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

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

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Synonym(s):
ABDA, Single Oxygen Probe
Empirical Formula (Hill Notation):
C22H18O8
CAS Number:
Molecular Weight:
410.37
Beilstein/REAXYS Number:
3503804
MDL number:
PubChem Substance ID:
NACRES:
NA.32

product line

BioReagent

assay

≥90% (HPCE)

form

powder

solubility

DMSO: soluble

fluorescence

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

suitability

suitable for fluorescence

SMILES string

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)

InChI key

DNUYOWCKBJFOGS-UHFFFAOYSA-N

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Quality Level

100

Quality Level

200

Quality Level

-

Quality Level

100

assay

≥90% (HPCE)

assay

~90% (TLC)

assay

≥98% (H-NMR), ≥98% (HPLC), ≥98% (LC/MS), ≥98% (elemental analysis)

assay

≥95% (HPCE)

form

powder

form

powder

form

-

form

solid

product line

BioReagent

product line

-

product line

-

product line

BioReagent

fluorescence

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

fluorescence

-

fluorescence

-

fluorescence

λex 390 nm; λem 478 nm in 0.1 M phosphate pH 7.5 (after derivatization with glutathione), λex 398 nm

General description

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Analysis Note

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

Other Notes

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

pictograms

Exclamation markEnvironment

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

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, Gloves


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Juan Wu et al.
Photodiagnosis and photodynamic therapy, 15, 34-39 (2016-05-15)
Vibrio parahaemolyticus (V. parahaemolyticus) is currently a major cause of bacterial diarrhoea associated with seafood consumption. The objective of this study was to determine the inactivation effect of curcumin-mediated photodynamic action on V. parahaemolyticus. First of all, V. parahaemolyticus suspended
Saya Otake et al.
Bioconjugate chemistry, 29(6), 2068-2073 (2018-05-16)
FLNBD-BAMPEG2k, bearing a nitrobenzoxadiazole (NBD) unit and an oleyl terminus conjugated via a poly(ethylene glycol) (PEG) spacer ( Mn = 2,000), was designed to fluorescently label cell membranes by docking its hydrophobic oleyl terminus. During laser scanning microscopy in a
Roxana Jijie et al.
Colloids and surfaces. B, Biointerfaces, 170, 347-354 (2018-06-26)
In the last years, carbon-based nanomaterials have attracted considerable attention in a wide range of fields, particularly in biomedicine, owing to their remarkable photo-physical and chemical properties. In this study, we demonstrate that amine-terminated carbon dots (CDs-NH2) functionalized with ampicillin
Vladimíra Pavlíčková et al.
Molecules (Basel, Switzerland), 24(24) (2019-12-11)
Purpurin 18 derivatives with a polyethylene glycol (PEG) linker were synthesized as novel photosensitizers (PSs) with the goal of using them in photodynamic therapy (PDT) for cancer. These compounds, derived from a second-generation PS, exhibit absorption at long wavelengths; considerable
N.A. Kuznetsova et al.
Russ. J. Gen. Chem., 71, 36-36 (2001)

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