Chapter 3 Biosynthesis of Oleamide

Vitamins and Hormones

Volumn 81, Issue C, 2009, Pages 55-78

  Mueller, Gregory P ^a   Driscoll, William J ^a  

^a Uniformed Services University of the Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME C; DRUG DERIVATIVE; GLYCINE; MIXED FUNCTION OXIDASE; MULTIENZYME COMPLEX; OLEIC ACID; OLEOYLGLYCINE; OLEYLAMIDE; PEPTIDYLGLYCINE MONOOXYGENASE;

ANIMAL; APOPTOSIS; BIOSYNTHESIS; HUMAN; KINETICS; METABOLISM; REVIEW;

ANIMALS; APOPTOSIS; CYTOCHROMES C; GLYCINE; HUMANS; KINETICS; MIXED FUNCTION OXYGENASES; MULTIENZYME COMPLEXES; OLEIC ACIDS;

EID: 67651177458     PISSN: 00836729     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0083-6729(09)81003-0     Document Type: Review

References (127)

1. Alberts G.L., Chio C.L., and Im W.B. Allosteric modulation of the human 5-HT(7A) receptor by lipidic amphipathic compounds. Mol. Pharmacol. 60 (2001) 1349-1355
2. Andrade-Rozental A.F., Rozental R., Hopperstad M.G., Wu J.K., Vrionis F.D., and Spray D.C. Gap junctions: The "kiss of death" and the "kiss of life". Brain Res. Brain Res. Rev. 32 (2000) 308-315
3. Arafat E.S., Trimble J.W., Andersen R.N., Dass C., and Desiderio D.M. Identification of fatty acid amides in human plasma. Life Sci. 45 (1989) 1679-1687
4. Bannerman P., Nichols W., Puhalla S., Oliver T., Berman M., and Pleasure D. Early migratory rat neural crest cells express functional gap junctions: Evidence that neural crest cell survival requires gap junction function. J. Neurosci. Res. 61 (2000) 605-615
5. Barros M.H., Netto L.E., and Kowaltowski A.J. H(2)O(2) generation in Saccharomyces cerevisiae respiratory pet mutants: Effect of cytochrome c. Free Radic. Biol. Med. 35 (2003) 179-188
6. Basile A.S., Hanus L., and Mendelson W.B. Characterization of the hypnotic properties of oleamide. Neuroreport 10 (1999) 947-951
7. Bernstein S.A., and Morley G.E. Gap junctions and propagation of the cardiac action potential. Adv. Cardiol. 42 (2006) 71-85
8. Bisogno T., Sepe N., De Petrocellis L., Mechoulam R., and Di Marzo V. The sleep inducing factor oleamide is produced by mouse neuroblastoma cells. Biochem. Biophys. Res. Commun. 239 (1997) 473-479
9. Bisogno T., Katayama K., Melck D., Ueda N., De Petrocellis L., et al. Biosynthesis and degradation of bioactive fatty acid amides in human breast cancer and rat pheochromocytoma cells-Implications for cell proliferation and differentiation. Eur. J. Biochem. 254 (1998) 634-642
10. Boengler K., Dodoni G., Rodriguez-Sinovas A., Cabestrero A., Ruiz-Meana M., et al. Connexin 43 in cardiomyocyte mitochondria and its increase by ischemic preconditioning. Cardiovasc. Res. 67 (2005) 234-244
11. Boengler K., Schulz R., and Heusch G. Connexin 43 signalling and cardioprotection. Heart 92 (2006) 1724-1727
12. Boengler K., Konietzka I., Buechert A., Heinen Y., Garcia-Dorado D., et al. Loss of ischemic preconditioning's cardioprotection in aged mouse hearts is associated with reduced gap junctional and mitochondrial levels of connexin 43. Am. J. Physiol. Heart Circ. Physiol. 292 (2007) H1764-H1769
