Browsing by Subject "NANOPARTICLES"

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  • Costa, Clarinda; Liu, Zehua; Martins, João Pedro; Correia, Alexandra; Rahikkala, Antti Tuomas Antero; Li, Wei; Seitsonen, Jani; Ruokolainen, Janne; Hirvonen, Sami-Pekka; Aguiar- Ricardo, Ana; Corvo, M. Luísa; Santos, Hélder A. (2020)
    Here, a continuous two-step glass-capillary microfluidic technique to produce a multistage oral delivery system is reported. Insulin is successfully encapsulated into liposomes, which are coated with chitosan to improve their mucoadhesion. The encapsulation in an enteric polymer offers protection from the harsh gastric conditions. Insulin permeability is enhanced across an intestinal monolayer.
  • Osipova, Olga; Sharoyko, Vladimir; Zashikhina, Natalia; Zakharova, Natalya; Tennikova, Tatiana; Urtti, Arto; Korzhikova-Vlakh, Evgenia (2020)
    Polyethyleneimine, poly-L-lysine, chitosan and some others cationic polymers have been thoroughly studied as nucleic acid delivery systems in gene therapy. However, the drug release from these systems proceeds at a very low rate due to extremely high binding between a carrier and gene material. To reduce these interactions and to enhance drug release, we developed a set of amphiphilic polypeptides containing positively and negatively charged amino acids as well as a hydrophobic one. The copolymers obtained were characterized by size-exclusion chromatography, static light scattering, HPLC amino acid analysis and (HNMR)-H-1 spectroscopy. All copolymers formed particles due to a self-assembly in aqueous media. Depending on polypeptide composition, the formation of particles with hydrodynamic diameters from 180 to 900 nm was observed. Stability of polymer particles, loading and release efficiency were carefully studied. Cellular uptake of the particles was efficient and their cytotoxicity was negligible. The application of polymer carriers, containing siRNA, to vascular endothelial growth factor (VEGF-A165) silencing of ARPE-19 cells was successful. The gene silencing was confirmed by suppression of both messenger RNA and protein expression.
  • Sakari Lintinen, Kalle; Luiro, Sanna; Figueiredo, Patricia; Sakarinen, Ekaterina; Mousavi, Zekra; Seitsonen, Jani; N. S. Rivière, Guillaume; Mattinen, Ulriika; Niemelä, Matti; Tammela, Päivi; Österberg, Monika; Johansson, Leena-Sisko; Bobacka, Johan; Santos, Hélder A.; A. Kostiainen, Mauri (2019)
    Acid-precipitated lignin nanoparticles with a cationic polymer coating exhibit antibacterial activity when infused with silver. While the use of such particles would be beneficial due to their high antibacterial activity with a low silver content, their production holds steps that are difficult to scale up to inexpensive industrial manufacture. For example, the production of acid-precipitated lignin nanoparticles requires the use of ethylene glycol, which is not easily recycled. Furthermore, the binding of silver to these particles is weak, and thus the particles need to be used rapidly after preparation. Here, we show that with a deprotonation reaction of an organic solution of anhydrous lignin and subsequent ion exchange with silver nitrate and colloid formation by solvent exchange, highly spherical silver carboxylate colloidal lignin particles (AgCLPs) can be prepared. Silver is not released from the particles in deionized water but can be released in physiological conditions, shown by their high antibacterial efficacy with low silver loading. In comparison to lignin nanoparticles with weakly bound silver, AgCLPs have high antibacterial activity even without cationic polyelectrolyte coating, and they retain their antibacterial activity for days. While the rapid depletion of silver from silver-infused lignin nanoparticles can be considered beneficial for some applications, the sustained antibacterial activity of the AgCLPs with ionically bound silver will enable their use in applications where silver nanoparticles have been previously used. Our results demonstrate that CLPs, which can be produced with a closed cycle process on a large scale, can be rapidly and quantitatively functionalized into active materials.
