MD4399C1 - Polymeric material with antibacterial properties - Google Patents
Polymeric material with antibacterial properties Download PDFInfo
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- MD4399C1 MD4399C1 MDA20150029A MD20150029A MD4399C1 MD 4399 C1 MD4399 C1 MD 4399C1 MD A20150029 A MDA20150029 A MD A20150029A MD 20150029 A MD20150029 A MD 20150029A MD 4399 C1 MD4399 C1 MD 4399C1
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- Moldova
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- polymeric material
- isofural
- mol
- antibacterial
- antibacterial properties
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- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 24
- 239000000463 material Substances 0.000 title claims abstract description 21
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 21
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229920001577 copolymer Polymers 0.000 claims abstract description 8
- -1 compound (E) -N '- ((5-nitrofuran- 2-yl) methylene) isonicotinhydrazide Chemical class 0.000 claims abstract description 4
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims abstract description 3
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000003814 drug Substances 0.000 abstract description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000002861 polymer material Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 6
- 244000005700 microbiome Species 0.000 description 5
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical compound NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 5
- 230000009471 action Effects 0.000 description 4
- 230000003385 bacteriostatic effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229960001907 nitrofurazone Drugs 0.000 description 4
- 235000015097 nutrients Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000010899 nucleation Methods 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 2
- 241000194032 Enterococcus faecalis Species 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- 241000588767 Proteus vulgaris Species 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940032049 enterococcus faecalis Drugs 0.000 description 2
- PLHJDBGFXBMTGZ-WEVVVXLNSA-N furazolidone Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)OCC1 PLHJDBGFXBMTGZ-WEVVVXLNSA-N 0.000 description 2
- 229960001625 furazolidone Drugs 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 229940007042 proteus vulgaris Drugs 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical class [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 206010008631 Cholera Diseases 0.000 description 1
- 201000000628 Gas Gangrene Diseases 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000224526 Trichomonas Species 0.000 description 1
- 241000607598 Vibrio Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
- 229960000723 ampicillin Drugs 0.000 description 1
- 229920002118 antimicrobial polymer Polymers 0.000 description 1
- 229940027988 antiseptic and disinfectant nitrofuran derivative Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000004098 cellular respiration Effects 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 231100000045 chemical toxicity Toxicity 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Изобретение относится к полимерному материалу с антибактериальными свойствами и может найти применение в медицине и ветеринарии.Полимерный материал, согласно изобретению, состоит из сополимера N-винилпирролидона с метакриловой или кротоновой кислотой, привитого соединением (E)-N'-((5-нитрофуран-2-ил)метилен)изоникотингидразид (изофурал).The invention relates to a polymeric material with antibacterial properties and can be used in medicine and veterinary medicine. The polymeric material according to the invention consists of a copolymer of N-vinylpyrrolidone with methacrylic or crotonic acid, grafted with compound (E) -N '- ((5-nitrofuran- 2-yl) methylene) isonicotinhydrazide (isofural).
Description
Invenţia se referă la un material polimeric cu proprietăţi antibacteriene şi poate fi aplicată în medicină şi medicina veterinară. The invention relates to a polymeric material with antibacterial properties and can be applied in medicine and veterinary medicine.
La preparatele antibacteriene se referă aşa preparate ca furacilina, furazolidonul şi altele. Aceste preparate fac parte din grupa derivaţilor nitrofuranului şi reprezintă chimioterapice de sinteză cu spectru larg de acţiune. Substanţele menţionate, fiind acceptori de oxigen, dereglează procesul respiraţiei celulare bacteriene, inhibă biosinteza acizilor nucleici, iar în dependenţă de concentraţie pot provoca efect bacteriostatic sau bactericid. Nitrofuranii se caracterizează printr-un spectru larg de acţiune, fiind activi faţă de multe bacterii gram-negative (Escherichia coli, Klebsiella pneumoniae) şi gram-pozitive, unele anaerobe, faţă de micoze (Candida). Furazolidonul este activ în infecţii cu lamblii, tricomonas, paratifos, Salmonella, vibrionul choleric, Staphylococcus, virusuri mari, agentul gangrenei gazoase. Antibacterial preparations include such preparations as furacilin, furazolidone and others. These preparations are part of the group of nitrofuran derivatives and represent synthetic chemotherapeutics with a broad spectrum of action. The mentioned substances, being oxygen acceptors, deregulate the process of bacterial cellular respiration, inhibit the biosynthesis of nucleic acids, and depending on the concentration can cause a bacteriostatic or bactericidal effect. Nitrofurans are characterized by a wide spectrum of action, being active against many gram-negative bacteria (Escherichia coli, Klebsiella pneumoniae) and gram-positive, some anaerobic, against mycoses (Candida). Furazolidone is active in infections with lamblia, trichomonas, paratyphoid, Salmonella, cholera vibrio, Staphylococcus, large viruses, the agent of gas gangrene.