13. Boger D.L., Patterson J.E., and Jin Q. Structural requirements for 5-HT2A and 5-HT1A serotonin receptor potentiation by the biologically active lipid oleamide. Proc. Natl. Acad. Sci. USA 95 (1998) 4102-4107
14. Boger D.L., Patterson J.E., Guan X., Cravatt B.F., Lerner R.A., and Gilula N.B. Chemical requirements for inhibition of gap junction communication by the biologically active lipid oleamide. Proc. Natl. Acad. Sci. USA 95 (1998) 4810-4815
15. Boitano S., and Evans W.H. Connexin mimetic peptides reversibly inhibit Ca(2+) signaling through gap junctions in airway cells. Am. J. Physiol. Lung Cell Mol. Physiol. 279 (2000) L623-L630
16. Bonafe L., Troxler H., Kuster T., Heizmann C.W., Chamoles N.A., et al. Evaluation of urinary acylglycines by electrospray tandem mass spectrometry in mitochondrial energy metabolism defects and organic acidurias. Mol. Genet. Metab. 69 (2000) 302-311
17. Burstein S.H., Rossetti R.G., Yagen B., and Zurier R.B. Oxidative metabolism of anandamide. Prostaglandins Other Lipid Mediat. 61 (2000) 29-41
18. Butovich I.A., Uchiyama E., and McCulley J.P. Lipids of human meibum: Mass-spectrometric analysis and structural elucidation. J. Lipid Res. 48 (2007) 2220-2235
19. Chaturvedi S., Driscoll W.J., Elliot B.M., Faraday M.M., Grunberg N.E., and Mueller G.P. In vivo evidence that N-oleoylglycine acts independently of its conversion to oleamide. Prostaglandins Other Lipid Mediat. 81 (2006) 136-149
20. Coleman A.M., and Sengelaub D.R. Patterns of dye coupling in lumbar motor nuclei of the rat. J. Comp. Neurol. 454 (2002) 34-41
21. Cotrina M.L., Kang J., Lin J.H., Bueno E., Hansen T.W., et al. Astrocytic gap junctions remain open during ischemic conditions. J. Neurosci. 18 (1998) 2520-2537
22. Cravatt B.F., Prospero-Garcia O., Siuzdak G., Gilula N.B., Henriksen S.J., et al. Chemical characterization of a family of brain lipids that induce sleep. Science 268 (1995) 1506-1509
23. Czyzyk T.A., Ning Y., Hsu M.S., Peng B., Mains R.E., et al. Deletion of peptide amidation enzymatic activity leads to edema and embryonic lethality in the mouse. Dev. Biol. 287 (2005) 301-313
24. Danial N.N., and Korsmeyer S.J. Cell death: Critical control points. Cell 116 (2004) 205-219
25. DeBlassio J.L., deLong M.A., Glufke U., Kulathila R., Merkler K.A., et al. Amidation of salicyluric acid and gentisuric acid: A possible role for peptidylglycine alpha-amidating monooxygenase in the metabolism of aspirin. Arch. Biochem. Biophys. 383 (2000) 46-55
26. Decrouy X., Gasc J.M., Pointis G., and Segretain D. Functional characterization of Cx43 based gap junctions during spermatogenesis. J. Cell Physiol. 200 (2004) 146-154
27. Driscoll W.J., Konig S., Fales H.M., Pannell L.K., Eipper B.A., and Mueller G.P. Peptidylglycine-alpha-hydroxylating monooxygenase generates two hydroxylated products from its mechanism-based suicide substrate, 4-phenyl-3-butenoic acid. Biochemistry 39 (2000) 8007-8016
28. Driscoll W.J., Chaturvedi S., and Mueller G.P. Oleamide synthesizing activity from rat kidney: Identification as cytochrome c. J. Biol. Chem. 282 (2007) 22353-22363
29. Droghetti E., Oellerich S., Hildebrandt P., and Smulevich G. Heme coordination states of unfolded ferrous cytochrome C. Biophys. J. 91 (2006) 3022-3031
