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Exogenous nitric oxide donors and inhibitors of its formation (the chemical aspects)

Vladimir Grigor'evich Granik 1
Vladimir Grigor'evich Granik
, 
Svetlana Yur'evna Ryabova 1
Svetlana Yur'evna Ryabova
, 
Nikita Borisovich Grigoriev 1
Nikita Borisovich Grigoriev
1 Centre for Medicinal Chemistry, All-Russian Research Chemical-Pharmaceutical Institute, Moscow
10.1070/RC1997v066n08ABEH000317
Published 30 November 1996
Communication , Volume 66, Issue 8, 717-731
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Granik V. G., Ryabova S. Y., Grigoriev N. B. Exogenous nitric oxide donors and inhibitors of its formation (the chemical aspects) // Russian Chemical Reviews. 1997. Vol. 66. No. 8. pp. 717-731.
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Granik V. G., Ryabova S. Y., Grigoriev N. B. Exogenous nitric oxide donors and inhibitors of its formation (the chemical aspects) // Russian Chemical Reviews. 1997. Vol. 66. No. 8. pp. 717-731.
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TY - JOUR
DO - 10.1070/RC1997v066n08ABEH000317
UR - https://rcr.colab.ws/publications/10.1070/RC1997v066n08ABEH000317
TI - Exogenous nitric oxide donors and inhibitors of its formation (the chemical aspects)
T2 - Russian Chemical Reviews
AU - Granik, Vladimir Grigor'evich
AU - Ryabova, Svetlana Yur'evna
AU - Grigoriev, Nikita Borisovich
PY - 1997
DA - 1996/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 717-731
IS - 8
VL - 66
ER -
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@article{1997_Granik,
author = {Vladimir Grigor'evich Granik and Svetlana Yur'evna Ryabova and Nikita Borisovich Grigoriev},
title = {Exogenous nitric oxide donors and inhibitors of its formation (the chemical aspects)},
journal = {Russian Chemical Reviews},
year = {1997},
volume = {66},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1997v066n08ABEH000317},
number = {8},
pages = {717--731},
doi = {10.1070/RC1997v066n08ABEH000317}
}
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Granik, Vladimir Grigor'evich, et al. “Exogenous nitric oxide donors and inhibitors of its formation (the chemical aspects).” Russian Chemical Reviews, vol. 66, no. 8, Nov. 1997, pp. 717-731. https://rcr.colab.ws/publications/10.1070/RC1997v066n08ABEH000317.
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Abstract

The published data on the biological role of nitric oxide formed in vivo by enzymatic oxidation of L-arginine are generalised. Special attention is given to exogenous nitric oxide donors, which can release NO in vitro and in vivo in oxidation, reduction, or hydrolytic cleavage. Also considered are the data on the chemical nature of inhibitors of NO-synthase responsible for nitric oxide formation from L-arginine. The bibliography includes 161 references.

References

1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
2.
Biochemistry of Nitric Oxide and Its Redox-Activated Forms
Stamler J.S., Singel D.J., Loscalzo J.
Science , 1992
3.
Nitric oxide synthase structure and mechanism
Marletta M.A.
Journal of Biological Chemistry , 1993
4.
Approaches toward Selective Inhibition of Nitric Oxide Synthase
Marletta M.A.
Journal of Medicinal Chemistry , 1994
5.
The arginine-nitric oxide pathway: A target for new drugs
Kerwin J.F., Heller M.
Medicinal Research Reviews , 1994
6.
Nitric Oxide: A New Paradigm for Second Messengers
Kerwin J.F., Lancaster J.R., Feldman P.L.
Journal of Medicinal Chemistry , 1995
8.
Free radicals (nitric oxide)
Kostka P.
Analytical Chemistry , 1995
9.
Subject Index
&NA;
Journal of Cardiovascular Pharmacology , 2006
11.
Vascular endothelial cells synthesize nitric oxide from L-arginine
Palmer R.M., Ashton D.S., Moncada S.
Nature , 1988
12.
Hydroxylamine is a vasorelaxant and a possible intermediate in the oxidative conversion of L-arginine to nitric oxide.
