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Methods for the synthesis of tritium-labelled fatty acids and their derivatives, oxylipins and steroids

Valerii Pavlovich Shevchenko 1
Valerii Pavlovich Shevchenko
, 
Igor Yulianovich Nagaev 1
Igor Yulianovich Nagaev
, 
Nikolai Fedorovich Myasoedov 1
Nikolai Fedorovich Myasoedov
1 Institute of Molecular Genetics of the Russian Academy of Sciences, Moscow
10.1070/RC1999v068n10ABEH000528
Published 30 November 1998
Communication , Volume 68, Issue 10, 859-879
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Shevchenko V. P., Nagaev I. Y., Myasoedov N. F. Methods for the synthesis of tritium-labelled fatty acids and their derivatives, oxylipins and steroids // Russian Chemical Reviews. 1999. Vol. 68. No. 10. pp. 859-879.
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Shevchenko V. P., Nagaev I. Y., Myasoedov N. F. Methods for the synthesis of tritium-labelled fatty acids and their derivatives, oxylipins and steroids // Russian Chemical Reviews. 1999. Vol. 68. No. 10. pp. 859-879.
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TY - JOUR
DO - 10.1070/RC1999v068n10ABEH000528
UR - https://rcr.colab.ws/publications/10.1070/RC1999v068n10ABEH000528
TI - Methods for the synthesis of tritium-labelled fatty acids and their derivatives, oxylipins and steroids
T2 - Russian Chemical Reviews
AU - Shevchenko, Valerii Pavlovich
AU - Nagaev, Igor Yulianovich
AU - Myasoedov, Nikolai Fedorovich
PY - 1999
DA - 1998/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 859-879
IS - 10
VL - 68
ER -
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@article{1999_Shevchenko,
author = {Valerii Pavlovich Shevchenko and Igor Yulianovich Nagaev and Nikolai Fedorovich Myasoedov},
title = {Methods for the synthesis of tritium-labelled fatty acids and their derivatives, oxylipins and steroids},
journal = {Russian Chemical Reviews},
year = {1999},
volume = {68},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1999v068n10ABEH000528},
number = {10},
pages = {859--879},
doi = {10.1070/RC1999v068n10ABEH000528}
}
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Shevchenko, Valerii Pavlovich, et al. “Methods for the synthesis of tritium-labelled fatty acids and their derivatives, oxylipins and steroids.” Russian Chemical Reviews, vol. 68, no. 10, Nov. 1999, pp. 859-879. https://rcr.colab.ws/publications/10.1070/RC1999v068n10ABEH000528.
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Abstract

The achievements in the field of synthesis and application of tritium-labelled oxylipins, steroids, fatty acids, phospho-, sphingo- and other lipids are reviewed. The importance of these studies for the solution of current problems of biochemistry, biology and pharmacology is exemplified in the application of labelled compounds. The bibliography includes 148 references.

References

1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
2.
Synthesis of tritium-labelled biologically important diazines
Sidorov G.V., Myasoedov N.F.
Russian Chemical Reviews , 1999
3.
4
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
4.
5
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1953
5.
6
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
6.
The effect of catalytic reaction conditions on the incorporation of tritium in unsaturated compounds
Shevchenko V.P., Yu. Nagayev I., Myasoedov N.F.
Journal of Labelled Compounds and Radiopharmaceuticals , 1989
8.
Introduction of tritium into organic compounds by isotope exchange reactions
Myasoedov N.F.
Journal of Labelled Compounds and Radiopharmaceuticals , 1993
9.
10
T. A. Kryukova
"Polyaro-graficheskii Analiz" (Polarographic Analysis) , 1959
10.
11
T. T. Bannister
Diss. Abstr. , 1959
11.
12
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
12.
13
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
13.
14
V. B. Evstigneev
Zhur. Fiz. Khim. , 1958
14.
15
A. S. Holt
"Research in Photosynthesis" , 1957
15.
16
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
16.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
17.
18
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
18.
19
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1959
19.
