PURPOSE: Plasmonic photothermal cancer therapy by gold nanorods (GNRs) emerges as a promising tool for cancer treatment. The goal of this study was to design cationic oligoethylene glycol (OEG) compounds varying in hydrophobicity and molecular electrostatic potential as ligand shells of GNRs. Three series of ligands with different length of OEG chain (ethylene glycol units = 3, 4, 5) and variants of quaternary ammonium salts (QAS) as terminal functional group were synthesized and compared to a prototypical quaternary ammonium ligand with alkyl chain - (16-mercaptohexadecyl)trimethylammonium bromide (MTAB). METHODS: Step-by-step research approach starting with the preparation of compounds characterized by NMR and HRMS spectra, GNRs ligand exchange evaluation through characterization of cytotoxicity and GNRs cellular uptake was used. A method quantifying the reshaping of GNRs was applied to determine the effect of ligand structure on the heat transport from GNRs under fs-laser irradiation. RESULTS: Fourteen out of 18 synthesized OEG compounds successfully stabilized GNRs in the water. The colloidal stability of prepared GNRs in the cell culture medium decreased with the number of OEG units. In contrast, the cellular uptake of OEG+GNRs by HeLa cells increased with the length of OEG chain while the structure of the QAS group showed a minor role. Compared to MTAB, more hydrophilic OEG compounds exhibited nearly two order of magnitude lower cytotoxicity in free state and provided efficient cellular uptake of GNRs close to the level of MTAB. Regarding photothermal properties, OEG compounds evoked the photothermal reshaping of GNRs at lower peak fluence (14.8 mJ/cm2) of femtosecond laser irradiation than the alkanethiol MTAB. CONCLUSION: OEG+GNRs appear to be optimal for clinical applications with systemic administration of NPs not-requiring irradiation at high laser intensity such as drug delivery and photothermal therapy inducing apoptosis.

• Klíčová slova
• cellular uptake, gold nanorods, oligoethylene glycol, photothermal stability, quaternary ammonium salts,
• MeSH
• biologický transport MeSH
• HeLa buňky MeSH
• hydrofobní a hydrofilní interakce MeSH
• koloidy MeSH
• kvartérní amoniové sloučeniny chemie   MeSH
• lidé MeSH
• ligandy MeSH
• nanotrubičky chemie   MeSH
• polyethylenglykoly chemie   MeSH
• stabilita léku MeSH
• teplota * MeSH
• zlato chemie   metabolismus   MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• koloidy MeSH
• kvartérní amoniové sloučeniny MeSH
• ligandy MeSH
• polyethylenglykoly MeSH
• zlato MeSH

Nosocomial infections, which greatly increase morbidity among hospitalized patients, together with growing antibiotic resistance still encourage many researchers to search for novel antimicrobial compounds. Picolinium salts with different lengths of alkyl chains (C12, C14, C16) were prepared by Menshutkin-like reaction and evaluated with respect to their biological activity, i.e., lipophilicity and critical micellar concentration. Picolinium salts with C14 and C16 side chains achieved similar or even better results when in terms of antimicrobial efficacy than benzalkoniums; notably, their fungicidal efficiency was substantially more potent. The position of the methyl substituent on the aromatic ring does not seem to affect antimicrobial activity, in contrast to the effect of length of the N-alkyl chain. Concurrently, picolinium salts exhibited satisfactory low cytotoxicity against mammalian cells, i.e., lower than that of benzalkonium compounds, which are considered as safe.

• Klíčová slova
• antimicrobial activity, critical micellar concentration, cytotoxicity, picolinium salts, quaternary ammonium compounds, surfactant,
• MeSH
• antibakteriální látky farmakologie   MeSH
• antiinfekční látky farmakologie   MeSH
• antivirové látky farmakologie   MeSH
• Candida účinky léků   MeSH
• CHO buňky MeSH
• Cricetulus MeSH
• gramnegativní bakterie účinky léků   MeSH
• grampozitivní bakterie účinky léků   MeSH
• houby účinky léků   MeSH
• kvartérní amoniové sloučeniny chemie   farmakologie   MeSH
• kyseliny pikolinové chemická syntéza   chemie   farmakologie   MeSH
• mikrobiální testy citlivosti MeSH
• povrchově aktivní látky chemie   farmakologie   MeSH
• viabilita buněk účinky léků   MeSH
• virus varicella zoster účinky léků   MeSH
• vztahy mezi strukturou a aktivitou MeSH
• zvířata MeSH
• Check Tag
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• antibakteriální látky MeSH
• antiinfekční látky MeSH
• antivirové látky MeSH
• kvartérní amoniové sloučeniny MeSH
• kyseliny pikolinové MeSH
• picolinic acid MeSH Prohlížeč
• povrchově aktivní látky MeSH