  • Ahmadian, Zainab; Rebelo Correia, Alexandra Maria; Hasany, Masoud; Figueiredo, Patricia; Dobakhti, Faramarz; Reza Eskandari, Mohammad; Hosseini, Seyed; Abiri, Ramin; Khorshid, Shiva; Hirvonen, Jouni; Santos, Hélder A.; Shahbazi, Mohammad-Ali (2021)
    Extracellular matrix‐mimicking hydrogels with antioxidant, hemostasis, and antibacterial properties offer translating avenues towards wound repair through the promotion of fibroblast proliferation. In article number 2001122 by Hélder A. Santos, Mohammad‐Ali Shahbazi, and co‐workers, hydrogen bonding among the functional groups of gelatin and tannic acid creates a biocompatible hydrogel, where the improvement of re‐epithelialization and collagen deposition are its main features to treat full‐thickness wounds.
  • Fusciello, Manlio; Fontana, Flavia; Tähtinen, Siri; Capasso, Cristian; Feola, Sara; da Silva Lopes Martins, Beatriz; Chiaro, Jacopo; Peltonen, Karita; Ylösmäki, Leena; Ylösmäki, Erkko; Hamdan Hissaoui, Firas; Kari, Otto K.; Ndika, Joseph; Alenius, Harri; Urtti, Arto; Hirvonen, Jouni T.; Santos, Hélder A.; Cerullo, Vincenzo (2019)
    Virus-based cancer vaccines are nowadays considered an interesting approach in the field of cancer immunotherapy, despite the observation that the majority of the immune responses they elicit are against the virus and not against the tumor. In contrast, targeting tumor associated antigens is effective, however the identification of these antigens remains challenging. Here, we describe ExtraCRAd, a multi-vaccination strategy focused on an oncolytic virus artificially wrapped with tumor cancer membranes carrying tumor antigens. We demonstrate that ExtraCRAd displays increased infectivity and oncolytic effect in vitro and in vivo. We show that this nanoparticle platform controls the growth of aggressive melanoma and lung tumors in vivo both in preventive and therapeutic setting, creating a highly specific anti-cancer immune response. In conclusion, ExtraCRAd might serve as the next generation of personalized cancer vaccines with enhanced features over standard vaccination regimens, representing an alternative way to target cancer.
  • Väyrynen, Katja; Hatanpää, Timo; Mattinen, Miika; Mizohata, Kenichiro; Meinander, Kristoffer; Räisänen, Jyrki; Link, Joosep; Stern, Raivo; Ritala, Mikko; Leskela, Markku (2019)
    Intermetallics form a versatile group of materials that possess unique properties ranging from superconductivity to giant magnetoresistance. The intermetallic Co-Sn and Ni-Sn compounds are promising materials for magnetic applications as well as for anodes in lithium- and sodium-ion batteries. Herein, a method is presented for the preparation of Co3Sn2 and Ni3Sn2 thin films using diamine adducts of cobalt(II) and nickel(II) chlorides, CoCl2(TMEDA) and NiCl2(TMPDA) (TMEDA = N,N,N ',N '-tetramethylethylenediamine, TMPDA = N,N,N ',N '-tetramethyl-1,3-propanediamine) combined with tributyltin hydride. The films are grown by atomic layer deposition (ALD), a technique that enables conformal film deposition with sub-nanometer thickness control. The Co3Sn2 process fulfills the typical ALD qualifications, such as self-limiting growth, excellent film uniformity, and conformal coverage of a trench structure. X-ray diffraction (XRD) shows reflections characteristic to the hexagonal Co3Sn2 phase, which confirms that the films are, indeed, intermetallic instead of being mere alloys of Co and Sn. The films are extremely pure with impurity levels each below 1.0 at.%. Ni3Sn2 films similarly exhibit the expected XRD reflections for the intermetallic phase and are of high purity. The Co3Sn2 film show magnetic hysteresis with high coercivity values exceeding 500 Oe, indicating great potential in terms of applicability of the films.
