MD4252C1 - Catena-(µ-nitrato)[µ-(2-hydroxybenzylidene)-4-prop-2-en-1-ylthiocarbazone-S]silver with antimicrobial activity against bacteria Salmonella abony - Google Patents
Catena-(µ-nitrato)[µ-(2-hydroxybenzylidene)-4-prop-2-en-1-ylthiocarbazone-S]silver with antimicrobial activity against bacteria Salmonella abony Download PDFInfo
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- MD4252C1 MD4252C1 MDA20120044A MD20120044A MD4252C1 MD 4252 C1 MD4252 C1 MD 4252C1 MD A20120044 A MDA20120044 A MD A20120044A MD 20120044 A MD20120044 A MD 20120044A MD 4252 C1 MD4252 C1 MD 4252C1
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- 230000000845 anti-microbial effect Effects 0.000 title claims abstract description 12
- 241001148132 Salmonella enterica subsp. enterica serovar Abony Species 0.000 title claims abstract description 10
- 229910052709 silver Inorganic materials 0.000 title claims abstract description 9
- 239000004332 silver Substances 0.000 title claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 239000013081 microcrystal Substances 0.000 claims abstract description 4
- 239000003814 drug Substances 0.000 abstract description 7
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 abstract description 3
- 239000004599 antimicrobial Substances 0.000 abstract description 2
- 229910052723 transition metal Inorganic materials 0.000 abstract description 2
- 150000003624 transition metals Chemical class 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 10
- 244000005700 microbiome Species 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 5
- 150000003378 silver Chemical group 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical group [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- -1 monodeprotonated 2-formylpyridine dimethylphenylthiosemicarbazone Chemical class 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 241000193755 Bacillus cereus Species 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 241000607142 Salmonella Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- IGRCWJPBLWGNPX-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-(4-chlorophenyl)-n,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl IGRCWJPBLWGNPX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000003385 Diospyros ebenum Nutrition 0.000 description 1
- 241000792913 Ebenaceae Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 238000012404 In vitro experiment Methods 0.000 description 1
- 241000607760 Shigella sonnei Species 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010835 comparative analysis Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229940006477 nitrate ion Drugs 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 229940115939 shigella sonnei Drugs 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 150000003379 silver compounds Chemical class 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 150000003584 thiosemicarbazones Chemical class 0.000 description 1
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Invenţia se referă la chimie şi medicină, şi anume la un compus coordinativ polinuclear de argint(I) din clasa tiosemicarbazonaţilor metalelor de tranziţie, care poate găsi aplicare în medicină şi medicina veterinară în calitate de preparat antimicrobian. The invention relates to chemistry and medicine, namely to a polynuclear coordination compound of silver(I) from the thiosemicarbazonate class of transition metals, which can find application in medicine and veterinary medicine as an antimicrobial preparation.
Din compuşii coordinativi care inhibă creşterea şi multiplicarea bacteriilor din specia Salmonella abony cel mai înalt efect antimicrobian a fost obţinut în cazul di(µ-S)-bis{cloro-[2-picoliden-4-(2,6-dimetilfenil)tiosemicarbazido-(1-)]cupru} tetrahidrat (cea mai apropiată soluţie şi analogul structural) [1]. Of the coordinating compounds that inhibit the growth and multiplication of Salmonella abony bacteria, the highest antimicrobial effect was obtained in the case of di(µ-S)-bis{chloro-[2-picolidene-4-(2,6-dimethylphenyl)thiosemicarbazido- (1-)]copper} tetrahydrate (closest solution and structural analogue) [1].
Dezavantajele complexului dat constau în faptul că deşi el inhibă creşterea şi multiplicarea bacteriilor din specia Salmonella abony în concentraţie de 9,37 µg/ml, acesta nu găseşte aplicare în practica medicală din cauza activităţii scăzute faţă de alte tipuri de microorganisme gram-pozitive şi gram-negative. The disadvantages of this complex consist in the fact that although it inhibits the growth and multiplication of bacteria from the species Salmonella abony in a concentration of 9.37 µg/ml, it does not find application in medical practice due to its low activity against other types of gram-positive and gram-negative microorganisms - negative.