Synthesis of tritium‐labelled natural prostaglandins of series 1,2,3
Shevchenko V.P., Myagkova G.I., Yu. Lazurkina T., Dyomin P.M., Shram S.I., Zabolotsky D.A., Yu. Nagayev I., Belosludtsev Y.Y., Evstigneeva R.P., Myasoyedov N.F.
Journal of Labelled Compounds and Radiopharmaceuticals , 1989
20.
21
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
21.
22
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
22.
23
N. V. Vostrilova
Dokl. Akad. Nauk Uzbek. SSR , 1958
23.
24
M. S. Ashkinazi
Dokl. Akad. Nauk SSSR , 1951
24.
25
G. W. Robinson
J. Chem. Phys. , 1955
25.
26
B. Ya. Dain
1957
26.
Regulation of gene transcription by polyunsaturated fatty acids
Clarke S.D., Jump D.B.
Progress in Lipid Research , 1993
29.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
30.
31
A. A. Krasnovskii
Biokhimiya , 1960
31.
32
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1952
32.
The Synthesis of Lepidoptera Pheromones
Matveeva E.D., Kurts A.L., Bundel' Y.G.
Russian Chemical Reviews , 1986
33.
35
Z. K. Maizus
Dokl. Akad. Nauk SSSR , 1960
34.
36
J. Billon
Bull. Soc. chim. France , 1960
35.
37
L. M. Kosobutskaya
Dokl. Akad. Nauk SSSR , 1950
36.
38
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
37.
Synthesis of novel tritium labeled oxamyristic acids
Devadas B., Adams S.P., Gordon J.I.
Journal of Labelled Compounds and Radiopharmaceuticals , 1991
38.
40
A. A. Krasnovskii
Biofizika , 1960
39.
235. Pseudo-metallic bonding of hydrides
Ubbelohde A.R.
Journal of the Chemical Society (Resumed) , 1950
40.
Primary Solid Hydrides
Gibb T.R.
Progress in Inorganic Chemistry , 1962
42.
44
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
45.
2-Arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain.
Sugiura T., Kondo S., Sukagawa A., Nakane S., Shinoda A., Itoh K., Yamashita A., Waku K.
Biochemical and Biophysical Research Communications , 1995
46.
Molecular characterization of a peripheral receptor for cannabinoids
Munro S., Thomas K.L., Abu-Shaar M.
Nature , 1993
47.
Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors.
Mechoulam R., Ben-Shabat S., Hanus L., Ligumsky M., Kaminski N.E., Schatz A.R., Gopher A., Almog S., Martin B.R., Compton D.R., Pertwee R.G., Griffin G., Bayewitch M., Barg J., Vogel Z., et. al.
Biochemical Pharmacology , 1995
48.
Two novel classes of neuroactive fatty acid amides are substrates for mouse neuroblastoma ‘anandamide amidohydrolase’
Maurelli S., Bisogno T., De Petrocellis L., Di Luccia A., Marino G., Di Marzo V.
FEBS Letters , 1995
49.
51
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
50.
Brain cannabinoids in chocolate
di Tomaso E., Beltramo M., Piomelli D.
Nature , 1996
51.
53
D. Porretand E. Rabinowitch
Nature , 1937
52.
54
R. Livingston
J. Phys. Chem. , 1941
53.
55
G. A. Bogdanovskii
1958
56.
The synthesis of 1,2-dioleoyl-sn-[2-3H]glycero-3-phosphoserine
Binaglia L., Alunni-Bistocchi G., Orlando M., Orlando P., Rosa G., Trenta R.
Journal of Labelled Compounds and Radiopharmaceuticals , 1991
57.
Chemical synthesis of diphosphoinositide
Shevchenko V.P., Tsirenina M.L., Molotkovsky J.G., Bergelson L.D.
Chemistry and Physics of Lipids , 1975
58.
CV-3988 - a specific antagonist of platelet activating factor (PAF).
Terashita Z., Tsushima S., Yoshioka Y., Nomura H., Inada Y., Nishikawa K.
Life Sciences , 1983
61.
