Dopamine- and tyramine-based derivatives of triazenes: Activation by tyrosinase and implications for prodrug design

European Journal of Medicinal Chemistry

Volumn 44, Issue 8, 2009, Pages 3228-3234

  Perry, M Jesus ^a   Mendes, Eduarda ^a   Simplício, Ana Luísa ^b   Coelho, Ana ^b   Soares, Ricardo V ^a   Iley, Jim ^c   Moreira, Rui ^a   Francisco, Ana Paula ^a  

^a RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

^b INSTITUTO DE TECNOLOGIA QUÍMICA E BIOLÓGICA   (Portugal)

^c OPEN UNIVERSITY   (United Kingdom)

Author keywords

Melanoma; Prodrugs; Triazenes; Tyrosinase

Indexed keywords

DOPAMINE; MONOPHENOL MONOOXYGENASE; PHOSPHATE BUFFERED SALINE; PRODRUG; TRIAZENE DERIVATIVE; TYRAMINE;

ARTICLE; CONTROLLED STUDY; DRUG DEGRADATION; DRUG DESIGN; DRUG HALF LIFE; DRUG HYDROLYSIS; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVATION; ENZYME PRODRUG THERAPY; ENZYME SUBSTRATE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MELANOMA; PARTITION COEFFICIENT; PLASMA;

AGARICALES; ALKYLATION; DOPAMINE; DRUG DESIGN; DRUG STABILITY; ENZYME ACTIVATION; HUMANS; MONOPHENOL MONOOXYGENASE; PRODRUGS; TRIAZENES; TYRAMINE;

EID: 67349149632     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.03.025     Document Type: Article

References (22)

1. Balch C.M., Soong S.J., Gershenwald J.E., Thompson J.F., Reintgen D.S., Cascinelli N., Urist M., McMasters K.M., Ross M.I., Kirkwood J.M., Atkins M.B., Thompson J.A., Coit D.G., Byrd D., Desmond R., Zhang Y., Liu P.Y., Lyman G., and Morabito A. J. Clin. Oncol. 19 (2001) 3622-3643
2. Kasper B., D'Hondt V., Vereecken P., and Awada A. Crit. Rev. Oncol. Hematol. 62 (2007) 16-22
3. Smalley K.S.M., and Herlyn M. Mini Rev. Med. Chem. 6 (2006) 387-393
4. Jordan A.M., Khan T.H., Osborn H.M., Photiou A., and Riley P.A. Bioorg. Med. Chem. 7 (1999) 1775-1780
5. Riley P.A. Pigment Cell Res. 6 (2003) 548-552
6. Rooseboom M., Commandeur J.N.M., and Vermeulen N.P.E. Pharmacol. Rev. 56 (2004) 53-102
7. Jordan A.M., Khan T.H., Malkin H., Osborn H.M., Photiou A., and Riley P.A. Bioorg. Med. Chem. 9 (2001) 1549-1558
8. Jordan A.M., Khan T.H., Malkin H., and Osborn H.M. Bioorg. Med. Chem. 10 (2002) 2625-2633
9. Knaggs S., Malkin H., Osborn H.M., Williams N.A.O., and Yaqoob P. Org. Biomol. Chem. 3 (2005) 4002-4010
10. Tarhini A.A., and Agarwala S.S. Dermatol. Ther. 19 (2006) 19-25
11. Chin L., Garraway L.A., and Fisher D.E. Genes Dev. 20 (2006) 2149-2182
12. Connors T.A., Goddard P.M., Merai K., Ross W.C.J., and Wilman D.E.V. Biochem. Pharmacol. 25 (1976) 241-246
13. Vaughan K., and Stevens M.F.G. Q. Rev. 7 (1978) 377-397
14. Skibba J.L., Beal D.D., Ramirez G., and Bryan G.T. Cancer Res. 30 (1970) 147-150
15. Krüger F.W., Preusssman R., and Niepelt N. Biochem. Pharmacol. 20 (1971) 529-533
16. Sparc. Sparc Performs Automated Reasoning in Chemistry V.4.2 (2008). http://ibmlc2.chem.uga.edu/sparc
17. Carvalho E., Iley J., Perry M.J., and Rosa E. J. Chem. Soc., Perkin Trans. 2 (1998) 2375-2380
18. Espin J.C., Varon R., Fenoll L.G., Gilabert M.A., Garcia-Ruiz P.A., Tudela J., and Garcia-Canovas F. Eur. J. Biochem. 267 (2000) 1270-1279
19. Seo S.Y., Sharma V.K., and Sharma N. J. Agric. Food Chem. 51 (2003) 2837-2853
20. Osborn H.M., and Williams N.A. Org. Lett. 18 (2004) 3111-3113
21. Gasowska-Bajer B., and Wojtasek H. Bioorg. Med. Chem. Lett. (2008) 10.1016/j.bmcl.2008.04.041
22. Borovansky J., Edge R., Land E.J., Navaratnam S., Pavel S., Ramsden C.A., Riley P.A., and Smit N.P.M. Pigment Cell Res. 19 (2006) 170-178