3,4-DIHYDROXYBENZYLAMINE HYDROBROMIDE

Names

[ Name ]:
3,4-DIHYDROXYBENZYLAMINE HYDROBROMIDE

[Synonym ]:
EINECS 240-382-8
4-(Aminomethyl)catechol hydrobromide,DHBA hydrobromide
MFCD00012859
4-(aminomethyl)benzene-1,2-diol,hydrobromide
3,4-Dihydroxybenzylamine hydrobromide

Biological Activity

[Description]:

3,4-Dihydroxybenzylamine hydrobromide (NSC 263475 hydrobromide) is an improved dopamine analog cytotoxic and inhibits DNA polymerase activity in melanoma cells[2]. 3,4-Dihydroxybenzylamine hydrobromide (NSC 263475 hydrobromide) displays growth inhibitory activity in melanoma cell lines with varying degrees of tyrosinase activity[2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

[In Vitro]

3,4-Dihydroxybenzylamine hydrobromide (1 μM-10 mM; 48 hours) inhibits the growth of all melanoma cell lines with an IC50 of 100 μM, while the SK-MELB cell line exhibits an IC50 of 122 μM. The IC50 values are 30, 84,90, and 68 μM for Human SK-MEL-30, SK-MEL-2, SK-MEL-3,RPMI-7951 cells, respectively. It exhibits IC50values of 10, 25, 67, and 184 μM for S91A,S91B, L1210, and SCC-25 cells, respectively[2]. 3,4-Dihydroxybenzylamine hydrobromide (1 μM-10 mM; 48 hours) cytotoxicity in SK-MEL-2 and SK-MEL-28 cell lines can be enhanced by application of buthionine sulfoximine (BSO). BSO treatment sensitizes marginally pigmented cells to the effects of 3,4-DHBA, and the presence of decreses IC50 values of 3,4-DHBA by 127% in the SK-MEL-28 cell line and by 148% in the SK-MEL-2 cell line[2]. Cell Viability Assay[1] Cell Line: Human and Murine Melanoma Cell Lines; Non-Melanoma Cell Lines Concentration: 1 μM-10 mM Incubation Time: 48 hours Result: Inhibited melanoma cell Lines growth.

[In Vivo]

3,4-Dihydroxybenzylamine hydrobromide (intraperitoneal injection; 1000 mg/kg; 7 days) has the least toxic effect in non-tumor-bearing B6D2F1 mice,and mice is tolerated at this dose[3]. 3,4-Dihydroxybenzylamine hydrobromide (intraperitoneal injection; 200-800 mg/kg; 21 days) has different effects at different doses, the median life-span are 17, 24.5, 26, 29 and 25 days for 0 mg/kg, 200 mg/kg, 400 mg/kg, 600 mg/kg, and 800 mg/kg, respectively[3]. Animal Model: C57BL/6 mice with B6D2F1 cells[3] Dosage: 200 mg/kg, 400 mg/kg, 600 mg/kg, and 800 mg/kg Administration: Intraperitoneal injection Result: Exhibited increased life-span of 44%,46%, 70% and 50% for 200 mg/kg, 400 mg/kg, 600 mg/kg, and 800 mg/kg, respectively.

[References]

[1]. FitzGerald GB, et al. 3,4-Dihydroxybenzylamine: an improved dopamine analog cytotoxic for melanoma cells in part through oxidation products inhibitory to dna polymerase.J Invest Dermatol. 1983 Feb;80(2):119-23.

[2]. Prezioso JA1,et al.Effects of tyrosinase activity on the cytotoxicity of 3,4-dihydroxybenzylamine and buthionine sulfoximine in human melanoma cells.Pigment Cell Res. 1990 Mar-Apr;3(2):49-54.

[3]. Mlchael M. Wick,et al. 3,4-Dihydroxybenzylamine: Antitumor Activity Against A Dopamine Analog B16 Melanoma.

Chemical & Physical Properties

[ Density]:
1.309g/cm3

[ Boiling Point ]:
333.4ºC at 760mmHg

[ Melting Point ]:
184-186 °C(lit.)

[ Molecular Formula ]:
C₇H₁₀BrNO₂

[ Molecular Weight ]:
220.06400

[ Flash Point ]:
155.5ºC

[ Exact Mass ]:
218.98900

[ PSA ]:
66.48000

[ LogP ]:
2.21490

[ Vapour Pressure ]:
1.32E-05mmHg at 25°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2922299090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2922299090

[ Summary ]:
2922299090. other amino-naphthols and other amino-phenols, other than those containing more than one kind of oxygen function, their ethers and esters; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Simultaneous determination of electroactive and non-electroactive food preservatives by novel capillary electrophoresis with amperometric detection.

Anal. Chim. Acta 678(1) , 39-43, (2010)

A novel capillary electrophoresis and amperometric detection method was achieved by adding an electroactive additive (3,4-dihydroxybenzylamine, 3,4-DHBA) to the running buffer, so that both electroact...

Selective extraction of catecholamines by packed fiber solid-phase using composite nanofibers composing of polymeric crown ether with polystyrene.

Biomed. Chromatogr. 29(1) , 103-9, (2014)

For the first time, electrospun composite nanofibers comprising polymeric crown ether with polystyrene (PCE-PS) have been used for the selective extraction of catecholamines - dopamine (DA), norepinep...

ERK5 induces ankrd1 for catecholamine biosynthesis and homeostasis in adrenal medullary cells.

Cell. Signal. 28 , 177-89, (2016)

Extracellular signal-regulated kinases (ERKs) play important roles in proliferation, differentiation and gene expression. In our previous study, we demonstrated that both ERK5 and ERK1/2 were responsi...