Isolation and Structure of a Brain Constituent That Binds to the Cannabinoid Receptor
Devane W.A., Hanuš L., Breuer A., Pertwee R.G., Stevenson L.A., Griffin G., Gibson D., Mandelbaum A., Etinger A., Mechoulam R.
Science , 1992
63.
Anandamide, an endogenous ligand of the cannabinoid receptor, induces hypomotility and hypothermia in vivo in rodents
Crawley J.N., Corwin R.L., Robinson J.K., Felder C.C., Devane W.A., Axelrod J.
Pharmacology Biochemistry and Behavior , 1993
64.
66
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
66.
Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction.
Felder C.C., Briley E.M., Axelrod J., Simpson J.T., Mackie K., Devane W.A.
Proceedings of the National Academy of Sciences of the United States of America , 1993
67.
Effects of anandamide on cannabinoid receptors in rat brain membranes.
Childers S.R., Sexton T., Roy M.B.
Biochemical Pharmacology , 1994
68.
70
N. Bubnov
Biofizika , 1960
69.
Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor
Hanus L., Gopher A., Almog S., Mechoulam R.
Journal of Medicinal Chemistry , 1993
70.
72
A. F. Lukovnikov
"Starenie i Stabilizatsiya Polimerov" (Aging arid Stabilisation of Polymers) , 1963
73.
Enzymatic synthesis of anandamide, an endogenous ligand for the cannabinoid receptor, by brain membranes.
Devane W.A., Axelrod J.
Proceedings of the National Academy of Sciences of the United States of America , 1994
74.
Formation and inactivation of endogenous cannabinoid anandamide in central neurons
Di Marzo V., Fontana A., Cadas H., Schinelli S., Cimino G., Schwartz J., Piomelli D.
Nature , 1994
75.
Lipoxygenase-catalyzed oxygenation of arachidonylethanolamide, a cannabinoid receptor agonist.
Ueda N., Yamamoto K., Yamamoto S., Tokunaga T., Shirakawa E., Shinkai H., Ogawa M., Sato T., Kudo I., Inoue K., Takizawa H., Nagano T., Hirobe M., Matsuki N., Saito H., et. al.
Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism , 1995
76.
78
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
77.
Anandamide hydroxylation by brain lipoxygenase:metabolite structures and potencies at the cannabinoid receptor
Hampson A.J., Hill W.A., Zan-Phillips M., Makriyannis A., Leung E., Eglen R.M., Bornheim L.M.
Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism , 1995
78.
Anandamide Amidohydrolase Activity in Rat Brain Microsomes
Desarnaud F., Cadas H., Piomelli D.
Journal of Biological Chemistry , 1995
79.
81
J. C. Ghosh
J. Indian Chem. Soc. , 1934
81.
Double dioxygenation of arachidonic acid by soybean lipoxygenase-1. Kinetics and regio-stereo specificities of the reaction steps.
Van Os C.P., Rijke-Schilder G.P., Van Halbeek H., Verhagen J., Vliegenthart J.F.
Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism , 1981
82.
Substrate specificity of soybean lipoxidase.
Holman R.T., Egwim P.O., Christie W.W.
Journal of Biological Chemistry , 1969
83.
85
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
84.
Structural requirements for long-chain (sphingoid) base inhibition of protein kinase C in vitro and for the cellular effects of these compounds
Merrill A.H., Nimkar S., Menaldino D., Hannun Y.A., Loomis C., Bell R.M., Tyagi S.R., Lambeth J.D., Stevens V.L.
Biochemistry , 1989
85.
Activation of the Sphingomyelin Cycle Through the Low-Affinity Neurotrophin Receptor
Dobrowsky R.T., Werner M.H., Castellino A.M., Chao M.V., Hannun Y.A.
Science , 1994
86.
Role of ceramide as a lipid mediator of 1 alpha,25-dihydroxyvitamin D3-induced HL-60 cell differentiation.
Okazaki T., Bielawska A., Bell R.M., Hannun Y.A.
Journal of Biological Chemistry , 1990
87.
