A series of novel Ga(III)-pyridine carboxylates ([Ga(Pic)3]·H2O (GaPic; HPic = picolinic acid), H3O[Ga(Dpic)2]·H2O (GaDpic; H2Dpic = dipicolinic acid), [Ga(Chel)(H2O)(OH)]2·4H2O (GaChel; H2Chel = chelidamic acid) and [Ga(Cldpic)(H2O)(OH)]2 (GaCldpic; H2Cldpic = 4-chlorodipicolinic acid)) have been synthesized by simple one-step procedure. Vibrational spectroscopy (mid-IR), elemental analysis, thermogravimetric analysis and X-ray diffraction confirmed complexes molecular structure, inter and intramolecular interactions and their influence to spectral and thermal properties. Moreover, complex species speciation was described in Ga(III)-HPic and Ga(III)-H2Dpic systems by potentiometry and 1H NMR spectroscopy and mononuclear complex species were determined; [Ga(Pic)2]+ (logβ021 = 16.23(6)), [Ga(Pic)3] (logβ031 = 20.86(2)), [Ga(Dpic)2]- (logβ021 = 15.42(9)) and [Ga(Dpic)2(OH)]2- (logβ-121 = 11.08(4)). To confirm the complexes stability in 1% DMSO (primary solvent for biological testing), timescale 1H NMR spectra were measured (immediately after dissolution up to 96 h). Antimicrobial activity evaluated by IC50 (0.05 mM) is significant for GaDpic and GaCldpic against difficult to treat and multi-resistant P. aeruginosa. On the other hand, the GaPic complex is most effective against Jurkat, MDA-MB-231 and A2058 cancer cell lines and significantly also decreases the HepG2 cancer cells viability at 75 and 100 μM concentrations in a relatively short time (up to 48 h). In addition, fluorescence measurements have been used to elucidate bovine serum albumin binding activity between ligands, Ga(III) complexes and bovine serum albumin.
A series of novel acridine N-acylhydrazone derivatives have been synthesized as potential topoisomerase I/II inhibitors, and their binding (calf thymus DNA-ctDNA and human serum albumin-HSA) and biological activities as potential anticancer agents on proliferation of A549 and CCD-18Co have been evaluated. The acridine-DNA complex 3b (-F) displayed the highest Kb value (Kb = 3.18 × 103 M-1). The HSA-derivatives interactions were studied by fluorescence quenching spectra. This method was used for the calculation of characteristic binding parameters. In the presence of warfarin, the binding constant values were found to decrease (KSV = 2.26 M-1, Kb = 2.54 M-1), suggesting that derivative 3a could bind to HSA at Sudlow site I. The effect of tested derivatives on metabolic activity of A549 cells evaluated by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide or MTT assay decreased as follows 3b(-F) > 3a(-H) > 3c(-Cl) > 3d(-Br). The derivatives 3c and 3d in vitro act as potential dual inhibitors of hTopo I and II with a partial effect on the metabolic activity of cancer cells A594. The acridine-benzohydrazides 3a and 3c reduced the clonogenic ability of A549 cells by 72% or 74%, respectively. The general results of the study suggest that the novel compounds show potential for future development as anticancer agents.
- MeSH
- akridiny chemie MeSH
- antitumorózní látky * chemie MeSH
- inhibitory topoisomerasy II farmakologie MeSH
- interkalátory MeSH
- lidé MeSH
- lidský sérový albumin chemie MeSH
- vazebná místa MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
V súčasnej dobe existuje 750 druhov húb rodu Cordyceps. Vysoká cena prírodného Cordycepsu a jej nedostatok v prírode spôsobil, že sa pozornosť upriamila na jej pestovanie, kultiváciu v laboratórnych podmienkach. Dopyt po tejto "hube-parazitovi" je aj v dnešnej dobe pomerne vysoký, čo dokazuje aj množstvo komerčných výživových doplnkov. Fytochemická diverzita zabezpečila, že Cordyceps sa používa ako imunomodulátor, antioxidant; má protirakovinové, protizápalové, antidiabetické, antibakteriálne a anti-HIV účinky. Práca sa zaoberá NMR a IR analýzou prírodných látok izolovaných z dvoch druhov húb rodu Cordyceps: Cordyceps sinensis MFTCCB025/0216, MFTCCB026/0216 a Paecilomyces hepiali MFTCCB023/0216. Tie boli umelo kultivované na dvoch substrátoch ryže (Oryza sativa Indica a Oryza sativa Japonica). Celkovo sa analyzovalo päť metanolových extraktov, ktoré boli pripravené refluxovaním pomletého materiálu húb. Na stanovenie kvality a kvantity majoritných chemických zlúčenín sa využila 1D a 2D NMR analýza, ktorej riešením 1H, 13C, COSY, NOESY, HSQC, HMBC a DEPT spektier sa priradili protóny a uhlíky jednotlivým organickým zlúčeninám. Ako doplnková analýza na stanovenie funkčných skupín sa zvolila IR spektroskopia. V extraktoch boli identifikované ako majoritné nasledujúce chemické zlúčeniny: kyselina linolová, kyselina olejová, manitol; ako minoritné tyrozín, alanín, močovina a iné biologicky zaujímavé látky.
There exist about 750 species of Cordyceps at present. A high price of natural Cordyceps and its lack in nature caused that the attention has been focused to its cultivation in laboratory conditions. The demand for this "fungus-parasite" is still quite high nowadays, as shown by the amount of commercial nutritional supplements. Phytochemical diversity has ensured that Cordyceps is used as an immunomodulatory and an antioxidant; it has anti-cancer, anti-inflammatory, anti-diabetic, antibacterial, anti-HIV effects. In the present study we focused on NMR and IR analyses of natural substances isolated from two species of Cordyceps: Cordyceps sinensis MFTCCB025/0216, MFTCCB026/0216 and Paecilomyces hepiali MFTCCB023/0216. Two types of rice substrates (Oryza sativa Indica and Oryza sativa Japonica) were used for cultivation. A total of five methanol extracts obtained by a reflux method of the ground mushroom were analysed. To determine the quality and quantity of the major chemical compounds, 1D and 2D NMR analysis has been used with 1H, 13C, COSY, NOESY, HSQC, HMBC and DEPT spectra. IR spectroscopy was chosen as a complementary analysis to determine functional groups. Linoleic acid, oleic acid and mannitol were identified as major compounds of the methanol extracts. Tyrosine, alanine, urea and the others biologically interesting substances were found as minor components.
- Klíčová slova
- Paecilomyces hepiali,
- MeSH
- Cordyceps * chemie MeSH
- kyselina linolová MeSH
- kyselina olejová MeSH
- magnetická rezonanční spektroskopie MeSH
- mannitol MeSH
- Paecilomyces * chemie MeSH
- spektrofotometrie infračervená MeSH
- tradiční čínská medicína MeSH
- Publikační typ
- práce podpořená grantem MeSH
