Ruthenium red
Ammoniated ruthenium oxychloride
Identifiers
ChEMBL
ChemSpider
ECHA InfoCard
100.228.922
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
Cl 6 H 42 N 14 O 2 Ru 3
Molar mass
786.34 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
The inorganic dye ammoniated ruthenium oxychloride , also known as ruthenium red , is used in histology to stain aldehyde fixed mucopolysaccharides .
Ruthenium red (RR) has also 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.[ 1] These include mammalian ion channels (CatSper1 , TASK , RyR1 , RyR2 , RyR3 , TRPM6 , TRPM8 , TRPV1 , TRPV2 , TRPV3 , TRPV4 , TRPV5 , TRPV6 , TRPA1 , mCa1 , mCa2 , CALHM1 [ 2] [ 3] ) TRPP3 ,[ 4] a plant ion channel, Ca2+ -ATPase , mitochondrial Ca2+ uniporter ,[ 5] 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).[ 6] 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.[ 7]
References
^ Vincent, F; Duncton, MA (2011). "TRPV4 agonists and antagonists". Curr Top Med Chem . 11 (17): 2216–26. doi :10.2174/156802611796904861 . PMID 21671873 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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
TRPA
Activators
4-Hydroxynonenal
4-Oxo-2-nonenal
4,5-EET
12S-HpETE
15-Deoxy-Δ12,14 -prostaglandin J2
α-Sanshool (ginger , Sichuan and melegueta peppers )
Acrolein
Allicin (garlic )
Allyl isothiocyanate (mustard , radish , horseradish , wasabi )
AM404
ASP-7663
Bradykinin
Cannabichromene (cannabis )
Cannabidiol (cannabis )
Cannabigerol (cannabis )
Cinnamaldehyde (cinnamon )
CR gas (dibenzoxazepine; DBO)
CS gas (2-chlorobenzal malononitrile)
Cuminaldehyde (cumin )
Curcumin (turmeric )
Dehydroligustilide (celery )
Diallyl disulfide
Dicentrine (Lindera spp.)
Farnesyl thiosalicylic acid
Formalin
Gingerols (ginger )
Hepoxilin A3
Hepoxilin B3
Hydrogen peroxide
Icilin
Isothiocyanate
JT-010
Ligustilide (celery , Angelica acutiloba )
Linalool (Sichuan pepper , thyme )
Methylglyoxal
Methyl salicylate (wintergreen )
N-Methylmaleimide
Nicotine (tobacco )
Oleocanthal (olive oil )
Paclitaxel (Pacific yew )
Paracetamol (acetaminophen)
PF-4840154
Phenacyl chloride
Polygodial (Dorrigo pepper )
Shogaols (ginger , Sichuan and melegueta peppers )
Tear gases
Tetrahydrocannabinol (cannabis )
Tetrahydrocannabiorcol
Thiopropanal S-oxide (onion )
Umbellulone (Umbellularia californica )
WIN 55,212-2
Blockers
TRPC
TRPM
TRPML
TRPP
TRPV
Activators
2-APB
5',6'-EET
9-HODE
9-oxoODE
12S-HETE
12S-HpETE
13-HODE
13-oxoODE
20-HETE
α-Sanshool (ginger , Sichuan and melegueta peppers )
Allicin (garlic )
AM404
Anandamide
Bisandrographolide (Andrographis paniculata )
Camphor (camphor laurel , rosemary , camphorweed , African blue basil , camphor basil )
Cannabidiol (cannabis )
Cannabidivarin (cannabis )
Capsaicin (chili pepper )
Carvacrol (oregano , thyme , pepperwort , wild bergamot , others)
DHEA
Diacyl glycerol
Dihydrocapsaicin (chili pepper )
Estradiol
Eugenol (basil , clove )
Evodiamine (Euodia ruticarpa )
Gingerols (ginger )
GSK1016790A
Heat
Hepoxilin A3
Hepoxilin B3
Homocapsaicin (chili pepper )
Homodihydrocapsaicin (chili pepper )
Incensole (incense )
Lysophosphatidic acid
Low pH (acidic conditions)
Menthol (mint )
N-Arachidonoyl dopamine
N-Oleoyldopamine
N-Oleoylethanolamide
Nonivamide (PAVA) (PAVA spray )
Nordihydrocapsaicin (chili pepper )
Paclitaxel (Pacific yew )
Paracetamol (acetaminophen)
Phenylacetylrinvanil
Phorbol esters (e.g., 4α-PDD )
Piperine (black pepper , long pepper )
Polygodial (Dorrigo pepper )
Probenecid
Protons
RhTx
Rutamarin (Ruta graveolens )
Resiniferatoxin (RTX) (Euphorbia resinifera /pooissonii )
Shogaols (ginger , Sichuan and melegueta peppers )
Tetrahydrocannabivarin (cannabis )
Thymol (thyme , oregano )
Tinyatoxin (Euphorbia resinifera /pooissonii )
Tramadol
Vanillin (vanilla )
Zucapsaicin
Blockers