DeMaster E.G., Raij L., Stephen L.A., Weir E.K.
Biochemical and Biophysical Research Communications , 1989
13.
Novel time-dependent inhibitors of human placental aromatase
Burkhart J.P., Peet N.P., Wright C.L., Johnston J.O.
Journal of Medicinal Chemistry , 1991
14.
Macrophage oxidation of L-arginine to nitrite and nitrate: nitric oxide is an intermediate
Marletta M.A., Yoon P.S., Iyengar R., Leaf C.D., Wishnok J.S.
Biochemistry , 1988
16.
N omega-hydroxy-L-arginine is an intermediate in the biosynthesis of nitric oxide from L-arginine.
Stuehr D.J., Kwon N.S., Nathan C.F., Griffith O.W., Feldman P.L., Wiseman J.
Journal of Biological Chemistry , 1991
17.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
19.
19
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1959
21.
L-N6-(1-Iminoethyl)lysine: A Selective Inhibitor of Inducible Nitric Oxide Synthase
Moore W.M., Webber R.K., Jerome G.M., Tjoeng F.S., Misko T.P., Currie M.G.
Journal of Medicinal Chemistry , 1994
23.
23
N. V. Vostrilova
Dokl. Akad. Nauk Uzbek. SSR , 1958
24.
S-nitrosylation of proteins with nitric oxide: synthesis and characterization of biologically active compounds.
Stamler J.S., Simon D.I., Osborne J.A., Mullins M.E., Jaraki O., Michel T., Singel D.J., Loscalzo J.
Proceedings of the National Academy of Sciences of the United States of America , 1992
28.
NO accounts completely for the oxygenated nitrogen species generated by enzymic l-arginine oxygenation
Mülsch A., Vanin A., Mordvintcev P., Hauschildt S., Busse R.
Biochemical Journal , 1992
29.
29
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
30.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
31.
31
A. A. Krasnovskii
Biokhimiya , 1960
32.
Nitric oxide-triggered heme-mediated hydrolysis: a possible model for biological reactions of NO
Traylor T.G., Duprat A.F., Sharma V.S.
Journal of the American Chemical Society , 1993
33.
33
M. B. Neiman
"Issledovanie Mekhanizma Okisleniya Butana" (Research on the Mechanism of the Oxidation of Butane) , 1939
34.
34
G. W. Robinson
J. Chem. Phys. , 1886
35.
New Thionitrites: Synthesis, Stability, and Nitric Oxide Generation
Roy B., du Moulinet d'Hardemare A., Fontecave M.
Journal of Organic Chemistry , 1994
36.
36
J. Billon
Bull. Soc. chim. France , 1960
37.
Direct evidence for nitric oxide formation from glyceryl trinitrate during incubation with intact bovine pulmonary artery
Marks G.S., McLaughlin B.E., Nakatsu K., Brien J.F.
Canadian Journal of Physiology and Pharmacology , 1992
38.
Interaction of glyceryl trinitrate and sodium nitroprusside with bovine pulmonary vein homogenate and 10 000 × g supernatant: biotransformation and nitric oxide formation
Marks G.S., McLaughlin B.E., Brown L.B., Beaton D.E., Booth B.P., Nakatsu K., Brien J.F.
Canadian Journal of Physiology and Pharmacology , 1991
39.
Nitric Oxide-Releasing Polymers Containing the [N(O)NO]- Group
Smith D.J., Chakravarthy D., Pulfer S., Simmons M.L., Hrabie J.A., Citro M.L., Saavedra J.E., Davies K.M., Hutsell T.C., Mooradian D.L., Hanson S.R., Keefer L.K.
Journal of Medicinal Chemistry , 1996
41.
41
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1950
42.
42
L. K. Obukhova
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1960
43.
43
N. Bunge
Ber. Deutsch. Chem. Ges. , 1870
44.
44
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
45.
45
W. Hendrich
Roczniki Chemii , 1958
46.
Ocular Hypotensive Effects of L-Arginine and its Derivatives and Their Actions on Ocular Blood Flow
CHIOU G.C., LIU S.X., LI B.H., CHIANG C.H., VARMA R.S.
