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Merck

P2297

Acide picrylsulfonique solution

5 % (w/v) in H2O, BioReagent, suitable for determination of primary amines

Synonyme(s) :

Acide 2,4,6-trinitrobenzènesulfonique solution, TNBS

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A propos de cet article

Formule empirique (notation de Hill) :
C6H3N3O9S
Numéro CAS:
2508-19-2
Poids moléculaire :
293.17
UNSPSC Code:
12352005
NACRES:
NA.25
PubChem Substance ID:
24898307
MDL number:
MFCD00064382
Beilstein/REAXYS Number:
572358
Concentration:
5 % (w/v) in H2O
Form:
liquid

Principaux documents

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InChI key

NHJVRSWLHSJWIN-UHFFFAOYSA-N

SMILES string

OS(=O)(=O)c1c(cc(cc1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O

InChI

1S/C6H3N3O9S/c10-7(11)3-1-4(8(12)13)6(19(16,17)18)5(2-3)9(14)15/h1-2H,(H,16,17,18)

product line

BioReagent

Quality Level

200

form

liquid

concentration

5 % (w/v) in H2O

solubility

soluble

suitability

suitable for determination of primary amines

storage temp.

2-8°C

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Catégories apparentées

Application

L'acide picrylsulfonique en solution a été utilisé :
  • pour évaluer l'efficacité de modifications par la carboxyméthyl-lysine (CML) d'amines primaires exposées.
  • pour incuber des embryons de bovin à zone pellucide intacte en vue du marquage différentiel de blastocystes.
  • pour induire le syndrome du côlon irritable (IBS) chez des souris et étudier ses effets sur Clostridium butyricum.

Réactif de modification hydrophile. Les dérivés contenant des composés amino peuvent être régénérés avec de l′hydrazine.

General description

L'acide picrylsulfonique en solution est un haptène capable de se lier aux protéines tissulaires et de se transformer en antigène. Cette transformation provoque plusieurs réponses immunologiques. La colite induite par l'acide 2,4,6-trinitrobenzènesulfonique (TNBS) est un type de réaction d'hypersensibilité retardée face aux protéines hapténisées. Le leucotriène B4 (LTB4) et les acides gras monohydroxylés que sont l'acide 5-hydroxyeicosatétraénoïque (5-HETE), le 12-HETE et le 15-HETE sont les principaux médiateurs inflammatoires impliqués dans cette colite induite par le TNBS. L'éthanol à forte concentration sert de véhicule pour l'administration du TNBS.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

hcodes

H314,H317

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1

Classe de stockage

8B - Non-combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000500119
0000500119
0000487337
0000487337
0000457677

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. Is Product P2297, Picrylsulfonic acid solution, supposed to be yellow?

    Yes. This product is a clear to slightly hazy yellow solution at room temperature. The solution has a concentration of 5 w/v % in H2O (5g per 100 mL).

  4. In general, what is Product P2297, Picrylsulfonic acid solution, used for?

    Picrylsulfonic acid has been used 1) As a hydrophilic modifying reagent[1]; 2) To make derivatives with amino compounds, which can be regenerated with hydrazine [2].

  5. How is Product P2297, Picrylsulfonic acid solution, tested? Do you have any references for its use besides Sigma's method?

    Sigma's suitability assay is based on a published method.1 We use a 500-fold dilution as a working solution, with glycine as a standard. Hydrochloric acid is used to stop the reaction, and to reduce yellow background due to picric acid.  Sodium phosphate is used as a buffer in place of sodium bicarbonate to avoid formation of CO2 when HCl is added.  Absorbance is read at 420 nm.Other procedures have been published. For example:---Twenty-five mL of 0.03 M TNBS is added to 1 mL of sample (in borate buffer), agitated to ensure complete mixing, and allowed to stand for 30 minutes at room temperature (25±1°C).  No quenching step is used.  In the blank, buffer replaces sample.  Absorbance is read at 420 nm.2---Protocols using a more concentrated solution of picric acid (1.1 M) have been published.3Note: TNBS forms an orange complex with amines, monitored at 420 nm, but the EmM of the complexes will vary with the reacting group:  for alpha-amino groups, 22.0; for epsilon-amino groups, somewhat lower; and for thiol groups, 2.25.3References:1. Satake, K. et al., J. Biochem., 47, 654 (1960).2. Snyder, S.L. and Sobocinski P.Z., Anal. Biochem., 64, 284-288 (1975).3. Fields, R., Methods in Enzymology, 25, 464-468 (1972).

  6. What are the suggested storage conditions for Product P2297, Picrylsulfonic acid solution?

    Store Product No. P2297 at 2-8°C in the dark.

  7. Is Product P2297, Picrylsulfonic acid solution, considered to be stable?

    It is explosive when it is dry. The solution should be stored at 2-8°C in the dark. Under these conditions less than 5% decomposition will occur over five months. At 37°C, 50% decomposition occurred in 60 days.  Picrylsulfonic acid decomposes to picric acid, crystals of which may form in the solution, but this impurity causes no interference in usage. The solution may also contain a trace amount of 2,4-dinitrophenol (typically <0.5%).  Storage at -20°C may enhance shelf-life of stock solutions.

  8. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  9. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Mara Perrone et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 115, 168-176 (2017-03-10)
The aim of this study was to synthesize, characterize and evaluate the mucoadhesive properties of the first thiolated hyperbranched natural polysaccharide with biodegradability and biocompatibility features. In detail, glycogen-cysteamine conjugates were synthesized through a first step of oxidative ring opening
Mengdie Shen et al.
Mediators of inflammation, 2020, 3070345-3070345 (2020-10-27)
To explore the treatment effect of mica on 2,4,6-trinitrobenzenesulfonic acid solution- (TNBS-) induced colitis in mice. Thirty male BALB/C mice were randomly divided into the control group, the TNBS group, and the mica group. Control mice were treated with saline
Elliot Yi-Hsin Lin et al.
Biomedicines, 8(8) (2020-08-09)
Aberrant neutrophil extracellular trap (NET) formation and the loss of barrier integrity in inflamed intestinal tissues have long been associated with inflammatory bowel disease (IBD). However, whether NETs alter intestinal epithelium permeability during colitis remains elusive. Here, we demonstrated that
Joel Castro et al.
Gastroenterology, 145(6), 1334-1346 (2013-08-21)
Linaclotide is a minimally absorbed agonist of guanylate cyclase-C (GUCY2C or GC-C) that reduces symptoms associated with irritable bowel syndrome with constipation (IBS-C). Little is known about the mechanism by which linaclotide reduces abdominal pain in patients with IBS-C. We
Florian Bär et al.
Gastroenterology, 145(5), 1055-1063 (2013-07-23)
Dysregulated energy homeostasis in the intestinal mucosa frequently is observed in patients with ulcerative colitis (UC). Intestinal tissues from these patients have reduced activity of the mitochondrial oxidative phosphorylation (OXPHOS) complex, so mitochondrial dysfunction could contribute to the pathogenesis of
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