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75068

Sigma-Aldrich

9,10-Anthracenediyl-bis(methylene)dimalonic acid

BioReagent, suitable for fluorescence, ≥90% (HPCE)

Synonyme(s) :

ABDA, Single Oxygen Probe

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About This Item

Formule empirique (notation de Hill):
C22H18O8
Numéro CAS:
307554-62-7
Poids moléculaire :
410.37
Numéro Beilstein :
3503804
Numéro MDL:
MFCD03095464
Code UNSPSC :
12352106
ID de substance PubChem :
329766104
Nomenclature NACRES :
NA.32

Gamme de produits

BioReagent

Pureté

≥90% (HPCE)

Forme

powder

Solubilité

DMSO: soluble

Fluorescence

λex 380 nm; λem 407 nm in 0.1 M phosphate pH 7.0

Adéquation

suitable for fluorescence

Chaîne SMILES 

OC(=O)C(Cc1c2ccccc2c(CC(C(O)=O)C(O)=O)c3ccccc13)C(O)=O

InChI

1S/C22H18O8/c23-19(24)17(20(25)26)9-15-11-5-1-2-6-12(11)16(10-18(21(27)28)22(29)30)14-8-4-3-7-13(14)15/h1-8,17-18H,9-10H2,(H,23,24)(H,25,26)(H,27,28)(H,29,30)

Clé InChI

DNUYOWCKBJFOGS-UHFFFAOYSA-N

Description générale

9,10-Anthracenediyl-bis(methylene)dimalonic acid or ABDA is a singlet oxygen probe. It is highly fluorescent and soluble in water and binds to lipopolysaccharides (LPS) found in the cell membrane. 9,10-Anthracenediyl-bis(methylene)dimalonic acid takes four negative charges upon fully deprotonation in neutral aqueous solutions, stabilizing the ion-pair complex and facilitating selective recognition of LPS over other common ionic species of clinical significance. In addition to the emission maximum at 407 nm, there are lower maxima at 431, 457, and 485 nm.

Application

9,10-Anthracenediyl-bis(methylene)dimalonic acid is widely used as a singlet oxygen detector probe. 9,10-Anthracenediyl-bis(methylene)dimalonic acid is suitable for assessing the photodynamic effect of curcumin Vibrio parahaemolyticus, which is a significant cause of bacterial diarrhea.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Remarque sur l'analyse

In addition to the emission maximum at 407 nm, there are lower maxima at 431, 457 and 485 nm.

Autres remarques

Reagent for the assay of singlett oxygen; it has better characteristics than 9,10-anthracenediyl-bis-dipropionic acid

Pictogrammes

Exclamation markEnvironment
GHS07,GHS09

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335,H400

Classification des risques

Aquatic Acute 1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Eun Jo Du et al.
Proceedings of the National Academy of Sciences of the United States of America, 116(24), 12013-12018 (2019-05-30)
Pigments often inflict tissue-damaging and proaging toxicity on light illumination by generating free radicals and reactive oxygen species (ROS). However, the molecular mechanism by which organisms sense phototoxic pigments is unknown. Here, we discover that Transient Receptor Potential Ankyrin 1-A
Tiago Entradas et al.
Journal of photochemistry and photobiology. B, Biology, 204, 111787-111787 (2020-01-21)
The sensitivity for singlet oxygen (1O2) of two convenient 1O2 probes, 1,3-diphenylisobenzofuran (DPBF) and 9,10-Anthracenediyl-bis(methylene)dimalonic acid (ABDA), has been investigated in different aqueous environments. Both probes are commercially available at reasonable cost and can be used with standard UV-vis spectrometers.
Renlu Han et al.
Biomaterials science, 8(2), 607-618 (2019-12-04)
Although combined chemotherapy (Chemo), photothermal (PTT) and photodynamic (PDT) in cancer therapy has drawn significant attention due to its superior anticancer ability, the required high intensity of irradiation results in serious photo-toxicity to healthy neighboring cells, and thus limits its
Mikkel Bregnhøj et al.
Photochemistry and photobiology, 95(1), 202-210 (2018-07-05)
Uric acid and/or its monoanion has long been used as chemical-trapping agents to demonstrate the presence of singlet oxygen, O2 (a1 Δg ), in aqueous systems. "Oxidative bleaching" of uric acid, generally monitored through changes in the uric acid absorption
Shodai Hino et al.
Chemistry, an Asian journal, 15(3), 365-370 (2019-12-13)
5,15-Diazaporphyrins, which have a large absorption at wavelengths over 600 nm, were dissolved in water by complex formation with β-(1,3-1,6)-d-glucans. Aqueous solutions of these complexes were relatively stable compared with their trimethyl-β-cyclodextrin-complexed analogues. β-Glucan-complexed diazaporphyrins showed quenched fluorescence and had low
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