Paweł Misiak | University of Bialystok (original) (raw)

Papers by Paweł Misiak

Research paper thumbnail of Optimization of Multilayer Films Composed of Chitosan and Low-Methoxy Amidated Pectin as Multifunctional Biomaterials for Drug Delivery

International Journal of Molecular Sciences

Polyelectrolyte multilayers (PEMs) based on polyelectrolyte complex (PEC) structures are recogniz... more Polyelectrolyte multilayers (PEMs) based on polyelectrolyte complex (PEC) structures are recognized as interesting materials for manufacturing functionalized coatings or drug delivery platforms. Difficulties in homogeneous PEC system development generated the idea of chitosan (CS)/low-methoxy amidated pectin (LM PC) multilayer film optimization with regard to the selected variables: the polymer ratio, PC type, and order of polymer mixing. Films were formulated by solvent casting method and then tested to characterize CS/LM PC PECs, using thermal analysis, Fourier transform infrared spectroscopy (FTIR), turbidity, and zeta potential measurements. The internal structure of the films was visualized by using scanning electron microscopy. Analysis of the mechanical and swelling properties enabled us to select the most promising formulations with high uniformity and mechanical strength. Films with confirmed multilayer architecture were indicated as a promising material for the multifuncti...

Research paper thumbnail of Doxorubicin-loaded polymeric nanoparticles containing ketoester-based block and cholesterol moiety as specific vehicles to fight estrogen-dependent breast cancer

Cancer Nanotechnology

The presented research concerns the preparation of polymer nanoparticles (PNPs) for the delivery ... more The presented research concerns the preparation of polymer nanoparticles (PNPs) for the delivery of doxorubicin. Several block and statistical copolymers, composed of ketoester derivative, N-isopropylacrylamide, and cholesterol, were synthesized. In the nanoprecipitation process, doxorubicin (DOX) molecules were kept in spatial polymeric systems. DOX-loaded PNPs show high efficacy against estrogen-dependent MCF-7 breast cancer cell lines despite low doses of DOX applied and good compatibility with normal cells. Research confirms the effect of PNPs on the degradation of the biological membrane, and the accumulation of reactive oxygen species (ROS), and the ability to cell cycle arrest are strictly linked to cell death. Graphical Abstract

Research paper thumbnail of Additional file 1 of Synergistic effect of folate-conjugated polymers and 5-fluorouracil in the treatment of colon cancer

Additional file 1: Table S1. Synthesis details of the PHEA-b-PNVCL conjugation with folic acid. F... more Additional file 1: Table S1. Synthesis details of the PHEA-b-PNVCL conjugation with folic acid. Figure S1. 1H NMR spectrum of PX-4 in DMSO-d6. Figure S2. 1H NMR spectrum of PHEA (DMSO-d6, 400 MHz). Figure S3. 1H NMR spectrum of PHEA-b-PNVCL (DMSO-d6, 400 MHz). Figure S4. FT IR spectra of PX-0, PX-1, PX-2, PX-3, PX-4, and folic acid. Figure S5. UV–Vis spectra of PX-0, PX-1, PX-2, PX-3, and PX-4 polymers. Figure S6. (A) The calibration curve of FA absorbance at 280 nm in distilled H2O vs. concentration and (B) calculations of exact folic acid content in polymers. Figure S7. (A) SEC-RI and (B) SEC-UV traces of PHEA-b-PVCL copolymer before and after post-modification with folic acid. Figure S8. (A) TGA and (B) DTG curves of FA, PHEA-b-PNVCL, and folate-conjugated polymers.