Problema pe care o rezolvă invenţia constă în obţinerea unui compus coordinativ nou, care posedă activitate bacteriostatică şi bactericidă înaltă faţă de bacteriile din specia Salmonella abony şi alte tipuri de microorganisme. The problem that the invention solves consists in obtaining a new coordinating compound, which possesses high bacteriostatic and bactericidal activity against bacteria of the species Salmonella abony and other types of microorganisms.
Esenţa invenţiei constă în sinteza compusului catena-(µ-nitrato)[µ-(2-hidroxibenziliden)-4-prop-2-en-l-iltiosemicarbazon-S]argint cu formula: The essence of the invention consists in the synthesis of the catena-(µ-nitrato)[µ-(2-hydroxybenzylidene)-4-prop-2-en-l-ylthiosemicarbazone-S]silver compound with the formula:
unde n este limitat de mărimile microcristalelor; where n is limited by the microcrystal sizes;
, ,
care manifestă activitate antimicrobiană faţă de bacteriile Salmonella abony. which exhibits antimicrobial activity against Salmonella abony bacteria.
Rezultatul tehnic al invenţiei constă în stabilirea la compusul revendicat a activităţii antimicrobiene faţă de bacteriile din specia Salmonella abony, care depăşeşte de 66,9 ori caracteristicile analoage ale di(µ-S)-bis{cloro-[2-picoliden-4-(2,6-dimetilfenil)tiosemicarbazido-(1-)]cupru} tetrahidrat (cea mai apropiată soluţie şi analogul structural). The technical result of the invention consists in the establishment of the claimed compound's antimicrobial activity against the bacteria of the species Salmonella abony, which exceeds by 66.9 times the analogous characteristics of di(µ-S)-bis{chloro-[2-picolidene-4-( 2,6-dimethylphenyl)thiosemicarbazido-(1-)]copper} tetrahydrate (closest solution and structural analogue).
Rezultatul tehnic al invenţiei este condiţionat de faptul că pentru prima dată în calitate de inhibitori de creştere şi multiplicare a bacteriilor din specia Salmonella abony se propune catena-(µ-nitrato)[µ-(2-hidroxibenziliden)-4-prop-2-en-l-iltiosemicarbazon-S]argint, care conţine o combinaţie nouă de legături chimice deja cunoscute. The technical result of the invention is conditioned by the fact that, for the first time, catena-(µ-nitrato)[µ-(2-hydroxybenzylidene)-4-prop-2- en-l-ylthiosemicarbazone-S]argint, which contains a new combination of already known chemical bonds.
Complexul dat, proprietăţile lui şi metoda de sinteză nu sunt descrise în literatură. The given complex, its properties and the synthesis method are not described in the literature.
Analiza comparativă a compusului revendicat cu cea mai apropiată soluţie demonstrează că ei se deosebesc prin aceea că în comparaţie cu analogul structural este schimbat atomul central, la care numărul de coordinare a crescut până la şapte, dimetilfeniltiosemicarbazona 2-formilpiridinei monodeprotonată din cea mai apropiată soluţie este înlocuită cu 4-aliltiosemicarbazona aldehidei salicilice nedeprotonată, acido-ligandul - clorul este înlocuit cu nitrat-ion. Acest ligand uneşte fragmente complexe în lanţuri polimerice. Datorită acestor particularităţi în structura complexului revendicat se realizează o combinaţie nouă de legături chimice deja cunoscute. The comparative analysis of the claimed compound with the nearest solution demonstrates that they differ in that compared to the structural analogue the central atom is changed, where the coordination number has increased to seven, the monodeprotonated 2-formylpyridine dimethylphenylthiosemicarbazone from the nearest solution is replaced by unprotonated salicylic aldehyde 4-allylthiosemicarbazone, the acid-ligand - chlorine is replaced by nitrate-ion. This ligand joins complex fragments into polymer chains. Due to these particularities in the structure of the claimed complex, a new combination of already known chemical bonds is achieved.
