Indirect oxidation of the antitumor agent procarbazine by tyrosinase—Possible application in designing anti-melanoma prodrugs

Gąsowska-Bajger, Beata; Wojtasek, Hubert

doi:10.1016/j.bmcl.2008.04.041

Cited by 17 publications

(12 citation statements)

References 28 publications

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“…Our results are consistent with recent studies that show that in urea or carbamate derivatives of dopamine the nitrogen atom is not sufficiently nucleophilic to effect the necessary cyclization that results in release of the antitumour agent [21,22]. …”

Section: Figure 1 Near Heresupporting

confidence: 93%

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

Perry

Mendes

Simplı́cio

et al. 2009

European Journal of Medicinal Chemistry

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Section: Figure 1 Near Heresupporting

confidence: 93%

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

Perry

Mendes

Simplı́cio

et al. 2009

European Journal of Medicinal Chemistry

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“…Hyperpigmentation, such as melasma, ephelide, and lentigo in human skin and enzymatic browning in fruits and vegetables is not desirable. The occurrence of these phenomena has encouraged researchers to seek potent new safe tyrosinase inhibitors for use in anti-browning in farm products 40) and skin whitening for medicinal 41) and cosmetic purposes. 42) Recent expansion of the global market has resulted in an ever-growing demand for new products for depigmentation, cosmeceutical, and skin lightening purposes.…”

Section: Discussionmentioning

confidence: 99%

A Novel Synthesized Tyrosinase Inhibitor: (E)-2-((2,4-Dihydroxyphenyl)diazenyl)phenyl 4-Methylbenzenesulfonate as an Azo-Resveratrol Analog

Bae

Kim

et al. 2013

Bioscience, Biotechnology, and Biochemistry

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We synthesized a novel series of (E)-2-((substituted phenyl)diazenyl)phenyl 4-methylbenzenesulfonate derivatives (2 and 3) and (E)-2-((substituted phenyl)diazenyl)phenol derivatives (4 and 5), and conducted an evaluation in order to determine their inhibitory effects on mushroom tyrosinase, with the aim of discovering a tyrosinase inhibitor. Most of the compounds (3-5) exhibited higher inhibitory effects than kojic acid (IC(50) = 49.08 µM), a representative tyrosinase inhibitor. A novel synthesized compound, (E)-2-((2,4-dihydroxyphenyl)diazenyl)phenyl 4-methylbenzenesulfonate (3), showed the best results with an IC(50) of 17.85 µM, and showed competitive inhibition on Lineweaver-Burk plots, as further confirmed by the docking results. In addition, active compounds 3-5 were not cytotoxic to cultured B16F10 cells at the concentrations tested, and inhibited both tyrosinase and melanin synthesis. Therefore the active compounds (3-5) might be considered excellent candidates for use in the development of therapeutic agents for diseases associated with hyperpigmentation.

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“…In particular, it has been demonstrated that tyrosinase is able to contribute to the oxidation of the hydrazine group in the anticancer agent procarbazine. 41 Tyrosinase is able to contribute via oxidation of substrates, namely, phenols such as quercetin, to reactive species. 42,43 These reactive o-quinone species are then able to oxidize the hydrazine linker on procarbazine and initiate procarbazine's antitumor activity.…”

Section: Tyrosinase-based Therapiesmentioning

confidence: 99%

“…42,43 These reactive o-quinone species are then able to oxidize the hydrazine linker on procarbazine and initiate procarbazine's antitumor activity. 41 Tyrosinase also mediates the release of cytotoxic agents from carbamate and urea prodrugs via a cyclization-drug release mechanism. 44 In murine models, tyrosinase-activated conditionally replicative adenoviruses have been reported to enhance prolongation of survival in mice with experimental brain tumors.…”

Section: Tyrosinase-based Therapiesmentioning

confidence: 99%

Exploiting Tyrosinase Expression and Activity in Melanocytic Tumors

et al. 2011

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Melanoma is an aggressive tumor that expresses the pigmentation enzyme tyrosinase. Tyrosinase expression increases during tumorigenesis, which could allow for selective treatment of this tumor type by strategies that use tyrosinase activity. Approaches targeting tyrosinase would involve gene transcription or signal transduction pathways mediated by p53 in a direct or indirect manner. Two pathways are proposed for exploiting tyrosinase expression: (a) a p53-dependent pathway leading to apoptosis or arrest and (b) a reactive oxygen species-mediated induction of endoplasmic reticulum stress in p53 mutant tumors. Both strategies could use tyrosinase-mediated activation of quercetin, a dietary polyphenol that induces the expression of p53 and modulates reactive oxygen species. In addition to antitumor signaling properties, activation of quercetin could complement conventional cancer therapy by the induction of phase II detoxification enzymes resulting in p53 stabilization and transduction of its downstream targets. In conclusion, recent advances in tyrosinase enzymology, prodrug chemistry, and modern chemotherapeutics present an intriguing and selective multitherapy targeting system where dietary bioflavonoids could be used to complement conventional cancer treatments.

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Indirect oxidation of the antitumor agent procarbazine by tyrosinase—Possible application in designing anti-melanoma prodrugs

Cited by 17 publications

References 28 publications

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

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

A Novel Synthesized Tyrosinase Inhibitor: (E)-2-((2,4-Dihydroxyphenyl)diazenyl)phenyl 4-Methylbenzenesulfonate as an Azo-Resveratrol Analog

Exploiting Tyrosinase Expression and Activity in Melanocytic Tumors

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