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H2380

Sigma-Aldrich

6-Hydroxy-DL-DOPA

≥98% (HPLC), powder, APE1 inhibitor

Sinónimos:

2,4,5-Trihydroxy-DL-phenylalanine, 2,5-Dihydroxy-DL-tyrosine

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About This Item

Fórmula empírica (notación de Hill):
C9H11NO5
Número de CAS:
21373-30-8
Peso molecular:
213.19
Beilstein/REAXYS Number:
2860065
MDL number:
MFCD00004272
UNSPSC Code:
12352200
PubChem Substance ID:
24278464
NACRES:
NA.32

product name

6-Hydroxy-DL-DOPA, ≥98% (HPLC), powder

assay

≥98% (HPLC)

form

powder

color

off-white

solubility

H2O: 3 mg/mL
1 M HCl: 50 mg/mL (Solutions should be freshly prepared and protected from exposure to light.)

storage temp.

−20°C

SMILES string

NC(Cc1cc(O)c(O)cc1O)C(O)=O

InChI

1S/C9H11NO5/c10-5(9(14)15)1-4-2-7(12)8(13)3-6(4)11/h2-3,5,11-13H,1,10H2,(H,14,15)

InChI key

YLKRUSPZOTYMAT-UHFFFAOYSA-N

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General description

Dissolve in oxygen-free boiled water containing 0.1% sodium metabisulfite or other antioxidant. Solutions should be freshly prepared and protected from exposure to light.

Biochem/physiol Actions

6-Hydroxy-DL-DOPA is an inhibitor of APE1 (apurinic/apyrimidinic endonuclease) repair-function activity. APE1 is a nuclease crucial for DNA base excision repair pathway. 6-Hydroxy-DL-DOPA also blocks RAD52 (DNA repair protein) single-stranded DNA binding domain.
Precursor of the catecholaminergic neurotoxin, 6-hydroxydopamine; converted to 6-hydroxydopamine by L-aromatic amino acid decarboxylase.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Caution

Hygroscopic; photosensitive

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Gurushankar Chandramouly et al.
Chemistry & biology, 22(11), 1491-1504 (2015-11-10)
Suppression of RAD52 causes synthetic lethality in BRCA-deficient cells. Yet pharmacological inhibition of RAD52, which binds single-strand DNA (ssDNA) and lacks enzymatic activity, has not been demonstrated. Here, we identify the small molecule 6-hydroxy-DL-dopa (6-OH-dopa) as a major allosteric inhibitor
Mass spectrometric studies of the primary sequence and structure of bovine liver and serum amine oxidase.
G W Adams et al.
Methods in enzymology, 258, 90-114 (1995-01-01)
E K Y Chung et al.
Neuro-Signals, 15(5), 238-248 (2007-04-17)
Overactivity of the glutamatergic system is suggested to be closely related to the onset and pathogenesis of Parkinson's disease. Vesicular glutamate transporters (VGLUT1, T2 and T3) are a group of glutamate transporters in neurons that are responsible for transporting glutamate
F Karoum et al.
Journal of neurochemistry, 61(4), 1369-1375 (1993-10-01)
Formation of 6-hydroxydopamine (6-OHDA) from dopamine has been hypothesized to mediate neurodegeneration induced by some psychostimulants. Although the emergence of a 6-OHDA-like substance was reported in the striatum of methamphetamine-treated rats, this substance has not been identified by a direct
A J Nappi et al.
Pigment cell research, 8(6), 283-293 (1995-12-01)
High pressure liquid chromatography with electrochemical detection (HPLC-ED) was employed in conjugation with a sensitive and specific salicylate hydroxylation assay to evaluate the immediate effects of hydroxyl radical (.OH) attack on four catechol intermediates of eumelanin, dopamine (3,4-dihydroxyphenylethylamine), its precursor
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