  • Fontana, Flavia; Fusciello, Manlio; Groeneveldt, Christianne; Capasso, Cristian; Chiaro, Jacopo; Feola, Sara; Liu, Zehua; Mäkilä, Ermei; Salonen, Jarno; Hirvonen, Jouni; Cerullo, Vincenzo; Santos, Hélder A. (2019)
    Recent approaches in the treatment of cancer focus on involving the immune system to control the tumor growth. The administration of immunotherapies, like checkpoint inhibitors, has shown impressive results in the long term survival of patients. Cancer vaccines are being investigated as further tools to prime tumor-specific immunity. Biomaterials show potential as adjuvants in the formulation of vaccines, and biomimetic elements derived from the membrane of tumor cells may widen the range of antigens contained in the vaccine. Here, we show how mice presenting an aggressive melanoma tumor model treated twice with the complete nanovaccine formulation showed control on the tumor progression, while in a less aggressive model, the animals showed remission and control on the tumor progression, with a modification in the immunological profile of the tumor microenvironment. We also prove that co-administration of the nanovaccine together with a checkpoint inhibitor increases the efficacy of the treatment (87.5% of the animals responding, with 2 remissions) compared to the checkpoint inhibitor alone in the B16.OVA model. Our platform thereby shows potential applications as a cancer nanovaccine in combination with the standard clinical care treatment for melanoma cancers.
  • Abu Saleh, Doaa; Niskanen, Jukka; Xue, Yanming; Golberg, Dmitri; Winnik, Francoise M.; Sosnik, Alejandro (2017)
    We report an organic-inorganic hybrid core-shell nanomaterial obtained by conjugation of an amphiphilic monomethoxy-poly(ethylene glycol)-b-poly(epsilon-caprolactone) diblock copolymer to hydroxylated boron nitride nanotubes (BNNTs). The extent of copolymer grafting reached 64% w/w, an exceptionally high value. The hybrid materials exhibit excellent physical stability in water and an outstanding loading capacity (31.3% w/w) for curcumin, a hydrophobic drug. Moreover, they present good compatibility with the Caco2 cell line, a model of intestinal epithelium. Our findings demonstrate the potential of multifunctional hybrid BNNTs to serve as a platform for complex amphiphilic nanoparticle architectures with improved features. (c) 2017 Elsevier Ltd. All rights reserved.
  • Quiroz, Jhon; de Oliveira, Paulo F. M.; Shetty, Shwetha; Oropeza, Freddy E.; de la Pena O'Shea, Victor A.; Rodrigues, Lucas C.; Rodrigues, Maria P. de S.; Torresi, Roberto Manuel; Emmerling, Franziska; Camargo, Pedro H. C. (2021)
    The localized surface plasmon resonance (LSPR) excitation in plasmonic nanoparticles (NPs) in the visible and near-infrared ranges is currently at the forefront of improving photocatalytic performances via plasmonic photocatalysis. One bottleneck of this field is that the NPs that often display the best optical properties in the visible and near-infrared ranges are based on expensive noble metals such as silver (Ag) and gold (Au). While earth-abundant plasmonic materials have been proposed together with catalytic metals in antenna-reactor systems, their performances remain limited by their optical properties. Importantly, the synthesis of plasmonic photocatalysts remains challenging in terms of scalability while often requiring several steps, high temperatures, and special conditions. Herein, we address these challenges by developing a one-pot, gram-scale, room-temperature synthesis of earth-abundant plasmonic photocatalysts while improving their activities beyond what has been dictated by the LSPR excitation of the plasmonic component. We describe the mechanochemical synthesis of earth-abundant plasmonic photocatalysts by using MoO3 (antenna) and Au (reactor) NPs as a proof-of-concept example and demonstrate that the dual plasmonic excitation of antenna and reactor sites enables the tuning of plasmonic photocatalytic performances toward the reductive coupling of nitrobenzene to azobenzene as a model reaction. In addition to providing a pathway to the facile and gramscale synthesis of plasmonic photocatalysts, the results reported herein may open pathways to improved activities in plasmonic catalysis.