30. Eipper B.A., Stoffers D.A., and Mains R.E. The biosynthesis of neuropeptides: Peptide alpha-amidation. Annu. Rev. Neurosci. 15 (1992) 57-85
31. Elshami A.A., Saavedra A., Zhang H., Kucharczuk J.C., Spray D.C., Fishman G.I., Amin K.M., Kaiser L.R., and Albelda S.M. Gap junctions play a role in the 'bystander effect' of the herpes simplex virus thymidine kinase/ganciclovir system in vitro. Gene Ther. 3 (1996) 85-92
32. Farrell E.K., and Merkler D.J. Biosynthesis, degradation and pharmacological importance of the fatty acid amides. Drug Discov. Today 13 (2008) 558-568
33. Fedorova I., Hashimoto A., Fecik R.A., Hedrick M.P., Hanus L.O., Boger D.L., Rice K.C., and Basile A.S. Behavioral evidence for the interaction of oleamide with multiple neurotransmitter systems. J. Pharmacol. Exp. Ther. 299 (2001) 332-342
34. Ford T.A., and Mueller G.P. Induction of peptidylglycine alpha-hydroxylating monooxygenase activity by nerve growth factor in PC12 cells. J. Mol. Neurosci. 4 (1993) 97-105
35. Gilleron J., Nebout M., Scarabelli L., Senegas-Balas F., Palmero S., Segretain D., and Pointis G. A potential novel mechanism involving connexin 43 gap junction for control of sertoli cell proliferation by thyroid hormones. J. Cell Physiol. 209 (2006) 153-161
36. Guan X., Cravatt B.F., Ehring G.R., Hall J.E., Boger D.L., Lerner R.A., and Gilula N.B. The sleep-inducing lipid oleamide deconvolutes gap junction communication and calcium wave transmission in glial cells. J. Cell Biol. 139 (1997) 1785-1792
37. Halestrap A.P. Mitochondria and preconditioning: A connexin connection?. Circ. Res. 99 (2006) 10-12
38. Hanus L.O., Fales H.M., Spande T.F., and Basile A.S. A gas chromatographic-mass spectral assay for the quantitative determination of oleamide in biological fluids. Anal. Biochem. 270 (1999) 159-166
39. Hedlund P.B., Carson M.J., Sutcliffe J.G., and Thomas E.A. Allosteric regulation by oleamide of the binding properties of 5-hydroxytryptamine7 receptors. Biochem. Pharmacol. 58 (1999) 1807-1813
40. Hedlund P.B., Danielson P.E., Thomas E.A., Slanina K., Carson M.J., and Sutcliffe J.G. No hypothermic response to serotonin in 5-HT7 receptor knockout mice. Proc. Natl. Acad. Sci. USA 100 (2003) 1375-1380
41. Huang G.Y., Cooper E.S., Waldo K., Kirby M.L., Gilula N.B., and Lo C.W. Gap junction-mediated cell-cell communication modulates mouse neural crest migration. J. Cell Biol. 143 (1998) 1725-1734
42. Huidobro-Toro J.P., and Harris R.A. Brain lipids that induce sleep are novel modulators of 5-hydroxytrypamine receptors. Proc. Natl. Acad. Sci. USA 93 (1996) 8078-8082
43. Huitron-Resendiz S., Gombart L., Cravatt B.F., and Henriksen S.J. Effect of oleamide on sleep and its relationship to blood pressure, body temperature, and locomotor activity in rats. Exp. Neurol. 172 (2001) 235-243
44. Hu Y., Benedict M.A., Ding L., and Nunez G. Role of cytochrome c and dATP/ATP hydrolysis in Apaf-1-mediated caspase-9 activation and apoptosis. EMBO J. 18 (1999) 3586-3595
45. Jann M.W., and Slade J.H. Antidepressant agents for the treatment of chronic pain and depression. Pharmacotherapy 27 (2007) 1571-1587