Din această grupă este cunoscut şi compusul (E)-N'-((5-nitrofuran-2-il)metilen) isonicotinohidrazidă, numit şi izofural, propus ca preparat antibacterian valoros pe piaţa medicamentelor din Republica Moldova, ce are o activitate de 4...5 ori mai înaltă decât alte preparate antibacteriene [1]. Însă acest compus posedă şi dezavantaje: From this group is also known the compound (E)-N'-((5-nitrofuran-2-yl)methylene) isonicotinohydrazide, also called isofural, proposed as a valuable antibacterial preparation on the drug market in the Republic of Moldova, which has an activity of 4 ...5 times higher than other antibacterial preparations [1]. But this compound also has disadvantages:
- timp real, dar scurt de acţiune în organism; - real, but short action time in the body;
- solubilitate neînsemnată în apă; - negligible solubility in water;
- toxicitate chimică (ca la toate preparatele medicinale sintetice). - chemical toxicity (as with all synthetic medicinal preparations).
În calitate de cea mai apropiată soluţie serveşte un grup de copolimeri biologic activi din N-vinilpirolidonă cu anhidridă maleică sau acizi nesaturaţi, cuplaţi cu preparate antibacteriene ca penicilina, ampicilina, care posedă activitate biologică comparabilă cu preparatele antibacteriene [2], dar au şi un şir de dezavantaje: As the closest solution serves a group of biologically active copolymers of N-vinylpyrrolidone with maleic anhydride or unsaturated acids, coupled with antibacterial preparations such as penicillin, ampicillin, which possess biological activity comparable to antibacterial preparations [2], but also have a string of disadvantages:
- toxicitate relativ mare; - relatively high toxicity;
- efect de prolongare neînsemnat din cauza masei moleculare mici a polimerilor suport; - insignificant prolongation effect due to the low molecular weight of the support polymers;
- compatibilitate neînsemnată cu organismul uman, ce micşorează posibilitatea utilizării lor in vivo. - insignificant compatibility with the human body, which reduces the possibility of their use in vivo.
Problema pe care o rezolvă prezenta invenţie constă în obţinerea unor materiale polimerice cu proprietăţi antibacteriene, care ar asigura micşorarea toxicităţii şi majorarea timpului de acţiune în organism. The problem that the present invention solves consists in obtaining polymeric materials with antibacterial properties, which would ensure the reduction of toxicity and the increase of the time of action in the body.
Problema se rezolvă prin aceea că a fost obţinut un material polimeric cu proprietăţi antibacteriene care constă dintr-un copolimer de N-vinilpirolidonă cu acid metacrilic sau crotonic, grefat cu compusul (E)-N'-((5-nitrofuran-2-il)metilen)izonicotinohidrazidă (izofural), în care conţinutul compusului este de 10…50% mol. The problem is solved by the fact that a polymeric material with antibacterial properties was obtained which consists of a copolymer of N-vinylpyrrolidone with methacrylic or crotonic acid, grafted with the compound (E)-N'-((5-nitrofuran-2-yl )methylene)isonicotinohydrazide (isofural), in which the content of the compound is 10...50% mol.
Rezultatul tehnic al invenţiei constă în faptul că polimerii propuşi în prezenta invenţie posedă un efect antibacterian la nivelul izofuralului micromolecular, toxicitate redusă şi o prolongare de 5...6 ori mai mare, faţă de cea mai apropiată soluţie. The technical result of the invention consists in the fact that the polymers proposed in the present invention possess an antibacterial effect at the level of micromolecular isofural, reduced toxicity and a 5...6 times greater prolongation, compared to the closest solution.
