Skip to Content
Merck
All Photos(1)

Documents

75068

Sigma-Aldrich

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

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

Synonym(s):

ABDA, Single Oxygen Probe

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C22H18O8
CAS Number:
Molecular Weight:
410.37
Beilstein:
3503804
MDL number:
UNSPSC Code:
12352106
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

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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
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
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service