Synthesis and analysis of activity of a potential anti-melanoma prodrug with a hydrazine linker

Frąckowiak-Wojtasek, Bożena; Gąsowska-Bajger, Beata; Mazurek, Magdalena; Raniszewska, Agnieszka; Logghe, Marieke; Smolarczyk, Ryszard; Cichoń, Tomasz; Szala, Stanisław; Wojtasek, Hubert

doi:10.1016/j.ejmech.2013.10.080

Cited by 8 publications

(4 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In more recent years, a novel prodrug containing a hydrazine linker was synthesized [139]. However, these phenylhydrazine derivatives were quickly abandoned as an option due to their intrinsic toxicity and lack of tyrosinase selectivity, displaying higher susceptibility to oxidation by different enzymes (Figure 4c) [139].…”

Section: Advancing Melanoma Systemic Treatment—potential Targets Amentioning

confidence: 99%

Emergent Nanotechnological Strategies for Systemic Chemotherapy against Melanoma

2019

View full text Add to dashboard Cite

Melanoma is an aggressive form of skin cancer, being one of the deadliest cancers in the world. The current treatment options involve surgery, radiotherapy, targeted therapy, immunotherapy and the use of chemotherapeutic agents. Although the last approach is the most used, the high toxicity and the lack of efficacy in advanced stages of the disease have demanded the search for novel bioactive molecules and/or efficient drug delivery systems. The current review aims to discuss the most recent advances on the elucidation of potential targets for melanoma treatment, such as aquaporin-3 and tyrosinase. In addition, the role of nanotechnology as a valuable strategy to effectively deliver selective drugs is emphasized, either incorporating/encapsulating synthetic molecules or natural-derived compounds in lipid-based nanosystems such as liposomes. Nanoformulated compounds have been explored for their improved anticancer activity against melanoma and promising results have been obtained. Indeed, they displayed improved physicochemical properties and higher accumulation in tumoral tissues, which potentiated the efficacy of the compounds in pre-clinical experiments. Overall, these experiments opened new doors for the discovery and development of more effective drug formulations for melanoma treatment.

show abstract

Section: Advancing Melanoma Systemic Treatment—potential Targets Amentioning

confidence: 99%

Emergent Nanotechnological Strategies for Systemic Chemotherapy against Melanoma

2019

View full text Add to dashboard Cite

show abstract

“…Gasowska-Bajger and Wojtasek [6] have described that not only carbamate or urea linkers, but also hydrazine linkers and phenolic substrates (4-tert-butylcatechol or N-acetyl-L-tyrosine) can be used in drug design for MDEPT. Therefore, they synthetized an aniline mustard prodrug (19) containing a hydrazine linker and a phenolic activator (Figure 8) [29]. The prodrug (N-{4-[bis-(2-chloroethyl) amino]benzoyl}-N-(4-hydroxybenzyl)hydrazine) (19) showed in vivo low specificity for the melanoma cells and weak activity to reduce melanoma solid tumor size compared to melphalan (cytostatic agent) at doses of 100 μg.…”

Section: Tyramine (R' = H) or Dopamine (R' = Oh) Subunitmentioning

confidence: 99%

“…Glutathione (GSH) is also overexpressed in tumor cells at levels 1000times superior to that of the blood plasma [29]. Based on this ) of triazene derivatives (18a-18f) in PBS buffer, 80% human plasma and in the presence of tyrosinase (300 U/mL) at 37ºC.…”

Section: Tyramine (R' = H) or Dopamine (R' = Oh) Subunitmentioning

confidence: 99%

Targeted Prodrug Design for the Treatment of Malignant Melanoma

Mendes¹,

Renato²,

dos³

et al. 2016

J Dermatol Res Ther

View full text Add to dashboard Cite

Malignant melanoma is a serious health problem once the current chemotherapy exhibits resistance to traditional drugs. Several challenges must be overcome during drug design in order to increase the efficacy and safety of the new drugs. Therefore, the specific chemical release of cytotoxic agents near to the target is an attractive approach to improve the anticancer activity and reduce the systemic toxicity. Herein, this review article describes the advances in the development of targeted prodrugs for the treatment of malignant melanoma.

show abstract

“…In addition to the well-known substrates (mono-and diphenols), the enzyme exhibits substrate specificity to phenolic oligomers and polymers, phenolic derivatives with tyrosine residues, aminophenols and various aromatic amines (Gąsowska et al, 2004). The most widespread mushroom tyrosinase has also been applied to detoxify waste water or soil contaminated with phenolic compounds, xenobiotics and *Corresponding author, e-mail: jolanta.bryjak@pwr.edu.pl Brought to you by | New York University Bobst Library Technical Services Authenticated Download Date | 7/2/15 1:58 PM amines (Ikehata & Nicelli, 2000;Xu & Yang, 2013;Kampmann et al, 2014), to detect phenolic compounds (Tembe et al, 2006;Sigolaeva et al, 2014;Karim et al, 2014), in the cosmetics, food and pharmaceutical industries (Ates et al, 2007;Morales et al, 2002;Wang et al, 2006), in the cross-linking of proteins (Thalmann & Lötzbeyer, 2006), as a part of the electrode in biofuel cells (Min et al, 2010), in the synthesis of antioxidant hydroxytyrosol (Espín et al, 2001) and even in tumour-suppressing and pro-drug therapy agents (Seo et al, 2003;Frąckowiak-Wojtasek et al, 2014). However, the operational stability of a native enzyme is fairly limited and its immobilisation is needed in order to mitigate this limitation (Burton, 2003).…”

Section: Introductionmentioning

confidence: 99%

Immobilisation of tyrosinase on siliceous cellular foams affording highly effective and stable biocatalysts

et al. 2015

View full text Add to dashboard Cite

Tyrosinase from Agaricus bisporus was immobilised covalently on mesostructured siliceous foam (MCF) and three mesoporous silicas of SBA-15 type of different pore sizes, regarded as the reference, to reveal that MCF was the superior enzyme support. All the carriers were functionalised using 3-aminopropyltrimethoxysilane and the enzyme was attached covalently via glutaraldehyde or by simple adsorption and it was also cross-linked with glutaraldehyde in selected samples. The experiments indicated that only tyrosinase attached covalently was highly active and that postimmobilisation cross-linking slightly reduced its activity with no improvement in stability. MCFbound tyrosinase was the best biocatalyst with monophenolase and diphenolase activities of 3627 U mL −1 and 53040 U mL −1 of carrier sediment, respectively. Inactivation studies at 55 • C showed that MCF-bound tyrosinase was 20 times more stable than the native enzyme, whereas for typical SBA-15 it was only 12 times. A comparative study with other, non-siliceous enzyme supports indicated that aminated MCF appeared to be the carrier of choice for the covalent attachment of tyrosinase.

show abstract

Synthesis and analysis of activity of a potential anti-melanoma prodrug with a hydrazine linker

Cited by 8 publications

References 20 publications

Emergent Nanotechnological Strategies for Systemic Chemotherapy against Melanoma

Emergent Nanotechnological Strategies for Systemic Chemotherapy against Melanoma

Targeted Prodrug Design for the Treatment of Malignant Melanoma

Immobilisation of tyrosinase on siliceous cellular foams affording highly effective and stable biocatalysts

Contact Info

Product

Resources

About