Related to the article: [https://hdl.handle.net/21.15107/rcub_dais_9814]Supplementary data for: [https://doi.org/10.1039/D0RA08085C

Ignjatović, Nenad

Janković, Nenad

Marković, Smilja

Ristovski (Trifunović), Jovana

Žižak, Željko

RSC Advances

PubMed

H and 13C NMR spectraRelated to the article: [https://hdl.handle.net/21.15107/rcub_dais_9814]Supplementary data for: [https://doi.org/10.1039/D0RA08085C

Serbian Academy of Science and Arts Digital Archive (DAIS)

RSC AdvancesElectronic Supplementary Information associated with the paperChitosan nanobeads loaded with Biginelli hybrids as cell-selective toxicity systems with a homogeneous distribution of the cell cycle in cancer treatment Jovana Ristovski(Trifunović),a Željko Žizak,b Smilja Marković,c Nenad Jankovićd* and Nenad Ignjatovićc*aDepartment of Pharmacology, Toxicology and Clinical Pharmacology, Faculty of Medicine, University of Novi Sad, SerbiabInstitute of Oncology and Radiology of Serbia, Pasterova 14, 11000, Belgrade Serbia.cInstitute of Technical Sciences of the Serbian Academy of Science and Arts, Knez Mihailova 35/IV, P.O. Box 377, 11000, Belgrade, Serbia.d University of Kragujevac, Institute for Information of Technologies Kragujevac, Department of Science, Jovana Cvijića bb, 34000 Kragujevac, Serbia. Corresponding author’s e-mail addresses: nenad.jankovic@kg.ac.rs and nenad.ignjatovic@itn.sanu.ac.rsElectronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 202021H and 13C NMR spectra of A, B and C                                                                                                                  Ethyl 6-chloromethyl-1-methyl-2-oxo-4-(4′-hydroxy-3′-methoxyphenyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate (A)Figure S1 1H NMR spectrum of AFigure S2 13C NMR spectrum of A3Ethyl 6- (chloromethyl)-1-methyl-2-oxo-4-(4′-benzyloxyphenyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate (B)Figure S3 1H NMR spectrum of BFigure S4 13C NMR spectrum of B4Ethyl 6-chloromethyl-1-methyl-2-oxo-4-(4′-hydroxy-5′-iodo-3′-methoxyphenyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate (C)Figure S5 1H NMR spectrum of CFigure S6 13C NMR spectrum of C

Electronic Supplementary Information associated with the paper: Ristovski (Trifunović), J., Žižak, Ž., Marković, S., Janković, N., Ignjatović, N., 2020. Chitosan nanobeads loaded with Biginelli hybrids as cell-selective toxicity systems with a homogeneous distribution of the cell cycle in cancer treatment. RSC Adv. 10, 41542–41550. https://doi.org/10.1039/D0RA08085C

Tetrahydropyrimidines are a class of azaheterocycles, also called Biginelli hybrids (obtained from the Biginelli reaction), that have attracted an enormous interest in the medicinal chemistry community in recent years, due to a broad biological activity, such as anticancer, antiviral, anti-inflammatory, antidiabetic, antituberculosis activities, etc. According to SciFinder®, more than 70 000 different Biginelli-like compounds have been covered in publications. However, although the Biginelli reaction can yield a large number of compounds with a broad range of activities, none of them have been captured in a carrier. In this study, chitosan-based (Ch) nanoparticles (NPs) containing three different molecules (Biginelli hybrids) were developed and tested for the first time as simple and promising vehicles for anticancer Biginelli-based drugs. The key features of NPs, such as size, surface morphology, drug encapsulation efficiency, and in vitro release were systematically investigated. Rather weak cell selectivity of pure Biginelli hybrids (A–C) to selected cancer cell lines has improved and this has been accompanied with two-to-four times stronger cytotoxic effect of A–C loaded Ch NPs, with a triple reduction in toxicity to healthy cells (MRC-5). It has been observed that the examined NPs induce apoptosis. The cell cycle analysis has confirmed the influence of A-loaded Ch (A-Ch), B-loaded Ch (B-Ch), and C-loaded Ch (C-Ch) on the cell cycle distribution, which was homogenously affected. This is the difference with regard to the effect of A, B, and C on the cell cycle. It has been established that the increased selectivity and antitumor activity of NPs are related to the presence of the carrier

PubMed Central

Chitosan nanobeads loaded with Biginelli hybrids as cell-selective toxicity systems with a homogeneous distribution of the cell cycle in cancer treatment

Tetrahydropyrimidines are a class of azaheterocycles, also called Biginelli hybrids (obtained from the Biginelli reaction), that have attracted an enormous interest in the medicinal chemistry community in recent years, due to a broad biological activity, such as anticancer, antiviral, anti-inflammatory, antidiabetic, antituberculosis activities, etc. According to SciFinder®, more than 70 000 different Biginelli-like compounds have been covered in publications. However, although the Biginelli reaction can yield a large number of compounds with a broad range of activities, none of them have been captured in a carrier. In this study, chitosan-based (Ch) nanoparticles (NPs) containing three different molecules (Biginelli hybrids) were developed and tested for the first time as simple and promising vehicles for anticancer Biginelli-based drugs. The key features of NPs, such as size, surface morphology, drug encapsulation efficiency, and in vitro release were systematically investigated. Rather weak cell selectivity of pure Biginelli hybrids (A–C) to selected cancer cell lines has improved and this has been accompanied with two-to-four times stronger cytotoxic effect of A–C loaded Ch NPs, with a triple reduction in toxicity to healthy cells (MRC-5). It has been observed that the examined NPs induce apoptosis. The cell cycle analysis has confirmed the influence of A-loaded Ch (A-Ch), B-loaded Ch (B-Ch), and C-loaded Ch (C-Ch) on the cell cycle distribution, which was homogenously affected. This is the difference with regard to the effect of A, B, and C on the cell cycle. It has been established that the increased selectivity and antitumor activity of NPs are related to the presence of the carrier.Supplementary material: [https://hdl.handle.net/21.15107/rcub_dais_9815

http://dais.sanu.ac.rs/bitstream/id/40695/Ristovski_RSC-Advances_2020.pdf

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