Martins Rucins
University of Latvia
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Publication
Featured researches published by Martins Rucins.
New Journal of Chemistry | 2013
Karlis Pajuste; Zanna Hyvönen; Oksana Petrichenko; Dainis Kaldre; Martins Rucins; Brigita Cekavicus; Velta Ose; Baiba Skrivele; Marina Gosteva; Emmanuelle Morin-Picardat; Mara Plotniece; Arkadij Sobolev; Gunars Duburs; Marika Ruponen; Aiva Plotniece
Seventeen 1,4-dihydropyridine (1,4-DHP) amphiphiles including differently substituted pyridinium, pyrazinium, N-methyl piperidinium or N-methyl morpholinium moieties as the cationic head-group of the molecule have been designed and synthesised. 1,4-DHP amphiphiles have been earlier proposed as a promising tool for plasmid DNA (pDNA) delivery in vitro. In this work the ability of the 1,4-DHP amphiphiles to self-assemble, to bind pDNA and to transfer it into the cells as well as the cytotoxicity of 1,4-DHP amphiphiles–pDNA complexes was studied. Furthermore, antiradical activity (ARA) of the 1,4-DHP derivatives was determined. We have revealed that all new 1,4-DHP amphiphiles possessed self-assembling properties and formed nanoparticles in an aqueous environment. The structure of the cationic head-group of 1,4-DHP amphiphiles influenced the size of nanoparticles. Additionally, we demonstrated for the first time that the electronic nature of the substituent of the pyridinium as the cationic head-group of the 1,4-DHP amphiphiles strongly affected the ability of these compounds to bind pDNA and transfer it into the cells. The amphiphiles with electron-donating properties possessing substituents at pyridinium moieties were able to bind pDNA and to deliver it more efficiently than amphiphiles containing electron-withdrawing properties possessing substituents at pyridinium moieties. Moreover, in this study we have established that the presence of the cationic part in the molecule was essential for the expression of ARA among tested 1,4-DHP amphiphiles. Cationic 1,4-DHP derivatives containing pyrazinium or N-methyl morpholinium substituents in the cationic head-group of the molecule displayed the highest ARA.
Chemistry and Physics of Lipids | 2015
Oksana Petrichenko; Martins Rucins; Aleksandra Vezane; Irena Timofejeva; Arkadij Sobolev; Brigita Cekavicus; Karlis Pajuste; Mara Plotniece; Marina Gosteva; Tatjana Kozlovska; Aiva Plotniece
New amphiphilic pyridine derivatives containing dodecyloxycarbonyl substituents at positions 3 and 5 and cationic moieties at positions 2 and 6 have been designed and synthesised. Compounds of this type can be considered as synthetic lipids. The corresponding 1,4-dihydropyridine (1,4-DHP) derivatives have earlier been proposed as a promising tool for plasmid DNA (pDNA) delivery in vitro. In this work studies of the self-assembling properties of amphiphilic pyridine derivatives leading to the formation of liposomes, determination of particle size, zeta-potential and critical micelle concentration (CMC) with dynamic light scattering (DLS) measurements are described. Furthermore, thermal analysis of pyridine derivatives was performed using thermogravimetry analysis (TGA) and differential thermal analysis (DTA) as well as the ability to deliver the pEGFP-C1 plasmid DNA (that encodes GFP reporter) into the Baby hamster kidney-derived (BHK-21) cell line was used for evaluation of gene delivery properties. We have revealed that the new pyridine derivatives possessed self-assembling properties which were proved by formation of nanoparticles with the average size from 115 to 743nm, the zeta-potentials in the range of 48-79mV and CMC values in the range of 2-67μM. DTA data showed that all processes were endothermic for all compounds. Additionally, we established that among the tested pyridines the representatives with N-methylpyrrolidinium or pyridinium moieties as cationic head-group at the positions 2 and 6 possessed higher pEGFP-C1 transfection activity into the BHK-21 cell line. Nevertheless, the obtained results indicated that correlation of the physicochemical, structural properties and gene delivery activities of the tested compounds were not completely elucidated yet. On the other hand, the synthesised pyridines as possible metabolites of promising delivery systems on the 1,4-DHP core possessed lower pDNA transfection activity than the corresponding 1,4-DHP amphiphiles.
