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Chemical Compound Review:

PubChem21986 4-(aminomethyl)benzene-1,2- diol

Synonyms: SureCN110644, AG-C-58602, HMDB12153, KB-28324, LS-29922, ...

FitzGerald, G.B. et al., Tsuchiya, H. et al., Boomsma, F. et al., Santagostino, G. et al., Wick, M.M., et al.

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of NSC263475

3,4-Dihydroxybenzylamine was active in 3 of 8 melanomas and 1 of 5 nonmelanomas [1].
Several analogues have been prepared with significant antitumor activity against experimental melanoma models, and these include levodopa, dopamine, and the nonneurotoxic analogue 3,4-dihydroxybenzylamine [2].

High impact information on NSC263475

It was found that drugs that have an indirect effect on this enzyme--methotrexate (MTX), hydroxyurea (HU), and 3,4-dihydroxybenzylamine (3,4-DHBA)--acted as noncompetitive inhibitors and the inhibition of thymidylate synthase by these drugs did not result in the accumulation of its substrate, dUMP [3].
Potentiation by alpha-difluoromethylornithine of the activity of 3,4-dihydroxybenzylamine, a tyrosinase-dependent melanolytic agent, against B16 melanoma [4].
Breakdown of 3,4-dihydroxybenzylamine and dopamine in plasma of various animal species by semicarbazide-sensitive amine oxidase [5].
Under optimal extraction conditions, L-3,4-dihydroxyphenylalanine and 3,4-dihydroxybenzylamine used as an internal standard are extracted from blood plasma by a simple procedure and in a short time and then separated by reversed-phase ion-pair chromatography [6].
Among catecholamines tested, only DA and 3,4-dihydroxybenzylamine (DHBA, the internal standard of most catecholamine assays using high-performance liquid chromatography (HPLC) with electrochemical detection) were good substrates for the pig plasma SSAO [7].

Chemical compound and disease context of NSC263475

Melanoma cytotoxicity of buthionine sulfoximine (BSO) alone and in combination with 3,4-dihydroxybenzylamine and melphalan [8].

Biological context of NSC263475

An internal standard of 3,4 dihydroxybenzylamine is added to the diluted urine and acidic hydrolysis of the conjugates is followed by reverse-phase HPLC separation and coulometric detection in the redox mode [9].

Analytical, diagnostic and therapeutic context of NSC263475

3,4-Dihydroxybenzylamine (DHBA) is commonly used as the internal standard in HPLC catecholamine assays [10].

References

Structure-activity relationships defining the cytotoxicity of catechol analogues against human malignant melanoma. Kern, D.H., Shoemaker, R.H., Hildebrand-Zanki, S.U., Driscoll, J.S. Cancer Res. (1988) [Pubmed]
The chemotherapy of malignant melanoma. Wick, M.M. J. Invest. Dermatol. (1983) [Pubmed]
Comparison of the inhibitory effects of hydroxyurea, 5-fluorodeoxyuridine, 3,4-dihydroxybenzylamine, and methotrexate on human squamous cell carcinoma. FitzGerald, G.B., Wick, M.M. J. Invest. Dermatol. (1987) [Pubmed]
Potentiation by alpha-difluoromethylornithine of the activity of 3,4-dihydroxybenzylamine, a tyrosinase-dependent melanolytic agent, against B16 melanoma. Prakash, N.J., Sunkara, P.S., Sjoerdsma, A. Biochem. Pharmacol. (1985) [Pubmed]
Breakdown of 3,4-dihydroxybenzylamine and dopamine in plasma of various animal species by semicarbazide-sensitive amine oxidase. Boomsma, F., Alberts, G., Bevers, M.M., Koning, M.M., Man in 't Veld, A.J., Schalekamp, M.A. J. Chromatogr. (1993) [Pubmed]
Determination of L-3,4-dihydroxyphenylalanine in blood by high-performance liquid chromatography after solvent extraction. Tsuchiya, H., Hayashi, T. J. Chromatogr. (1989) [Pubmed]
High activity of semicarbazide-sensitive amine oxidase (SSAO): an important source of errors in the determination of the concentration of dopamine in pig plasma. Boomsma, F., van Woerkens, L.J., Man in 't Veld, A.J., Verdouw, P.D., Schalekamp, M.A. J. Cardiovasc. Pharmacol. (1993) [Pubmed]
Melanoma cytotoxicity of buthionine sulfoximine (BSO) alone and in combination with 3,4-dihydroxybenzylamine and melphalan. Prezioso, J.A., FitzGerald, G.B., Wick, M.M. J. Invest. Dermatol. (1992) [Pubmed]
Simultaneous measurement of total catecholamines and metanephrines in human urine by liquid chromatography with coulometric detection. Santagostino, G., Preda, S., Cucchi, M.L., Frattini, P. Farmaco (1991) [Pubmed]
Determination of catecholamines in sheep plasma by high-performance liquid chromatography with electrochemical detection: comparison of deoxyepinephrine and 3,4-dihydroxybenzylamine as internal standard. He, H., Stein, C.M., Christman, B., Wood, A.J. J. Chromatogr. B Biomed. Sci. Appl. (1997) [Pubmed]

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