46. Kase B.F., and Bjorkhem I. Peroxisomal bile acid-CoA:amino-acid N-acyltransferase in rat liver. J. Biol. Chem. 264 (1989) 9220-9223
47. Kase B.F., Prydz K., Bjorkhem I., and Pedersen J.I. Conjugation of cholic acid with taurine and glycine by rat liver peroxisomes. Biochem. Biophys. Res. Commun. 138 (1986) 167-173
48. Kelley M., and Vessey D.A. Characterization of the acyl-CoA:amino acid N-acyltransferases from primate liver mitochondria. J. Biochem. Toxicol. 9 (1994) 153-158
49. King III L., Barnes S., Glufke U., Henz M.E., Kirk M., Merkler K.A., Vederas J.C., Wilcox B.J., and Merkler D.J. The enzymatic formation of novel bile acid primary amides. Arch. Biochem. Biophys. 374 (2000) 107-117
50. Kluck R.M., Bossy-Wetzel E., Green D.R., and Newmeyer D.D. The release of cytochrome c from mitochondria: A primary site for Bcl-2 regulation of apoptosis. Science 275 (1997) 1132-1136
51. Koga D., Santa T., Fukushima T., Homma H., and Imai K. Liquid chromatographic-atmospheric pressure chemical ionization mass spectrometric determination of anandamide and its analogs in rat brain and peripheral tissues. J. Chromatogr. B Biomed. Sci. Appl. 690 (1997) 7-13
52. Kuida K., Haydar T.F., Kuan C.Y., Gu Y., Taya C., Karasuyama H., Su M.S., Rakic P., and Flavell R.A. Reduced apoptosis and cytochrome c-mediated caspase activation in mice lacking caspase 9. Cell 94 (1998) 325-337
53. Laposky A.D., Homanics G.E., Basile A., and Mendelson W.B. Deletion of the GABA(A) receptor beta 3 subunit eliminates the hypnotic actions of oleamide in mice. Neuroreport 12 (2001) 4143-4147
54. Lees G., Edwards M.D., Hassoni A.A., Ganellin C.R., and Galanakis D. Modulation of GABA(A) receptors and inhibitory synaptic currents by the endogenous CNS sleep regulator cis-9,10-octadecenoamide (cOA). Br. J. Pharmacol. 124 (1998) 873-882
55. Leithe E., Sirnes S., Omori Y., and Rivedal E. Downregulation of gap junctions in cancer cells. Crit. Rev. Oncog. 12 (2006) 225-256
56. Lerner R.A. A hypothesis about the endogenous analogue of general anesthesia. Proc. Natl. Acad. Sci. USA 94 (1997) 13375-13377
57. Lerner R.A., Siuzdak G., Prospero-Garcia O., Henriksen S.J., Boger D.L., and Cravatt B.F. Cerebrodiene: A brain lipid isolated from sleep-deprived cats. Proc. Natl. Acad. Sci. USA 91 (1994) 9505-9508
58. Lichtman A.H., Hawkins E.G., Griffin G., and Cravatt B.F. Pharmacological activity of fatty acid amides is regulated, but not mediated, by fatty acid amide hydrolase in vivo. J. Pharmacol. Exp. Ther. 302 (2002) 73-79
59. Lin J.H., Weigel H., Cotrina M.L., Liu S., Bueno E., Hansen A.J., Hansen T.W., Goldman S., and Nedergaard M. Gap-junction-mediated propagation and amplification of cell injury. Nat. Neurosci. 1 (1998) 494-500
60. Liu X., Kim C.N., Yang J., Jemmerson R., and Wang X. Induction of apoptotic program in cell-free extracts: Requirement for dATP and cytochrome c. Cell 86 (1996) 147-157
61. Maccarrone M., and Finazzi-Agro A. Endocannabinoids and their actions. Vitam. Horm. 65 (2002) 225-255
62. Mains R.E., Park L.P., and Eipper B.A. Inhibition of peptide amidation by disulfiram and diethyldithiocarbamate. J. Biol. Chem. 261 (1986) 11938-11941