Research paper thumbnail of Membrane-active diacylglycerol-terminated thermoresponsive polymers: RAFT synthesis and biocompatibility evaluation

European Polymer Journal, 2022

Research paper thumbnail of Evaluation of Cytotoxic Effect of Cholesterol End-Capped Poly(N-Isopropylacrylamide)s on Selected Normal and Neoplastic Cells

International Journal of Nanomedicine, 2020

Purpose: Efficient intracellular delivery of a therapeutic compound is an important feature of sm... more Purpose: Efficient intracellular delivery of a therapeutic compound is an important feature of smart drug delivery systems (SDDS). Modification of a carrier structure with a cellpenetrating ligand, ie, cholesterol moiety, is a strategy to improve cellular uptake. Cholesterol end-capped poly(N-isopropylacrylamide)s offer a promising foundation for the design of efficient thermoresponsive drug delivery systems. Methods: A series of cholesterol end-capped poly(N-isopropylacrylamide)s (PNIPAAm) with number-average molar masses ranging from 3200 to 11000 g•mol-1 were synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization from original xanthate-functionalized cholesterol and self-assembled into micelles. The physicochemical characteristics and cytotoxicity of cholesterol end-capped poly(N-isopropylacrylamide)s have been thoroughly investigated. Results: Phase transition temperature dependence on the molecular weight and hydrophilic/ hydrophobic ratio in the polymers were observed in water. Biological test results showed that the obtained materials, both in disordered and micellar form, are non-hemolytic, highly compatible with fibroblasts, and toxic to glioblastoma cells. It was found that the polymer termini dictates the mode of action of the system. Conclusion: The cholesteryl moiety acts as a cell-penetrating agent, which enables disruption of the plasma membrane and in effect leads to the restriction of the tumor growth. Cholesterol end-capped PNIPAAm showing in vitro anticancer efficacy can be developed not only as drug carriers but also as components of combined/synergistic therapy.

Research paper thumbnail of Doxorubicin delivery systems with an acetylacetone-based block in cholesterol-terminated copolymers: diverse activity against estrogen-dependent and estrogen-independent breast cancer cells

Chemistry and Physics of Lipids

Research paper thumbnail of Characterization of Nanofluids Using Multifractal Analysis of a Liquid Droplet Trace

This paper presents a novel approach to the analysis of nanofluids by using a nonlinear multifrac... more This paper presents a novel approach to the analysis of nanofluids by using a nonlinear multifractal algorithm. Multifractal analysis allows to present detailed local descriptions of complex scaling behavior using a spectrum of singularity exponents. Nanoliquids prepared from nanoparticles of SiO2 (~0,01g) suspended in 100 ml of demineralized water and in 100 ml of 99,5% isopropanol were subjected to classical methods of analysis: determination of the contact angle, determination of the zeta potential, pH, and examination with a particle size analyzer. The obtained results show that the obtained nanofluid is stable and well prepared, while further nonlinear analyzes show that the usage of multifractal analysis for nanofluids can significantly improve both the process of analyzing this issue as well as its preparation, based on the multifractional spectrum.

Research paper thumbnail of Synergistic effect of folate-conjugated polymers and 5-fluorouracil in the treatment of colon cancer

Cancer Nanotechnology

Background In recent years, targeted drug delivery strategies have received special attention fro... more Background In recent years, targeted drug delivery strategies have received special attention from the scientific world due to advantages such as more effective therapy and reduction of side effects. The principle of operation is delayed excretion from the bloodstream of the drug delivery system compared to the drug itself, as well as facilitated penetration into diseased cells thanks to the use of ligands recognized by appropriate receptors. Particularly interesting drug carriers are amphiphilic copolymers that form nano-sized micelles with a drug, which can release the drug at a specific place in the body under the influence of appropriate stimuli. Results We describe the synthesis of the diblock polymer, poly(2-hydroxyethyl acrylate)-b-poly(N-vinylcaprolactam) using RAFT/MADIX (Reversible Addition-Fragmentation chain Transfer/MAcromolecular Design by Interchange of Xanthate) controlled polymerization affording polymers with good dispersity according to SEC (Size-Exclusion Chromat...