  • Kinaret, Pia Anneli Sofia; Scala, Giovanni; Federico, Antonio; Sund, Jukka; Greco, Dario (2020)
    Toxic effects of certain carbon nanomaterials (CNM) have been observed in several exposure scenarios both in vivo and in vitro. However, most of the data currently available has been generated in a high-dose/acute exposure setup, limiting the understanding of their immunomodulatory mechanisms. Here, macrophage-like THP-1 cells, exposed to ten different CNM for 48 h in low-cytotoxic concentration of 10 mu g mL(-1), are characterized by secretion of different cytokines and global transcriptional changes. Subsequently, the relationships between cytokine secretion and transcriptional patterns are modeled, highlighting specific pathways related to alternative macrophage activation. Finally, time- and dose-dependent activation of transcription and secretion of M1 marker genes IL-1 beta and tumor necrosis factor, and M2 marker genes IL-10 and CSF1 is confirmed among the three most responsive CNM, with concentrations of 5, 10, and 20 mu g mL(-1) at 24, 48, and 72 h of exposure. These results underline CNM effects on the formation of cell microenvironment and gene expression leading to specific patterns of macrophage polarization. Taken together, these findings imply that, instead of a high and toxic CNM dose, a sub-lethal dose in controlled exposure setup can be utilized to alter the cell microenvironment and program antigen presenting cells, with fascinating implications for novel therapeutic strategies.
  • Ora, Ari; Järvihaavisto, Erika; Zhang, Hongbo; Auvinen, Henni; Santos, Helder A.; Kostiainen, Mauri A.; Linko, Veikko (2016)
    In this communication, we show that active enzymes can be delivered into HEK293 cells in vitro when they are attached to tubular DNA origami nanostructures. We use bioluminescent enzymes as a cargo and monitor their activity from a cell lysate. The results show that the enzymes stay intact and retain their activity in the transfection process. The method is highly modular, which makes it a compelling candidate for a great variety of delivery applications.
  • Cai, Runlong; Attoui, Michel; Jiang, Jingkun; Korhonen, Frans; Hao, Jiming; Petäjä, Tuukka; Kangasluoma, Juha (2018)
    Classifying sub-3 nm particles effectively with relatively high penetration efficiencies and sizing resolutions is important for atmospheric new particle formation studies. A high-resolution supercritical differential mobility analyzer (half-mini DMA) was recently improved to classify aerosols at a sheath flow rate less than 100 L/min. In this study, we characterized the transfer functions, the penetration efficiencies, and the sizing resolution of the new half-mini DMA at the aerosol flow rate of 2.5-10 L/min and the sheath flow rate of 25-250 L/min using tetra-alkyl ammonium ions and tungsten oxide particles. The transfer functions of the new half-mini DMA at an aerosol flow rate lower than 5 L/min and a sheath flow rate lower than 150 L/min agree well with predictions using a theoretical diffusing transfer function. The penetration efficiencies can be approximated using an empirical formula. When classifying 1.48 nm molecular ions at an aerosol-to-sheath flow ratio of 5/50 L/min, the penetration efficiency, the sizing resolution, and the multiplicative broadening factor of the new half-mini DMA are 0.18, 6.8, and 1.11, respectively. Compared to other sub-3 nm DMAs applied in atmospheric measurements (e.g. the mini-cyDMA, the TSI DMA 3086, the TSI nanoDMA 3085, and the Grimm S-DMA), the new half-mini DMA characterized in this study is able to classify particles at higher aerosol and sheath flow rates, leading to a higher sizing resolution at the same aerosol-to-sheath flow ratio. Accordingly, the new half-mini DMA can reduce the uncertainties in atmospheric new particle formation measurement if coupled with an aerosol detector that could work at the corresponding high aerosol flow rate. (c) 2018 American Association for Aerosol Research
  • Kangasluoma, Juha; Hering, Susanne; Picard, David; Lewis, Gregory; Enroth, Joonas; Korhonen, Frans; Kulmala, Markku; Sellegri, Karine; Attoui, Michel; Petäjä, Tuukka (2017)
