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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
Annalisa Pinna et al.
Synapse (New York, N.Y.), 61(8), 606-614 (2007-05-04)
Evidence obtained in rodent and primate models of Parkinson's disease (PD) and preliminary clinical trials, indicates that adenosine A(2A) receptor antagonists might represent a promising nondopaminergic therapeutic tool for the treatment of PD. Those studies demonstrated the ability of adenosine
Adnan Azeem et al.
International journal of pharmaceutics, 422(1-2), 436-444 (2011-11-08)
Ropinirole, a recent introduction in the clinical treatment of Parkinson's disease, suffers with the problems of low oral bioavailability and frequent dosing. An effective transdermal nano-emulsion drug delivery system can however resolve these issues effectively with greater therapeutic benefits and
A J Nappi et al.
Biochimica et biophysica acta, 1201(3), 498-504 (1994-12-15)
The interactions of ascorbic acid (AA) and reduced glutathione (GSH) in the oxidations of the catecholaminergic neurotoxins 6-hydroxydopa (TOPA) and 6-hydroxydopamine (6-OHDA) were investigated by both high performance liquid chromatography with electrochemical detection (HPLC-ED) and spectrometric methods. These comparative studies
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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