Modulation of cell growth and differentiation by ceramide
Bielawska A., Linardic C.M., Hannun Y.A.
FEBS Letters , 1992
88.
A Mediator Role of Ceramide in the Regulation of Neuroblastoma Neuro2a Cell Differentiation
Riboni L., Prinetti A., Bassi R., Caminiti A., Tettamanti G.
Journal of Biological Chemistry , 1995
90.
Induction of apoptotic DNA fragmentation and cell death by natural ceramide
Ji L., Zhang G., Uematsu S., Akahori Y., Hirabayashi Y.
FEBS Letters , 1995
91.
Ceramide activates heterotrimeric protein phosphatase 2A.
Dobrowsky R.T., Kamibayashi C., Mumby M.C., Hannun Y.A.
Journal of Biological Chemistry , 1993
92.
Role of ceramide-activated protein phosphatase in ceramide-mediated signal transduction.
Wolff R.A., Dobrowsky R.T., Bielawska A., Obeid L.M., Hannun Y.A.
Journal of Biological Chemistry , 1994
93.
Ceramide Inactivates Cellular Protein Kinase Cα*
Lee J.Y., Hannun Y.A., Obeid L.M.
Journal of Biological Chemistry , 1996
94.
Ceramide Inhibits Phospholipase D in a Cell-free System*
Venable M.E., Bielawska A., Obeid L.M.
Journal of Biological Chemistry , 1996
95.
97
A. N. Terenin
Dokl. Akad. Nauk SSSR , 1952
96.
Specific tritium labelling of sphingosines at the 3-position
Birk R., Brenner-Weiß G., Giannis A., Sandhoff K., Schmidt R.R.
Journal of Labelled Compounds and Radiopharmaceuticals , 1991
97.
A facile and regiospecific tritiation of sphingosine: Synthesis of (2S,3R,4E)‐2‐amino‐4‐octadecene‐1,3‐diol‐1‐3H
Toyokuni T., Nisar M., Dean B., Hakomori S.
Journal of Labelled Compounds and Radiopharmaceuticals , 1991
98.
100
V. V. Zolotarev
Chem. Abs. , 1941
99.
Role of Gangliosides in Reception of Influenza Virus
BERGELSON L.D., BUKRINSKAYA A.G., PROKAZOVA N.V., SHAPOSHNIKOVA G.I., KOCHAROV S.L., SHEVCHENKO V.P., KORNILAEVA G.V., FOMINA-AGEEVA E.V.
FEBS Journal , 2005
100.
102
F. Fichter
Helv. Chim. Acta , 1922
101.
Lipoxin biosynthesis and its impact in inflammatory and vascular events
Serhan C.N.
Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism , 1994
102.
Hepoxilins
Pace-Asciak C.R.
General Pharmacology The Vascular System , 1993
103.
105
F. F. Litvin
Dokl. Akad. Nauk SSSR , 1958
104.
106
F. Fichter
Helv. Chim. Acta , 1927
105.
107
M. F. Shostakovskii
Zhur. Obshch. Khim. , 1961
107.
109
F. Ficher
Bull. Soc. chim. France (4) , 1916
108.
110
M. F. Shostakovskii
Dokl. Akad. Nauk SSSR , 1960
109.
111
M. Calvin
1956
110.
Synthesis and biological evaluation of 14,15-dehydro-LTA4 analog
Garcia M., Durand T., Rossi J.C., Zarini S., Bolla M., Folco G., Wheelan P., Sala A.
Bioorganic and Medicinal Chemistry Letters , 1997
112.
Enzymatic synthesis of tritium labelled eicosanoids
Shram S.I., Lazurkina T.Y., Shevchenko V.P., Nagayev I.Y., Myasoedov N.F.
Journal of Labelled Compounds and Radiopharmaceuticals , 1998
113.
115
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1957
114.
Enzymatic synthesis of tritium - labelled prostaglandin D2 and its conversion to other prostaglandins
Shram S.I., Lazurkina T.Y., Shevchenko V.P., Nagaev I.Y., Myasoedov N.F.