    In this study we characterized the performance of three new particle counters able to detect particles smaller than 3 nm during the Helsinki condensation particle counter (CPC) workshop in summer 2016: the Aerosol Dynamics Inc. (ADI; Berkeley, USA) versatile water condensation particle counter (vWCPC), TSI 3777 nano enhancer (TSI Inc., Shoreview, USA) and modified and boosted TSI 3010-type CPC from Universite Blaise Pascal called a B3010. The performance of all CPCs was first measured with charged tungsten oxide test particles at temperature settings which resulted in supersaturation low enough to not detect any ions produced by a radioactive source. Due to similar measured detection efficiencies, additional comparison between the 3777 and vWCPC were conducted using electrically neutral tungsten oxide test particles and with positively charged tetradodecylammonium bromide. Furthermore, the detection efficiencies of the 3777 and vWCPC were measured with boosted temperature settings yielding supersaturation which was at the onset of homogeneous nucleation for the 3777 or confined within the range of liquid water for the ADI vWCPC. Finally, CPC-specific tests were conducted to probe the response of the 3777 to various inlet flow relative humidities, of the B3010 to various inlet flow rates and of the vWCPC to various particle concentrations. For the 3777 and vWCPC the measured 50% detection diameters (d50s) were in the range of 1.3-2.4 nm for the tungsten oxide particles, depending on the particle charging state and CPC temperature settings, between 2.5 and 3.3 nm for the organic test aerosol, and in the range of 3.2-3.4 nm for tungsten oxide for the B3010.
  • Liu, Zehua; Li, Yunzhan; Li, Wei; Lian, Wenhua; Kemell, Marianna; Hietala, Sami; Figueiredo, Patricia; Li, Li; Mäkilä, Ermei; Ma, Ming; Salonen, Jarno; Hirvonen, Jouni T.; Liu, Dongfei; Zhang, Hongbo; Deng, Xianming; Santos, Helder A. (2019)
    Here, an oxidation/acid dual-responsive nanohybrids/ark system was produced. The microfluidics-produced nanohybrids endow the system with an orchestrated cascade from wound detection, reactive oxygen species scavenging, drug release to hydrogel formation. The drug release behavior imitates the dynamic wound healing process, thus rendering an enhanced bio-mimetic regeneration.
  • Fang, Jiaxi; Wang, Yang; Kangasluoma, Juha; Attoui, Michel; Junninen, Heikki; Kulmala, Markku; Petäjä, Tuukka; Biswas, Pratim (2017)
    Few studies reported the formation of Ti-containing clusters in the initial stages of TiO2 flame synthesis. The conversion from synthesis precursor to TiO2 monomers was commonly assumed to take place through global reaction such as thermal decomposition and/or hydrolysis at high temperatures. More recent studies have been able to identify stable intermediates of Ti-containing monomers, most commonly Ti(OH)(4), as the final step before the formation of TiO2. However, no larger Ti-containing cluster formation mechanisms or interactions between these monomers have been tracked. To investigate cluster formation pathways of TiO2 during flame synthesis, Charged clusters were measured in an atmospheric pressure interface time-of-flight (APi-TOF) mass spectrometer. TiO2 nanoparticles were synthesized by adding titanium tetraisopropoxide (TTIP) precursor to a premixed CH4/O-2/N-2 flat flame aerosol reactor. Pure TiO2 clusters were not detected by the APi-TOF. Results from measured mass spectra and mass defect plots show that for positively charged clusters, the abstraction of CH2 groups occurs simultaneously with the clustering of larger intermediate organometallic species. For negatively charged clusters, NOx formation pathways in the flame may play a role during the initial stages of TiO2 formation, since a lot of Ti-containing clusters were attached with nitrate-related species. These research findings provide insights on quantum dot synthesis and molecular doping where rapid dilution of the flame synthesized nanoparticles is needed to better control the particle size and chemical composition. The possible influences of and potential artifacts brought by the dilution system on observing the incipient particle formation in flames were also discussed.
