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Dinitrosyl iron complexes with thiolate ligands: Physico-chemistry, biochemistry and physiology
Abstract
Some present-day concepts on the origin and functional activities of dinitrosyl iron complexes (DNIC) with thiolate ligands are considered. Nitric oxide (NO) including to DNIC increases its stability and ensures effective targeting of NO to organs and tissues. DNIC have a square-planar structure; unpaired electron is localized on the d(z2) orbital of the d(7) iron atom. The formula of DNIC appears as [(RS(-))(2)Fe(+)(NO(+))(2)....((-)SR)(2)](-); electron spin is S=1/2. Conversion of an originally diamagnetic group, Fe(2+)(NO)(2) with electron configuration d(8), into a paramagnetic Fe(+)(NO(+))(2) group is a result of disproportionation of NO ligands and substitution of newly generated NO(-) for NO. The nitrosonium ions present in DNIC impart to them high nitrosylating activity, e.g., ability to induce S-nitrosylation of thiols. The ability of S-nitrosothiols to form DNIC in a direct reaction with bivalent iron is a prerequisite to effective mutual conversions of DNIC and S-nitrosothiols. In this work, I consider some mechanisms of destructive effects of low-molecular DNIC on active centers of iron-sulfur proteins, ability of DNIC to express certain genes, to activate guanylate cyclase, to exert hypotensive, vasodilator effects, to inhibit platelet aggregation, to accelerate wound healing and to produce potent erective action. Recently a stabilized powder-like polymeric composition based on dimeric glutathione DNIC the water-soluble polymer in which was used as a filling agent was designed. The advantages of this stable DNIC-glutathione preparation include their ability to retain their physico-chemical and functional activities within at least one year. At present, the preparation undergo testing as a base for the design of a wide variety of broad-spectrum drugs.
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“It was proposed that DNICs are formed in the vasculature from nitrosothiols and that they are in equilibrium with the nitrosothiol pool [103,104].”
From On the chemical biology of the nitrite/sulfide interaction (2015) · cites this paper as [103]
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Davidson, C. A., Kaminski, P. M., Wu, M., & Wolin, M. S. (1996) · American Journal of Physiology-Heart and Circulatory Physiology · doi:10.1152/ajpheart.1996.270.3.h1038 · Cited by 34
Ferry‐Dumazet, H., Mamani‐Matsuda, M., Dupouy, M., Belloc, F., Thiolat, D., Marit, G., Arock, M., Reiffers, J. J., & Mossalayi, M. D. (2002) · Leukemia · doi:10.1038/sj.leu.2402404 · Cited by 30
Voevodskaya, N. V., Сереженков, В. А., Cooper, C. E., Kubrina, L. N., & Vanin, A. F. (2002) · Biochemical Journal · doi:10.1042/bj20020788 · Cited by 29
Self-citationButyl Isocyanide as a Probe of the Activation Mechanism of Soluble Guanylate Cyclase
Derbyshire, E. R., & Marletta, M. A. (2007) · Journal of Biological Chemistry · doi:10.1074/jbc.m705557200 · Cited by 29
Lancaster, J. R., Werner‐Felmayer, G., & Wächter, H. (1994) · Free Radical Biology and Medicine · doi:10.1016/0891-5849(94)90206-2 · Cited by 28
[Dinitrosyl-iron complexes with cysteine or glutathione accelerate skin wound healing in animals].
Shekhter, A. B., Руденко, Т. Г., Сереженков, В. А., & Vanin, A. F. (2007) · PubMed · Cited by 25
Self-citationDNICs: physico-chemical properties and their observations in cells and tissues
Vanin, A. F., & van Faassen, E. E. (2007) · Elsevier eBooks · doi:10.1016/b978-044452236-8/50002-2 · Cited by 22
Self-citationA role of iron ions in the SOS DNA repair response induced by nitric oxide in Escherichia coli.
Stupakova, M. V., Lobysheva, I. I., Vd, M., Vanin, A. F., & Vasilieva, S. V. (2000) · PubMed · Cited by 14
Self-citationJersild, C., Dupont, B., SVEJGAARD, A., Platz, P., Ciongoli, K. A., & Fog, T. (1975) · Neurology · doi:10.1212/wnl.25.5.488 · Cited by 13
Ludbrook, S. B., Scrutton, M. C., Joannou, C. L., Cammack, R., & Hughes, M. (1995) · Platelets · doi:10.3109/09537109509078457 · Cited by 12
[Paramagnetic nitrosyl complexes of heme and nonheme iron].
