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HomeProduct name list6-Nitroveratraldehyde

6-Nitroveratraldehyde

Synonym(s):DMNB, 4,5- Di methoxy-2- nitro benzaldehyde, DNA-Dependent Protein Kinase Inhibitor;DMNB, 4,5-Dimethoxy-2-nitrobenzaldehyde, DNA-Dependent Protein Kinase Inhibitor;DNA-PK Inhibitor - CAS 20357-25-9 - Calbiochem

  • CAS NO.:20357-25-9
  • Empirical Formula: C9H9NO5
  • Molecular Weight: 211.17
  • MDL number: MFCD00007134
  • EINECS: 243-762-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-09 19:38:33
6-Nitroveratraldehyde  Structural

What is 6-Nitroveratraldehyde ?

Chemical properties

yellow fluffy powder

The Uses of 6-Nitroveratraldehyde

6-Nitroveratraldehyde has been used in the preparation of no-carrier-added 6-18F-fluoro-L-dopa, fundamental tracer for cerebral positron emission tomography studies of dopaminergic system in humans and o-nitroaryl-bis(5-methylfur-2-yl)methanes, versatile synthons for the synthesis of nitrogen-containing heterocycles. DMNB is also an enzyme involved in the non-homologous end-joining (NHEJ) pathway of double-stranded DNA break (DSB) repair. It is also used for synthesizing analogs of alpha-asarone.

What are the applications of Application

DMNB is a vanillin derivative and potent inhibitor of DNA-PK

Definition

ChEBI: 4,5-dimethoxy-2-nitrobenzaldehyde is a C-nitro compound and an aromatic ether.

General Description

A cell-permeable vanillin derivative that acts as a potent and selective inhibitor of DNA-dependent protein kinase (DNA-PK) activity (IC50 = 15 μM) and DNA-PK-mediated double strand break (DSB) DNA repair by non-homologous DNA-end-joining (NHEJ). Reported to effectively sensitize cells to Cisplatin (Cat. No. 232120). Does not affect the activities of PKC or Chk2.

Biological Activity

Inhibitor of DNA-dependent protein kinase (DNA-PK) (IC 50 = 15 μ M), an enzyme involved in the non-homologous end-joining (NHEJ) pathway of double-stranded DNA break (DSB) repair in human cells. Displays 100-fold higher potency than its analog vanillin and does not affect PKC activity. Produces lethal effects on cisplatin-treated D5037 cells upon continuous exposure.

Biochem/physiol Actions

Cell permeable: yes

Purification Methods

The aldehyde is purified by dissolving 9g in 200mL of boiling 95% EtOH, and set aside overnight to crystallise. It is then dried in vacuo at 50o and recrystallised from 110mL of 95% EtOH to give 6-7g of aldehyde with m 132-133o. Crystallisation from aqueous EtOH provides light yellow needles. It is light sensitive and should be stored in the dark [Fetscher Org Synth Coll Vol 4 735 1963]. [Beilstein 8 H 262, 8 I 610, 8 II 290, 6 III 2065, 6 IV 1785.]

Properties of 6-Nitroveratraldehyde

Melting point: 131-133 °C (lit.)
Boiling point: 350.84°C (rough estimate)
Density  1.4194 (rough estimate)
refractive index  1.5700 (estimate)
storage temp.  Keep in dark place,Sealed in dry,Room Temperature
solubility  DMSO: 22 mg/mL
form  solid
color  yellow
Water Solubility  Insoluble in water. Soluble to 25 mM in ethanol with gentle warming and to 100 mM in DMSO.
Sensitive  Air & Light Sensitive
BRN  395599
CAS DataBase Reference 20357-25-9(CAS DataBase Reference)
NIST Chemistry Reference 6-Nitroveratraldehyde(20357-25-9)

Safety information for 6-Nitroveratraldehyde

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 6-Nitroveratraldehyde

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