Rezultatul tehnic obţinut se datorează grefării izofuralului la catena polimerică din N-vinilpirolidonă (N-VP) cu acid metacrilic (ACM), care disociază mai lent şi se reţine mai mult timp în organism. The technical result obtained is due to the grafting of isofural to the polymer chain of N-vinylpyrrolidone (N-VP) with methacrylic acid (ACM), which dissociates more slowly and is retained longer in the body.
Invenţia se explică cu ajutorul desenelor din fig. 1-2, care reprezintă: The invention is explained with the help of the drawings in fig. 1-2, which represents:
- fig. 1, spectrul IR al copolimerului N-VP:ACM (1:1); - fig. 1, IR spectrum of N-VP:ACM (1:1) copolymer;
- fig. 2, spectrul IR al materialului polimeric cu proprietăţi antibacteriene. - fig. 2, the IR spectrum of the polymeric material with antibacterial properties.
Polimerii medicinali se obţin prin tratarea soluţiei de copolimeri N-VP:ACM în dimetilformamidă (DMF) cu adaos de trietilamină (TEA) şi cloroformiat de etil (CFE) conform schemei: Medicinal polymers are obtained by treating the solution of N-VP:ACM copolymers in dimethylformamide (DMF) with the addition of triethylamine (TEA) and ethyl chloroformate (CFE) according to the scheme:
Cloroformiatul de etil, ce conţine gruparea chimica activă , reacţionează uşor la temperatura de 0±2ºC cu grupa -COOH din catena polimerică formând un compus dicetonic nestabil, ce uşor reacţionează cu grupe amine primare sau secundare. Structura chimică a copolimerului N-vinilpirolidonă:acid metacrilic grefat cu izofural a fost confirmată cu ajutorul spectroscopiei IR şi analizei elementale. Din spectre se observă apariţia vibraţiilor noi la ν=2487 cm-1, ceea ce confirmă existenţa grupării , cât şi altele (fig.1 şi 2). Ethyl chloroformate, which contains the active chemical group, reacts easily at a temperature of 0±2ºC with the -COOH group in the polymer chain, forming an unstable diketonic compound, which easily reacts with primary or secondary amine groups. The chemical structure of the N-vinylpyrrolidone:isofural-grafted methacrylic acid copolymer was confirmed by IR spectroscopy and elemental analysis. The spectra show the appearance of new vibrations at ν=2487 cm-1, which confirms the existence of the group, as well as others (fig. 1 and 2).
Exemplu de realizare a invenţiei Example of realization of the invention
Într-un pahar de 50 ml se depozitează 1,0 g de copolimer de N-vinilpirolidonă cu acid metacrilic (1:1, 50% mol N-vinilpirolidonă şi 50% mol acid metacrilic), care se dizolvă în 10 ml de dimetilformamidă (soluţia 1). În alt pahar se dizolvă 1,5 g de izofural (calculat teoretic după reacţia chimică, ce constituie 50% mol izofural în materialul polimeric (copolimer-izofural)) în 30 ml de dimetilformamidă (soluţia 2). Conţinutul maxim al izofuralului în materialul polimeric (1) (unde N-VP:ACM (1:1)) poate fi de 50% mol. In a 50 ml glass, store 1.0 g of N-vinylpyrrolidone copolymer with methacrylic acid (1:1, 50% mol N-vinylpyrrolidone and 50% mol methacrylic acid), which is dissolved in 10 ml of dimethylformamide ( solution 1). In another glass, dissolve 1.5 g of isofural (calculated theoretically after the chemical reaction, which constitutes 50% mol of isofural in the polymer material (copolymer-isofural)) in 30 ml of dimethylformamide (solution 2). The maximum content of isofural in the polymeric material (1) (where N-VP:ACM (1:1)) can be 50% mol.