Vanin, A. F., & Chetverikov, A. G. (1968) · PubMed · Cited by 12
Self-citationGenetic Signal Transduction by Nitrosyl-Iron Complexes in Escherichia coli
Vasilieva, S. V., Moshkovskaya, E. Y., Санина, Н. А., Aldoshin, S. M., & Vanin, A. F. (2004) · Biochemistry (Moscow) · doi:10.1023/b:biry.0000040220.13586.45 · Cited by 11
Self-citationSerezhenkov, V. A., Kalinina, E. V., Glazunova, V. A., Saprin, A. N., & Vanin, A. F. (2007) · PubMed · Cited by 11
Self-citationVeliev, E. I., Kotov, S. V., Vk, S., Serezhenkov, V. A., Lozinskiĭ, V. I., & Vanin, A. F. (2008) · PubMed · Cited by 8
Self-citationEffect of sodium nitroprusside on hemodynamics of corpus cavernosum in Chinese.
Fu, Q., Yao, D.-H., & Jiang, Y. (2001) · PubMed · Cited by 7
Quasi-Adaptive Response to Alkylating Agents in Escherichia coli: A New Phenomenon
Vasilieva, S. V., & Moshkovskaya, E. Y. (2005) · Russian Journal of Genetics · doi:10.1007/s11177-005-0115-8 · Cited by 7
The Rearrangement Reaction of CH3SNO2to CH3SONO Studied by a Density Functional Theory Method
Choi, Y. J. (2004) · Bulletin of the Korean Chemical Society · doi:10.5012/bkcs.2004.25.11.1657 · Cited by 6
Intracellular iron ions regulate the genetic activity of NO-donating agents
Vasilieva, S. V., Moshkovskaya, E. Y., Terekhov, A. S., Санина, Н. А., & Aldoschin, S. M. (2006) · Russian Journal of Genetics · doi:10.1134/s1022795406070064 · Cited by 6
Vanin, A. F. (1993) · PubMed · Cited by 6
Self-citationS-nitrosated proteins: formation, metabolism, and function
Yang, Y. A., & Loscalzo, J. (2007) · Elsevier eBooks · doi:10.1016/b978-044452236-8/50010-1 · Cited by 5
Vanin, A. F. (2005) · PubMed · Cited by 4
Self-citationKanazawa (1996) · doi:10.1002/(sici)1097-0142(19960415)77:8+
Flagged first, then by citations
Research works printed but not linked: 19
- Vanin, 1967, Investigation of non-heme iron complexes in cells and tissues by the EPR method, Biofizika (Rus), 12, 829
- Vanin, 1967, Identification of divalent iron complexes with cysteine in biological systems, Biokhimiya (Rus), 32, 228
- A.F. Vanin, L.A. Blumenfeld, D.Sh. Burbaev, I.L. Lisovskaya, A.G. Chetverikov, Investigations of some iron complexes in biological objects, Proceedings of the International Jubilee Conference on Paramagnetic Resonance, 1969 June 15–20, Kazan, Part 1 (1970) 218–223.
- Vanin, 1971, Endogenous heme and non-heme nitrosyl iron complexes in cells and tissues, Biofizika (Rus), 16, 650
- Mikoyan, 2004, Formation of paramagnetic nitrosyl complexes of nonheme iron in the animal organism with the participation of nitric oxide from exogenous and endogenous sources, Biophysics (Translation from Russian), 41, 110
- Vanin, 1992, Dinitrosyl-iron complexes with thiol-containing ligands and their reversible transformation into nitrosothiols, Biokhimiya (Rus), 58, 1103
- A.F. Vanin, Nitrosyl non-heme iron complexes in animal tissues and microorganisms, D.Sc.Thesis, Institute of Chemical Physics, Moscow, 1980.
