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MedKoo Cat#: 598997 | Name: Lissamine rhodamine B sulfonyl chloride
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lissamine rhodamine B sulfonyl chloride is a fluorescent protein label forming stable conjugates.

Chemical Structure

Lissamine rhodamine B sulfonyl chloride
CAS#62796-29-6

Theoretical Analysis

MedKoo Cat#: 598997

Name: Lissamine rhodamine B sulfonyl chloride

CAS#: 62796-29-6

Chemical Formula: C27H29ClN2O6S2

Exact Mass: 576.1156

Molecular Weight: 577.11

Elemental Analysis: C, 56.19; H, 5.07; Cl, 6.14; N, 4.85; O, 16.63; S, 11.11

Price and Availability

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1g USD 950.00 2 Weeks
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Synonym
Lissamine rhodamine B sulfonyl chloride;
IUPAC/Chemical Name
2-(3,6-bis(diethylamino)xanthylium-9-yl)-5-(chlorosulfonyl)benzenesulfonate
InChi Key
YERWMQJEYUIJBO-UHFFFAOYSA-N
InChi Code
InChI=1S/C27H29ClN2O6S2/c1-5-29(6-2)18-9-12-21-24(15-18)36-25-16-19(30(7-3)8-4)10-13-22(25)27(21)23-14-11-20(37(28,31)32)17-26(23)38(33,34)35/h9-17H,5-8H2,1-4H3
SMILES Code
CCN(C1=CC2=[O+]C3=C(C=CC(N(CC)CC)=C3)C(C4=CC=C(S(=O)(Cl)=O)C=C4S(=O)([O-])=O)=C2C=C1)CC
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Lissamine rhodamine B sulfonyl chloride is a fluorescent protein label forming stable conjugates.
In vitro activity:
The interaction of iridium(iii) with a new lissamine rhodamine B sulfonyl derivative, bearing alanine as a building block, (1) with an orange emission in water results in a green highly emissive Ir@1 complex at room temperature. Reference: Dalton Trans. 2016 Jan 21;45(3):1254-8. https://pubmed.ncbi.nlm.nih.gov/26671832/
In vivo activity:
A new simple, fast and sensitive analytical method, based on in situ derivatization-ultrasound-assisted dispersive liquid-liquid microextraction (in situ DUADLLME) in a single step, has been proposed for the quantitative determination of catecholamines and their biosynthesis precursors and metabolites in rat brain microdialysates. The optimum conditions of in situ DUADLLME were found to be 30μL of microdialysates, 150μL of acetonitrile containing LRSC (lissamine rhodamine B sulfonyl chloride), 50μL of bromobenzene and 800μL of NaHCO3-Na2CO3 buffer (pH 10.5) for 3.0min at 37°C. Under the optimized conditions, good linearity was observed with LODs (S/N>3) and LOQs (S/N>10) of LRSC derivatized-NTs in the range of 0.002-0.004 and 0.007-0.015 nmol/L, respectively. It also brought good precision (3.2-12.8%, peak area CVs%), accuracy (94.2-108.6%), recovery (94.5-105.5%) and stability (3.8-8.1%, peak area CVs%) results. Reference: J Chromatogr A. 2016 Aug 5;1458:70-81. https://pubmed.ncbi.nlm.nih.gov/27372412/

