Biomimetic synthesis of hemiketal eicosanoids for biological testing

Juan A. Giménez-Bastida; Takashi Suzuki; Katie C. Sprinkel; William E. Boeglin; Claus Schneider

doi:10.1016/j.prostaglandins.2016.09.001

Biomimetic synthesis of hemiketal eicosanoids for biological testing

Juan A. Giménez-Bastida, Takashi Suzuki, Katie C. Sprinkel, William E. Boeglin, Claus Schneider

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

9 Scopus citations

Abstract

The hemiketal (HK) eicosanoids HKE₂ and HKD₂ are the major products resulting from the biosynthetic cross-over of the 5-lipoxygenase and cyclooxygenase-2 pathways. They are formed by activated human leukocytes ex vivo, and, therefore, may be involved in regulation of the inflammatory response as autocrine or paracrine mediators. HKE₂ and HKD₂ are not commercially available and, so far, no method for their total chemical synthesis has been reported. The limited availability has impeded the characterization of their biological effects. Here, we describe a method for biomimetic preparation of HKE₂ and HKD₂ by reaction of recombinant human cyclooxygenase-2 with chemically synthesized 5S-HETE. We found that HKE₂ did not induce or inhibit the release of TNFα and IL-1β by human THP-1 monocytes and phorbol ester treatment-derived macrophages.

Original language	English (US)
Pages (from-to)	41-46
Number of pages	6
Journal	Prostaglandins and Other Lipid Mediators
Volume	132
DOIs	https://doi.org/10.1016/j.prostaglandins.2016.09.001
State	Published - Sep 2017
Externally published	Yes

Keywords

Cyclooxygenase
Cytokine
Di-endoperoxide
Hemiketal
Lipoxygenase
Macrophage

ASJC Scopus subject areas

Biochemistry
Physiology
Pharmacology
Cell Biology

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10.1016/j.prostaglandins.2016.09.001

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@article{4ed04726d5e9444e9b03e9081aca2a40,

title = "Biomimetic synthesis of hemiketal eicosanoids for biological testing",

abstract = "The hemiketal (HK) eicosanoids HKE2 and HKD2 are the major products resulting from the biosynthetic cross-over of the 5-lipoxygenase and cyclooxygenase-2 pathways. They are formed by activated human leukocytes ex vivo, and, therefore, may be involved in regulation of the inflammatory response as autocrine or paracrine mediators. HKE2 and HKD2 are not commercially available and, so far, no method for their total chemical synthesis has been reported. The limited availability has impeded the characterization of their biological effects. Here, we describe a method for biomimetic preparation of HKE2 and HKD2 by reaction of recombinant human cyclooxygenase-2 with chemically synthesized 5S-HETE. We found that HKE2 did not induce or inhibit the release of TNFα and IL-1β by human THP-1 monocytes and phorbol ester treatment-derived macrophages.",

keywords = "Cyclooxygenase, Cytokine, Di-endoperoxide, Hemiketal, Lipoxygenase, Macrophage",

author = "Gim{\'e}nez-Bastida, {Juan A.} and Takashi Suzuki and Sprinkel, {Katie C.} and Boeglin, {William E.} and Claus Schneider",

note = "Publisher Copyright: {\textcopyright} 2016 Elsevier Inc.",

year = "2017",

month = sep,

doi = "10.1016/j.prostaglandins.2016.09.001",

language = "English (US)",

volume = "132",

pages = "41--46",

journal = "Prostaglandins and Other Lipid Mediators",

issn = "1098-8823",

publisher = "Elsevier BV",

}

TY - JOUR

T1 - Biomimetic synthesis of hemiketal eicosanoids for biological testing

AU - Giménez-Bastida, Juan A.

AU - Suzuki, Takashi

AU - Sprinkel, Katie C.

AU - Boeglin, William E.

AU - Schneider, Claus

PY - 2017/9

Y1 - 2017/9

N2 - The hemiketal (HK) eicosanoids HKE2 and HKD2 are the major products resulting from the biosynthetic cross-over of the 5-lipoxygenase and cyclooxygenase-2 pathways. They are formed by activated human leukocytes ex vivo, and, therefore, may be involved in regulation of the inflammatory response as autocrine or paracrine mediators. HKE2 and HKD2 are not commercially available and, so far, no method for their total chemical synthesis has been reported. The limited availability has impeded the characterization of their biological effects. Here, we describe a method for biomimetic preparation of HKE2 and HKD2 by reaction of recombinant human cyclooxygenase-2 with chemically synthesized 5S-HETE. We found that HKE2 did not induce or inhibit the release of TNFα and IL-1β by human THP-1 monocytes and phorbol ester treatment-derived macrophages.

AB - The hemiketal (HK) eicosanoids HKE2 and HKD2 are the major products resulting from the biosynthetic cross-over of the 5-lipoxygenase and cyclooxygenase-2 pathways. They are formed by activated human leukocytes ex vivo, and, therefore, may be involved in regulation of the inflammatory response as autocrine or paracrine mediators. HKE2 and HKD2 are not commercially available and, so far, no method for their total chemical synthesis has been reported. The limited availability has impeded the characterization of their biological effects. Here, we describe a method for biomimetic preparation of HKE2 and HKD2 by reaction of recombinant human cyclooxygenase-2 with chemically synthesized 5S-HETE. We found that HKE2 did not induce or inhibit the release of TNFα and IL-1β by human THP-1 monocytes and phorbol ester treatment-derived macrophages.

KW - Cyclooxygenase

KW - Cytokine

KW - Di-endoperoxide

KW - Hemiketal

KW - Lipoxygenase

KW - Macrophage

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UR - http://www.scopus.com/inward/citedby.url?scp=85011085666&partnerID=8YFLogxK

U2 - 10.1016/j.prostaglandins.2016.09.001

DO - 10.1016/j.prostaglandins.2016.09.001

M3 - Review article

C2 - 27596332

AN - SCOPUS:85011085666

SN - 1098-8823

VL - 132

SP - 41

EP - 46

JO - Prostaglandins and Other Lipid Mediators

JF - Prostaglandins and Other Lipid Mediators

ER -

Biomimetic synthesis of hemiketal eicosanoids for biological testing

Abstract

Keywords

ASJC Scopus subject areas

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