Soluţia 1 se răceşte într-o baie cu gheaţă pâna la 0ºC la care se adaugă cu picătura 0,6 ml de trietilamină, iar peste 20 min se adaugă la agitare 0,8 ml de cloroformiat de etil. Agitarea la 0ºC se mai prelungeşte 20 min, după care cu picătura se adaugă soluţia 2. După 30 min amestecul obţinut se aduce la temperatura camerei şi se menţine 2…3 ore. Soluţia obţinută se evaporă până la o concentraţie de 15…20%, apoi se separă prin filtrare şi pe filtru se mai spală cu apă rece, apoi se usucă la temperatura camerei şi în etuvă cu vid la t~40ºC. Randamentul reacţiei constituie 80%. Materialul polimeric (copolimer-izofural) obţinut se supune testărilor antibacteriene. Solution 1 is cooled in an ice bath to 0ºC, to which 0.6 ml of triethylamine is added dropwise, and after 20 min, 0.8 ml of ethyl chloroformate is added with stirring. Stirring at 0ºC is prolonged for another 20 min, after which solution 2 is added drop by drop. After 30 min, the obtained mixture is brought to room temperature and maintained for 2...3 hours. The obtained solution is evaporated to a concentration of 15...20%, then it is separated by filtration and the filter is washed with cold water, then it is dried at room temperature and in a vacuum oven at t~40ºC. The yield of the reaction is 80%. The polymer material (copolymer-isofural) obtained is subject to antibacterial testing.
Alte materiale polimerice medicinale cu rapoarte procentuale ale monomerilor diferite şi, respectiv, conţinutul de izofural diferit au fost obţinute conform metodicii sus-menţionate. Other medicinal polymer materials with different percentage ratios of monomers and, respectively, different isofural content were obtained according to the above-mentioned methodology.
În al doilea material polimeric elaborat conţinutul monomerilor este de 70% mol N-vinilpirolidonă şi 30% mol acid metacrilic (N-VP:ACM (7:3)). Conţinutul maxim al izofuralului în materialul polimeric (unde N-VP:ACM (7:3)) poate fi de 30% mol. In the second polymeric material developed, the monomer content is 70% mol N-vinylpyrrolidone and 30% mol methacrylic acid (N-VP:ACM (7:3)). The maximum content of isofural in the polymer material (where N-VP:ACM (7:3)) can be 30% mol.
În al treilea material polimeric elaborat conţinutul monomerilor este de 90% mol N-vinilpirolidonă şi 10% mol acid metacrilic, (N-VP:ACM (9:1)). Conţinutul maxim al izofuralului în materialul polimeric (unde N-VP:ACM (9:1)) poate fi de 10% mol. In the third developed polymeric material, the monomer content is 90% mol N-vinylpyrrolidone and 10% mol methacrylic acid, (N-VP:ACM (9:1)). The maximum content of isofural in the polymer material (where N-VP:ACM (9:1)) can be 10% mol.
Cercetarea activităţii antibacteriene (bacteriostatice şi bactericide) a materialului polimeric a fost efectuată faţă de microorganismele: Staphylococcus aureus (tulpina 209-P), Enterococcus faecalis, Escherichia coli (tulpina ATCC25922), Proteus vulgaris (tulpina HX 19222), Pseudomonas aeruginosa (tulpina ATCC 27853) prin metoda diluărilor în serie în mediu nutritiv lichid (bulion peptonat din carne 2%, pH=7,0). Materialul polimeric a fost dizolvat în dimetilformamidă (cu concentraţia de 10 mg/ml). Pentru însămânţare au fost folosite culturi ale microorganismelor indicate, crescute pe geloză timp de 18 ore, spălate cu soluţie izotonică de clorură de sodiu. Doza de însămânţare constituie 500 de mii de corpi microbieni la 1 ml de mediu nutritiv. În calitate de control au servit mediile nutritive însămânţate cu aceleaşi tulpini fără conţinutul materialelor cercetate. Evaluarea activităţii bacteriostatice (concentraţia minimă de inhibiţie (CMI)) a fost efectuată vizual prin confirmarea lipsei creşterii microorganismelor în mediul nutritiv lichid. Activitatea bactericidă (concentraţia minimă bactericidă (CMB)) s-a determinat în baza lipsei creşterii microorganismelor după însămânţare repetată pe geloză peptonată cu termostatarea ulterioară timp de 24, 48 de ore. Rezultatele obţinute sunt prezentate în tabel. Pentru comparaţie în acelaşi tabel sunt prezentate date privind