  • Peltonen, Leena; Strachan, Clare J. (2020)
    Poor aqueous solubility is currently a prevalent issue in the development of small molecule pharmaceuticals. Several methods are possible for improving the solubility, dissolution rate and bioavailability of Biopharmaceutics Classification System (BCS) class II and class IV drugs. Two solid state approaches, which rely on reductions in order, and can theoretically be applied to all molecules without any specific chemical prerequisites (compared with e.g. ionizable or co-former groups, or sufficient lipophilicity), are the use of the amorphous form and nanocrystals. Research involving these two approaches is relatively extensive and commercial products are now available based on these technologies. Nevertheless, their formulation remains more challenging than with conventional dosage forms. This article describes these two technologies from both theoretical and practical perspectives by briefly discussing the physicochemical backgrounds behind these approaches, as well as the resulting practical implications, both positive and negative. Case studies demonstrating the benefits and challenges of these two techniques are presented.
  • Nieminen, H. J.; Ylitalo, T.; Karhula, S.; Suuronen, J. -P.; Kauppinen, S.; Serimaa, R.; Haeggstrom, E.; Pritzker, K. P. H.; Valkealahti, M.; Lehenkari, P.; Finnila, M.; Saarakkala, S. (2015)
    Objective: Collagen distribution within articular cartilage (AC) is typically evaluated from histological sections, e.g., using collagen staining and light microscopy (LM). Unfortunately, all techniques based on histological sections are time-consuming, destructive, and without extraordinary effort, limited to two dimensions. This study investigates whether phosphotungstic acid (PTA) and phosphomolybdic acid (PMA), two collagen-specific markers and X-ray absorbers, could (1) produce contrast for AC X-ray imaging or (2) be used to detect collagen distribution within AC. Method: We labeled equine AC samples with PTA or PMA and imaged them with micro-computed tomography (micro-CT) at pre-defined time points 0, 18, 36, 54, 72, 90, 180, 270 h during staining. The micro-CT image intensity was compared with collagen distributions obtained with a reference technique, i.e., Fourier-transform infrared imaging (FTIRI). The labeling time and contrast agent producing highest association (Pearson correlation, BlandeAltman analysis) between FTIRI collagen distribution and micro-CT -determined PTA distribution was selected for human AC. Results: Both, PTA and PMA labeling permitted visualization of AC features using micro-CT in non-calcified cartilage. After labeling the samples for 36 h in PTA, the spatial distribution of X-ray attenuation correlated highly with the collagen distribution determined by FTIRI in both equine (mean +/- S.D. of the Pearson correlation coefficients, r = 0.96 +/- 0.03, n = 12) and human AC (r = 0.82 +/- 0.15, n = 4). Conclusions: PTA-induced X-ray attenuation is a potential marker for non-destructive detection of AC collagen distributions in 3D. This approach opens new possibilities in development of non-destructive 3D histopathological techniques for characterization of OA. (C) 2015 The Authors. Published by Elsevier Ltd and Osteoarthritis Research Society International.