Molecules | 2015
Brigita Vigante; Martins Rucins; Aiva Plotniece; Karlis Pajuste; Iveta Luntena; Brigita Cekavicus; Egils Bisenieks; Rufus Smits; Gunars Duburs; Arkadij Sobolev
The ethoxycarbonylmethyl esters of 1,4-dihydropyridines were directly converted into carbamoylmethyl esters in the presence of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) in good to excellent yields under mild conditions. The use of TBD is crucial for the successful aminolysis of ethoxycarbonylmethyl ester of 1,4-dihydropyridines with secondary amines as without it the reaction does not proceed at all. The aminolysis reaction proceeded regioselectively, as the alkyl ester conjugated with the 1,4-dihydropyridine cycle was not involved in the reaction. Screening of other N-containing bases, such as triethylamine (TEA), pyridine, 4-(N,N-dimethylamino)pyridine (DMAP), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), imidazole, tetramethyl guanidine (TMG) and 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) as catalysts revealed no activity in the studied reaction.
Oxidative Medicine and Cellular Longevity | 2017
Imanta Bruvere; Egils Bisenieks; Janis Poikans; Janis Uldrikis; Aiva Plotniece; Karlis Pajuste; Martins Rucins; Brigita Vigante; Zenta Kalme; Marina Gosteva; Ilona Domracheva; Astrida Velena; Tea Vukovic; Lidija Milkovic; Gunars Duburs; Neven Zarkovic
The effects of eleven 1,4-dihydropyridine derivatives (DHPs) used alone or together with prooxidant anticancer drug doxorubicin were examined on two cancer (HOS, HeLa) and two nonmalignant cell lines (HMEC, L929). Their effects on the cell growth (3H-thymidine incorporation) were compared with their antiradical activities (DPPH assay), using well-known DHP antioxidant diludine as a reference. Thus, tested DHPs belong to three groups: (1) antioxidant diludine; (2) derivatives with pyridinium moieties at position 4 of the 1,4-DHP ring; (3) DHPs containing cationic methylene onium (pyridinium, trialkylammonium) moieties at positions 2 and 6 of the 1,4-DHP ring. Diludine and DHPs of group 3 exerted antiradical activities, unlike compounds of group 2. However, novel DHPs had cell type and concentration dependent effects on 3H-thymidine incorporation, while diludine did not. Hence, IB-32 (group 2) suppressed the growth of HOS and HeLa, enhancing growth of L929 cells, while K-2-11 (group 3) enhanced growth of every cell line tested, even in the presence of doxorubicin. Therefore, growth regulating and antiradical activity principles of novel DHPs should be further studied to find if DHPs of group 2 could selectively suppress cancer growth and if those of group 3 promote wound healing.
Chemistry of Heterocyclic Compounds | 2015
Martins Rucins; Marina Gosteva; Ilona Domracheva; Iveta Kanepe-Lapsa; Sergey Belyakov; Māra Plotniece; Klāvs Pajuste; Brigita Cekavicus; M. Jekabsone; Arkadij Sobolev; I. Shestakova; А. Plotniece
Novel pyridinium salts based on 4-(3-pyridyl)-3,5-dipropargylcarbonyl-1,4-dihydropyridine were obtained by quaternization of pyridine moiety with different alkyl halides. The reducing capacity of the synthesized compounds was evaluated using the phosphomolybdenum complex method. The obtained results confirmed that all tested compounds possessed reducing capacity. Ca2+ channel antagonist and agonist activities of the compounds were additionaly assayed by changes in intracellular Ca2+ ion concentration in H9C2 and A7R5 cell lines. The obtained data confirmed that all synthesized 1,4-dihydropyridine derivatives have smooth muscle selective antagonist activities, and in the case of 4-phenyl derivative the activity was 4.7 times higher than that of amlodipine.
