Substrate specificity in the biocleavage of the O-alkyl bond: 1-alkyl-2-acetyl-sn-glycero-3-phosphocholine (a hypotensive and platelet-activating lipid) and its metabolites

Lee, Ten-ching; Blank, Merle L.; Fitzgerald, Veronica; Snyder, Fred

doi:10.1016/0003-9861(81)90519-1

Cited by 56 publications

(16 citation statements)

References 21 publications

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“…200 The monooxygenase activity of the microsomes was unaltered after 3 days at 4ЊC, and was slightly affected by freezing and thawing, losing 10% of the activity after 6 thaw-freeze cycles during 3 days. 138 At 25ЊC the activity decreased with a half life of 27 h, 209 at 60ЊC it dropped to 10%, 91 and was completely lost on boiling. 200,209 The protein was finally purified by affinity chromatography and gave a single band on SDS-polyacrylamide gel electrophoresis (SDS-PAGE) with an M r val-ue of 45K, 202 whereas the molecular weight of the native protein as measured by Sepharose 6B column chromatography in 20 mM Tris-HCl (pH 7.5) containing 0.1% Triton X-100 was ca.…”

Section: B General Propertiesmentioning

confidence: 96%

“…III-I). [89][90][91] This enzyme is thus capable of regulating the levels of a variety of glyceryl ethers either directly or indirectly.…”

Section: • Taguchi and Armaregomentioning

confidence: 99%

“…The livers from overnight starved rats that were decapitated, or killed in a CO 2 atmosphere, were homogenized in 0.25M sucrose in 0.125M Tris-HCl buffer (pH 7.5) in the absence, 1,89,138,192,197 or presence of 1 mM EDTA, 91,198,199 in 0.125M sucrose alone, 200 or in buffer containing 8 mM CaCl 2 . 201 We did not find it necessary to add EDTA to obtain optimal activity.…”

Section: G L Y C E R Y L -E T H E R M O N O O X Y G E N a S E A Occumentioning

confidence: 99%

“…The identity of the monooxygenase as glyceryl-ether monooxygenase was further confirmed by the stimulating effect of catalase and by comparative heat stability studies of the enzyme. 91 In a recent example of this approach to inhibition, it was shown that a monooxygenase cleaved the alkyl glycol ether 1-O-hexadecyl- 3 H]-ethan-1-ol (substrate) to the extent of 41, 31, and 19% of the chimyl alcohol-free assay reaction. This inhibition of alkyl ethylene glycol monooxygenase by chimyl alcohol exhibited competitive inhibition with a Ki value of 8 M which was very close in value to the Km (12 M) of chimyl alcohol in the same assay system.…”

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confidence: 99%

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Glyceryl-ether monooxygenase [EC 1.14.16.5]. A microsomal enzyme of ether lipid metabolism

Taguchi¹,

Armarego²

1998

Med. Res. Rev.

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Section: B General Propertiesmentioning

confidence: 96%

“…III-I). [89][90][91] This enzyme is thus capable of regulating the levels of a variety of glyceryl ethers either directly or indirectly.…”

Section: • Taguchi and Armaregomentioning

confidence: 99%

Section: G L Y C E R Y L -E T H E R M O N O O X Y G E N a S E A Occumentioning

confidence: 99%

mentioning

confidence: 99%

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Glyceryl-ether monooxygenase [EC 1.14.16.5]. A microsomal enzyme of ether lipid metabolism

Taguchi¹,

Armarego²

1998

Med. Res. Rev.

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“…The category of glycerolipids comprising the class of monoradylglycerols that contains the subclass of monoalkylglycerols (i.e., the four species found to be most significantly changed; see above) did not appear to be significantly enriched, because alkylglycerols with side-chain carbon atoms [16][17][18][19][20][21][22] were not yet listed in the version of LIPID MAPS used.…”

Section: Impact Of Agmo Activity Manipulation On Ifn-γ/lps-induced Nimentioning

confidence: 99%

Tetrahydrobiopterin and alkylglycerol monooxygenase substantially alter the murine macrophage lipidome

Watschinger

Keller

McNeill

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

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Tetrahydrobiopterin is a cofactor synthesized from GTP with well-known roles in enzymatic nitric oxide synthesis and aromatic amino acid hydroxylation. It is used to treat mild forms of phenylketonuria. Less is known about the role of tetrahydrobiopterin in lipid metabolism, although it is essential for irreversible ether lipid cleavage by alkylglycerol monooxygenase. Here we found intracellular alkylglycerol monooxygenase activity to be an important regulator of alkylglycerol metabolism in intact murine RAW264.7 macrophage-like cells. Alkylglycerol monooxygenase was expressed and active also in primary mouse bone marrowderived monocytes and "alternatively activated" M2 macrophages obtained by interleukin 4 treatment, but almost missing in M1 macrophages obtained by IFN-γ and lipopolysaccharide treatment. The cellular lipidome of RAW264.7 was markedly changed in a parallel way by modulation of alkylglycerol monooxygenase expression and of tetrahydrobiopterin biosynthesis affecting not only various ether lipid species upstream of alkylglycerol monooxygenase but also other more complex lipids including glycosylated ceramides and cardiolipins, which have no direct connection to ether lipid pathways. Alkylglycerol monooxygenase activity manipulation modulated the IFN-γ/lipopolysaccharide-induced expression of inducible nitric oxide synthase, interleukin-1β, and interleukin 1 receptor antagonist but not transforming growth factor β1, suggesting that alkylglycerol monooxygenase activity affects IFN-γ/lipopolysaccharide signaling. Our results demonstrate a central role of tetrahydrobiopterin and alkylglycerol monooxygenase in ether lipid metabolism of murine macrophages and reveal that alteration of alkylglycerol monooxygenase activity has a profound impact on the lipidome also beyond the class of ether lipids. alkylglycerols | lipidomics | macrophages | RAW264.7 | tetrahydrobiopterin

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Biologically active phospholipids as potential cardiovascular drugs

Blankley

Kaplan

1984

Drug Development Research

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Both useful and undesirable cardiovascular properties have been associated with naturally occurring and synthetically derived phospholipids. Certain phospholipids may function physiologically (or pathophysiologically) in such processes as blood pressure regulation, cardiac rhythm, and platelet aggregation. Drugs that can modify the synthesis or degradation of endogenous phospholipid mediators or selectively mimic or block their effects may be of interest as potentially useful cardiovascular agents. This article reviews the current literature in this area and defines in chemical, biochemical, and biological terms the potential of the phospholipid-type compounds in the development of useful cardiovascular drugs.

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Substrate specificity in the biocleavage of the O-alkyl bond: 1-alkyl-2-acetyl-sn-glycero-3-phosphocholine (a hypotensive and platelet-activating lipid) and its metabolites

Cited by 56 publications

References 21 publications

Glyceryl-ether monooxygenase [EC 1.14.16.5]. A microsomal enzyme of ether lipid metabolism

Glyceryl-ether monooxygenase [EC 1.14.16.5]. A microsomal enzyme of ether lipid metabolism

Tetrahydrobiopterin and alkylglycerol monooxygenase substantially alter the murine macrophage lipidome

Biologically active phospholipids as potential cardiovascular drugs

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