Compusul revendicat se obţine la temperatura camerei (≈ 20°C) la interacţiunea soluţiei metanolice a nitratului de argint cu 4-aliltiosemicarbazona aldehidei salicilice luate în raport molar 1:1. Reacţia decurge în 50…60 min conform următoarei scheme: The claimed compound is obtained at room temperature (≈ 20°C) by the interaction of the methanolic solution of silver nitrate with 4-allylthiosemicarbazone of salicylic aldehyde taken in a 1:1 molar ratio. The reaction proceeds in 50...60 min according to the following scheme:
unde n este limitat de mărimile microcristalelor; where n is limited by the microcrystal sizes;
. .
Mecanismul reacţiei date constă în coordinarea 4-aliltiosemicarbazonei aldehidei salicilice la ionul de argint(1+) prin atomul de sulf ca ligand-punte neutru. Al doilea loc coordinativ în sfera internă а atomului central îl ocupă atomul de sulf al moleculei vecine. La rândul său, în molecula vecină al doilea loc coordinativ este ocupat de atomul de sulf al următorului fragment coordinativ. Locurile al treilea, al patrulea, al cincilea şi al şaselea în sfera coordinativă а tuturor atomilor centrali de argint sunt ocupate de trei nitrat-ioni-punte. Ultimul loc coordinativ în sfera internă este ocupat de atomul de oxigen al grupei fenolice nedeprotonate а 4-aliltiosemicarbazonei aldehidei salicilice din lanţul polimeric vecin. The mechanism of the given reaction consists in the coordination of the 4-allylthiosemicarbazone of salicylic aldehyde to the silver ion(1+) through the sulfur atom as a neutral bridging ligand. The second coordinating place in the internal sphere of the central atom is occupied by the sulfur atom of the neighboring molecule. In turn, in the neighboring molecule the second coordinating place is occupied by the sulfur atom of the next coordinating fragment. The third, fourth, fifth and sixth places in the coordination sphere of all central silver atoms are occupied by three nitrate-ion-bridges. The last coordinating place in the inner sphere is occupied by the oxygen atom of the unprotonated phenolic group of the 4-allylthiosemicarbazone of salicylic aldehyde from the neighboring polymer chain.
Procedeul de obţinere а compusului coordinativ polinuclear revendicat este simplu în executare, substanţele iniţiale sunt accesibile, randamentul constituie 71% faţă de cel teoretic calculat. Complexul sintetizat are culoare brună deschisă, este stabil în contact cu aerul, bine solubil în alcooli alifatici, dimetilformamidă şi dimetilsulfoxid, practic insolubil în eter. The procedure for obtaining the claimed polynuclear coordination compound is simple in execution, the initial substances are accessible, the yield is 71% compared to the theoretically calculated one. The synthesized complex has a light brown color, is stable in contact with air, well soluble in aliphatic alcohols, dimethylformamide and dimethylsulfoxide, practically insoluble in ether.