activitatea materialelor polimerice (copolimer grefat cu izofural), izofuralului molecular, precum şi a furacilinei. Rezultatele investigaţiei demonstrează că substanţele cercetate au manifestat activitate antibacteriană înaltă faţă de culturile sus-menţionate. Materialul polimeric medicinal (izofural grefat pe matricea polimerică N-vinilpirolidonă:acid metacrilic) a demonstrat activitate bactericidă, bacteriostatică mai pronunţată de aproximativ 4 ori, comparativ cu furacilina faţă de Staphylococcus aureus, ceea ce demonstrează că materialul polimeric poate avea avantaje faţă de unele substanţe biologic active ce sunt utilizate pe larg în tratamentul infecţiilor bacteriene. The investigation of the antibacterial activity (bacteriostatic and bactericidal) of the polymeric material was carried out against the microorganisms: Staphylococcus aureus (strain 209-P), Enterococcus faecalis, Escherichia coli (strain ATCC25922), Proteus vulgaris (strain HX 19222), Pseudomonas aeruginosa (strain ATCC 27853) by the method of serial dilutions in a liquid nutrient medium (meat peptone broth 2%, pH=7.0). The polymeric material was dissolved in dimethylformamide (at a concentration of 10 mg/ml). Cultures of the indicated microorganisms were used for seeding, grown on agar for 18 hours, washed with isotonic sodium chloride solution. The seeding dose is 500 thousand microbial bodies per 1 ml of nutrient medium. Nutrient media seeded with the same strains without the content of the researched materials served as control. Evaluation of bacteriostatic activity (minimum inhibitory concentration (MIC)) was performed visually by confirming the lack of growth of microorganisms in the liquid nutrient medium. Bactericidal activity (minimum bactericidal concentration (MBC)) was determined based on the lack of growth of microorganisms after repeated seeding on peptone agar with subsequent thermostating for 24, 48 hours. The obtained results are presented in the table. For comparison, data on the activity of polymeric materials (copolymer grafted with isofural), molecular isofural, and furacilin are presented in the same table. The results of the investigation demonstrate that the investigated substances showed high antibacterial activity against the above-mentioned cultures. The medicinal polymer material (isofural grafted on the polymer matrix N-vinylpyrrolidone:methacrylic acid) demonstrated bactericidal, bacteriostatic activity about 4 times more pronounced compared to furacilin against Staphylococcus aureus, which proves that the polymer material can have advantages over some substances biologically active that are widely used in the treatment of bacterial infections.
Proprietăţile depistate ale materialului polimeric medicinal obţinut prezintă interes pentru medicină şi medicina veterinară din punct de vedere al extinderii arsenalului de remedii antibacteriene. The detected properties of the medicinal polymeric material obtained are of interest for medicine and veterinary medicine from the point of view of expanding the arsenal of antibacterial remedies.
Tabel Table
Activitatea antibacteriană (µg/ml) a materialului polimeric revendicat faţă de microorganismele gram-pozitive şi gram-negative Antibacterial activity (µg/ml) of the claimed polymeric material against gram-positive and gram-negative microorganisms
Material polimeric şi analogi micromoleculari Test cultură bactericidă (mg/ml) Staphylococcus aureus (tulpina 209-P) Enterococcus faecalis Escherichia coli (tulpina ATCC25922) Proteus vulgaris (tulpina HX 19222) Pseudomonas aeruginosa (tulpina ATCC 27853) CMI CMB CMI CMB CMI CMB CMI CMB CMI CMB Material polimeric (N-VP:ACM (1:1) grefat cu izofural (50% mol)) 4,68 9,37 18,75 150 37,5 75 37,5 300 37,5 75 Material polimeric (N-VP:ACM (7:3) grefat cu izofural (30% mol)) 9,62 13,98 23,3 177 43,5 171,5 57 >300 53 200 Material polmeric (N-VP:ACM (9:1) grefat cu izofural (10% mol)) 14,56 18,60 27,85 195 49,5 268 76,5 >300 68,5 129 Izofural 2,37 9,37 9,37 75 18,75 300 300 300 18,75 37,5 Furacilină 18,75 37,5 37,5 75 18,75 37,5 >300 >300 150 300 