicosa-5(Z),8(Z),14(Z)-trienoic acid and their 14,15-dehydro analogs",

abstract = "The title autacoids and acetylenic analogs were conveniently prepared from 2-deoxy-D-ribose via Barton deoxygenation, cuprate coupling, and Wittig homologation. 12(R)-HETrE, but not the 12(S)-isomer, significantly stimulated microvessel endothelial cell proliferation and proto-oncogene mRNA levels at sub-nano to picomolar concentrations. A high affinity binding site for 12(R)-HETrE was detected on microvessle endothelial cells.",

author = "Kamlesh Chauhan and Dhamjewar Ravi and Falck, {J R} and Stoltz, {Robert A.} and Michal Laniado-Schwartzman",

year = "1994",

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doi = "10.1016/S0960-894X(01)80697-1",

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T2 - syntheses of 12(R)- and 12(S)-hydroxyeicosa-5(Z),8(Z),14(Z)-trienoic acid and their 14,15-dehydro analogs

AU - Chauhan, Kamlesh

AU - Ravi, Dhamjewar

AU - Falck, J R

AU - Stoltz, Robert A.

AU - Laniado-Schwartzman, Michal

PY - 1994/11

Y1 - 1994/11

N2 - The title autacoids and acetylenic analogs were conveniently prepared from 2-deoxy-D-ribose via Barton deoxygenation, cuprate coupling, and Wittig homologation. 12(R)-HETrE, but not the 12(S)-isomer, significantly stimulated microvessel endothelial cell proliferation and proto-oncogene mRNA levels at sub-nano to picomolar concentrations. A high affinity binding site for 12(R)-HETrE was detected on microvessle endothelial cells.

AB - The title autacoids and acetylenic analogs were conveniently prepared from 2-deoxy-D-ribose via Barton deoxygenation, cuprate coupling, and Wittig homologation. 12(R)-HETrE, but not the 12(S)-isomer, significantly stimulated microvessel endothelial cell proliferation and proto-oncogene mRNA levels at sub-nano to picomolar concentrations. A high affinity binding site for 12(R)-HETrE was detected on microvessle endothelial cells.

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Angiogenic factors: syntheses of 12(R)- and 12(S)-hydroxyeicosa-5(Z),8(Z),14(Z)-trienoic acid and their 14,15-dehydro analogs

Abstract

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