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.

• Keywords
• cellular uptake, gold nanorods, oligoethylene glycol, photothermal stability, quaternary ammonium salts,
• MeSH
• Biological Transport MeSH
• HeLa Cells MeSH
• Hydrophobic and Hydrophilic Interactions MeSH
• Colloids MeSH
• Quaternary Ammonium Compounds chemistry   MeSH
• Humans MeSH
• Ligands MeSH
• Nanotubes chemistry   MeSH
• Polyethylene Glycols chemistry   MeSH
• Drug Stability MeSH
• Temperature * MeSH
• Gold chemistry   metabolism   MeSH
• Check Tag
• Humans MeSH
• Publication type
• Journal Article MeSH
• Names of Substances
• Colloids MeSH
• Quaternary Ammonium Compounds MeSH
• Ligands MeSH
• Polyethylene Glycols MeSH
• Gold 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.

• Keywords
• antimicrobial activity, critical micellar concentration, cytotoxicity, picolinium salts, quaternary ammonium compounds, surfactant,
• MeSH
• Anti-Bacterial Agents pharmacology   MeSH
• Anti-Infective Agents pharmacology   MeSH
• Antiviral Agents pharmacology   MeSH
• Candida drug effects   MeSH
• CHO Cells MeSH
• Cricetulus MeSH
• Gram-Negative Bacteria drug effects   MeSH
• Gram-Positive Bacteria drug effects   MeSH
• Fungi drug effects   MeSH
• Quaternary Ammonium Compounds chemistry   pharmacology   MeSH
• Picolinic Acids chemical synthesis   chemistry   pharmacology   MeSH
• Microbial Sensitivity Tests MeSH
• Surface-Active Agents chemistry   pharmacology   MeSH
• Cell Survival drug effects   MeSH
• Herpesvirus 3, Human drug effects   MeSH
• Structure-Activity Relationship MeSH
• Animals MeSH
• Check Tag
• Animals MeSH
• Publication type
• Journal Article MeSH
• Names of Substances
• Anti-Bacterial Agents MeSH
• Anti-Infective Agents MeSH
• Antiviral Agents MeSH
• Quaternary Ammonium Compounds MeSH
• Picolinic Acids MeSH
• picolinic acid MeSH Browser
• Surface-Active Agents MeSH