Exemplu de obţinere a catena-(µ-nitrato)[µ-(2-hidroxibenziliden)-4-prop- 2-en-l-iltiosemicarbazon-S]argintului Example of obtaining caten-(µ-nitrato)[µ-(2-hydroxybenzylidene)-4-prop-2-en-l-ylthiosemicarbazone-S]argin
La soluţia metanolică, care conţine 10 mmol de nitrat de argint în 25 ml de metanol, amestecată în permanenţă cu ajutorul agitatorului magnetic, se adaugă soluţie de 10 mmol de 4-aliltiosemicarbazonă a aldehidei salicilice în 25 ml de alcool. După aceasta, amestecul reactant se agită în permanenţă cu ajutorul agitatorului magnetic timp de 50...60 min. Peste o zi din amestecul reactant se depun cristale mărunte de culoare brună deschisă, care se filtrează prin filtru din sticlă, se spală cu metanol, eter şi se usucă în aer. A solution of 10 mmol of 4-allylthiosemicarbazone of salicylic aldehyde in 25 ml of alcohol is added to the methanolic solution, which contains 10 mmol of silver nitrate in 25 ml of methanol, constantly mixed with the aid of a magnetic stirrer. After this, the reactant mixture is constantly stirred with the help of the magnetic stirrer for 50...60 min. After one day, small light brown crystals are deposited from the reaction mixture, which are filtered through a glass filter, washed with methanol, ether and dried in air.
S-a determinat, %: С - 32,39; H - 3,15; Ag - 26,81; N - 13,77; S - 7,78. It was determined, %: С - 32.39; H - 3.15; Ag - 26.81; N - 13.77; S - 7.78.
Pentru C11H13AgN4O4S s-a calculat, %: С - 32,61; H - 3,23; Ag - 26,62; N -13,83; S - 7,91. For C11H13AgN4O4S it was calculated, %: С - 32.61; H - 3.23; Ag - 26.62; N -13.83; S - 7.91.
La recristalizarea compusului revendicat din soluţie metanolică au fost obţinute monocristale, structura cărora a fost stabilită cu ajutorul analizei cu raze X. Experimentul s-a efectuat la difractometrul Xcalibur-Gemini „Oxford Diffraction”. Structura a fost determinată prin metoda directă şi stabilită folosind metoda pătratelor minime în apropieri anizotrope pentru atomii de hidrogen după programele SHELX-97. Atomii de hidrogen sunt incluşi în poziţiile geometrice prevăzute, iar factorul lor de temperatură UH este luat de 1,2 ori mai mare decât în cazul atomilor de carbon şi oxigen legaţi cu ei. Parametrii principali ai experimentului sunt prezentaţi în tabelul 1. Coordonatele atomilor de bază ai structurii studiate sunt depuse în baza de date Cambridge (CCDC 860423). În compusul studiat atomul de argint coordinează cu molecula de 4-aliltiosemicarbazona aldehidei salicilice şi nitrat-ionii. A fost stabilit că atomii de sulf ai fragmentului tiosemicarbazonic unesc complecşii în lanţuri infinite în direcţia axei cristalografice с cu distanţele Ag(l)-S(l) 2,444(4) şi 2,464(3) Å (fig. 1 şi 2). Upon recrystallization of the claimed compound from methanolic solution, single crystals were obtained, the structure of which was established with the help of X-ray analysis. The experiment was performed on the Xcalibur-Gemini "Oxford Diffraction" diffractometer. The structure was determined by the direct method and established using the least squares method in anisotropic approximations for hydrogen atoms according to SHELX-97 programs. The hydrogen atoms are included in the predicted geometric positions, and their temperature factor UH is taken 1.2 times higher than in the case of the carbon and oxygen atoms bound to them. The main parameters of the experiment are presented in table 1. The coordinates of the basic atoms of the studied structure are deposited in the Cambridge database (CCDC 860423). In the studied compound, the silver atom coordinates with the 4-allylthiosemicarbazone molecule of salicylic aldehyde and nitrate ions. It was established that the sulfur atoms of the thiosemicarbazonic fragment unite the complexes in infinite chains in the direction of the crystallographic axis with Ag(l)-S(l) distances of 2.444(4) and 2.464(3) Å (figs. 1 and 2).