Journal of Ocular Pharmacology and Therapeutics , 2009
47.
Improvement of Retinal Functions After Ischemia with L-Arginine and its Derivatives
LIU S.X., CHIOU G.C., VARMA R.S.
Journal of Ocular Pharmacology and Therapeutics , 2009
48.
48
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
49.
49
A. A. Krasnovskii
Biofizika , 1958
50.
50
G. Glacomello
Gazzetta. , 1935
51.
51
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
53.
53
D. Porretand E. Rabinowitch
Nature , 1937
54.
54
R. Livingston
J. Phys. Chem. , 1941
55.
55
G. A. Bogdanovskii
1958
57.
57
R. Livingston
"Research in Photosynthesis" , 1957
58.
58
N. E. Khomutov
1953
59.
59
H. Linshitz
"Research in Photosynthesis" , 1957
60.
60
A. N. Terenin
Optika i Spektrosk. , 1956
61.
61
A. N. Terenin
1959
63.
The new NO donor SPM3672 increases cGMP and improves contraction in rat cardiomyocytes and isolated heart
Kojda G., Brixius K., Kottenberg K., Nix P., Schlüter K., Piper H.M., Noack E.
European Journal of Pharmacology , 1995
64.
64
Chem. Zentr. II , 1931
65.
65
A. A. Krasnovskii
Biofizika , 1959
66.
66
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
67.
67
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1940
69.
Generation of nitric oxide by enzymatic oxidation of N-hydroxy-N-nitrosamines.
Alston T.A., Porter D.J., Bright H.J.
Journal of Biological Chemistry , 1985
70.
70
N. Bubnov
Biofizika , 1960
71.
71
Yu. A. Shlyapnikov
Vysokomol. Soed. , 1962
72.
A redox-based mechanism for the neuroprotective and neurodestructive effects of nitric oxide and related nitroso-compounds
Lipton S.A., Choi Y., Pan Z., Lei S.Z., Chen H.V., Sucher N.J., Loscalzo J., Singel D.J., Stamler J.S.
Nature , 1993
73.
Nitric oxide formation during light-induced decomposition of phenyl N-tert-butylnitrone
Chamulitrat W., Jordan S.J., Mason R.P., Saito K., Cutler R.G.
Journal of Biological Chemistry , 1993
75.
75
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
76.
76
A. N. Terenin
"Fotokhimiya Krasitelei" (The Photochemistry of Dyes) , 1947
77.
77
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
78.
Reactions of nitric oxide with phenolic antioxidants and phenoxyl radicals
Janzen E.G., Wilcox A.L., Manoharan V.
Journal of Organic Chemistry , 1993
79.
79
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1952
80.
80
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1937
81.
81
J. C. Ghosh
J. Indian Chem. Soc. , 1934
82.
82
G. P. Brin
Biokhimiya , 1957
83.
83
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
84.
84
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
85.
85
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
86.
86
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
89.
89
A. A. Krasnovskii
Izd. Akad. Nauk SSSR, Moscow , 1955
90.
90
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1951
91.
91
L. M. Vorob'eva
Biokhimiya , 1956
92.
Comparative pharmacology of analogues of S-nitroso-N-acetyl-dl-penicillamine on human platelets
Salas E., Moro M.A., Askew S., Hodson H.F., Butler A.R., Radomski M.W., Moncada S.
British Journal of Pharmacology , 1994
93.
93
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
94.
94
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
95.
Complexes of .NO with nucleophiles as agents for the controlled biological release of nitric oxide. Vasorelaxant effects
Maragos C.M., Morley D., Wink D.A., Dunams T.M., Saavedra J.E., Hoffman A., Bove A.A., Isaac L., Hrabie J.A., Keefer L.K.
Journal of Medicinal Chemistry , 1991
96.
New nitric oxide-releasing zwitterions derived from polyamines
Hrabie J.A., Klose J.R., Wink D.A., Keefer L.K.
Journal of Organic Chemistry , 1993
97.
Diethylamine/Nitric Oxide (NO) Adduct, an NO Donor, Produces Potent Pulmonary and Systemic Vasodilation in Intact Newborn Lambs
Vanderford P.A., Wong J., Chang R., Keefer L.K., Soifer S.J., Fineman J.R.
