Ruthenium red

Ammoniated ruthenium oxychloride
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.228.922
EC Number
  • 802-133-7
UNII
  • InChI=1S/6ClH.14H3N.2H2O.3Ru/h6*1H;14*1H3;2*1H2;;;/q;;;;;;;;;;;;;;;;;;;;;;+4;2*+5/p-6 Y
    Key: CIBHIQPXTCXIRW-UHFFFAOYSA-H Y
  • InChI=1/6ClH.14H3N.2H2O.3Ru/h6*1H;14*1H3;2*1H2;;;/q;;;;;;;;;;;;;;;;;;;;;;+4;2*+5/p-6
    Key: CIBHIQPXTCXIRW-CYFPFDDLAK
  • [Ru+5].[Ru+5].[Ru+4].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].O.O.N.N.N.N.N.N.N.N.N.N.N.N.N.N
Properties
Cl6H42N14O2Ru3
Molar mass 786.34 g·mol−1
Appearance Brownish-red solid[1]
Hazards
GHS labelling:[1]
Warning
H302, H315, H319
P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Ruthenium red (RR), also known as ammoniated ruthenium oxychloride, is an inorganic compound used as a dye in histology to stain aldehyde fixed mucopolysaccharides.

Structure

The chloride has the chemical formula [Ru3O2(NH3)14]Cl6·4H2O.[2] A thiosulfate been characterized with the formula [Ru3O2(NH3)14](S2O3)3·4H2O.[3] The cation is composed of a linear [(NH3)5-RuIII-O-(NH3)4RuIV-O-RuIII-(NH3)5]6+ backbone formed from three ruthenium coordination octahedra.[3][4]

The inhibition of mitochondrial Ca2+ uptake is attributed to an impurity with the formula μ-O-[(HCO2)(NH3)4Ru]2Cl3.[4] This compound crystallizes in the orthorhombic system (space group Pnn2 (No. 34), a = 8.588 Å, b = 13.335 Å, c = 7.602 Å, cell volume = 870.6 Å3, Z = 2 units per cell).[4]

Preparation

The chloride is prepared by the aerial oxidation of ruthenium(III) chloride in aqueous ammonia solution.[3] The thiosulfate is prepared by treating an aqueous solution of the chloride with sodium thiosulfate.[3]

Uses

Ruthenium red has been used as a pharmacological tool to study specific cellular mechanisms. Selectivity is a significant issue in such studies as RR is known to interact with many proteins.[5] These include mammalian ion channels (CatSper1, TASK, RyR1, RyR2, RyR3, TRPM6, TRPM8, TRPV1, TRPV2, TRPV3, TRPV4, TRPV5, TRPV6, TRPA1, mCa1, mCa2, CALHM1[6][7]) TRPP3,[8] a plant ion channel, Ca2+-ATPase, mitochondrial Ca2+ uniporter,[9] tubulin, myosin light-chain phosphatase, and Ca2+ binding proteins such as calmodulin. Ruthenium red displays nanomolar potency against several of its binding partners (e.g. TRPV4, ryanodine receptors,...). For example, it is a potent inhibitor of intracellular calcium release by ryanodine receptors (Kd ~20 nM).[10] As a TRPA1 blocker, it assists in reducing the airway inflammation caused by pepper spray.

RR has been used on plant material since 1890 for staining pectins, mucilages, and gums. RR is a stereoselective stain for pectic acid, insofar as the staining site occurs between each monomer unit and the next adjacent neighbor.[11]

References

  1. ^ a b PubChem. "Ruthenium Red". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-02-02.
  2. ^ Fletcher, J. M.; Greenfield, B. F.; Hardy, C. J.; Scargill, D.; Woodhead, J. L. (1961-01-01). "382. Ruthenium red". Journal of the Chemical Society (Resumed) (0): 2000–2006. doi:10.1039/JR9610002000. ISSN 0368-1769.
  3. ^ a b c d de C.T. Carrondo, M. A. A. F.; Griffith, W. P.; Hall, J. P.; Skapski, A. C. (1980-02-07). "X-ray structure of [Ru3 O2 (NH3)14]6+, cation of the cytological reagent ruthenium red". Biochimica et Biophysica Acta (BBA) - General Subjects. 627 (3): 332–334. doi:10.1016/0304-4165(80)90464-X. ISSN 0304-4165.
  4. ^ a b c Emerson, Jeffrey; Clarke, M. J.; Ying, Wen Long; Sanadi, D. Rao (1993-12-01). "The component of "ruthenium red" responsible for inhibition of mitochondrial calcium ion transport. Spectra, electrochemistry, and aquation kinetics. Crystal structure of .mu.-O-[(HCO2)(NH3)4Ru]2Cl3". Journal of the American Chemical Society. 115 (25): 11799–11805. doi:10.1021/ja00078a019. ISSN 0002-7863.
  5. ^ Vincent, F; Duncton, MA (2011). "TRPV4 agonists and antagonists". Curr Top Med Chem. 11 (17): 2216–26. doi:10.2174/156802611796904861. PMID 21671873.
  6. ^ Ma, Z; Siebert, AP; Cheung, KH; Lee, RJ; Johnson, B; Cohen, AS; Vingtdeux, V; Marambaud, P; Foskett, JK (2012). "Calcium homeostasis modulator 1 (CALHM1) is the pore-forming subunit of an ion channel that mediates extracellular Ca2+ regulation of neuronal excitability". Proc Natl Acad Sci USA. 109 (28): E1963–71. Bibcode:2012PNAS..109E1963M. doi:10.1073/pnas.1204023109. PMC 3396471. PMID 22711817.
  7. ^ Dreses-Werringloer, U; Vingtdeux, V; Zhao, H; Chandakkar, P; Davies, P; Marambaud, P (2013). "CALHM1 controls Ca2+-dependent MEK/ERK/RSK/MSK signaling in neurons". J Cell Sci. 126 (Pt 5): 1199–206. doi:10.1242/jcs.117135. PMC 4481642. PMID 23345406.
  8. ^ Decaen, P. G.; Delling, M.; Vien, T. N.; Clapham, D. E. (2013). "Direct recording and molecular identification of the calcium channel of primary cilia". Nature. 504 (7479): 315–318. Bibcode:2013Natur.504..315D. doi:10.1038/nature12832. PMC 4073646. PMID 24336289.
  9. ^ Hajnóczky, G; Csordás, G; Das, S; Garcia-Perez, C; Saotome, M; Sinha Roy, S; Yi, M (2006). "Mitochondrial calcium signalling and cell death: approaches for assessing the role of mitochondrial Ca2+ uptake in apoptosis". Cell Calcium. 40 (5–6): 553–60. doi:10.1016/j.ceca.2006.08.016. PMC 2692319. PMID 17074387.
  10. ^ Tripathy, Le Xu Ashutosh; Pasek, Daniel A.; Meissner, Gerhard (1998). "Potential for Pharmacology of Ryanodine Receptor/Calcium Release Channels". Ann NY Acad Sci. 853 (1): 130–148. Bibcode:1998NYASA.853..130T. doi:10.1111/j.1749-6632.1998.tb08262.x. PMID 10603942. S2CID 86436194. Archived from the original on 2008-04-23. Retrieved 2006-10-22.
  11. ^ Mariani Colombo P, Rascio N. "Ruthenium red staining for electron microscopy of plant material". Journal of Ultrastructure Research Volume 60, Issue 2, August 1977, Pages 135–139
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