Preparing Stock Solutions

The following data is based on the product molecular weight 577.11 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Oliveira E, Santos SM, Núñez C, Capelo JL, Lodeiro C. An unusual highly emissive water-soluble iridium lissamine-alanine complex and its use in a molecular logic gate. Dalton Trans. 2016 Jan 21;45(3):1254-8. doi: 10.1039/c5dt03666f. PMID: 26671832. 2. Hay CE, Marken F, Blanchard GJ. Detection and characterization of liquid|solid and liquid|liquid|solid interfacial gradients of water nanodroplets in wet N-octyl-2-pyrrolidone. Langmuir. 2014 Aug 26;30(33):9951-61. doi: 10.1021/la502743j. Epub 2014 Aug 14. PMID: 25101792. 3. He Y, Zhao XE, Zhu S, Wei N, Sun J, Zhou Y, Liu S, Liu Z, Chen G, Suo Y, You J. In situ derivatization-ultrasound-assisted dispersive liquid-liquid microextraction for the determination of neurotransmitters in Parkinson's rat brain microdialysates by ultra high performance liquid chromatography-tandem mass spectrometry. J Chromatogr A. 2016 Aug 5;1458:70-81. doi: 10.1016/j.chroma.2016.06.059. Epub 2016 Jun 18. PMID: 27372412. 4. Ogilvy CS, Borges LF. A quantitative analysis of the retrograde axonal transport of 4 different fluorescent dyes in peripheral sensory and motor neurons and lack of anterograde transport in the corticospinal system. Brain Res. 1988 Dec 20;475(2):244-53. doi: 10.1016/0006-8993(88)90612-9. PMID: 2463856.
In vitro protocol:
1. Oliveira E, Santos SM, Núñez C, Capelo JL, Lodeiro C. An unusual highly emissive water-soluble iridium lissamine-alanine complex and its use in a molecular logic gate. Dalton Trans. 2016 Jan 21;45(3):1254-8. doi: 10.1039/c5dt03666f. PMID: 26671832. 2. Hay CE, Marken F, Blanchard GJ. Detection and characterization of liquid|solid and liquid|liquid|solid interfacial gradients of water nanodroplets in wet N-octyl-2-pyrrolidone. Langmuir. 2014 Aug 26;30(33):9951-61. doi: 10.1021/la502743j. Epub 2014 Aug 14. PMID: 25101792.
In vivo protocol:
1. He Y, Zhao XE, Zhu S, Wei N, Sun J, Zhou Y, Liu S, Liu Z, Chen G, Suo Y, You J. In situ derivatization-ultrasound-assisted dispersive liquid-liquid microextraction for the determination of neurotransmitters in Parkinson's rat brain microdialysates by ultra high performance liquid chromatography-tandem mass spectrometry. J Chromatogr A. 2016 Aug 5;1458:70-81. doi: 10.1016/j.chroma.2016.06.059. Epub 2016 Jun 18. PMID: 27372412. 2. Ogilvy CS, Borges LF. A quantitative analysis of the retrograde axonal transport of 4 different fluorescent dyes in peripheral sensory and motor neurons and lack of anterograde transport in the corticospinal system. Brain Res. 1988 Dec 20;475(2):244-53. doi: 10.1016/0006-8993(88)90612-9. PMID: 2463856.
1: Lefevre C, Kang HC, Haugland RP, Malekzadeh N, Arttamangkul S, Haugland RP. Texas Res-X and rhodamine Red-X, new derivatives of sulforhodamine 101 and lissamine rhodamine B with improved labeling and fluorescence properties. Bioconjug Chem. 1996 Jul-Aug;7(4):482-9. PubMed PMID: 8853462. 2: Oliveira E, Santos SM, Núñez C, Capelo JL, Lodeiro C. An unusual highly emissive water-soluble iridium lissamine-alanine complex and its use in a molecular logic gate. Dalton Trans. 2016 Jan 21;45(3):1254-8. doi: 10.1039/c5dt03666f. PubMed PMID: 26671832. 3: He Y, Zhao XE, Zhu S, Wei N, Sun J, Zhou Y, Liu S, Liu Z, Chen G, Suo Y, You J. In situ derivatization-ultrasound-assisted dispersive liquid-liquid microextraction for the determination of neurotransmitters in Parkinson's rat brain microdialysates by ultra high performance liquid chromatography-tandem mass spectrometry. J Chromatogr A. 2016 Aug 5;1458:70-81. doi: 10.1016/j.chroma.2016.06.059. Epub 2016 Jun 18. PubMed PMID: 27372412. 4: McKenna N, Meigs JB, Wang YL. Identical distribution of fluorescently labeled brain and muscle actins in living cardiac fibroblasts and myocytes. J Cell Biol. 1985 Jan;100(1):292-6. PubMed PMID: 3965475; PubMed Central PMCID: PMC2113464. 5: Thazhathveetil AK, Liu ST, Indig FE, Seidman MM. Psoralen conjugates for visualization of genomic interstrand cross-links localized by laser photoactivation. Bioconjug Chem. 2007 Mar-Apr;18(2):431-7. PubMed PMID: 17373769. 6: Hock RS, Sanger JM, Sanger JW. Talin dynamics in living microinjected nonmuscle cells. Cell Motil Cytoskeleton. 1989;14(2):271-87. PubMed PMID: 2515003. 7: Hay CE, Marken F, Blanchard GJ. Detection and characterization of liquid|solid and liquid|liquid|solid interfacial gradients of water nanodroplets in wet N-octyl-2-pyrrolidone. Langmuir. 2014 Aug 26;30(33):9951-61. doi: 10.1021/la502743j. Epub 2014 Aug 14. PubMed PMID: 25101792. 8: Wei N, Zhao XE, Zhu S, He Y, Zheng L, Chen G, You J, Liu S, Liu Z. Determination of dopamine, serotonin, biosynthesis precursors and metabolites in rat brain microdialysates by ultrasonic-assisted in situ derivatization-dispersive liquid-liquid microextraction coupled with UHPLC-MS/MS. Talanta. 2016 Dec 1;161:253-264. doi: 10.1016/j.talanta.2016.08.036. Epub 2016 Aug 16. PubMed PMID: 27769404. 9: Houghten RA, Dooley CT, Appel JR. De novo identification of highly active fluorescent kappa opioid ligands from a rhodamine labeled tetrapeptide positional scanning library. Bioorg Med Chem Lett. 2004 Apr 19;14(8):1947-51. PubMed PMID: 15050634. 10: Kosík O, Farkas V. One-pot fluorescent labeling of xyloglucan oligosaccharides with sulforhodamine. Anal Biochem. 2008 Apr 15;375(2):232-6. Epub 2007 Nov 28. PubMed PMID: 18158908. 11: Sanger JW, Mittal B, Sanger JM. Interaction of fluorescently-labeled contractile proteins with the cytoskeleton in cell models. J Cell Biol. 1984 Sep;99(3):918-28. PubMed PMID: 6540785; PubMed Central PMCID: PMC2113417. 12: Kagan JM. Local immunity to Bacteroides gingivalis in periodontal disease. J Dent Res. 1980 Nov;59:1750-6. PubMed PMID: 6159380. 13: Bai M, Wyatt SK, Han Z, Papadopoulos V, Bornhop DJ. A novel conjugable translocator protein ligand labeled with a fluorescence dye for in vitro imaging. Bioconjug Chem. 2007 Jul-Aug;18(4):1118-22. Epub 2007 Jun 7. PubMed PMID: 17552492. 14: Rosenecker J, Zhang W, Hong K, Lausier J, Geppetti P, Yoshihara S, Papahadjopoulos D, Nadel JA. Increased liposome extravasation in selected tissues: effect of substance P. Proc Natl Acad Sci U S A. 1996 Jul 9;93(14):7236-41. PubMed PMID: 8692975; PubMed Central PMCID: PMC38966. 15: Kreis TE. Preparation, assay, and microinjection of fluorescently labeled cytoskeletal proteins: actin, alpha-actinin, and vinculin. Methods Enzymol. 1986;134:507-19. PubMed PMID: 3102901.