Antioxidant and neuroprotective properties of N-arachidonoyldopamine

被引：40

作者：

Bobrov, Mikhail Yu. ^{[1
]}

Lizhin, Anatoly A. ^{[2
]}

Andrianova, Ekaterina L. ^{[1
]}

Gretskaya, Natalia M. ^{[1
]}

Frumkina, Lidia E. ^{[2
]}

Khaspekov, Leonid G. ^{[2
]}

Bezuglov, Vladimir V. ^{[1
]}

机构：

[1] Russian Acad Sci, Shemyakin Ovchinnikov Inst Biorgan Chem, Oxylipin Lab, Moscow 117997, Russia

[2] Russian Acad Sci, Ctr Neurol Sci, Moscow, Russia

来源：

NEUROSCIENCE LETTERS | 2008年 / 431卷 / 01期

基金：

俄罗斯基础研究基金会;

关键词：

N-arachidonoyldopamine; N-acyldopamine; cannabinoid; vanilloid; antioxidant; neuroprotection;

D O I：

10.1016/j.neulet.2007.11.010

中图分类号：

Q189 [神经科学];

学科分类号：

071006 ;

摘要：

N-Acyldopamines were recently described as putative endogenous substances in the rat brain. Among them, N-arachidonoyldopamine (AADA) was characterized as cannabinoid CBI and vanilloid TRPV1 receptor ligand. The physiological significance of such compounds is yet poorly understood. In this study, we describe the novel properties of AADA as antioxidant and neuroprotectant. Antioxidant potential of AADA and its analogs were first tested in the galvinoxyl assay. It was found that N-acyldopamines are potent antioxidants and that the number of free hydroxyl groups in the phenolic moiety of dopamine is essential for the activity. AADA dose dependently (0.1-10 mu M) protected cultured cerebellar granule neurons (CGN) in the model of oxidative stress induced by hydrogen peroxide. N-Oleoyldopamine, another endogenous substance, was much less potent in these conditions while the natural antioxidant a-tocopherol was inactive. In this test, AADA decreased the peroxide level in CGN preparations and its neuroprotection was independent of cannabinoid/vanilloid receptors blockade. AADA (10 mu M) also protected CGN from death induced by K+/serum deprivation and glutamate exitotoxicity. These data indicate that AADA may act as endogenous antioxidant in different pathological conditions. (C) 2007 Elsevier Ireland Ltd. All rights reserved.

引用

页码：6 / 11

页数：6

共 29 条

[1] INHIBITION OF NA+/CA2+ EXCHANGE ENHANCES DELAYED NEURONAL DEATH ELICITED BY GLUTAMATE IN CEREBELLAR GRANULE CELL-CULTURES [J].

ANDREEVA, N ;

KHODOROV, B ;

STELMASHOOK, E ;

CRAGOE, E ;

VICTOROV, I .

BRAIN RESEARCH, 1991, 548 (1-2) :322-325

[2] Synthesis and biological evaluation of novel amides of polyunsaturated fatty acids with dopamine [J].

Bezuglov, V ;

Bobrov, M ;

Gretskaya, N ;

Gonchar, A ;

Zinchenko, G ;

Melck, D ;

Bisogno, T ;

Di Marzo, V ;

Kuklev, D ;

Rossi, JC ;

Vidal, JP ;

Durand, T .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (04) :447-449

[3]

Bezuglov VV, 1997, BIOORG KHIM+, V23, P211

[4] N-acyl-dopamines:: novel synthetic CB1 cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo [J].

Bisogno, T ;

Melck, D ;

Bobrov, MY ;

Gretskaya, NM ;

Bezuglov, VV ;

De Petrocellis, L ;

Di Marzo, V .

BIOCHEMICAL JOURNAL, 2000, 351 (03) :817-824

[5] Endocannabinoids in Neuroimmunology and Stress [J].

Carrier, E. J. ;

Patel, S. ;

Hillard, C. J. .

CNS & NEUROLOGICAL DISORDERS-DRUG TARGETS, 2005, 4 (06) :657-665

[6] Oxidative stress, mitochondrial function, and acute glutamate excitotoxicity in cultured cerebellar granule cells [J].

Castilho, RF ;

Ward, MW ;

Nicholls, DG .

JOURNAL OF NEUROCHEMISTRY, 1999, 72 (04) :1394-1401

[7] N-oleoyldopamine, a novel endogenous capsaicin-like lipid that produces hyperalgesia [J].

Chu, CJ ;

Huang, SM ;

De Petrocellis, L ;

Bisogno, T ;

Ewing, SA ;

Miller, JD ;

Zipkin, RE ;

Daddario, N ;

Appendino, G ;

Di Marzo, V ;

Walker, JM .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (16) :13633-13639

[8] INDUCTION OF APOPTOSIS IN CEREBELLAR GRANULE NEURONS BY LOW POTASSIUM - INHIBITION OF DEATH BY INSULIN-LIKE GROWTH FACTOR-I AND CAMP [J].

D'MELLO, SR ;

GALLI, C ;

CIOTTI, T ;

CALISSANO, P .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (23) :10989-10993

[9] The involvement of p53 in dopamine-induced apoptosis of cerebellar granule neurons and leukemic cells overexpressing p53 [J].

Daily, D ;

Barzilai, A ;

Offen, D ;

Kamsler, A ;

Melamed, E ;

Ziv, I .

CELLULAR AND MOLECULAR NEUROBIOLOGY, 1999, 19 (02) :261-276

[10] Perchloric acid enhances sensitivity and reproducibility of the ferric-xylenol orange peroxide assay [J].

Gay, CA ;

Gebicki, JM .

ANALYTICAL BIOCHEMISTRY, 2002, 304 (01) :42-46

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