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S0252

Sigma-Aldrich

Sulfobromophthalein disodium salt hydrate

used to study hepatocyte transport functions

Synonym(s):

BSP, Bromsulfalein sodium disodium salt hydrate

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About This Item

Empirical Formula (Hill Notation):
C20H8Br4Na2O10S2 · xH2O
CAS Number:
123359-42-2
Molecular Weight:
838.00 (anhydrous basis)
EC Number:
200-761-0
MDL number:
MFCD00150017
UNSPSC Code:
12171500
PubChem Substance ID:
24899433
NACRES:
NA.47

Quality Level

200

form

powder

composition

Water (by Karl Fischer): ≤ 8%

Sodium (Na) anhydrous: 4.6-5.8%

color

white to light gray

solubility

water: 50 mg/mL, clear to hazy

λmax

575-581 nm

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

[Na+].[Na+].[H]O[H].Oc1ccc(cc1S([O-])(=O)=O)C2(OC(=O)c3c(Br)c(Br)c(Br)c(Br)c23)c4ccc(O)c(c4)S([O-])(=O)=O

InChI

1S/C20H10Br4O10S2.2Na.H2O/c21-15-13-14(16(22)18(24)17(15)23)20(34-19(13)27,7-1-3-9(25)11(5-7)35(28,29)30)8-2-4-10(26)12(6-8)36(31,32)33;;;/h1-6,25-26H,(H,28,29,30)(H,31,32,33);;;1H2/q;2*+1;/p-2

InChI key

CDTNUNQQEUGDSD-UHFFFAOYSA-L

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Application

Sulfobromophthalein disodium salt hydrate has been used as a positive control to study the interaction of 11-keto-β-boswellic acid (KBA) and 3-acetyl-11-keto-β-boswellic acid (AKBA) with organic anion transporter OATP1B3.

Biochem/physiol Actions

Sulfobromophthalein (BSP) is a high affinity organic ion substrate for organic anion transporting polypeptides (OATPs) and has been used as a substrate for multidrug resistance associated protein 2 (Mrp2). BSP is transported into hepatocytes by OATPs and, after conjugation to glutathione, is excreted into bile by Mrp2. It was found to inhibit the aldo-keto reductase ARK1C20.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H317,H334

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR4273
SHBP9196
SHBN0832
SHBL8816
MKBW7618V

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Jing-Dong Zhou et al.
Journal of cellular and molecular medicine, 21(8), 1468-1481 (2017-04-30)
Promoter hypermethylation-mediated inactivation of ID4 plays a crucial role in the development of solid tumours. This study aimed to investigate ID4 methylation and its clinical relevance in myeloid malignancies. ID4 hypermethylation was associated with higher IPSS scores, but was not
Substrate- and pH-specific antifolate transport mediated by organic anion-transporting polypeptide 2B1 (OATP2B1-SLCO2B1).
Visentin M
Molecular Pharmaceutics, 81(2), 134-142 (2012)
Induction of multidrug resistance-associated protein 2 in liver, intestine and kidney of streptozotocin-induced diabetic rats.
Xenobiotica, 42(8) (2012)
Organic Anion Transporting Polypeptide Mediates Organic Anion/HCO3- Exchange*
Lisa M
The Journal of Biological Chemistry (1997)
Permeation of Boswellia extract in the Caco-2 model and possible interactions of its constituents KBA and AKBA with OATP1B3 and MRP2
Philip Kruger
European Journal of Pharmaceutical Sciences, 36 (2009)
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