Journal of Labelled Compounds and Radiopharmaceuticals , 1994
115.
117
V. V. Levchenko
Zhur. Obshch. Khim. , 1948
116.
118
V. M. Rodionov
Zhur. Obshch. Khim. , 1935
117.
119
V. V. Levchenko
Zhur. Obshch. Khim. , 1947
118.
120
V. V. Levchenko
Zhur. Obshch. Khim. , 1948
119.
121
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
120.
122
S. R. Rafikov
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
121.
123
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
122.
124
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
123.
125
K. A. Andrianov
Vysokomol. Soed. , 1960
124.
Labeling of steroids by activated tritium
Tang G.Z., Peng C.T.
Journal of Labelled Compounds and Radiopharmaceuticals , 1988
125.
Synthesis of canrenone and related steroids labelled with tritium, carbon-14, and sulfur-35
Markos C.S., Dorn C.R., Zitzewitz D.J.
Journal of Labelled Compounds and Radiopharmaceuticals , 1988
126.
Synthesis of highly tritiated 7-deoxy-7 dihydroantheridiol and antheriodiol
Meyer M.D., Carlson G.L., Toft D.O., Greaves A.M., Ng K.E., McMorris T.C.
Journal of Labelled Compounds and Radiopharmaceuticals , 1987
127.
Synthesis of [5,6-3H2]CP-88,818 (β-[5,6-3H2]tigogenin cellobioside)
McCarthy P.A.
Journal of Labelled Compounds and Radiopharmaceuticals , 1990
129.
131
N. Thooi
Compt. rend. , 1958
130.
Synthesis of tritium-labelled biologically active analogues of progesterone by selective hydrogenation of 16α,17α-cyclohex-3′-en-pregna-1,4-dien-3,20-dione
Shevchenko V.P., Nagaev I.Y., Potapova A.V., Myasoedov N.F., Kamernitsky A.V., Levina I.S., Kulikova L.E., Smirnov A.N.
Journal of Labelled Compounds and Radiopharmaceuticals , 1998
131.
High specific activity steroids I: 17α-ethynylestradiol-[9,11-3H] and norethindrone-[9,11-3H]
Parnes H., Shelton E.J.
Journal of Labelled Compounds and Radiopharmaceuticals , 1991
134.
Synthesis of [14α, 15α-3H]-norgestrel
Wagner H., Römer J.
Journal of Labelled Compounds and Radiopharmaceuticals , 1988
135.
Total synthesis of (S)-12-hydroxy-5,8,14-cis,-10-trans-eicosatetraenoic acid (Samuelsson's HETE)
Corey E.J., Niwa H., Knolle J.
Journal of the American Chemical Society , 1978
136.
Synthesis of tritiated 1α,25-dihydroxy-22-oxavitamin D3
Watanabe H., Akiyama M., Kawanishi T., Kubodera N.
Journal of Labelled Compounds and Radiopharmaceuticals , 1995
137.
139
I. L. Knunyants
1959
138.
140
1912
139.
The Synthesis of Tritium-Labeled 16α,17α-Cyclohex-3′-eno-progesterone as Probe for the Study of Steroid–Receptor Binding
Shevchenko V.P., Nagaev I.Y., Myasoedov N.F., Kamernitsky A.V., Levina I.S., Kulikova L.E., Pokrovskaya E.V., Shchelkunova T.A., Smirnov A.N.
Bioorganic Chemistry , 1999
140.
142
1913
141.
143
Friedl.
142.
144
1912
143.
145
Friedl.
144.
146
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1952
145.
147
Y. Sasada
Acta Cryst. , 1898
146.
148
P. Kresse
Chem. Abs. , 1960
148.
Direct tritium labeling of multifunctional compounds using organoiridium catalysis
Chen W., Garnes K.T., Levinson S.H., Saunders D., Senderoff S.G., Shu A.Y., Villani A.J., Heys J.R.
Journal of Labelled Compounds and Radiopharmaceuticals , 1997
149.
151
V. M. Rodionov
Zhur. Obshch. Khim. , 1936