63. Martinez-Gonzalez D., Bonilla-Jaime H., Morales-Otal A., Henriksen S.J., Velazquez-Moctezuma J., and Prospero-Garcia O. Oleamide and anandamide effects on food intake and sexual behavior of rats. Neurosci. Lett. 364 (2004) 1-6
64. Matono S., Tanaka T., Sueyoshi S., Yamana H., Fujita H., and Shirouzu K. Bystander effect in suicide gene therapy is directly proportional to the degree of gap junctional intercellular communication in esophageal cancer. Int. J. Oncol. 23 (2003) 1309-1315
65. Mawal Y.R., and Qureshi I.A. Purification to homogeneity of mitochondrial acyl coa:glycine n-acyltransferase from human liver. Biochem. Biophys. Res. Commun. 205 (1994) 1373-1379
66. McCue J.M., Driscoll W.J., and Mueller G.P. Cytochrome c catalyzes the in vitro synthesis of arachidonoyl glycine. Biochem. Biophys. Res. Commun. 365 (2008) 322-327
67. McIntyre N.R., Lowe Jr. E.W., Chew G.H., Owen T.C., and Merkler D.J. Thiorphan, tiopronin, and related analogs as substrates and inhibitors of peptidylglycine alpha-amidating monooxygenase (PAM). FEBS Lett. 580 (2006) 521-532
68. Mendelson W.B., and Basile A.S. The hypnotic actions of the fatty acid amide, oleamide. Neuropsychopharmacology 25 (2001) S36-S39
69. Merkler D.J., Merkler K.A., Stern W., and Fleming F.F. Fatty acid amide biosynthesis: A possible new role for peptidylglycine alpha-amidating enzyme and acyl-coenzyme A:glycine N-acyltransferase. Arch. Biochem. Biophys. 330 (1996) 430-434
70. Merkler D.J., Chew G.H., Gee A.J., Merkler K.A., Sorondo J.P., and Johnson M.E. Oleic acid derived metabolites in mouse neuroblastoma N18TG2 cells. Biochemistry 43 (2004) 12667-12674
71. Mesnil M., Piccoli C., Tiraby G., Willecke K., and Yamasaki H. Bystander killing of cancer cells by herpes simplex virus thymidine kinase gene is mediated by connexins. Proc. Natl. Acad. Sci. USA 93 (1996) 1831-1835
72. Miller L.A., Baumgart L.E., Chew G.H., deLong M.A., Galloway L.C., Jung K.W., Merkler K.A., Nagle A.S., Poore D.D., Yoon C.H., and Merkler D.J. Glutathione, S-substituted glutathiones, and leukotriene C4 as substrates for peptidylglycine alpha-amidating monooxygenase. Arch. Biochem. Biophys. 412 (2003) 3-12
73. Miura T., Ohnuma Y., Kuno A., Tanno M., Ichikawa Y., Nakamura Y., Yano T., Miki T., Sakamoto J., and Shimamoto K. Protective role of gap junctions in preconditioning against myocardial infarction. Am. J. Physiol. Heart Circ. Physiol. 286 (2004) H214-H221
74. Moltzen E.K., and Bang-Andersen B. Serotonin reuptake inhibitors: The corner stone in treatment of depression for half a century-A medicinal chemistry survey. Curr. Top. Med. Chem. 6 (2006) 1801-1823
75. Mueller G.P., and Driscoll W.J. In vitro synthesis of oleoylglycine by cytochrome c points to a novel pathway for the production of lipid signaling molecules. J. Biol. Chem. 282 31 (2007) 22364-22369
76. Mueller G.P., Husten E.J., Mains R.E., and Eipper B.A. Peptide alpha-amidation and peptidylglycine alpha-hydroxylating monooxygenase: Control by disulfiram. Mol. Pharmacol. 44 (1993) 972-980
77. Mueller G.P., Driscoll W.J., and Eipper B.A. In vivo inhibition of peptidylglycine-alpha-hydroxylating monooxygenase by 4-phenyl-3-butenoic acid. J. Pharmacol. Exp. Ther. 290 (1999) 1331-1336