În polimer atomul de argint coordinează prin atomii de oxigen ai tiosemicarbazonei din lanţul vecin şi trei nitrato-grupe, cu distanţa Ag-O egală cu 2,804(14); 2,877(15); 2,999(15); 3,20(2) Å (fig. 2). Distanţa dintre atomii de argint apropiaţi din lanţul polimeric este egală cu 3,674 Å. Astfel în compusul studiat numărul de coordinare al atomului de argint este şapte. Atomii de sulf, oxigenul fenolic al ligandului organic din lanţul vecin şi atomul de oxigen al uneia din grupările NO3 - constituie planul ecuatorial al poliedrului de coordinare al atomului de argint. Deplasarea atomilor daţi de la acest plan constituie -0,121; -0,035; 0,041; 0,116 şi 0,036 Å. Pe de o parte a planului ecuatorial al poliedrului de coordinare al atomului de argint, a doua nitrato-grupă coordinează la atomul de metal prin doi atomi de oxigen cu distanţe 2,739 şi 2,999 Å, iar pe de altă parte a acestui plan, atomul de oxigen din a treia grupă NO3 - formează cea mai lungă legătură Ag-O pentru acest complex egală cu 3,200 Å. Unghiurile între această legătură coordinativă şi două alte legături apicale constituie 162,2 şi 151,9°. In the polymer, the silver atom coordinates through the oxygen atoms of the thiosemicarbazone in the neighboring chain and three nitrato-groups, with the Ag-O distance equal to 2.804(14); 2,877(15); 2,999(15); 3.20(2) Å (Fig. 2). The distance between the adjacent silver atoms in the polymer chain is equal to 3.674 Å. Thus, in the studied compound, the coordination number of the silver atom is seven. The sulfur atoms, the phenolic oxygen of the organic ligand in the neighboring chain and the oxygen atom of one of the NO3 - groups constitute the equatorial plane of the coordination polyhedron of the silver atom. The displacement of the given atoms from this plane is -0.121; -0.035; 0.041; 0.116 and 0.036 Å. On one side of the equatorial plane of the coordination polyhedron of the silver atom, the second nitrate group coordinates to the metal atom through two oxygen atoms with distances of 2.739 and 2.999 Å, and on the other side of this plane, the oxygen atom of the third group NO3 - forms the longest Ag-O bond for this complex equal to 3,200 Å. The angles between this coordinating link and two other apical links are 162.2 and 151.9°.
Astfel, în baza rezultatelor analizei cu raze X a fost stabilită structura compusului revendicat. Thus, based on the results of the X-ray analysis, the structure of the claimed compound was established.
Activitatea antimicrobiană a catenei-(µ-nitrato)[µ-(2-hidroxibenziliden)-4-prop-2-en-l-iltiosemicarbazon-S]argintului a fost determinată în mediu nutritiv lichid (bulion peptonat din carne de 2%, pH 7,0) prin metoda diluţiilor succesive. În calitate de cultură de referinţă în experimentul in vitro au fost folosite tulpinile standard de Staphylococcus aureus (АТСС 25923), Bacillus cereus (ГИСК 8035), Escherichia coli (АТСС 25922), Shigela sonnei şi Salmonella abony (ГИСК 03/03). Dizolvarea substanţei studiate în dimetilsulfoxid, cultivarea microorganismelor, obţinerea suspensiei, determinarea concentraţiei minime de inhibare (CMI) şi concentraţiei minime bactericide (CMB) au fost efectuate după metoda standard descrisă în literatură. The antimicrobial activity of (µ-nitrato)[µ-(2-hydroxybenzylidene)-4-prop-2-en-l-ylthiosemicarbazone-S]argin chain was determined in liquid nutrient medium (2% meat peptonate broth, pH 7.0) by the method of successive dilutions. The standard strains of Staphylococcus aureus (АТСС 25923), Bacillus cereus (ГИСК 8035), Escherichia coli (АТСС 25922), Shigella sonnei and Salmonella ebony (ГИСК 03/03) were used as reference culture in the in vitro experiment. The dissolution of the studied substance in dimethylsulfoxide, the cultivation of microorganisms, the preparation of the suspension, the determination of the minimum inhibition concentration (MIC) and the minimum bactericidal concentration (MBC) were performed according to the standard method described in the literature.