Polymeric material and micromolecular analogs Bactericidal culture test (mg/ml) Staphylococcus aureus (strain 209-P) Enterococcus faecalis Escherichia coli (strain ATCC25922) Proteus vulgaris (strain HX 19222) Pseudomonas aeruginosa (strain ATCC 27853) CMI CMB CMI CMB CMI CMB CMI CMB CMI CMB Polymeric material (N-VP:ACM (1:1) grafted with isofural (50% mol)) 4.68 9.37 18.75 150 37.5 75 37.5 300 37.5 75 Polymeric material ( N-VP:ACM (7:3) grafted with isofural (30% mol)) 9.62 13.98 23.3 177 43.5 171.5 57 >300 53 200 Polymeric material (N-VP:ACM (9 :1) grafted with isofural (10% mol)) 14.56 18.60 27.85 195 49.5 268 76.5 >300 68.5 129 Isofural 2.37 9.37 9.37 75 18.75 300 300 300 18.75 37.5 Furacilin 18.75 37.5 37.5 75 18.75 37.5 >300 >300 150 300
1. MD 196 B1 1995.05.31 1. MD 196 B1 1995.05.31
2. Timofeeva L., Kleshcheva N. Antimicrobial polymers: mechanism of action, factors of activity, and applications. Applied Microbiology and Biotechnology, 2011, vol. 89, nr. 3, p. 475-492 2. Timofeeva L., Kleshcheva N. Antimicrobial polymers: mechanism of action, factors of activity, and applications. Applied Microbiology and Biotechnology, 2011, vol. 89, no. 3, pp. 475-492
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20150029A MD4399C1 (en) | 2015-02-19 | 2015-02-19 | Polymeric material with antibacterial properties |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20150029A MD4399C1 (en) | 2015-02-19 | 2015-02-19 | Polymeric material with antibacterial properties |
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| Publication Number | Publication Date |
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| MD4399B1 MD4399B1 (en) | 2016-02-29 |
| MD4399C1 true MD4399C1 (en) | 2016-09-30 |
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| MDA20150029A MD4399C1 (en) | 2015-02-19 | 2015-02-19 | Polymeric material with antibacterial properties |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MD4506C1 (en) * | 2016-11-24 | 2018-03-31 | Государственный Университет Молд0 | Polymeric material with antibacterial properties based on lignin grafted with N'-(5-nitrofurfurylidene)isonicotinehydrazide |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2042892A (en) * | 1979-02-05 | 1980-10-01 | Chinoin Gyogyszer Es Vegyeszet | Compositions of Improved Dispersability and Preparation Thereof |
| SU1731037A3 (en) * | 1986-04-11 | 1992-04-30 | Басф Аг (Фирма) | Method of producing pellets |
| MD196B1 (en) * | 1994-07-22 | 1995-05-31 | Univ De Stat De Medicina N Tes | Izonicotinoylhydrazone of 5-nitro-2-furanic aldehyde |
| MD2380B2 (en) * | 2001-03-22 | 2004-02-29 | Heraeus Kulzer Gmbh & Co Kg | Polymer combination of antibiotic(s) and use thereof |
| RU2519679C2 (en) * | 2008-06-30 | 2014-06-20 | Эббетт ГмбХ унд Ко. КГ | Pharmaceutical dosed form, containing polymer carrier composition |
-
2015
- 2015-02-19 MD MDA20150029A patent/MD4399C1/en not_active IP Right Cessation
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2042892A (en) * | 1979-02-05 | 1980-10-01 | Chinoin Gyogyszer Es Vegyeszet | Compositions of Improved Dispersability and Preparation Thereof |
| SU1731037A3 (en) * | 1986-04-11 | 1992-04-30 | Басф Аг (Фирма) | Method of producing pellets |
| MD196B1 (en) * | 1994-07-22 | 1995-05-31 | Univ De Stat De Medicina N Tes | Izonicotinoylhydrazone of 5-nitro-2-furanic aldehyde |
| MD2380B2 (en) * | 2001-03-22 | 2004-02-29 | Heraeus Kulzer Gmbh & Co Kg | Polymer combination of antibiotic(s) and use thereof |
| RU2519679C2 (en) * | 2008-06-30 | 2014-06-20 | Эббетт ГмбХ унд Ко. КГ | Pharmaceutical dosed form, containing polymer carrier composition |
Non-Patent Citations (1)
| Title |
|---|
| Timofeeva L., Kleshcheva N. Antimicrobial polymers: mechanism of action, factors of activity, and applications. Applied Microbiology and Biotechnology, 2011, vol. 89, nr. 3, p. 475-492 * |
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| Publication number | Publication date |
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| MD4399B1 (en) | 2016-02-29 |
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