Journal of Cardiovascular Pharmacology , 2006
98.
Inhibition of cytochromes P450 by nitric oxide and a nitric oxide-releasing agent.
Wink D.A., Osawa Y., Darbyshire J.F., Jones C.R., Eshenaur S.C., Nims R.W.
Archives of Biochemistry and Biophysics , 1993
99.
Secondary amine/nitric oxide complex ions, R2N[N(O)NO]-. O-Functionalization chemistry
Saavedra J.E., Dunams T.M., Flippen-Anderson J.L., Keefer L.K.
Journal of Organic Chemistry , 1992
100.
100
V. V. Zolotarev
Chem. Abs. , 1941
101.
Kinetics of Nitric Oxide Liberation by 3,4-Dihydro-1,2-Diazete 1,2-Dioxides and Their Vasodilatory Properties in Vitro and in Vivo
Utepbergenov D.I., Khramtsov V.V., Vlassenko L.P., Markel A.L., Mazhukin D.G., Tikhonov A.Y., Volodarsky L.B.
Biochemical and Biophysical Research Communications , 1995
102.
Thiol-mediated generation of nitric oxide accounts for the vasodilator action of furoxans
Feelisch M., Schönafingeri K., Noack H.
Biochemical Pharmacology , 1992
103.
Furoxans as Nitric Oxide Donors. 4-Phenyl-3-furoxancarbonitrile: Thiol-Mediated Nitric Oxide Release and Biological Evaluation
Medana C., Ermondi G., Fruttero R., Di Stilo A., Ferretti C., Gasco A.
Journal of Medicinal Chemistry , 1994
104.
A new class of furoxan derivatives as NO donors: mechanism of action and biological activity
Ferioli R., Folco G.C., Ferretti C., Gasco A.M., Medana C., Fruttero R., Civelli M., Gasco A.
British Journal of Pharmacology , 1995
105.
Cardiovascular actions of the furoxan CAS 1609, a novel nitric oxide donor
Bohn H., Brendel J., Martorana P.A., Schönafinger K.
British Journal of Pharmacology , 1995
106.
Characterization of furoxans as a new class of tolerance-resistant nitrovasodilators
Hecker M., Vorhoff W., Bara A., Mordvintcev P., Busse R.
Naunyn-Schmiedeberg's Archives of Pharmacology , 1995
107.
107
M. F. Shostakovskii
Zhur. Obshch. Khim. , 1961
109.
Molsidomine
Scholtholt J.
Handbook of Experimental Pharmacology , 1985
112.
Antithrombotic Properties of a Novel Sydnonimine Derivative
Just M., Sch??nafinger K.
Journal of Cardiovascular Pharmacology , 2006
113.
Oxygen and Oxidation Promote the Release of Nitric Oxide from Sydnonimines
Bohn H., Schönafinger K.
Journal of Cardiovascular Pharmacology , 2007
114.
Molecular Aspects Underlying the Vasodilator Action of Molsidomine
Noack E., Feelisch M.
Journal of Cardiovascular Pharmacology , 2007
115.
On the Mechanism of NO Release from Sydnonimines
Feelisch M., Ostrowski J., Noack E.
Journal of Cardiovascular Pharmacology , 2007
116.
116
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1957
118.
118
V. M. Rodionov
Zhur. Obshch. Khim. , 1935
120.
120
V. V. Levchenko
Zhur. Obshch. Khim. , 1948
121.
121
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
122.
122
S. R. Rafikov
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
123.
123
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
124.
124
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
125.
125
K. A. Andrianov
Vysokomol. Soed. , 1960
126.
126
J. Wiemannand Ch. Clachet
Compt. rend. , 1948
128.
128
J. Wiemann
Bull. Soc. chim. France , 1952
129.
129
J. Wiemann
Bull. Soc. chim. France , 1955
130.
Aminoguanidine, a novel inhibitor of nitric oxide formation, prevents diabetic vascular dysfunction
Corbett J.A., Tilton R.G., Chang K., Hasan K.S., Ido Y., Wang J.L., Sweetland M.A., Lancaster J.R., Williamson J.R., McDaniel M.L.