Rezultatele studiului activităţii antimicrobiene a catenei-(µ-nitrato)[µ-(2-hidroxibenziliden)-4-prop-2-en-l-iltiosemicarbazon-S]argintului sunt prezentate în tabelul 2, din care se vede că complexul revendicat posedă activitate bacteriostatică şi bactericidă în limitele concentraţiilor 0,59…2,34 µg/mL faţă de bacteriile gram-pozitive şi 0,07…0,59 µg/mL faţă de microorganismele gram-negative. Pentru comparaţie în acelaşi tabel sunt prezentate rezultatele activităţii antimicrobiene caracteristice di(µ-S)-bis{cloro-[2-picoliden-4-(2,6-dimetilfenil)tiosemicarbazido-(1-)]cupru} tetrahidrat (celei mai apropiate soluţii şi analogului structural), care manifestă cea mai înaltă activitate faţă de bacteriile din specia Salmonella abony dintre substanţele din şirul tiosemicarbazonic, cunoscute în literatură. Datele experimentale obţinute demonstrează că catena-(µ-nitrato)[µ-(2-hidroxibenziliden)-4-prop-2-en-l-iltiosemicarbazon-S]argint manifestă activitate antimicrobiană faţă de microorganismele din specia Salmonella abony de 66,9 ori mai înaltă decât di(µ-S)-bis{cloro-[2-picoliden-4-(2,6-dimetilfenil)tiosemicarbazido-(1-)]cupru} tetrahidrat. The results of the study of the antimicrobial activity of the (µ-nitrato)[µ-(2-hydroxybenzylidene)-4-prop-2-en-l-ylthiosemicarbazone-S]argent chain are presented in table 2, from which it can be seen that the claimed complex possesses bacteriostatic and bactericidal activity within the concentration limits of 0.59...2.34 µg/mL against gram-positive bacteria and 0.07...0.59 µg/mL against gram-negative microorganisms. For comparison, the same table shows the results of the characteristic antimicrobial activity of di(µ-S)-bis{chloro-[2-picolidene-4-(2,6-dimethylphenyl)thiosemicarbazido-(1-)]copper} tetrahydrate (the closest solutions and the structural analogue), which shows the highest activity against the bacteria of the species Salmonella abony among the substances of the thiosemicarbazone series, known in the literature. The obtained experimental data demonstrate that catena-(µ-nitrato)[µ-(2-hydroxybenzylidene)-4-prop-2-en-l-ylthiosemicarbazone-S]argin exhibits antimicrobial activity against microorganisms from the species Salmonella abony of 66.9 times higher than di(µ-S)-bis{chloro-[2-picolidene-4-(2,6-dimethylphenyl)thiosemicarbazido-(1-)]copper} tetrahydrate.
Proprietăţile depistate ale compusului revendicat prezintă interes din punct de vedere al extinderii arsenalului de remedii antimicrobiene, iar complexul respectiv poate fi utilizat în cazul rezistenţei microorganismelor faţă de medicamentele tradiţionale. The detected properties of the claimed compound are of interest from the point of view of expanding the arsenal of antimicrobial remedies, and the respective complex can be used in the case of resistance of microorganisms to traditional drugs.
