Can QSAR Models Describing Small‐Molecule Xenobiotics Give Useful Tips for Predicting Uptake and Localization of Nanoparticles in Living Cells? And If Not, Why Not?

Horobin, Richard W.

doi:10.1002/9780470875780.ch11

Cited by 13 publications

(5 citation statements)

References 47 publications

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“…Regarding lysosomes, they finally become multivesicular or residual bodies (often containing lipofuscins and myelin figures) when their contents are indigestible materials, and they are not generally extruded to the outside but normally remain indefinitely within cells (Pitt, 1975). The fate of possible degradation products from boron compounds would be the same as colloidal metals, metal oxides, carbon, polymeric nanoparticles, vital dyes and fluorescent probes, which are selectively accumulated within lysosomes and melanosomes (Allison, 1968;Rashid et al, 1991;Horobin, 2010;.…”

Section: Resultsmentioning

confidence: 99%

In vivo polymerization of the dopamine-borate melanin precursor: A proof-of-concept regarding boron neutron-capture therapy for melanoma

Stockert¹,

ROMERO²,

Felix-Pozzi³

et al. 2023

Biocell

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The 10 boron neutron-capture therapy (BNCT) is an emerging antitumoral method that shows increasing biomedical interest. BNCT is based on the selective accumulation of the 10 boron isotope within the tumor, which is then irradiated with low-energy thermal neutrons, generating nuclear fission that produces 7 lithium, 4 helium, and γ rays. Simple catechol-borate esters have been rather overlooked as precursors of melanin biosynthesis, and therefore, a proof-of-concept approach for using dopamine-borate (DABO) as a suitable boron-containing candidate for potential BNCT is presented here. DABO can spontaneously oxidize and autopolymerize in vitro, giving a soluble, eumelaninlike brown-black poly-DABO product. Melanotic melanoma cell cultures treated with 1 mM DABO for 24 and 48 h were viable and showed no signs of damage or cell death. The stability and possible trans-esterification of DABO is shortly discussed. Chemical calculations and quantitative structure-activity relationships (QSAR) analysis of DABO and the BNCT agent BPA indicated that they should be cell permeant and accumulate within lysosomes and melanosomes. Molecular modeling allows visualization of both the DABO precursor and the structure of a borate derivative of the proposed catechol-porphycene model for eumelanin, showing interesting features from molecular orbital calculations. The main difference between DABO and other agents, such as BPA, is that it is not a boronic acid nor a boron cluster. This simple catechol-borate ester (protected from oxidation and blackening) could be administrated to living cells and organisms, in which biosynthesis of boron-melanin in melanoma melanocytes can lead to improved BNCT.

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Section: Resultsmentioning

confidence: 99%

In vivo polymerization of the dopamine-borate melanin precursor: A proof-of-concept regarding boron neutron-capture therapy for melanoma

Stockert¹,

ROMERO²,

Felix-Pozzi³

et al. 2023

Biocell

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“…The morphology, size, and surface charge affect the ability of polymeric nanoparticles for internalization into cancer cells 43, 44. The mechanisms of cellular internalization nanoparticles include merging with cellular membranes or uptake by endocytosis 45–47. The preferential accumulation of nanoparticles in tumor tissues is known as the enhanced permeability and retention (EPR) effect 48.…”

Section: Resultsmentioning

confidence: 99%

Encapsulation of Quercetin in a Mixed Nanomicellar System to Enhance its Cytotoxicity against Breast Cancer Cells

et al. 2022

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The therapeutic potential of quercetin-loaded Pluronic F-127 (PF-127)/Tween 80 mixed nanomicelles as a passive targeted drug delivery system for breast cancer therapy is evaluated. Quercetin-loaded mixed nanomicelles with different mass ratios of drug/PF-127/Tween 80 were prepared by thin-film hydration method. The physical interactions of quercetin with PF-127 and Tween 80 in an optimal ratio were investigated. The results of in vitro drug release experiments showed that the mixed micellar system exhibits a prolonged and sustained release behavior compared to the solution of free quercetin. The in vitro cytotoxicity studies of quercetin-loaded mixed nanomicelles on breast cancer cells revealed that the encapsulated drug has a lower half-maximal inhibitory concentration (IC 50 ) value compared to the free drug.