78. Murillo-Rodriguez E., Giordano M., Cabeza R., Henriksen S.J., Mendez Diaz M., Navarro L., and Prospero-Garcia O. Oleamide modulates memory in rats. Neurosci. Lett. 313 (2001) 61-64
79. Nagasawa K., Chiba H., Fujita H., Kojima T., Saito T., Endo T., and Sawada N. Possible involvement of gap junctions in the barrier function of tight junctions of brain and lung endothelial cells. J. Cell Physiol. 208 (2006) 123-132
80. Nakase T., and Naus C.C. Gap junctions and neurological disorders of the central nervous system. Biochim. Biophys. Acta 1662 (2004) 149-158
81. Nichols K.K., Ham B.M., Nichols J.J., Ziegler C., and Green-Church K.B. Identification of fatty acids and fatty acid amides in human meibomian gland secretions. Invest Ophthalmol. Vis. Sci. 48 (2007) 34-39
82. Nodin C., Nilsson M., and Blomstrand F. Gap junction blockage limits intercellular spreading of astrocytic apoptosis induced by metabolic depression. J. Neurochem. 94 (2005) 1111-1123
83. O'Byrne J., Hunt M.C., Rai D.K., Saeki M., and Alexson S.E. The human bile acid-CoA:amino acid N-acyltransferase functions in the conjugation of fatty acids to glycine. J. Biol. Chem. 278 (2003) 34237-34244
84. Patricelli M.P., and Cravatt B.F. Proteins regulating the biosynthesis and inactivation of neuromodulatory fatty acid amides. Vitam. Horm. 62 (2001) 95-131
85. Perez Velazquez J.L., Kokarovtseva L., Sarbaziha R., Jeyapalan Z., and Leshchenko Y. Role of gap junctional coupling in astrocytic networks in the determination of global ischaemia-induced oxidative stress and hippocampal damage. Eur. J. Neurosci. 23 (2006) 1-10
86. Pinheiro T.J., Elove G.A., Watts A., and Roder H. Structural and kinetic description of cytochrome c unfolding induced by the interaction with lipid vesicles. Biochemistry 36 (1997) 13122-13132
87. Quist A.P., Rhee S.K., Lin H., and Lal R. Physiological role of gap-junctional hemichannels. Extracellular calcium-dependent isosmotic volume regulation. J. Cell Biol. 148 (2000) 1063-1074
88. Rami A., Volkmann T., and Winckler J. Effective reduction of neuronal death by inhibiting gap junctional intercellular communication in a rodent model of global transient cerebral ischemia. Exp. Neurol. 170 (2001) 297-304
89. Ransjo M., Sahli J., and Lie A. Expression of connexin 43 mRNA in microisolated murine osteoclasts and regulation of bone resorption in vitro by gap junction inhibitors. Biochem. Biophys. Res. Commun. 303 (2003) 1179-1185
90. Rathmell J.C., and Thompson C.B. Pathways of apoptosis in lymphocyte development, homeostasis, and disease. Cell 109 Suppl (2002) S97-S107
91. Rawanduzy A., Hansen A., Hansen T.W., and Nedergaard M. Effective reduction of infarct volume by gap junction blockade in a rodent model of stroke. J. Neurosurg. 87 (1997) 916-920
92. Reznikov K., Kolesnikova L., Pramanik A., Tan-No K., Gileva I., Yakovleva T., Rigler R., Terenius L., and Bakalkin G. Clustering of apoptotic cells via bystander killing by peroxides. FASEB J. 14 (2000) 1754-1764
93. Ritenour-Rodgers K.J., Driscoll W.J., Merkler K.A., Merkler D.J., and Mueller G.P. Induction of peptidylglycine alpha-amidating monooxygenase in N(18)TG(2) cells: A model for studying oleamide biosynthesis. Biochem. Biophys. Res. Commun. 267 (2000) 521-526