Tabelul 1 Table 1
Caracteristicile cristalografice ale catena-(µ-nitrato)[µ-(2-hidroxibenziliden)-4-prop-2-en-1-iltiosemicarbazon-S]argintului Crystallographic characteristics of catena-(µ-nitrato)[µ-(2-hydroxybenzylidene)-4-prop-2-en-1-ylthiosemicarbazone-S]argin
Formula moleculară C11H13Ag1N4O4S1 Masa molară, g/mol 403,97 Singonia, grupa spaţială, Z hexagonală, R3C, 18 a, Å 300,3891 (10) b, Å 30,3891 (10) c, Å 9,2144 (6) α, grad 90 β, grad 90 γ, grad 120 V, Å3 7369,4 (6) Dx, g/cm3 1,643 Radiaţia; λ, Å MoKα; 0,7107 µ, cm-1 1,376 T, K 293 (2) Dimensiunea monocristalului, mm 0,10 x 0,30 x 0,35 Difractometrul Xcalibur-Gemini Tipul scanării θ/2θ θmax, grad 24,99 Limitele h, k, l -36≤ h ≤34 -34≤ k ≤33 -10≤ 1 ≤5 Reflexe colectate/independente (N1), / cu I >2σ(I), (N2) 4494/1852 [R(int) = 0,0641] Metoda aprecierii Metoda pătratelor minime Numărul parametrilor 192 R1/wR2 (N2) 0,0585 / 0,0821 S 0,968 Δρ(max), Δρ(min), e/A3 0,460, -0,361 Programe SHELX-97 Molecular formula C11H13Ag1N4O4S1 Molar mass, g/mol 403.97 Singonia, space group, Z hexagonal, R3C, 18 a, Å 300.3891 (10) b, Å 30.3891 (10) c, Å 9.2144 (6) α, degree 90 β, degree 90 γ, degree 120 V, Å3 7369.4 (6) Dx, g/cm3 1.643 Radiation; λ, Å MoKα; 0.7107 µ, cm-1 1.376 T, K 293 (2) Single crystal size, mm 0.10 x 0.30 x 0.35 Xcalibur-Gemini diffractometer Scan type θ/2θ θmax, degree 24.99 Limits h, k , l -36≤ h ≤34 -34≤ k ≤33 -10≤ 1 ≤5 Collected/independent reflexes (N1), / with I >2σ(I), (N2) 4494/1852 [R(int) = 0 .0641] Assessment method Least squares method Number of parameters 192 R1/wR2 (N2) 0.0585 / 0.0821 S 0.968 Δρ(max), Δρ(min), e/A3 0.460, -0.361 SHELX-97 programs
Tabelul 2 Table 2
Concentraţia minimă de înhibare (CMI) şi concentraţia minimă bactericidă (CMB) a compusului coordinativ revendicat faţă de microorganismele gram-pozitive şi gram-negative (mg/ml) The minimum inhibitory concentration (MIC) and the minimum bactericidal concentration (MBC) of the claimed coordinating compound against gram-positive and gram-negative microorganisms (mg/ml)
Compusul Microorganismele gram-pozitive Microorganismele gram-negative Staphylococcus aureus, ATCC 25923 Bacillus cereus, ГИСК Escherichia coli, ATCC 25922 Shigela sonnei Salmonella adony ГИСК 03/03 CMI CMB CMI CMB CMI CMB CMI CMB CMI CMB Cea mai apropiată soluţie 0,009 0,018 0,009 0,018 9,37 37,5 0,07 0,07 9,37 9,37 Catena-(µ-nitrato)[µ-(2-hidroxibenziliden)-4-prop-2-en-1-iltiosemicarbazon-S]argint 0,59 1,17 1,17 2,34 0,29 0,59 0,15 0,29 0,07 0,14 Compound Gram-positive microorganisms Gram-negative microorganisms Staphylococcus aureus, ATCC 25923 Bacillus cereus, ГИСК Escherichia coli, ATCC 25922 Shigela sonnei Salmonella adony ГИСК 03/03 CMI CMB CMI CMB CMI CMB CMI CMB CMI CMB Closest solution 0.009 0.018 0.009 0.018 9 .37 37.5 0.07 0.07 9.37 9.37 Chain-(µ-nitrato)[µ-(2-hydroxybenzylidene)-4-prop-2-en-1-ylthiosemicarbazone-S]Silver 0, 59 1.17 1.17 2.34 0.29 0.59 0.15 0.29 0.07 0.14
1. MD 4112 B1 2011.05.31 1. MD 4112 B1 2011.05.31
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| MD195B1 (en) * | 1994-12-05 | 1995-05-31 | Univ De Stat De Medicina N Tes | Copper complexes with antistaphylococcal properties |