Australian Journal of Chemistry | 2015
Martins Rucins; Marina Gosteva; Sergey Belyakov; Arkadij Sobolev; Karlis Pajuste; Mara Plotniece; Brigita Cekavicus; Dace Tirzite; Aiva Plotniece
New bispyridinium dibromides based on the 1,4-dihydropyridine (1,4-DHP) cycle were synthesised in the reaction between 4-pyridyl-1,4-DHP derivatives and propargyl bromide. It has been shown that variation of the substituent position on the pyridine as well as small changes in the electronic nature of the 1,4-DHP cycle as a result of the substituent nature at the 3 and 5 positions do not affect the course of the reaction and in all cases the corresponding bispyridinium dibromides 4a–e were formed. The antiradical activity, using 1,1-diphenyl-2-picrylhydrazine as a free radical scavenger, and the reducing capacity using phosphomolybdenum complexes have been evaluated for the newly synthesised compounds 4a–e. It has been shown that all tested 1,4-DHP bispyridinium dibromides 4a–e possess reducing capacity and antiradical properties. Moreover, the reducing capacity results could be explained by the influence of the electronic nature of the substituent at the 3 and 5 positions of the 1,4-DHP cycle.
Molecules | 2018
Gunita Apsite; Irena Timofejeva; Aleksandra Vezane; Brigita Vigante; Martins Rucins; Arkadij Sobolev; Mara Plotniece; Karlis Pajuste; Tatjana Kozlovska; Aiva Plotniece
New amphiphilic 1,4-DHP derivative C12-Man-Q with remoted cationic moieties at positions 2 and 6 was synthesised to study DNA delivery activity. The results were compared with data obtained for cationic 1,4-DHP derivative D19, which is known to be the most efficient one among the previously tested 1,4-DHP amphiphiles. We analysed the effects of C12-Man-Q concentration, complexation media, and complex/cell contact time on the gene delivery effectiveness and cell viability. Transmission electron microscopy data confirms that lipoplexes formed by the compound C12-Man-Q were quite uniform, vesicular-like structures with sizes of about 50 nm, and lipoplexes produced by compound D19 were of irregular shapes, varied in size in the range of 25–80 nm. Additionally, confocal microscopy results revealed that both amphiphiles effectively delivered green fluorescent protein expression plasmid into BHK-21 cells and produced a fluorescent signal with satisfactory efficiency, although compound C12-Man-Q was more cytotoxic to the BHK-21 cells with an increase of concentration. It can be concluded that optimal conditions for C12-Man-Q lipoplexes delivery in BHK-21 cells were the serum free media without 0.15 M NaCl, at an N/P ratio of 0.9. Compound D19 showed higher transfection efficiency to transfect BHK-21 and Cos-7 cell lines, when transfecting active proliferating cells. Although D19 was not able to transfect all studied cell lines we propose that it could be cell type specific. The compound C12-Man-Q showed modest delivery activity in all used cell lines, and higher activity was obtained in the case of H2-35 and B16 cells. The transfection efficiency in cell lines MCF-7, HeLa, and Huh-7 appears to be comparable to the reference compound D19 and minimal in the HepG2 cell line.
Comptes Rendus Chimie | 2014
Martins Rucins; Dainis Kaldre; Karlis Pajuste; Maria A.S. Fernandes; Joaquim A.F. Vicente; Linda Klimaviciusa; Elina Jaschenko; Iveta Kanepe-Lapsa; I. Shestakova; Mara Plotniece; Marina Gosteva; Arkadij Sobolev; Baiba Jansone; Ruta Muceniece; Vija Klusa; Aiva Plotniece
Tetrahedron | 2013
Brigita Cekavicus; Brigita Vigante; Martins Rucins; Kintija Birkmane; M. V. Petrova; Sergey Belyakov; Liga Zuka; Aiva Plotniece; Karlis Pajuste; Marina Gosteva; Arkadij Sobolev
Tetrahedron Letters | 2014
Brigita Cekavicus; Brigita Vigante; Martins Rucins; A. Plotniece; Karlis Pajuste; M. Petrova; Sergey Belyakov; Gunars Duburs; Arkadij Sobolev