Sulforhodamine B

Sulforhodamine B
Names
	IUPAC name 2-(3-diethylamino-6-diethylazaniumylidene-xanthen-9-yl)-5-sulfo-benzenesulfonate
Identifiers
CAS Number	3520-42-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	58690 ;
ECHA InfoCard	100.020.482
EC Number	220-025-2;
PubChem CID	65191;
UNII	821LWZ3R6R ;
	InChI InChI=1S/C27H30N2O7S2/c1-5-28(6-2)18-9-12-21-24(15-18)36-25-16-19(29(7-3)8-4)10-13-22(25)27(21)23-14-11-20(37(30,31)32)17-26(23)38(33,34)35/h9-17H,5-8H2,1-4H3,(H-,30,31,32,33,34,35) Key: IOOMXAQUNPWDLL-UHFFFAOYSA-N ; InChI=1/C27H30N2O7S2/c1-5-28(6-2)18-9-12-21-24(15-18)36-25-16-19(29(7-3)8-4)10-13-22(25)27(21)23-14-11-20(37(30,31)32)17-26(23)38(33,34)35/h9-17H,5-8H2,1-4H3,(H-,30,31,32,33,34,35) Key: IOOMXAQUNPWDLL-UHFFFAOYAJ;
	SMILES O=S(=O)(O)c4ccc(C=1c3c(OC=2C=1\C=C/C(=[N+](/CC)CC)/C=2)cc(cc3)N(CC)CC)c(c4)S([O-])(=O)=O;
Properties
Chemical formula	C27H30N2O7S2
Molar mass	558.666 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Sulforhodamine B or Kiton Red 620 (C₂₇H₃₀N₂O₇S₂) is a fluorescent dye with uses spanning from laser-induced fluorescence (LIF) to the quantification of cellular proteins of cultured cells. This red solid dye is very water-soluble.^[1]

Spectroscopy

The dye has maximal absorbance at 565 nm light and maximal fluorescence emission at 586 nm light.^[1] It does not exhibit pH-dependent absorption or fluorescence over the range of 3 to 10.^[2]

Applications

Sulforhodamine B is often used as a membrane-impermeable polar tracer^[3] or used for cell density determination via determination of cellular proteins (cytotoxicity assay).^[4]

References

^ ^a ^b "Sulforhodamine B sodium salt (CAS 3520-42-1)". Santa Cruz Biotechnology.
^ Coppeta, J.; Rogers, C. (1998). "Dual Emission Laser Induced Fluorescence for Direct Planar Scalar Behavior Measurements". Experiments in Fluids. 25: 1–15. doi:10.1007/s003480050202. S2CID 37649159.
^ Viricel W; Mbarek A; Leblond J (2015). "Switchable Lipids: Conformational Change for Fast pH-Triggered Cytoplasmic Delivery" (PDF). Angewandte Chemie International Edition. 54 (43): 12743–12747. doi:10.1002/anie.201504661. PMID 26189870.
^ Vichai V; Kirtikara K (2006). "Sulforhodamine B colorimetric assay for cytotoxicity screening". Nature Protocols. 1 (3): 1112–1116. doi:10.1038/nprot.2006.179. PMID 17406391. S2CID 1245354.

[SCBT-1] "Sulforhodamine B sodium salt (CAS 3520-42-1)". Santa Cruz Biotechnology.

[2] Coppeta, J.; Rogers, C. (1998). "Dual Emission Laser Induced Fluorescence for Direct Planar Scalar Behavior Measurements". Experiments in Fluids. 25: 1–15. doi:10.1007/s003480050202. S2CID 37649159.

[3] Viricel W; Mbarek A; Leblond J (2015). "Switchable Lipids: Conformational Change for Fast pH-Triggered Cytoplasmic Delivery" (PDF). Angewandte Chemie International Edition. 54 (43): 12743–12747. doi:10.1002/anie.201504661. PMID 26189870.

[4] Vichai V; Kirtikara K (2006). "Sulforhodamine B colorimetric assay for cytotoxicity screening". Nature Protocols. 1 (3): 1112–1116. doi:10.1038/nprot.2006.179. PMID 17406391. S2CID 1245354.

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Names

IUPAC name 2-(3-diethylamino-6-diethylazaniumylidene-xanthen-9-yl)-5-sulfo-benzenesulfonate
Identifiers
CAS Number	3520-42-1
3D model (JSmol)	Interactive image
ChemSpider	58690
ECHA InfoCard	100.020.482
EC Number	220-025-2
PubChem CID	65191
UNII	821LWZ3R6R
InChI InChI=1S/C27H30N2O7S2/c1-5-28(6-2)18-9-12-21-24(15-18)36-25-16-19(29(7-3)8-4)10-13-22(25)27(21)23-14-11-20(37(30,31)32)17-26(23)38(33,34)35/h9-17H,5-8H2,1-4H3,(H-,30,31,32,33,34,35) Key: IOOMXAQUNPWDLL-UHFFFAOYSA-N InChI=1/C27H30N2O7S2/c1-5-28(6-2)18-9-12-21-24(15-18)36-25-16-19(29(7-3)8-4)10-13-22(25)27(21)23-14-11-20(37(30,31)32)17-26(23)38(33,34)35/h9-17H,5-8H2,1-4H3,(H-,30,31,32,33,34,35) Key: IOOMXAQUNPWDLL-UHFFFAOYAJ
SMILES O=S(=O)(O)c4ccc(C=1c3c(OC=2C=1\C=C/C(=[N+](/CC)CC)/C=2)cc(cc3)N(CC)CC)c(c4)S([O-])(=O)=O
Properties
Chemical formula	C₂₇H₃₀N₂O₇S₂
Molar mass	558.666 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).