| MD1650F1 (en) * | 1999-12-06 | 2001-04-30 | Univ Nicolae Testemitanu | 3,5-Dibromsalicylidenethiosemicarbazidopyridinecopper possessing antistaphylococcia and antistreptococcia activity |
| MD1812B1 (en) * | 2000-12-29 | 2001-12-31 | Univ Nicolae Testemitanu | Copper complexes as bacteria and fungi inhibitors |
| MD2003B1 (en) * | 2001-01-10 | 2002-09-30 | Univ Nicolae Testemitanu | Copper chelate compounds(II) with antimicrobial and antimycotic activity |
| MD2942B2 (en) * | 2004-04-27 | 2005-12-31 | Universitatea De Stat De Medicina Si Farmacie "Nicolae Testemitanu" Din Republica Moldova | Di(-O)-bis(3,5-dibromosalicylidene thiosemicarbazonatocopper) |
| MD3032F1 (en) * | 2005-10-31 | 2006-04-30 | Universitatea De Stat Din Moldova | Copper (II) naphthalidyosemicarbazides containing sulfanylamides |
| MD3124B1 (en) * | 2005-05-25 | 2006-08-31 | Universitatea De Stat De Medicina Si Farmacie "Nicolae Testemitanu" Din Republica Moldova | Copper (II) salicylidentesemicarbazidates containing sulfanylamides |
| MD4112B1 (en) * | 2010-05-17 | 2011-05-31 | Univ De Stat Din Moldova | Coordinative compounds of copper with 4-(dimethylphenyl)-thiosemicarbazones of 2-formylpyridine |
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2012
- 2012-05-31 MD MDA20120044A patent/MD4252C1/en not_active IP Right Cessation
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU979359A1 (en) * | 1981-07-20 | 1982-12-07 | Ордена Трудового Красного Знамени Институт Химии Ан Мсср | Derivatives of iron(iii) mu-oxo-bis-(s-alkyl-n1n4-di(salicylydene)thiosemicarbazidato) and process for producing the same |
| MD195B1 (en) * | 1994-12-05 | 1995-05-31 | Univ De Stat De Medicina N Tes | Copper complexes with antistaphylococcal properties |
| MD1650F1 (en) * | 1999-12-06 | 2001-04-30 | Univ Nicolae Testemitanu | 3,5-Dibromsalicylidenethiosemicarbazidopyridinecopper possessing antistaphylococcia and antistreptococcia activity |
| MD1812B1 (en) * | 2000-12-29 | 2001-12-31 | Univ Nicolae Testemitanu | Copper complexes as bacteria and fungi inhibitors |
| MD2003B1 (en) * | 2001-01-10 | 2002-09-30 | Univ Nicolae Testemitanu | Copper chelate compounds(II) with antimicrobial and antimycotic activity |
| MD2942B2 (en) * | 2004-04-27 | 2005-12-31 | Universitatea De Stat De Medicina Si Farmacie "Nicolae Testemitanu" Din Republica Moldova | Di(-O)-bis(3,5-dibromosalicylidene thiosemicarbazonatocopper) |
| MD3124B1 (en) * | 2005-05-25 | 2006-08-31 | Universitatea De Stat De Medicina Si Farmacie "Nicolae Testemitanu" Din Republica Moldova | Copper (II) salicylidentesemicarbazidates containing sulfanylamides |
| MD3032F1 (en) * | 2005-10-31 | 2006-04-30 | Universitatea De Stat Din Moldova | Copper (II) naphthalidyosemicarbazides containing sulfanylamides |
| MD4112B1 (en) * | 2010-05-17 | 2011-05-31 | Univ De Stat Din Moldova | Coordinative compounds of copper with 4-(dimethylphenyl)-thiosemicarbazones of 2-formylpyridine |
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