Tetracationic compounds based on 1,4-diazabicyclo[2.2.2]octane: antibacterial activity and reactions with N-containing nucleophiles

Буракова, Е. А.; Saranina, Irina V.; Tikunova, Nina; ́nikov, V. N. Sil

doi:10.1007/s11172-015-1023-2

Cited by 4 publications

(4 citation statements)

References 18 publications

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“…High antimicrobial activity of polycationic amphiphiles containing a quaternarized 1,4-diazabicyclo[2.2.2]octane (DABCO) subunit has been reported. [33,37,[56][57][58][59][60] Therefore, the library is based on ionenes containing alkylated DABCO as a positively charged moiety. It is essential to keep crucial structural parameters constant between PEGylated and nonPEGylated polymers to study the impact of PEG moiety as reliable as possible.…”

Section: Introductionmentioning

confidence: 99%

Influence of PEG Subunit on the Biological Activity of Ionenes: Synthesis of Novel Polycations, Antimicrobial and Toxicity Studies

Kopiasz

Kulbacka

Drężek

et al. 2022

Macromolecular Bioscience

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An alarming increase of antibiotic resistance among pathogens creates an urgent need to develop new antimicrobial agents. Many reported polycations show high antimicrobial activity along with low hemolytic activity. Unfortunately, most of those molecules remain highly cytotoxic against various mammalian cells. In this work, a systematic study on the impact of triethylene glycol monomethyl ether side groups (short polyethylene glycol (PEG) analog) on antimicrobial, hemolytic, and cytotoxic properties of novel amphiphilic ionenes is presented. A detailed description of synthesis, leading to well‐defined alternating polymers, which differ in structural elements responsible for hydrophilicity (PEG) and hydrophobicity (alkyl chain), is presented. Obtained results show that the PEG moiety and fine‐tuned hydrophilic‐lipophilic balance of ionenes synergistically lead to low cytotoxic, low hemolytic molecules with high activity against S. aureus, including methicillin‐resistant strains (MRSA). Additionally, the results of mechanistic studies on bacterial cells and fluorescently labeled liposomes are also discussed.

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Section: Introductionmentioning

confidence: 99%

Influence of PEG Subunit on the Biological Activity of Ionenes: Synthesis of Novel Polycations, Antimicrobial and Toxicity Studies

Kopiasz

Kulbacka

Drężek

et al. 2022

Macromolecular Bioscience

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“…S1). Antibacterial activity based on 1,4-diazabicyclo[2.2.2]octane bis-quaternary salts with dodecyl substituents bound by linker groups containing four carbon atoms was analysed and all the compounds displayed activity against the test strains [30]. Antibacterial activity was determined by the disc diffusion method using Muller-Hinton Agar (MHA) medium.…”

Section: Antibacterial Activitymentioning

confidence: 99%

Structural and Spectral Studies of Bis (1, 3, 5-triazinane-2, 4, 6-trione) 1, 4-diazabicyclo [2·2·2] Octane (TTDO).

Ponnuvel,

Nivithaa,

Kala

et al. 2023

J Chem Crystallogr

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1,3,5-triazinane-2,4,6-trione) 1,4-diazabicyclo[2.2.2]octane (TTDO) was prepared from 1,4-Diazabicyclo[2.2.2]octane (DABCO) and cyanuric acid (CA) by solvent evaporation method. The TTDO molecule crystallized in the centrosymmetric space group C2/c with a monoclinic crystal system. The structure has a salt bridge between N1(CA)-H1 and N4(DABCO)-H4. The DABCO comes in between two CA moieties linearly disposed on either side of the two nitrogen atoms of DABCO. On sidewise, the CA molecules extend H-bonding showing a supramolecular assembly. Hydrogen bonding as compelled by stereographic projection. The Hirshfeld surface analysis con rms that the crystal is formed by involving intermolecular interactions. FT-IR con rms the presence of N-H, C-H, C=O and CN stretching vibrations of the molecule. The photoluminescence spectra show intense peaks at 532 nm in the green region. TG-DTA analysis con rms that the molecule is stable up to 143°C and loses CA in the rst stage and DABCO decomposes subsequently. Antibacterial activity shows that TTDO inhibits Gram-positive (Staphylococcus aureus) and Gram-negative (Salmonella typhi) bacteria.

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“…4-Pyridine is also an important raw material for the synthesis of antibacterial active pyridine quaternary ammonium salts, 17 and the DABCO bis-quaternary salts also exhibit antibacterial activity. 18 Theophylline has also been shown to possess antiaging and anticytotoxic effects in human skin. 19 Caffeine is highly biologically active, has the ability to penetrate the skin barrier, and also prevents excessive accumulation of fat in skin cells.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Furthermore, it is known that 4-pyridine and 1,4-diazabicyclo[2.2.2]octane (DABCO) are effective antioxidants. 4-Pyridine is also an important raw material for the synthesis of antibacterial active pyridine quaternary ammonium salts, and the DABCO bis-quaternary salts also exhibit antibacterial activity . Theophylline has also been shown to possess antiaging and anticytotoxic effects in human skin .…”

Section: Introductionmentioning

confidence: 99%

Searching for Suitable Kojic Acid Coformers: From Cocrystals and Salt to Eutectics

Sun

Braun

Casali

et al. 2023

Crystal Growth & Design

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The possibility of obtaining cocrystals of kojic acid with organic coformers has been investigated by both computational and experimental approaches. Cocrystallization attempts have been carried out with about 50 coformers, in different stoichiometric ratios, by solution, slurry, and mechanochemical methods. Cocrystals were obtained with 3-hydroxybenzoic acid, imidazole, 4-pyridone, DABCO, and urotropine, while piperazine yielded a salt with the kojiate anion; cocrystallization with theophylline and 4-aminopyridine resulted in stoichiometric crystalline complexes that could not be described with certainty as cocrystals or salts. In the cases of panthenol, nicotinamide, urea, and salicylic acid the eutectic systems with kojic acid were investigated via differential scanning calorimetry. In all other preparations the resulting materials were constituted of a mixture of the reactants. All compounds were investigated by powder X-ray diffraction; the five cocrystals and the salt were fully characterized via single crystal X-ray diffraction. The stability of the cocrystals and the intermolecular interactions in all characterized compounds have been investigated by computational methods based on the electronic structure and pairwise energy calculations, respectively.

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Tetracationic compounds based on 1,4-diazabicyclo[2.2.2]octane: antibacterial activity and reactions with N-containing nucleophiles

Cited by 4 publications

References 18 publications

Influence of PEG Subunit on the Biological Activity of Ionenes: Synthesis of Novel Polycations, Antimicrobial and Toxicity Studies

Influence of PEG Subunit on the Biological Activity of Ionenes: Synthesis of Novel Polycations, Antimicrobial and Toxicity Studies

Structural and Spectral Studies of Bis (1, 3, 5-triazinane-2, 4, 6-trione) 1, 4-diazabicyclo [2·2·2] Octane (TTDO).

Searching for Suitable Kojic Acid Coformers: From Cocrystals and Salt to Eutectics

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