- Burbaev, 1971, Electronic and spatial structures of paramagnetic dinitrosyl ferrous complexes, Zhurnal Strukt. Khimii (Rus), 2, 252
- Sanina, 2004, Structure of neutral mononuclear dinitrosyl iron complex with 1,2,4-triazole-3-thione [Fe(SC3H3N3)2(NO)2]0.5H2O, Mendeleev Communs., 1, 1
- Vanin, 1975, On the origin of paramagnetic centers at g=2.03 in animal tissues and microorganisms, Studia Biofizika, 49, 13
- Vanin, 1980, On the mechanism of nitrosyl non-heme iron formation in animal tissue, Studia Biofizika, 80, 221
- Voevodskaya, 1999, The nitric oxide-mediated degradation of active center in an iron-sulphur protein adrenodoxin, Current Top. Biophys., 23, 31
- Kleschyov, 1985, Role of nitric oxide and iron in hypotensive action of nitrosyl iron complexes with various anionic ligands, Studia Biofizika, 105, 93
- Mordvintcev, 1988, Hypotensive activity of dinitrosyl complexes of iron in narcotized animals, Bulleten Vsesoyuznogo Kardiol. Nauchnogo Tsentra SSSR, 1, 46
- Galagan, 1988, Hypotensive effect of dinitrosyl complexes of iron in conscious animals, Bulleten Vsesoyuznogo Kardiol. Nauchnogo Centra SSSR, 2, 75
- Van der Viet, 1998, Formation of S-nitrosothiols via direct nucleophylic nitrosation of thiols by peroxynitrite with elimination of hydrogen peroxide, J. Biol. Chem., 273, 30225
- Mordvintcev, 1986, The inhibitory effect of low-molecular dinitrosyl iron complexes on platelet aggregation, Biokhimiya (Rus), 51, 1851
- Kuznetsov, 1988, Low-molecular and protein-bound dinitrosyl iron complexes as inhibitors of platelet aggregation, Voprosy Med. Khimii, 5, 43
- Kurbanov, 1989, Effects of thiol-containing compounds and iron on the formation of nitric oxide from nitroprusside and nitroglycerine, Voprosy Med Khimii (Rus), 6, 87
Cited by
Sorted by citations
Nitric oxide synthase in innate and adaptive immunity: an update
Bogdan, C. (2015) · Trends in Immunology · doi:10.1016/j.it.2015.01.003 · Cited by 862
Riener, K., Haslinger, S., Raba, A., Högerl, M. P., Cokoja, M., Herrmann, W. A., & Kühn, F. E. (2014) · Chemical Reviews · doi:10.1021/cr4006439 · Cited by 411
Koskenkorva-Frank, T. S., Weiss, G., Koppenol, W. H., & Burckhardt, S. (2013) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2013.09.001 · Cited by 406
Connecting the Chemical and Biological Properties of Nitric Oxide
Toledo, J. C., & Augusto, O. (2012) · Chemical Research in Toxicology · doi:10.1021/tx300042g · Cited by 294
Thomas, D. D. (2015) · Redox Biology · doi:10.1016/j.redox.2015.05.002 · Cited by 179
Metadata
- Authors
- Vanin, A. F.
- Affiliations
- Russian Academy of Sciences (RU)
- Corresponding author
- Vanin, Anatoly F.
- ORCID
- Vanin, Anatoly F.
- Venue
- Nitric Oxide
- Publisher
- Elsevier BV
- Published
- 2009-08
- Volume
- 21
- Issue
- 1
- Pages
- 1-13
- ISSN
- 1089-8603 (ISSN-L)
- OpenAlex
- W2044091187
- Cited by
- 217
- References
- 126
- Citations by year
- 2026: 2 · 2025: 3 · 2024: 2 · 2023: 9 · 2022: 10 · 2021: 11 · 2020: 12 · 2019: 9 · 2018: 15 · 2017: 15 · 2016: 13 · 2015: 16 · 2014: 28 · 2013: 21 · 2012: 19
- FWCI
- 1.87
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Nitric Oxide (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Russian Foundation for Basic Research
- Topics
- Health Sciences › Medicine › Physiology (medical) › Nitric Oxide and Endothelin Effects
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Hemoglobin structure and function
- Physical Sciences › Chemistry › Inorganic Chemistry › Metal-Catalyzed Oxygenation Mechanisms
- Keywords
- dinitrosyl iron complexes, thiolate ligands, nitrosonium ion, S-nitrosylation, S-nitrosothiols, iron-sulfur proteins, guanylate cyclase activation, platelet aggregation inhibition, wound healing, erectile function, glutathione, polymeric drug delivery
- MeSH terms
- Animals, Electron Spin Resonance Spectroscopy, Iron, Liver, Nitric Oxide, Nitrogen Oxides, Sulfhydryl Compounds, Chemical Phenomena
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