Lissamine rhodamine B | CAS#2609-88-3 | Radiotracer

MedKoo Cat#: 598993 | Name: Lissamine rhodamine B

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Description:

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

Lissamine rhodamine B is a new Radiotracer for Imaging Tumors by Positron Emission Tomography.

Chemical Structure

Lissamine rhodamine B

CAS#2609-88-3

Theoretical Analysis

MedKoo Cat#: 598993

Name: Lissamine rhodamine B

CAS#: 2609-88-3

Chemical Formula: C27H30N2O7S2

Exact Mass:

Molecular Weight: 558.66

Elemental Analysis: C, 58.05; H, 5.41; N, 5.01; O, 20.05; S, 11.48

Price and Availability

Size	Price	Availability	Quantity
1g	USD 250.00	2 Weeks
5g	USD 550.00	2 Weeks

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Related CAS #

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Synonym

Lissamine rhodamine B;

IUPAC/Chemical Name

hydrogen 4-(3,6-bis(diethylamino)xanthylium-9-yl)benzene-1,3-disulfonate

InChi Key

IOOMXAQUNPWDLL-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

O=S(C1=CC=C(C2=C3C=CC(N(CC)CC)=CC3=[O+]C4=C2C=CC(N(CC)CC)=C4)C(S(=O)([O-])=O)=C1)([O-])=O.[H+]

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 can be used as a fluorescent probe to develop competitive aptamer fluorescence anisotropy/polarization (FA/FP) assays.

In vitro activity:

The antimicrobial peptide (AMP) derived from lactoferricin B, LfcinB (4-9) (RRWQWR), and lissamine rhodamine B red-labeled peptide (Rh-LfcinB (4-9)) exhibit strong antimicrobial activities, and they can enter Escherichia coli cells without damaging the cell membranes. Thus, these peptides are cell-penetrating peptide (CPP) -type AMPs. In this study, to elucidate the effect of the membrane potential (Δφ) on the action of the CPP-type AMP, Rh-LfcinB (4-9), this study investigated the interactions of Rh-LfcinB (4-9) with single E. coli cells and spheroplasts containing calcein in the cytosol using confocal laser scanning microscopy. Reference: J Bacteriol. 2021 Feb 8;203(9):e00021-21. https://pubmed.ncbi.nlm.nih.gov/33558393/

In vivo activity:

The aim of this study is to synthesize and evaluate (68)Ga-labeled Lissamine Rhodamine B (LRB) as a new radiotracer for imaging MDA-MB-231 and MCF-7 cells induced tumor mice by positron emission tomography (PET). The radiochemical purity of (68)Ga(DOTA-LRB) was >95%. MicroPET dynamic imaging revealed that the uptake of (68)Ga(DOTA-LRB) was mainly in normal organs, such as kidney, heart, liver, and brain and mainly excreted from kidney. Reference: Biomed Res Int. 2016;2016:8549635. https://pubmed.ncbi.nlm.nih.gov/26949707/

Preparing Stock Solutions

The following data is based on the product molecular weight 558.66 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.

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. Hossain F, Dohra H, Yamazaki M. Effect of membrane potential on entry of lactoferricin B-derived 6-residue antimicrobial peptide into single Escherichia coli cells and lipid vesicles. J Bacteriol. 2021 Feb 8;203(9):e00021-21. doi: 10.1128/JB.00021-21. Epub ahead of print. PMID: 33558393; PMCID: PMC8092161. 2. Neufeld EB, Sato M, Gordon SM, Durbhakula V, Francone N, Aponte A, Yilmaz G, Sviridov D, Sampson M, Tang J, Pryor M, Remaley AT. ApoA-I-Mediated Lipoprotein Remodeling Monitored with a Fluorescent Phospholipid. Biology (Basel). 2019 Jul 12;8(3):53. doi: 10.3390/biology8030053. PMID: 31336888; PMCID: PMC6784057. 3. Boysen AT, Whitehead B, Stensballe A, Carnerup A, Nylander T, Nejsum P. Fluorescent Labeling of Helminth Extracellular Vesicles Using an In Vivo Whole Organism Approach. Biomedicines. 2020 Jul 14;8(7):213. doi: 10.3390/biomedicines8070213. PMID: 32674418; PMCID: PMC7399896. 4. Li X, Yin Y, Du B, Li N, Li Y. The Synthesis and Evaluations of the (6 8) Ga-Lissamine Rhodamine B (LRB) as a New Radiotracer for Imaging Tumors by Positron Emission Tomography. Biomed Res Int. 2016;2016:8549635. doi: 10.1155/2016/8549635. Epub 2016 Feb 2. PMID: 26949707; PMCID: PMC4754471.

