Unusual Enhancement of Doxorubicin Activity on Co-Delivery with Polyhedral Oligomeric Silsesquioxane (POSS)

Sobierajska, Ewelina; Konopka, Małgorzata; Janaszewska, Anna; Piorecka, Kinga; Błauż, Andrzej; Klajnert‐Maculewicz, Barbara; Stańczyk, M.; Stańczyk, Włodzimierz A.

doi:10.3390/ma10050559

Cited by 13 publications

(18 citation statements)

References 26 publications

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“…Thus, half maximal inhibitory concentration (IC 50 ) values for the POSS:DOX complex towards MCF-7 and HeLa cell lines were, respectively, 2.69 ± 0.15 and 0.92 ± 0.09 µM•L −1 , compared with 17.44 ± 5.23 and 1.45 ± 0.15 µM•L −1 for DOX itself. These findings pointed to increased transport effectiveness of DOX to the cells by means of octa(3-aminopropyl)silsesquioxane as the complexing nanocarrier [14]. Similar anti-cancer activity enhancement had been reported earlier by Ohta et al [15] for the interaction of amino-modified silicon quantum dots (Si-QDs) and DOX.…”

Section: Introductionsupporting

confidence: 84%

“…Figure 8 shows the cellular uptake of the selected most effective complexes by HeLa and MCF-7 cells. As in previous studies, cellular uptake of POSS complexed anthracyclines was higher than that of free drugs [14]. The MTT test using DAU was repeated with the same conditions and analogous complexes.…”

Section: Resultsmentioning

confidence: 70%

“…Materials 2020, 13, x; doi: FOR PEER REVIEW www.mdpi.com/journal/materials previous studies, cellular uptake of POSS complexed anthracyclines was higher than that of free drugs [14]. Figure 7.…”

Section: Resultsmentioning

confidence: 91%

“…However, we obtained such information from FTIR analysis because it clearly indicates that there are interactions of anthracycline OHAr groups with POSS. The decrease in the absorption intensity indicates the interaction of DOX/DAU with POSS via hydrogen bonding between the OH groups in the anthraquinone ring with the POSS OH moieties [14]. Moreover, IR spectra revealed that POSS strongly interacts with DOX via interaction of glycosidic and ketone oxygens and, as mentioned…”

Section: Discussionmentioning

confidence: 87%

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Hydrophilic Polyhedral Oligomeric Silsesquioxane, POSS(OH)32, as a Complexing Nanocarrier for Doxorubicin and Daunorubicin

et al. 2020

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A novel strategy, recently developed by us, to use polyhedral oligomeric silsesquioxanes (POSS) as an anti-cancer drug carrier is presented. Anthracycline:POSS complexes were prepared by simple co-addition of doxorubicin (DOX) or daunorubicin (DAU) with hydrophilic POSS(OH)32. Co-delivery of POSS and anthracyclines led to higher anti-cancer activity towards HeLa (cervical cancer endothelial) and MCF-7 (human breast adenocarcinoma) cell lines. The obtained supramolecular hybrid complexes were characterised by nuclear magnetic resonance (NMR) spectroscopy (nuclear Overhauser effect spectroscopy [NOESY] and homonuclear correlation spectroscopy [COSY]), Fourier transform infrared spectroscopy (FTIR), and dynamic light scattering (DLS). The two-dimensional (2D) NOESY spectra of the complexes showed the cross-correlation peaks for hydroxyl groups of POSS (~4.3–4.8 ppm) with OH groups of DOX and DAU. FTIR showed that hydroxyl group of POSS can interact with amine and hydroxyl groups of DOX and DAU. The viability of HeLa and MCF-7 was analysed with the MTT assay to evaluate the cytotoxicity of free DOX and DAU and the relevant complexes with POSS at different molar ratios. At a low DOX concentration (2.5 µM), for molar ratios 1:1, 1:4, and 1:8 (POSS:DOX), the complexes showed two and three times higher cytotoxicity towards HeLa and MCF-7 cells, respectively, than DOX itself after both 24- and 48-h incubation. The 1 µM concentration for a 1:4 POSS:DOX molecular ratio and the 2.5 µM concentration for all complexes were more toxic towards MCF-7 cells than free DOX after 48-h incubation. In the case of POSS:DAU complexes, there was higher toxicity than that of free drug after 48-h incubation. It can be concluded that the formation of non-covalent complexes increases toxicity of anthracycline drugs towards Hela and MCF-7 cells. The novel complexes are inexpensive to prepare and more effective than free drugs at low systemic toxicity.