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“…The main vital probes are acridine orange, acridine yellow, alizarin, auramine O, 3,4-benzpyrene, Bismarck brown, brilliant cresyl blue, coupled azo dyes, eosin Y, erythrosin B, euchrysine 3R, Evans blue, FITC-dextran, fluores-cein, hematein and hematoxylin, hydroethidine, inorganic nanoparticles, Lucifer yellow CH, methylene blue, neocyanine, neutral red, Nile blue, phloxine B, phosphine, primulin, proflavine, purpurin, quinacrine, thionine, toluidine blue, trypan blue, etc. [5,18,[130][131][132][133][134][135][136][137][138][139]. Numerous lysosome probes are also efficient photosensitizers for photodynamic therapy (PDT) [140,141].…”

Section: Lysosome and Melanosome Labelingmentioning

confidence: 99%

“…TiO 2 nanoparticles subjected to US (1 MHz, 1 W/cm 2 , 2 min) produced significant regression of the C32 melanoma [193]. It is tempting to assume that generic biomembranes and lysosome uptake of nanoparticles [138], and piezoelectric activity of TiO 2 are involved in the therapeutic response. As xanthene colorants accumulate into lysosomes, it would be expected that rose Bengal could also label melanosomes.…”

Section: Melanoma and Ultrasound Therapymentioning

confidence: 99%

Melanin-Binding Colorants: Updating Molecular Modeling, Staining and Labeling Mechanisms, and Biomedical Perspectives

2022

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Melanin and melanoma tumors are two fields of increasing interest in biomedical research. Melanins are ubiquitous biopigments with adaptive value and multiple functions, and occur in the malignant melanoma. Although several chemical structures have been proposed for eumelanin, molecular modeling and orbitals indicate that a planar or spiral benzoquinone-porphycene polymer would be the model that better explains the broad-band light and ultrasound absorption, electric conductivity, and graphite-like organization shown by X-ray crystallography and electron microscopy. Lysosomes and melanosomes are selectively labeled by vital probes, and melanin also binds to metal cations, colorants, and drugs, with important consequences in pharmacology, pathology, and melanoma therapy. In addition to traditional and recent oncologic treatments, photodynamic, photothermal, and ultrasound protocols represent novel modalities for melanoma therapy. Since eumelanin is practically the ideal photothermal and ultrasound sensitizer, the vibrational decay from photo-excited electrons after NIR irradiation, or the electrochemical production of ROS and radicals after ultrasound absorption, induce an efficient heating or oxidative response, resulting in the damage and death of tumor cells. This allows repetitive treatments due to the remaining melanin contained in tumoral melanophages. Given that evolution and prognosis of the advanced melanoma is still a concern, new biophysical procedures based on melanin properties can now be developed and applied.

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Can QSAR Models Describing Small‐Molecule Xenobiotics Give Useful Tips for Predicting Uptake and Localization of Nanoparticles in Living Cells? And If Not, Why Not?

Cited by 13 publications

References 47 publications

In vivo polymerization of the dopamine-borate melanin precursor: A proof-of-concept regarding boron neutron-capture therapy for melanoma

In vivo polymerization of the dopamine-borate melanin precursor: A proof-of-concept regarding boron neutron-capture therapy for melanoma

Encapsulation of Quercetin in a Mixed Nanomicellar System to Enhance its Cytotoxicity against Breast Cancer Cells

Melanin-Binding Colorants: Updating Molecular Modeling, Staining and Labeling Mechanisms, and Biomedical Perspectives

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