In vitro protocol:

In vivo protocol:

1. Boysen AT, Whitehead B, Stensballe A, Carnerup A, Nylander T, Nejsum P. Fluorescent Labeling of Helminth Extracellular Vesicles Using an In Vivo Whole Organism Approach. Biomedicines. 2020 Jul 14;8(7):213. doi: 10.3390/biomedicines8070213. PMID: 32674418; PMCID: PMC7399896. 2. Li X, Yin Y, Du B, Li N, Li Y. The Synthesis and Evaluations of the (6 8) Ga-Lissamine Rhodamine B (LRB) as a New Radiotracer for Imaging Tumors by Positron Emission Tomography. Biomed Res Int. 2016;2016:8549635. doi: 10.1155/2016/8549635. Epub 2016 Feb 2. PMID: 26949707; PMCID: PMC4754471.

1: Li X, Yin Y, Du B, Li N, Li Y. The Synthesis and Evaluations of the (6 8) Ga-Lissamine Rhodamine B (LRB) as a New Radiotracer for Imaging Tumors by Positron Emission Tomography. Biomed Res Int. 2016;2016:8549635. doi: 10.1155/2016/8549635. Epub 2016 Feb 2. PubMed PMID: 26949707; PubMed Central PMCID: PMC4754471. 2: Zhou Y, Kim YS, Yan X, Jacobson O, Chen X, Liu S. 64Cu-labeled lissamine rhodamine B: a promising PET radiotracer targeting tumor mitochondria. Mol Pharm. 2011 Aug 1;8(4):1198-208. doi: 10.1021/mp200025m. Epub 2011 May 24. PubMed PMID: 21545131; PubMed Central PMCID: PMC3148415. 3: Glunde K, Foss CA, Takagi T, Wildes F, Bhujwalla ZM. Synthesis of 6'-O-lissamine-rhodamine B-glucosamine as a novel probe for fluorescence imaging of lysosomes in breast tumors. Bioconjug Chem. 2005 Jul-Aug;16(4):843-51. PubMed PMID: 16029026. 4: Krishnamoorthy K, Begley TP. Reagent for the detection of protein thiocarboxylates in the bacterial proteome: lissamine rhodamine B sulfonyl azide. J Am Chem Soc. 2010 Aug 25;132(33):11608-12. doi: 10.1021/ja1034107. PubMed PMID: 20677756; PubMed Central PMCID: PMC2927480. 5: 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. 6: Massari S, Colonna R, Folena E. Interaction of the fluorescent probe N-(lissamine Rhodamine B sulfonyl)dipalmitoylphosphatidylethanolamine with phosphatidylcholine bilayers. Biochim Biophys Acta. 1988 May 9;940(1):149-57. PubMed PMID: 3365429. 7: Wessendorf MW, Appel NM, Molitor TW, Elde RP. A method for immunofluorescent demonstration of three coexisting neurotransmitters in rat brain and spinal cord, using the fluorophores fluorescein, lissamine rhodamine, and 7-amino-4-methylcoumarin-3-acetic acid. J Histochem Cytochem. 1990 Dec;38(12):1859-77. PubMed PMID: 1701460. 8: Chodosh J, Dix RD, Howell RC, Stroop WG, Tseng SC. Staining characteristics and antiviral activity of sulforhodamine B and lissamine green B. Invest Ophthalmol Vis Sci. 1994 Mar;35(3):1046-58. PubMed PMID: 7510270. 9: Khedkar JK, Jagtap KK, Pinjari RV, Ray AK, Gejji SP. Binding of rhodamine B and kiton red S to cucurbit[7]uril: density functional investigations. J Mol Model. 2012 Aug;18(8):3743-50. doi: 10.1007/s00894-012-1375-6. Epub 2012 Mar 1. PubMed PMID: 22392431. 