Research paper thumbnail of Polymeric Drug Delivery Systems Bearing Cholesterol Moieties: A Review

Polymers

This review aims to provide an overview of polymers comprising cholesterol moiety/ies designed to... more This review aims to provide an overview of polymers comprising cholesterol moiety/ies designed to be used in drug delivery. Over the last two decades, there have been many papers published in this field, which are summarized in this review. The primary focus of this article is on the methods of synthesis of polymers bearing cholesterol in the main chain or as side chains. The data related to the composition, molecular weight, and molecular weight distribution of polymers are presented. Moreover, other aspects, such as forms of carriers, types of encapsulated drugs, encapsulation efficiency and capacity, are also included.

Research paper thumbnail of Susceptibility of microbial cells to the modified PIP2-binding sequence of gelsolin anchored on the surface of magnetic nanoparticles

Journal of Nanobiotechnology

Research paper thumbnail of Effects of nonionic sugar surfactants on the structure of model membranes

Research paper thumbnail of Does the Intramolecular Hydrogen Bond Affect the Spectroscopic Properties of Bicyclic Diazole Heterocycles?

Journal of Spectroscopy

The formation of an intramolecular hydrogen bond in pyrrolo[1,2-a]pyrazin-1(2H)-one bicyclic diaz... more The formation of an intramolecular hydrogen bond in pyrrolo[1,2-a]pyrazin-1(2H)-one bicyclic diazoles was analyzed, and the influence of N-substitution on HB formation is discussed in this study. B3LYP/aug-cc-pVDZ calculations were performed for the diazole, and the quantum theory of atoms in molecules (QTAIM) approach as well as the natural bond orbital (NBO) method was applied to analyze the strength of this interaction. It was found that the intramolecular hydrogen bond that closes an extra ring between the C=O proton acceptor group and the CH proton donor, that is, C=O⋯H–C, influences the spectroscopic properties of pyrrolopyrazine bicyclic diazoles, particularly the carbonyl frequencies. The influence of N-substitution on the aromaticity of heterocyclic rings is also discussed in this report.

Research paper thumbnail of Optimization of Multilayer Films Composed of Chitosan and Low-Methoxy Amidated Pectin as Multifunctional Biomaterials for Drug Delivery

International Journal of Molecular Sciences

Polyelectrolyte multilayers (PEMs) based on polyelectrolyte complex (PEC) structures are recogniz... more Polyelectrolyte multilayers (PEMs) based on polyelectrolyte complex (PEC) structures are recognized as interesting materials for manufacturing functionalized coatings or drug delivery platforms. Difficulties in homogeneous PEC system development generated the idea of chitosan (CS)/low-methoxy amidated pectin (LM PC) multilayer film optimization with regard to the selected variables: the polymer ratio, PC type, and order of polymer mixing. Films were formulated by solvent casting method and then tested to characterize CS/LM PC PECs, using thermal analysis, Fourier transform infrared spectroscopy (FTIR), turbidity, and zeta potential measurements. The internal structure of the films was visualized by using scanning electron microscopy. Analysis of the mechanical and swelling properties enabled us to select the most promising formulations with high uniformity and mechanical strength. Films with confirmed multilayer architecture were indicated as a promising material for the multifuncti...

Research paper thumbnail of Doxorubicin-loaded polymeric nanoparticles containing ketoester-based block and cholesterol moiety as specific vehicles to fight estrogen-dependent breast cancer

Cancer Nanotechnology

The presented research concerns the preparation of polymer nanoparticles (PNPs) for the delivery ... more The presented research concerns the preparation of polymer nanoparticles (PNPs) for the delivery of doxorubicin. Several block and statistical copolymers, composed of ketoester derivative, N-isopropylacrylamide, and cholesterol, were synthesized. In the nanoprecipitation process, doxorubicin (DOX) molecules were kept in spatial polymeric systems. DOX-loaded PNPs show high efficacy against estrogen-dependent MCF-7 breast cancer cell lines despite low doses of DOX applied and good compatibility with normal cells. Research confirms the effect of PNPs on the degradation of the biological membrane, and the accumulation of reactive oxygen species (ROS), and the ability to cell cycle arrest are strictly linked to cell death. Graphical Abstract

