Synthesis, biological evaluation and structure-activity relationships of self-assembled and solubilization properties of amphiphilic quaternary ammonium derivatives of quinuclidine

被引：18

作者：

Burilova, E. A. ^{[1
,2
]}

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

Lukashenko, S. S. ^{[1
]}

Sapunova, A. S. ^{[1
]}

Voloshina, A. D. ^{[1
]}

Zhiltsova, E. P. ^{[1
]}

Campos, J. R. ^{[4
]}

Souto, E. B. ^{[4
,5
]}

Zakharova, L. Ya. ^{[1
,3
]}

机构：

[1] RAS, Arbuzov Inst Organ & Phys Chem, FRC Kazan Sci Ctr, Arbuzov St 8, Kazan 420088, Russia

[2] Kazan Fed Univ, Kremlevskaya Str 18, Kazan 420008, Russia

[3] Kazan Natl Res Technol Univ, Karl Marx St 68, Kazan 420015, Russia

[4] Univ Coimbra FFUC, Dept Pharmaceut Technol, Fac Pharm, Polo Ciencias Saude, P-3000548 Coimbra, Portugal

[5] Univ Coimbra, Grp Pharmaceut Technol, REQUIMTE LAQV, Fac Pharm, Coimbra, Portugal

来源：

JOURNAL OF MOLECULAR LIQUIDS | 2018年 / 272卷

基金：

俄罗斯科学基金会;

关键词：

Quatemary ammonium derivatives of quinuclidine; Solubilization; Quercetin; Rutin; Antimicrobial activity; Cytotoxicity; NICOTINIC ACETYLCHOLINE-RECEPTOR; ACID-BASED SURFACTANTS; ALKYLTRIMETHYLAMMONIUM BROMIDES; GEMINI SURFACTANTS; SYSTEMS; DESIGN; BEHAVIOR; AGGREGATION; SALTS; MICELLIZATION;

D O I：

10.1016/j.molliq.2018.10.008

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

This work deals with development of polyfunctional biocompatible cationic surfactant systems based on bioactive saturated bicyclic alkaloid quinuclidine. It is focused on the effect of the chemical structure of surfactants on their aggregation behavior, their physicochemical estimation of solubility of model water insoluble dye Orange OT and drugs, quercetin and rutin, microbiology and cytotoxicity. Quaternary ammonium derivatives of quinuclidine (Q-Nuc-n) with different hydrophobicity (R = CnH2n+1, where n = 14, 16, 18) were synthesized. Self-assembly of Q-Nuc-n was investigated by tensiometry, conductometry, spectrophotometry, fluorimetry and dynamic light scattering. The critical micelle concentration, thermodynamic and adsorption parameters at water-air interface, size and aggregation numbers of Q-Nuc-n micelles were determined. The looser packing of surfactant molecules in Q-Nuc-n micelles compared to its analogues, quatemized derivatives of 1,4-diazabicyclo[2.2.2]octane (DABCO-n), was established. The hydrophobic dye Orange OT and drugs quercetin and rutin were solubilized in micellar Q-Nuc-n solutions better than in solutions of classical surfactant CTAB and its analogue DABCO-n. Solubilization capacity of Q-Nuc-18 is 5 times higher than that of classical surfactant CTAB. Q-Nuc-18 1.95 mu g.mL(-1) has also bactericidal and fungicidal activity 2 times (against S. aureus 209P) and 8 times (against B. cereus 8035) higher than antibiotics Norfloxacin and antifungal Ketoconazole. Q-Nuc-16 has the highest bactericidal activity. It is 6 times (against S. aureus 209P) and 15 times (against B. cereus 8035) higher than the bactericidal activity value of Norfloxacin. Synthesized cationic surfactants based on quinuclidine are new multifunctional biocompatible compounds with high potential in nanomedicine and biotechnology. (C) 2018 Elsevier B.V. All rights reserved.

引用

页码：722 / 730

页数：9

共 53 条

[41] Micellar enhanced ultrafiltration (MEUF) of methylene blue with carboxylate surfactants [J].

Schwarze, M. ;

Schaefer, L. ;

Chiappisi, L. ;

Gradzielski, M. .

SEPARATION AND PURIFICATION TECHNOLOGY, 2018, 199 :20-26

[42] Chemistry of pyrimidinophanes: synthesis and applications: a review from 1990 until recently [J].

Semenov, Vyacheslav E. .

JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2013, 77 (1-4) :1-22

[43] Solid lipid nanoparticles for hydrophilic biotech drugs: Optimization and cell viability studies (Caco-2 & HEPG-2 cell lines) [J].

Severino, Patricia ;

Andreani, Tatiana ;

Jaeger, Alessandro ;

Chaud, Marco V. ;

Santana, Maria Helena A. ;

Silva, Amelia M. ;

Souto, Eliana B. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 81 :28-34

[44] Advances in the synthesis, molecular architectures and potential applications of gemini surfactants [J].

Sharma, Renu ;

Kamal, Ajar ;

Abdinejad, Maryam ;

Mahajan, Rakesh Kumar ;

Kraatz, Heinz-Bernhard .

ADVANCES IN COLLOID AND INTERFACE SCIENCE, 2017, 248 :35-68

[45] Structure-property relationship of quinuclidinium surfactants-Towards multifunctional biologically active molecules [J].

Skocibusic, Mirjana ;

Odsak, Renata ;

Stefanic, Zoran ;

Krizic, Ivana ;

Kristo, Lucija ;

Jovic, Ozren ;

Hrenar, Tomica ;

Primozic, Ines ;

Jurasin, Darija .

COLLOIDS AND SURFACES B-BIOINTERFACES, 2016, 140 :548-559

[46] LUMINESCENT PROBES FOR DETERGENT SOLUTIONS - SIMPLE PROCEDURE FOR DETERMINATION OF MEAN AGGREGATION NUMBER OF MICELLES [J].

TURRO, NJ ;

YEKTA, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (18) :5951-5952

[47] Synthesis and Antimicrobial and Toxic Poperties of Novel 1,3-bis(alkyl)-6-Methyluracil Derivatives Containing 1,2,3-and 1,2,4-Triazolium Fragments [J].

Voloshina, A. D. ;

Semenov, V. E. ;

Strobykina, A. S. ;

Kulik, N. V. ;

Krylova, E. S. ;

Zobov, V. V. ;

Reznik, V. S. .

RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2017, 43 (02) :170-176

[48] Self-assembly strategy for the design of soft nanocontainers with controlled properties [J].

Zakharova, Lucia Ya. ;

Kashapov, Ruslan R. ;

Pashirova, Tatiana N. ;

Mirgorodskaya, Alla B. ;

Sinyashin, Oleg G. .

MENDELEEV COMMUNICATIONS, 2016, 26 (06) :457-468

[49] Micellization of alkylated 1.4-diazabicyclo[2.2.2]octane by nuclear magnetic resonance technique using pulsed gradient of static magnetic field [J].

Zakharova, Lucia Ya ;

Gaysin, Nail K. ;

Gnezdilov, Oleg I. ;

Bashirov, Farid I. ;

Kashapov, Ruslan R. ;

Zhiltsova, Elena P. ;

Pashirova, Tatiana N. ;

Lukashenko, Svetlana S. .

JOURNAL OF MOLECULAR LIQUIDS, 2012, 167 :89-93

[50] Dimeric (gemini) surfactants: Effect of the spacer group on the association behavior in aqueous solution [J].

Zana, R .

JOURNAL OF COLLOID AND INTERFACE SCIENCE, 2002, 248 (02) :203-220

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