Thiosemicarbazones with tyrosinase inhibitory activity

Hałdys, Katarzyna; Latajka, Rafał

doi:10.1039/c9md00005d

Cited by 48 publications

(30 citation statements)

References 85 publications

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“…In the case of pheomelanin the biosynthesis involves the binding of cysteine in the positions 2 or 5 of the benzene ring, forming 5-S- and 2-S-cysteinyldopa from DOPAquinone. Subsequently, pheomelanin is formed via the oxidation of the substrates to cysteinyldopa-quinones, that cyclize in 1,4 benzothiazine intermediates [ 51 ]. Even if the supramolecular structures of the two biopigments remain still indefinite, eumelanin can be considered a heterogeneous polymer consisting of DHI and DHICA in various ratios, while pheomelanin is composed from the oxidative polymerization of 5-S- and 2-S-cysteinyldopa and consists of benzothiazine and benzothiazole units.…”

Section: Introductionmentioning

confidence: 99%

Bio-Applications of Multifunctional Melanin Nanoparticles: From Nanomedicine to Nanocosmetics

et al. 2020

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Bioinspired nanomaterials are ideal components for nanomedicine, by virtue of their expected biocompatibility or even complete lack of toxicity. Natural and artificial melanin-based nanoparticles (MNP), including polydopamine nanoparticles (PDA NP), excel for their extraordinary combination of additional optical, electronic, chemical, photophysical, and photochemical properties. Thanks to these features, melanin plays an important multifunctional role in the design of new platforms for nanomedicine where this material works not only as a mechanical support or scaffold, but as an active component for imaging, even multimodal, and simple or synergistic therapy. The number of examples of bio-applications of MNP increased dramatically in the last decade. Here, we review the most recent ones, focusing on the multiplicity of functions that melanin performs in theranostics platforms with increasing complexity. For the sake of clarity, we start analyzing briefly the main properties of melanin and its derivative as well as main natural sources and synthetic methods, moving to imaging application from mono-modal (fluorescence, photoacoustic, and magnetic resonance) to multi-modal, and then to mono-therapy (drug delivery, anti-oxidant, photothermal, and photodynamic), and finally to theranostics and synergistic therapies, including gene- and immuno- in combination to photothermal and photodynamic. Nanomedicine aims not only at the treatment of diseases, but also to their prevention, and melanin in nature performs a protective action, in the form of nanopigment, against UV-Vis radiations and oxidants. With these functions being at the border between nanomedicine and cosmetics nanotechnology, recently examples of applications of artificial MNP in cosmetics are increasing, paving the road to the birth of the new science of nanocosmetics. In the last part of this review, we summarize and discuss these important recent results that establish evidence of the interconnection between nanomedicine and cosmetics nanotechnology.

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Section: Introductionmentioning

confidence: 99%

Bio-Applications of Multifunctional Melanin Nanoparticles: From Nanomedicine to Nanocosmetics

et al. 2020

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“…However, there is no clear relationship between location of the substituent on the pyridine ring and anti-tyrosinase activity. Literature reports that the case of different group of compounds (e. g., thiosemicarbazones), [28] introducing smaller 5-mem-bered heterocyclic rings gives better results than 6membered rings what could be hint for further investigations.…”

Section: Structure-activity Relationshipmentioning

confidence: 94%

“…[7] The main strategy to avoid the expression of these undesirable effects is controlling melanin biosynthesis by the inhibition of tyrosinase. Over the past few decades, a lot of inhibitors of the enzyme have been characterized and described in the literature (see reviews [13 -17] ) including kojic acid, [18] azelaic acid, [19] arbutin [20] and aloesin, [20,21] aurones, [11] flavonoids, [22] simple aldehydes, [23,24] stilbenes, [25] 4-substituted resorcinols, [26,27] thiosemicarbazones, [28] tropolone [29] and captopril. [30] Derivatives of organophosphorus are a class of compounds containing phosphorus atom bonded directly to the organic moieties or bonded through a heteroatom (nitrogen, sulfur or oxygen).…”

