Biological evaluation of tetracationic compounds based on two 1,4-diazabicyclo[2.2.2]octane moieties connected by different linkers

Буракова, Е. А.; Saranina, Irina V.; Tikunova, Nina; Nazarkina, Zhanna K.; Laktionov, Pavel P.; Karpinskaya, Lubov’ A.; Anikin, Vadim; Zarubaev, Vladimir V.; Silnikov, Vladimir N.

doi:10.1016/j.bmc.2016.09.064

Cited by 16 publications

(15 citation statements)

References 51 publications

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“…DABCO-based polycationic amphiphiles containing rigid L linker groups have the same antibacterial activity against both Staphylococcus aureus and Enterococcus faecalis. We obtained similar results for ciprofloxacin [8]. However, in the case of conjugates of cationic amphiphiles with an antibiotic containing a similar rigid linker group there is a significantly lower activity against both gram-positive and all tested gram-negative microorganisms.…”

Section: Discussionsupporting

confidence: 75%

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Antibacterial activity of cationic amphiphil conjugates with ciprofloxacin

Zadvornykh

Zhang²,

Liu³

et al. 2022

ijhs

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The aim: Design and synthesis of new compounds with antibacterial activity. Determination of the minimum inhibitory and minimum bactericidal concentration of conjugates of cationic amphiphiles based on quaternary salts of 1,4-diazabicyclo[2.2.2]octane with ciprofloxacin. Materials and methods: The article is dedicated to the synthesis and primary assessment of antibacterial activity in vitro of conjugates of cationic amphiphiles based on quaternary salts of 1,4-diazabicyclo[2.2.2]octane with ciprofloxacin against gram-negative and gram-positive microorganisms. Results: The present work provides hybrid structures which include the widely used antibiotic ciprofloxacin and tetra-cationic DABCO derivatives. The last ones previously showed a wide spectrum of antimicrobial activity as well as primary studies of their antibacterial activity against gram-positive and gram-negative microorganisms in vitro. There was a high in vitro antibacterial activity against gram-negative pathogens, moderate against Staphylococcus aureus and low against Enterococcus faecalis. Conclusions: A range of amphiphilic polycationic compounds based on quaternary salts of 1,4-diazabicyclo[2.2.2]octane (DABCO) was synthesized and their biological activity was studied. The compounds have demonstrated high antibacterial activity. We assume that they can serve as a basis for the development of new antibacterial drugs.

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Section: Discussionsupporting

confidence: 75%

“…Synthetic amphiphilic polycationic compounds based on quaternary salts of 1,4diazabicyclo [2.2.2] octane (DABCO) possess a similar spectrum of biological activity and they can serve as a basis for new antibacterial drugs that are an alternative to modern antibiotics [8][9].…”

Section: Introductionmentioning

confidence: 99%

Antibacterial activity of cationic amphiphil conjugates with ciprofloxacin

Zadvornykh

Zhang²,

Liu³

et al. 2022

ijhs

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“…Several reports also suggested a mild fibrinolytic activity of iloprost [ 53 , 54 , 55 , 56 ]. Antimicrobial effect was furnished by a cationic amphiphilic drug (CAD) 1,5-bis-(4-tetradecyl-1,4-diazoniabicyclo [2.2.2] octan-1-yl) pentane tetrabromide, which has RNase activity in contrast to other CADs and therefore has higher antibacterial and antiviral properties [ 33 , 57 , 58 , 59 ]. Both iloprost and CAD were conjugated to the TEVG luminal surface using a poly(vinylpyrrolidone) (PVP) hydrogel.…”

Section: Resultsmentioning

confidence: 99%

Controlled and Synchronised Vascular Regeneration upon the Implantation of Iloprost- and Cationic Amphiphilic Drugs-Conjugated Tissue-Engineered Vascular Grafts into the Ovine Carotid Artery: A Proteomics-Empowered Study

et al. 2022

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Implementation of small-diameter tissue-engineered vascular grafts (TEVGs) into clinical practice is still delayed due to the frequent complications, including thrombosis, aneurysms, neointimal hyperplasia, calcification, atherosclerosis, and infection. Here, we conjugated a vasodilator/platelet inhibitor, iloprost, and an antimicrobial cationic amphiphilic drug, 1,5-bis-(4-tetradecyl-1,4-diazoniabicyclo [2.2.2]octan-1-yl) pentane tetrabromide, to the luminal surface of electrospun poly(ε-caprolactone) (PCL) TEVGs for preventing thrombosis and infection, additionally enveloped such TEVGs into the PCL sheath to preclude aneurysms, and implanted PCLIlo/CAD TEVGs into the ovine carotid artery (n = 12) for 6 months. The primary patency was 50% (6/12 animals). TEVGs were completely replaced with the vascular tissue, free from aneurysms, calcification, atherosclerosis and infection, completely endothelialised, and had clearly distinguishable medial and adventitial layers. Comparative proteomic profiling of TEVGs and contralateral carotid arteries found that TEVGs lacked contractile vascular smooth muscle cell markers, basement membrane components, and proteins mediating antioxidant defense, concurrently showing the protein signatures of upregulated protein synthesis, folding and assembly, enhanced energy metabolism, and macrophage-driven inflammation. Collectively, these results suggested a synchronised replacement of PCL with a newly formed vascular tissue but insufficient compliance of PCLIlo/CAD TEVGs, demanding their testing in the muscular artery position or stimulation of vascular smooth muscle cell specification after the implantation.

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“…Nitrogen containing heterocycles and their derivatives have emerged as promising candidates in the field of medicinal chemistry, due to their ability to form hydrogen bonding with the target proteins as well as π-stacking interactions [1][2][3][4][5]. Among them indole [6], pyrrole [7], imidazole [8] and triazole [9] derivatives had received more attention due to the availability of several synthetic routes to access them with diversity in substituents.…”

Section: Introductionmentioning

confidence: 99%