Ammonium Amphiphiles Based on Natural Compounds: Design, Synthesis, Properties, and Biomedical Applications. A Review

被引：6

作者：

Pashirova, T. N. ^{[1
]}

Shaikhutdinova, Z. M. ^{[1
]}

Mironov, V. F. ^{[1
]}

Bogdanov, A. V. ^{[1
]}

机构：

[1] Russian Acad Sci, Arbuzov Inst Organ & Phys Chem, FRC Kazan Sci Ctr, Kazan 420088, Russia

来源：

DOKLADY CHEMISTRY | 2023年 / 509卷 / 01期

关键词：

ammonium salts; amphiphiles; antimicrobial activity; structure-activity; alkaloids; terpenoids; steroids; natural compounds; PROTIC IONIC LIQUID; ANTIBACTERIAL ACTIVITY; BIOLOGICAL EVALUATION; ANTICANCER ACTIVITY; PHENOLIC-COMPOUNDS; ESCHERICHIA-COLI; SELF-AGGREGATION; SIDE-CHAIN; QUATERNARY; SALTS;

D O I：

10.1134/S0012500823700179

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In order to search for new antibacterial and anticancer agents, the data of amphiphilic quaternary ammonium compounds (QAC) based on natural structures were analyzed and systematized over the past three years in this review. The analysis of publication is considered on the properties of QAS based on heterocyclic and pyridine alkaloids, alkylated phenols, terpenoids and steroids. The relationships between the structure of ammonium salts and their supramolecular self-assembly, biological activity, and cytotoxicity were tried to be revealed. In terms of synthetic ease of chemical modification, availability, biorelevance, and efficacy against strains of bacterial pathogens and antitumor activity, prospects for using natural platforms for extended trials have been identified.

引用

页码：71 / 88

页数：18

共 122 条

[1] Cationic gemini surfactant properties, its potential as a promising bioapplication candidate, and strategies for improving its biocompatibility: A review [J].

Ahmady, Azin Rashidy ;

Hosseinzadeh, Pakshid ;

Solouk, Atefeh ;

Akbari, Somaye ;

Szulc, Adrianna M. ;

Brycki, Bogumil E. .

ADVANCES IN COLLOID AND INTERFACE SCIENCE, 2022, 299

[2] Synthesis and Antiviral Evaluation of Nucleoside Analogues Bearing One Pyrimidine Moiety and Two D-Ribofuranosyl Residues [J].

Andreeva, Olga, V ;

Garifullin, Bulat F. ;

Zarubaev, Vladimir V. ;

Slita, Alexander, V ;

Yesaulkova, Iana L. ;

Volobueva, Alexandrina S. ;

Belenok, Mayya G. ;

Man'kova, Maria A. ;

Saifina, Liliya F. ;

Shulaeva, Marina M. ;

Voloshina, Alexandra D. ;

Lyubina, Anna P. ;

Semenov, Vyacheslav E. ;

Kataev, Vladimir E. .

MOLECULES, 2021, 26 (12)

[3] Quaternary ammonium salts of chitosan. A critical overview on the synthesis and properties generated by quaternization [J].

Andreica, Bianca-Iustina ;

Cheng, Xinjian ;

Marin, Luminita .

EUROPEAN POLYMER JOURNAL, 2020, 139

[4] Rapid membrane permeabilization of Listeria monocytogenes and Escherichia coli induced by antibacterial prenylated phenolic compounds from legumes [J].

Araya-Cloutier, Carla ;

Vincken, Jean-Paul ;

van Ederen, Roan ;

den Besten, Heidy M. W. ;

Gruppen, Harry .

FOOD CHEMISTRY, 2018, 240 :147-155

[5] NMR Hydrophilic Metabolomic Analysis of Bacterial Resistance Pathways Using Multivalent Antimicrobials with Challenged and Unchallenged Wild Type and Mutated Gram-Positive Bacteria [J].

Aries, Michelle L. ;

Cloninger, Mary J. .

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2021, 22 (24)

[6] Organocatalytic Activity of Cinchona Alkaloids: Which Nitrogen Is More Nucleophilic? [J].

Baidya, Mahiuddin ;

Horn, Markus ;

Zipse, Hendrik ;

Mayr, Herbert .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (18) :7157-7164

[7] Antiviral effects of quinine sulfate on HSV-1 HaCat cells infected: Analysis of the molecular mechanisms involved [J].

Baroni, A. ;

Paotetti, I. ;

Ruocco, E. ;

Ayala, F. ;

Wolf, R. ;

Tufano, M. A. .

JOURNAL OF DERMATOLOGICAL SCIENCE, 2007, 47 (03) :253-255

[8] Discovery of novel quaternary ammonium compounds based on quinuclidine-3-ol as new potential antimicrobial candidates [J].

Bazina, Linda ;

Maravic, Ana ;

Krce, Lucija ;

Soldo, Barbara ;

Odzak, Renata ;

Popovic, Viljemka Butevic ;

Aviani, Ivica ;

Primozic, Ines ;

Sprung, Matilda .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2019, 163 :626-635

[9] Bio-inspired surfactants capable of generating plant volatiles [J].

Bhadani, Avinash ;

Rane, Jayant ;

Veresmortean, Cristina ;

Banerjee, Sanjoy ;

John, George .

SOFT MATTER, 2015, 11 (15) :3076-3082

[10] Self-Aggregation and Liquid Crystalline Behavior of New Ester-Functionalized Quinuclidinolium Surfactants [J].

Bhadani, Avinash ;

Endo, Takeshi ;

Koura, Setsuko ;

Sakai, Kenichi ;

Abe, Masahiko ;

Sakai, Hideki .

LANGMUIR, 2014, 30 (30) :9036-9044

← 1 2 3 4 5 6 7 8 9 10 →