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Section: Introductionsupporting

confidence: 84%

Section: Resultsmentioning

confidence: 70%

Section: Resultsmentioning

confidence: 91%

Section: Discussionmentioning

confidence: 87%

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Hydrophilic Polyhedral Oligomeric Silsesquioxane, POSS(OH)32, as a Complexing Nanocarrier for Doxorubicin and Daunorubicin

et al. 2020

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“…In the preliminary phase of this effort, we evaluated the cytotoxic activities of 7a-u towards three human cancer cell lines including HCT-116 (colon cancer), MF-7 (breast cancer) and A549 (lung cancer), in addition to the normal human cell line MCF10A (breast cell line). This assessment was performed using the standard MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] colorimetric assay 32,33 , and utilizes doxorubicin as a reference anti-cancer agent [34][35][36][37][38] . For this purpose, three independent determinations were made using treatments with three concentrations (12.5, 25 and 50 μM) of 7a-u for a 48 h incubation period.…”

Section: Resultsmentioning

confidence: 99%

The first Q-Tube based high-pressure synthesis of anti-cancer active thiazolo[4,5-c]pyridazines via the [4 + 2] cyclocondensation of 3-oxo-2-arylhydrazonopropanals with 4-thiazolidinones

Ibrahim

Behbehani

2020

Sci Rep

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A novel and efficient protocol for the synthesis of thiazolo[4,5-c]pyridazine derivatives was developed. The approach utilizes a high pressure Q-Tube reactor to promote cyclocondensation reactions between 3-oxo-2-arylhydrazonopropanals and 4-thiazolidinones. The process has a significantly high atom economy and a broad substrate scope, as well as being applicable to gram scale syntheses. The in vitro cytotoxic activities of the synthesized thiazolo[4,5-c]pyridazine derivatives were examined utilizing a MTT colorimetric assay with doxorubicin as a reference anti-cancer drug and three human cancer cell lines including HCT-116 (colon), MCF-7 (breast) and A549 (lung). The results show that thiazolopyridazines 7c, h, k and p have high cytotoxic activity against the MCF-7 cell line with respective ic 50 values of 14.34, 10.39, 15.43 and 13.60 μM. Moreover, the thiazolopyridazine derivative 7s also show promising cytotoxic activity against the HCT-116 cell line with IC 50 = 6.90 μM . Observations made in this effort serve as a basis for further investigations into the design and preparation of new anti-cancer drugs.Thiazolopyridazine derivatives comprise a broad range of structurally interesting substances that display a variety of medicinally interesting properties including activities against cancers 1,2 , microbes 3,4 , viruses 5 and bacteria 6 , as well as antioxidant 7 , analgesic and pesticidal activities 8,9 . As a result of these important properties, thiazolopyridazines remain the focus of our continuing investigations aimed at developing new and green routes for the synthesis of novel fused nitrogen containing heterocycles [10][11][12][13][14][15][16][17][18] . Until now, several methods have been developed for the synthesis of fused thiazolopyridazines, most of which are targeted at the synthesis of thiazolo[4,5-d] pyridazines 1-3,5 , thiazolo[3,2-b]pyridazine 19 and thiazolo[5,4-c]pyridazine 6 . In contrast, current methods to prepare thiazolo [4,5-c]pyridazines are much less well-developed 20 , and they suffer from some major deficiencies. Specifically, the only method devised for this purpose involves reaction of pyridazine-3-carboxamide derivatives with Lawesson's reagent under reflux for 48 h, which forms mono-substituted thiazolo[4,5-c]pyridazines in only moderate yields (Scheme 1a) 20 .In the current study, we developed a novel and efficient green method for the synthesis members of a series o thiazolo[4,5-c]pyridazine derivatives. The new protocol, which involves cyclocondensation reactions between 4-thiazolidinones and 3-oxo-2-arylhydrazonopropanals utilizing a high pressure Q-Tube reactor, is simple and environmentally benign (Scheme 1b). In contrast to those utilizing microwave irradiation and conventional heating, processes carried out using the Q-Tube reactor employ a high pressures to promote organic reactions. Use of the Q-tube technique has many advantageous features 21-28 including higher yields, clean products, lower energy costs, lower reaction times and higher reproducibility than those as...

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Multifaceted applications of polyhedral oligomeric silsesquioxane and their composites

Kannan,

Muthuraj,

Mayavan

et al. 2023

Materials Today Chemistry

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Unusual Enhancement of Doxorubicin Activity on Co-Delivery with Polyhedral Oligomeric Silsesquioxane (POSS)

Cited by 13 publications

References 26 publications

Hydrophilic Polyhedral Oligomeric Silsesquioxane, POSS(OH)32, as a Complexing Nanocarrier for Doxorubicin and Daunorubicin

Hydrophilic Polyhedral Oligomeric Silsesquioxane, POSS(OH)32, as a Complexing Nanocarrier for Doxorubicin and Daunorubicin

The first Q-Tube based high-pressure synthesis of anti-cancer active thiazolo[4,5-c]pyridazines via the [4 + 2] cyclocondensation of 3-oxo-2-arylhydrazonopropanals with 4-thiazolidinones

Multifaceted applications of polyhedral oligomeric silsesquioxane and their composites

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