Section: Introductionmentioning

confidence: 99%

“…[14] Literature presents a number of bioactive heterocycles showing tyrosinase inhibitory potency. [28,42] The presence of electronegative oxygen, sulfur or nitrogen atoms in the potential inhibitor structure increases the coordination abilities of ligands. As tyrosinase possesses two copper ions in its active site, it is possible for phosphonic and phosphinic acid derivatives bearing pyridine moiety to chelate the ions and decrease catalytic activity of the enzyme.…”

Section: Introductionmentioning

confidence: 99%

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Phosphonic and Phosphinic Acid Derivatives as Novel Tyrosinase Inhibitors: Kinetic Studies and Molecular Docking

Wolińska

Hałdys

Góra

et al. 2019

Chemistry & Biodiversity

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A dozen of phosphonic and phosphinic acid derivatives containing pyridine moiety were synthesized and its inhibitory activity toward mushroom tyrosinase was investigated. Moreover, molecular docking of these compounds to the active site of the enzyme was performed. All the compounds (1–10) demonstrated the inhibitory effect with the IC50 and inhibition constants ranging millimolar concentrations. The obtained results indicate that the compounds show different types of inhibition (competitive, noncompetitive, mixed), but all of them are reversible inhibitors. The obtained outcomes allowed to make the structure–activity relationship (SAR) analysis. Compound 4 ([(benzylamino)(pyridin‐2‐yl)methyl]phenylphosphinic acid) revealed the lowest IC50 value of 0.3 mm and inhibitory constant of Ki 0.076 mm, with noncompetitive type and reversible mechanism of inhibition. According to SAR analysis, introducing bulky phenyl moieties to phosphonic and amino groups plays an important role in the inhibitory potency on activity of mushroom tyrosinase and could be useful in design and development of a new class of potent organophosphorus inhibitors of tyrosinase. Combined results of molecular docking and SAR analysis can be helpful in designing novel tyrosinase inhibitors of desired properties. They may have broad application in food industry and cosmetology.

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“…They can act as N, S-multidentate ligands, and moreover, it is possible to modulate the binding properties/stoichiometries through the insertion of other heteroatoms into the backbone structure (i.e., phenolic or pyridyl moieties). They have a great variety of biological properties, both as free ligands and as metal complexes, and several studies have been published reporting on thiosemicarbazone-based complexes with medicinal applications [12][13][14][15][16][17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Biological Applications of Thiocarbohydrazones and Their Metal Complexes: A Perspective Review

2019

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Although organic compounds account for more than 99% of currently approved clinical drugs, the established clinical use of cisplatin in cancer or auranofin in rheumatoid arthritis have paved the way to several research initiatives to identify metal-based drugs for a wide range of human diseases. Nitrogen and sulfur donor ligands, characterized by different binding motifs, have been the subject in recent years of one of the main research areas in coordination chemistry. Among the nitrogen/sulfur compounds, very little is known about thiocarbohydrazones (TCH), the higher homologues of the well-known thiosemicarbazones (TSC), and their metal complexes. The extra hydrazine moiety provides the ligands of variable metal binding modes, structural diversity and promising biological implications. The interesting coordination chemistry of TCH has mainly been focused on symmetric derivatives, which are relatively simple to synthesize while few examples of asymmetric ligands have been reported. This informative review on TCHs and their metal complexes will be helpful for improving the design of metal-based pharmaceuticals for applications ranging from anticancer to antinfective therapy.

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Thiosemicarbazones with tyrosinase inhibitory activity

Abstract: Thiosemicarbazones reveal strong anti-tyrosinase activity.

Cited by 48 publications

References 85 publications

Bio-Applications of Multifunctional Melanin Nanoparticles: From Nanomedicine to Nanocosmetics

Bio-Applications of Multifunctional Melanin Nanoparticles: From Nanomedicine to Nanocosmetics

Phosphonic and Phosphinic Acid Derivatives as Novel Tyrosinase Inhibitors: Kinetic Studies and Molecular Docking

Biological Applications of Thiocarbohydrazones and Their Metal Complexes: A Perspective Review

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