  • Kangasniemi, Oskari; Kuuluvainen, Heino; Heikkilä, Joni; Pirjola, Liisa; Niemi, Jarkko V.; Timonen, Hilkka; Saarikoski, Sanna; Rönkkö, Topi; Dal Maso, Miikka (2019)
    Traffic is a major source of ultrafine aerosol particles in urban environments. Recent studies show that a significant fraction of traffic-related particles are only few nanometers in diameter. Here, we study the dispersion of this nanocluster aerosol (NCA) in the size range 1.3-4 nm. We measured particle concentrations near a major highway in the Helsinki region of Finland, varying the distance from the highway. Additionally, modelling studies were performed to gain further information on how different transformation processes affect NCA dispersion. The roadside measurements showed that NCA concentrations fell more rapidly than the total particle concentrations, especially during the morning. However, a significant amount of NCA particles remained as the aerosol population evolved. Modelling studies showed that, while dilution is the main process acting on the total particle concentration, deposition also had a significant impact. Condensation and possibly enhanced deposition of NCA were the main plausible processes explaining why dispersion is faster for NCA than for total particle concentration, while the effect of coagulation on all size ranges was small. Based on our results, we conclude that NCA may play a significant role in urban environments, since, rather than being scavenged by larger particles, NCA particles remain in the particle population and grow by condensation.
  • Wester, Niklas; Mikladal, Bjorn F.; Varjos, Ilkka; Peltonen, Antti; Kalso, Eija; Lilius, Tuomas; Laurila, Tomi; Koskinen, Jari (2020)
    A disposable electrochemical test strip for the quantitative point-of-care (POC) determination of acetaminophen (paracetamol) in plasma and finger-prick whole blood was fabricated. The industrially scalable dry transfer process of single-walled carbon nanotubes (SWCNTs) and screen printing of silver were combined to produce integrated electrochemical test strips. Nafion coating stabilized the potential of the Ag reference electrode and enabled the selective detection in spiked plasma as well as in whole blood samples. The test strips were able to detect acetaminophen in small 40 mu L samples with a detection limit of 0.8 mu M and a wide linear range from 1 mu M to 2 mM, well within the required clinical range. After a simple 1:1 dilution of plasma and whole blood, a quantitative detection with good recoveries of 79% in plasma and 74% in whole blood was achieved. These results strongly indicate that these electrodes can be used directly to determine the unbound acetaminophen fraction without the need for any additional steps. The developed test strip shows promise as a rapid and simple POC quantitative acetaminophen assay.
  • Badazhkova, Veronika D.; Raik, Sergei; Polyakov, Dmitry S.; Poshina, Daria N.; Skorik, Yury A. (2020)
    Recently, much effort has been expended on the development of non-viral gene delivery systems based on polyplexes of nucleic acids with various cationic polymers. Natural polysaccharide derivatives are promising carriers due to their low toxicity. In this work, chitosan was chemically modified by a reaction with 4-formyl-n,n,n-trimethylanilinium iodide and pyridoxal hydrochloride and subsequent reduction of the imine bond with NaBH4. This reaction yielded three novel derivatives, n-[4-(n',n',n'-trimethylammonium)benzyl]chitosan chloride (TMAB-CS), n-[(3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridine)methyl]chitosan chloride (Pyr-CS), and n-[4-(n',n',n''-trimethylammonium)benzyl]-n-[(3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridine)methyl]chitosan chloride (PyrTMAB-CS). Their structures and degrees of substitution were established by H-1 NMR spectroscopy as DS1 = 0.22 for TMAB-CS, DS2 = 0.28 for Pyr-CS, and DS1 = 0.21, DS2 = 0.22 for PyrTMAB-CS. Dynamic light scattering measurements revealed that the new polymers formed stable polyplexes with plasmid DNA encoding the green fluorescent protein (pEGFP-N3) and that the particles had the smallest size (110-165 nm) when the polymer:DNA mass ratio was higher than 5:1. Transfection experiments carried out in the HEK293 cell line using the polymer:DNA polyplexes demonstrated that Pyr-CS was a rather poor transfection agent at polymer:DNA mass ratios less than 10:1, but it was still more effective than the TMAB-CS and PyrTMAB-CS derivatives that contained a quaternary ammonium group. By contrast, TMAB-CS and PyrTMAB-CS were substantially more effective than Pyr-CS at higher polymer:DNA mass ratios and showed a maximum efficiency at 200:1 (50%-70% transfected cells). Overall, the results show the possibility of combining substituent effects in a single carrier, thereby increasing its efficacy.