94. Sakono M., Goto M., and Furusaki S. Refolding of cytochrome c using reversed micelles. J. Biosci. Bioeng. 89 (2000) 458-462
95. Sanghera N., and Pinheiro T.J. Unfolding and refolding of cytochrome c driven by the interaction with lipid micelles. Protein Sci. 9 (2000) 1194-1202
96. Schafer Z.T., and Kornbluth S. The apoptosome: Physiological, developmental, and pathological modes of regulation. Dev. Cell 10 (2006) 549-561
97. Schiller P.C., D'Ippolito G., Balkan W., Roos B.A., and Howard G.A. Gap-junctional communication is required for the maturation process of osteoblastic cells in culture. Bone 28 (2001) 362-369
98. Schiller P.C., D'Ippolito G., Brambilla R., Roos B.A., and Howard G.A. Inhibition of gap-junctional communication induces the trans-differentiation of osteoblasts to an adipocytic phenotype in vitro. J. Biol. Chem. 276 (2001) 14133-14138
99. Schweitzer J.S., Wang H., Xiong Z.Q., and Stringer J.L. pH Sensitivity of non-synaptic field bursts in the dentate gyrus. J. Neurophysiol. 84 (2000) 927-933
100. Shonsey E.M., Sfakianos M., Johnson M., He D., Falany C.N., Falany J., Merkler D.J., and Barnes S. Bile acid coenzyme A:amino acid N-acyltransferase in the amino acid conjugation of bile acids. Methods Enzymol. 400 (2005) 374-394
101. SiuYi Leung D., Unsicker K., and Reuss B. Gap junctions modulate survival-promoting effects of fibroblast growth factor-2 on cultured midbrain dopaminergic neurons. Mol. Cell Neurosci. 18 (2001) 44-55
102. Sohl G., Maxeiner S., and Willecke K. Expression and functions of neuronal gap junctions. Nat. Rev. Neurosci. 6 (2005) 191-200
103. Stewart J.M., Blakely J.A., and Johnson M.D. The interaction of ferrocytochrome c with long-chain fatty acids and their CoA and carnitine esters. Biochem. Cell Biol. 78 (2000) 675-681
104. Subauste M.C., List B., Guan X., Hahn K.M., Lerner R., and Gilula N.B. A catalytic antibody produces fluorescent tracers of gap junction communication in living cells. J. Biol. Chem. 276 (2001) 49164-49168
105. Sugiura T., Kondo S., Kodaka T., Tonegawa T., Nakane S., Yamashita A., Ishima Y., and Waku K. Enzymatic synthesis of oleamide (cis-9, 10-octadecenoamide), an endogenous sleep-inducing lipid, by rat brain microsomes. Biochem. Mol. Biol. Int. 40 (1996) 931-938
106. Suzuki R., Rygh L.J., and Dickenson A.H. Bad news from the brain: Descending 5-HT pathways that control spinal pain processing. Trends Pharmacol. Sci. 25 (2004) 613-617
107. Theis M., Sohl G., Eiberger J., and Willecke K. Emerging complexities in identity and function of glial connexins. Trends Neurosci. 28 (2005) 188-195
108. Theiss C., Mazur A., Meller K., and Mannherz H.G. Changes in gap junction organization and decreased coupling during induced apoptosis in lens epithelial and NIH-3T3 cells. Exp. Cell Res. 313 (2007) 38-52
109. Thomas E.A., Carson M.J., Neal M.J., and Sutcliffe J.G. Unique allosteric regulation of 5-hydroxytryptamine receptor-mediated signal transduction by oleamide. Proc. Natl. Acad. Sci. USA 94 (1997) 14115-14119