Research paper thumbnail of Additional file 1 of Synergistic effect of folate-conjugated polymers and 5-fluorouracil in the treatment of colon cancer

Additional file 1: Table S1. Synthesis details of the PHEA-b-PNVCL conjugation with folic acid. F... more Additional file 1: Table S1. Synthesis details of the PHEA-b-PNVCL conjugation with folic acid. Figure S1. 1H NMR spectrum of PX-4 in DMSO-d6. Figure S2. 1H NMR spectrum of PHEA (DMSO-d6, 400 MHz). Figure S3. 1H NMR spectrum of PHEA-b-PNVCL (DMSO-d6, 400 MHz). Figure S4. FT IR spectra of PX-0, PX-1, PX-2, PX-3, PX-4, and folic acid. Figure S5. UV–Vis spectra of PX-0, PX-1, PX-2, PX-3, and PX-4 polymers. Figure S6. (A) The calibration curve of FA absorbance at 280 nm in distilled H2O vs. concentration and (B) calculations of exact folic acid content in polymers. Figure S7. (A) SEC-RI and (B) SEC-UV traces of PHEA-b-PVCL copolymer before and after post-modification with folic acid. Figure S8. (A) TGA and (B) DTG curves of FA, PHEA-b-PNVCL, and folate-conjugated polymers.

Research paper thumbnail of Membrane-active diacylglycerol-terminated thermoresponsive polymers: RAFT synthesis and biocompatibility evaluation

European Polymer Journal, 2022

Research paper thumbnail of Evaluation of Cytotoxic Effect of Cholesterol End-Capped Poly(N-Isopropylacrylamide)s on Selected Normal and Neoplastic Cells

International Journal of Nanomedicine, 2020

Purpose: Efficient intracellular delivery of a therapeutic compound is an important feature of sm... more Purpose: Efficient intracellular delivery of a therapeutic compound is an important feature of smart drug delivery systems (SDDS). Modification of a carrier structure with a cellpenetrating ligand, ie, cholesterol moiety, is a strategy to improve cellular uptake. Cholesterol end-capped poly(N-isopropylacrylamide)s offer a promising foundation for the design of efficient thermoresponsive drug delivery systems. Methods: A series of cholesterol end-capped poly(N-isopropylacrylamide)s (PNIPAAm) with number-average molar masses ranging from 3200 to 11000 g•mol-1 were synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization from original xanthate-functionalized cholesterol and self-assembled into micelles. The physicochemical characteristics and cytotoxicity of cholesterol end-capped poly(N-isopropylacrylamide)s have been thoroughly investigated. Results: Phase transition temperature dependence on the molecular weight and hydrophilic/ hydrophobic ratio in the polymers were observed in water. Biological test results showed that the obtained materials, both in disordered and micellar form, are non-hemolytic, highly compatible with fibroblasts, and toxic to glioblastoma cells. It was found that the polymer termini dictates the mode of action of the system. Conclusion: The cholesteryl moiety acts as a cell-penetrating agent, which enables disruption of the plasma membrane and in effect leads to the restriction of the tumor growth. Cholesterol end-capped PNIPAAm showing in vitro anticancer efficacy can be developed not only as drug carriers but also as components of combined/synergistic therapy.