10: van Tonder A, Joubert AM, Cromarty AD. Limitations of the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay when compared to three commonly used cell enumeration assays. BMC Res Notes. 2015 Feb 20;8:47. doi: 10.1186/s13104-015-1000-8. PubMed PMID: 25884200; PubMed Central PMCID: PMC4349615. 11: Kharge AB, Wu Y, Perlman CE. Sulforhodamine B interacts with albumin to lower surface tension and protect against ventilation injury of flooded alveoli. J Appl Physiol (1985). 2015 Feb 1;118(3):355-64. doi: 10.1152/japplphysiol.00818.2014. Epub 2014 Nov 20. PubMed PMID: 25414246; PubMed Central PMCID: PMC4312850. 12: Chazotte B. Labeling membranes with fluorescent phosphatidylethanolamine. Cold Spring Harb Protoc. 2011 May 1;2011(5):pdb.prot5621. doi: 10.1101/pdb.prot5621. PubMed PMID: 21536759. 13: Vichai V, Kirtikara K. Sulforhodamine B colorimetric assay for cytotoxicity screening. Nat Protoc. 2006;1(3):1112-6. PubMed PMID: 17406391. 14: Christomanos AA, Dimitriades A. On the chemical structure of antigens and antibodies bound to fluorescent dyes. I. Structure of the antihuman gamma-globulin of the goat bound to the fluorochrome lissamine rhodamine B. Enzymologia. 1966 Apr 30;30(4):223-36. PubMed PMID: 4913349. 15: Gosetti F, Bolfi B, Marengo E. Identification of sulforhodamine B photodegradation products present in nonpermanent tattoos by micro liquid chromatography coupled with tandem high-resolution mass spectrometry. Anal Bioanal Chem. 2015 Jun;407(16):4649-59. doi: 10.1007/s00216-015-8667-5. Epub 2015 May 5. PubMed PMID: 25939426. 16: McKay IC, Forman D, White RG. A comparison of fluorescein isothiocyanate and lissamine rhodamine (RB 200) as labels for antibody in the fluorescent antibody technique. Immunology. 1981 Jul;43(3):591-602. PubMed PMID: 6788685; PubMed Central PMCID: PMC1555036. 17: Sankhagowit S, Wu SH, Biswas R, Riche CT, Povinelli ML, Malmstadt N. The dynamics of giant unilamellar vesicle oxidation probed by morphological transitions. Biochim Biophys Acta. 2014 Oct;1838(10):2615-24. doi: 10.1016/j.bbamem.2014.06.020. Epub 2014 Jul 3. Erratum in: Biochim Biophys Acta. 2015 Feb;1848(2):433. PubMed PMID: 24998358. 18: Li HM, Wan DW, Li RT. New abietane-type diterpene glycosides from the roots of Tripterygium wilfordii. J Asian Nat Prod Res. 2015;17(7):761-6. doi: 10.1080/10286020.2014.1001379. Epub 2015 Jan 15. PubMed PMID: 25588600. 19: Zwolak I. Comparison of five different in vitro assays for assessment of sodium metavanadate cytotoxicity in Chinese hamster ovary cells (CHO-K1 line). Toxicol Ind Health. 2015 Aug;31(8):677-90. doi: 10.1177/0748233713483199. Epub 2013 Mar 22. PubMed PMID: 23524879. 20: Yan Y, Krishnakumar S, Yu H, Ramishetti S, Deng LW, Wang S, Huang L, Huang D. Nickel(II) dithiocarbamate complexes containing sulforhodamine B as fluorescent probes for selective detection of nitrogen dioxide. J Am Chem Soc. 2013 Apr 10;135(14):5312-5. doi: 10.1021/ja401555y. Epub 2013 Mar 29. PubMed PMID: 23530626; PubMed Central PMCID: PMC4138600.