110. Thomas E.A., Carson M.J., and Sutcliffe J.G. Oleamide-induced modulation of 5-hydroxytryptamine receptor-mediated signaling. Ann. NY Acad. Sci. 861 (1998) 183-189
111. Thompson C.B. Apoptosis in the pathogenesis and treatment of disease. Science 267 (1995) 1456-1462
112. Trosko J.E., and Ruch R.J. Gap junctions as targets for cancer chemoprevention and chemotherapy. Curr. Drug Targets 3 (2002) 465-482
113. Unger V.M., Kumar N.M., Gilula N.B., and Yeager M. Electron cryo-crystallography of a recombinant cardiac gap junction channel. Novartis Found Symp. 219 (1999) 22-30 discussion 1-43
114. van Veen T.A., van Rijen H.V., and Jongsma H.J. Physiology of cardiovascular gap junctions. Adv. Cardiol. 42 (2006) 18-40
115. Vempati U.D., Diaz F., Barrientos A., Narisawa S., Mian A.M., Millan J.L., Boise L.H., and Moraes C.T. Role of cytochrome C in apoptosis: Increased sensitivity to tumor necrosis factor alpha is associated with respiratory defects but not with lack of cytochrome C release. Mol. Cell Biol. 27 (2007) 1771-1783
116. Verdon B., Zheng J., Nicholson R.A., Ganelli C.R., and Lees G. Stereoselective modulatory actions of oleamide on GABA(A) receptors and voltage-gated Na(+) channels in vitro: A putative endogenous ligand for depressant drug sites in CNS. Br. J. Pharmacol. 129 (2000) 283-290
117. Wakamatsu K., Masaki T., Itoh F., Kondo K., and Sudo K. Isolation of fatty acid amide as an angiogenic principle from bovine mesentery. Biochem. Biophys. Res. Commun. 168 (1990) 423-429
118. Wang Z.B., Li M., Zhao Y., and Xu J.X. Cytochrome C is a hydrogen peroxide scavenger in mitochondria. Protein Pept. Lett. 10 (2003) 247-253
119. Watkins P.A. Fatty acid activation. Prog. Lipid Res. 36 (1997) 55-83
120. Wilcox B.J., Ritenour-Rodgers K.J., Asser A.S., Baumgart L.E., Baumgart M.A., Boger D.L., DeBlassio J.L., deLong M.A., Glufke U., Henz M.E., King III L., Merkler K.A., et al. N-acylglycine amidation: Implications for the biosynthesis of fatty acid primary amides. Biochemistry 38 (1999) 3235-3245
121. Yang J., Liu X., Bhalla K., Kim C.N., Ibrado A.M., Cai J., Peng T.I., Jones D.P., and Wang X. Prevention of apoptosis by Bcl-2: Release of cytochrome c from mitochondria blocked. Science 275 (1997) 1129-1132
122. Yang J.Y., Abe K., Xu N.J., Matsuki N., and Wu C.F. Oleamide attenuates apoptotic death in cultured rat cerebellar granule neurons. Neurosci. Lett. 328 (2002) 165-169
123. Yuan J., and Yankner B.A. Apoptosis in the nervous system. Nature 407 (2000) 802-809
124. Zhao Y., and Xu J.X. The operation of the alternative electron-leak pathways mediated by cytochrome c in mitochondria. Biochem. Biophys. Res. Commun. 317 (2004) 980-987
125. Zhao Y., Wang Z.B., and Xu J.X. Effect of cytochrome c on the generation and elimination of O2*- and H2O2 in mitochondria. J. Biol. Chem. 278 (2003) 2356-2360
126. Zohar J., and Westenberg H.G. Anxiety disorders: A review of tricyclic antidepressants and selective serotonin reuptake inhibitors. Acta Psychiatr. Scand. Suppl. 403 (2000) 39-49
127. Zou H., Li Y., Liu X., and Wang X. An APAF-1.cytochrome c multimeric complex is a functional apoptosome that activates procaspase-9. J. Biol. Chem. 274 (1999) 11549-11556