Research paper thumbnail of Doxorubicin delivery systems with an acetylacetone-based block in cholesterol-terminated copolymers: diverse activity against estrogen-dependent and estrogen-independent breast cancer cells

Chemistry and Physics of Lipids

Research paper thumbnail of Characterization of Nanofluids Using Multifractal Analysis of a Liquid Droplet Trace

This paper presents a novel approach to the analysis of nanofluids by using a nonlinear multifrac... more This paper presents a novel approach to the analysis of nanofluids by using a nonlinear multifractal algorithm. Multifractal analysis allows to present detailed local descriptions of complex scaling behavior using a spectrum of singularity exponents. Nanoliquids prepared from nanoparticles of SiO2 (~0,01g) suspended in 100 ml of demineralized water and in 100 ml of 99,5% isopropanol were subjected to classical methods of analysis: determination of the contact angle, determination of the zeta potential, pH, and examination with a particle size analyzer. The obtained results show that the obtained nanofluid is stable and well prepared, while further nonlinear analyzes show that the usage of multifractal analysis for nanofluids can significantly improve both the process of analyzing this issue as well as its preparation, based on the multifractional spectrum.

Research paper thumbnail of Synergistic effect of folate-conjugated polymers and 5-fluorouracil in the treatment of colon cancer

Cancer Nanotechnology

Background In recent years, targeted drug delivery strategies have received special attention fro... more Background In recent years, targeted drug delivery strategies have received special attention from the scientific world due to advantages such as more effective therapy and reduction of side effects. The principle of operation is delayed excretion from the bloodstream of the drug delivery system compared to the drug itself, as well as facilitated penetration into diseased cells thanks to the use of ligands recognized by appropriate receptors. Particularly interesting drug carriers are amphiphilic copolymers that form nano-sized micelles with a drug, which can release the drug at a specific place in the body under the influence of appropriate stimuli. Results We describe the synthesis of the diblock polymer, poly(2-hydroxyethyl acrylate)-b-poly(N-vinylcaprolactam) using RAFT/MADIX (Reversible Addition-Fragmentation chain Transfer/MAcromolecular Design by Interchange of Xanthate) controlled polymerization affording polymers with good dispersity according to SEC (Size-Exclusion Chromat...

Research paper thumbnail of Polymeric Drug Delivery Systems Bearing Cholesterol Moieties: A Review

Polymers

This review aims to provide an overview of polymers comprising cholesterol moiety/ies designed to... more This review aims to provide an overview of polymers comprising cholesterol moiety/ies designed to be used in drug delivery. Over the last two decades, there have been many papers published in this field, which are summarized in this review. The primary focus of this article is on the methods of synthesis of polymers bearing cholesterol in the main chain or as side chains. The data related to the composition, molecular weight, and molecular weight distribution of polymers are presented. Moreover, other aspects, such as forms of carriers, types of encapsulated drugs, encapsulation efficiency and capacity, are also included.

Research paper thumbnail of Susceptibility of microbial cells to the modified PIP2-binding sequence of gelsolin anchored on the surface of magnetic nanoparticles

Journal of Nanobiotechnology

Research paper thumbnail of Effects of nonionic sugar surfactants on the structure of model membranes

Research paper thumbnail of Does the Intramolecular Hydrogen Bond Affect the Spectroscopic Properties of Bicyclic Diazole Heterocycles?

Journal of Spectroscopy

The formation of an intramolecular hydrogen bond in pyrrolo[1,2-a]pyrazin-1(2H)-one bicyclic diaz... more The formation of an intramolecular hydrogen bond in pyrrolo[1,2-a]pyrazin-1(2H)-one bicyclic diazoles was analyzed, and the influence of N-substitution on HB formation is discussed in this study. B3LYP/aug-cc-pVDZ calculations were performed for the diazole, and the quantum theory of atoms in molecules (QTAIM) approach as well as the natural bond orbital (NBO) method was applied to analyze the strength of this interaction. It was found that the intramolecular hydrogen bond that closes an extra ring between the C=O proton acceptor group and the CH proton donor, that is, C=O⋯H–C, influences the spectroscopic properties of pyrrolopyrazine bicyclic diazoles, particularly the carbonyl frequencies. The influence of N-substitution on the aromaticity of heterocyclic rings is also discussed in this report.