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H2380

Sigma-Aldrich

6-Hydroxy-DL-DOPA

≥98% (HPLC), powder, APE1 inhibitor

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C9H11NO5
CAS Number:
21373-30-8
Molecular Weight:
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)

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’.

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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
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
A Padiglia et al.
Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry, 4(5), 608-613 (1999-11-07)
The reaction with substrates and carbonyl reagents of native lentil Cu-amine oxidase and its modified forms, i.e. Cu-fully-depleted, Cu-half-reconstituted, Cu-fully-reconstituted, Co-substituted, Ni-substituted and Zn-substituted, has been studied. Upon removal of only one of the two Cu ions, the enzyme loses
P Oguzkurt et al.
British journal of urology, 82(1), 104-108 (1998-08-12)
To evaluate the effects of vasodilator therapies and chemical sympathectomy on ipsilateral and contralateral testicular spermatogenetic activity after unilateral testicular torsion using DNA flow cytometry and thus determine whether contralateral testicular damage occurs through a reflexively decreased blood flow. The
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
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