Diabetes , 1992
132.
132
G. Shima
Kyoto Univ. , 1929
133.
133
C. Wilson
Trans. Electrochem. Soc. , 1941
134.
Chronic inhibition of nitric oxide synthesis. A new model of arterial hypertension.
Ribeiro M.O., Antunes E., de Nucci G., Lovisolo S.M., Zatz R.
Hypertension , 2012
135.
Inactivation of macrophage nitric oxide synthase activity by NG-Methyl-L-arginine
Olken N.M., Rusche K.M., Richards M.K., Marletta M.A.
Biochemical and Biophysical Research Communications , 1991
137.
137
S. R. Rafikov
Zh. Obshch. Khim. , 1944
138.
138
S. Ono
J. Chem. Soc. Japan , 1957
139.
139
I. L. Knunyants
1959
140.
140
1912
141.
141
Friedl.
142.
142
1913
144.
Selective inhibition of the inducible nitric oxide synthase by aminoguanidine
Misko T.P., Moore W.M., Kasten T.P., Nickols G.A., Corbett J.A., Tilton R.G., McDaniel M.L., Williamson J.R., Currie M.G.
European Journal of Pharmacology , 1993
145.
145
Friedl.
146.
146
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1952
147.
147
Y. Sasada
Acta Cryst. , 1898
148.
148
P. Kresse
Chem. Abs. , 1960
149.
Potent and selective inhibition of human nitric oxide synthases. Inhibition by non-amino acid isothioureas.
Garvey E.P., Oplinger J.A., Tanoury G.J., Sherman P.A., Fowler M., Marshall S., Harmon M.F., Paith J.E., Furfine E.S.
Journal of Biological Chemistry , 1994
150.
150
Ya. E. Bernadskaya
"Iskusstvennoe Volokno" (Artificial Fibres) , 1952
151.
2-Iminopiperidine and Other 2-Iminoazaheterocycles as Potent Inhibitors of Human Nitric Oxide Synthase Isoforms
Moore W.M., Webber R.K., Fok K.F., Jerome G.M., Connor J.R., Manning P.T., Wyatt P.S., Misko T.P., Tjoeng F.S., Currie M.G.
Journal of Medicinal Chemistry , 1996
154.
Selective inhibition of constitutive nitric oxide synthase by L-NG-nitroarginine
Furfine E.S., Harmon M.F., Paith J.E., Garvey E.P.
Biochemistry , 1993
155.
Characterization of three inhibitors of endothelial nitric oxide synthase in vitro and in vivo
Rees D.D., Palmer R.M., Schulz R., Hodson H.F., Moncada S.
British Journal of Pharmacology , 1990
158.
Inhibition of rat cerebellar nitric oxide synthase by 7‐nitro indazole and related substituted indazoles
Babbedge R.C., Bland-Ward P.A., Hart S.L., Moore P.K.
British Journal of Pharmacology , 1993
159.
159
J. Tafel
Z. Elektrochem. , 1911
160.
160
1912
161.
161
Friedl.
162.
Heme coordination of NO in NO synthase.
Wang J., Rousseau D.L., Abu-Soud H.M., Stuehr D.J.
Proceedings of the National Academy of Sciences of the United States of America , 1994
163.
163
Friedl.
165.
165
Friedl.
166.
Water Soluble Furoxan Derivatives as NO Prodrugs
Sorba G., Medana C., Fruttero R., Cena C., Di Stilo A., Galli U., Gasco A.
Journal of Medicinal Chemistry , 1997
167.
The aromatization of Hantzsch dihydropyridines with nitric oxide (NO)
Itoh T., Nagata K., Okada M., Ohsawa A.
Tetrahedron Letters , 1995
168.
cGMP mediates the vascular and platelet actions of nitric oxide: confirmation using an inhibitor of the soluble guanylyl cyclase.
Moro M.A., Russel R.J., Cellek S., Lizasoain I., Su Y., Darley-Usmar V.M., Radomski M.W., Moncada S.
Proceedings of the National Academy of Sciences of the United States of America , 1996