Chemistry of pyrimidinophanes: synthesis and applications: a review from 1990 until recently

The development of biotechnological protocols based on cationic surfactants is a modern trend focusing on the fabrication of antimicrobial and bioimaging agents, supramolecular catalysts, stabilizers of nanoparticles, and especially drug and gene nanocarriers. The main emphasis given to the design of novel ecologically friendly and biocompatible cationic surfactants makes it possible to avoid the drawbacks of nanoformulations preventing their entry to clinical trials. To solve the problem of toxicity various ways are proposed, including the use of mixed composition with nontoxic nonionic surfactants and/or hydrotropic agents, design of amphiphilic compounds bearing natural or cleavable fragments. Essential advantages of cationic surfactants are the structural diversity of their head groups allowing of chemical modification and introduction of desirable moiety to answer the green chemistry criteria. The latter can be exemplified by the design of novel families of ecological friendly cleavable surfactants, with improved biodegradability, amphiphiles with natural fragments, and geminis with low aggregation threshold. Importantly, the development of amphiphilic nanocarriers for drug delivery allows understanding the correlation between the chemical structure of surfactants, their aggregation behavior, and their functional activity. This review focuses on several aspects related to the synthesis of innovative cationic surfactants and their broad biological applications including antimicrobial activity, solubilization of hydrophobic drugs, complexation with DNA, and catalytic effect toward important biochemical reaction.

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“…An excellent review of pyrimidinophanes structure, synthesis, and application by V.E. Semenov is recommended for further, detailed reading [64].…”

Section: Structural Diversity Of Biocompatible and Ecologically Frmentioning

confidence: 99%

Cationic Surfactants: Self-Assembly, Structure-Activity Correlation and Their Biological Applications

Zakharova

Pashirova

Doktorovová

et al. 2019

IJMS

115

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“…La explotación sintética del carbono nucleofílico de los uracilos se ha convertido en un campo importante debido a la variedad de potenciales productos y aplicaciones, (45)(46)(47)(48)(49)(50) . La química de los derivados del uracilo, estudios y procedimientos sintéticos, se incrementó desde la década de 1980, debido al amplio rango de actividades y propiedades farmacológicas.…”

Section: Síntesis De Deazaflavinas a Partir De Uracilo Y Derivadosunclassified

5-Deazaflavinas: síntesis química

Trilleras¹,

Rodríguez²,

López³

2018

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Las 5-Deazaflavinas, están involucradas en reacciones enzimáticas redox de una variedad de sistemas biológicos y guardan similitud estructural con la riboflavina. Las propiedades electroquímicas y fotoquímicas son resultado de la sustitución del N-5 del anillo de la isoaloxazina por un átomo de carbono. En esta revisión, se describen los avances en la obtención de 5-deazaflavinas y análogos a partir de ácido barbitúrico, análogos de uracilo, triamino-tricloropirimidinas y quinolincarbonitrilos. El grado y tipo de sustitución de las 5-deazaflavinas, se obtiene a través de los aldehídos y aminas utilizadas, vía reacciones clásicas, simples y convergentes. Comparando las diferentes estrategias sintéticas reportadas, para la construcción de 5-deazaflavinas y análogos, estas se clasifican en dos estrategias generales: i) la construcción del anillo de quinolina sobre el anillo pirimidínico o ii) la construcción del anillo pirimidínico sobre el anillo quinolínico.

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“…For this purpose, сationic surfactants with low critical micelle concentrations such as gemini (dimeric) surfactants are the most attractive [19][20][21][22][23][24][25][26]. Cationic amphiphiles containing natural fragments, such as sugar- [27,28], peptide- [29,30] pyrimidine- [31,32] and amino acid-surfactants [33], biodegradable amphiphiles [34] are also promised. The long-chain cetalkonium chloride-cationic emulsions are attractive for reducing toxicity of cationic surfactants and for further development in eye drops [35] The increase of the antimicrobial efficacy by cationic nanoemulsions was shown [36].…”

Section: Introductionmentioning

confidence: 99%

Nontoxic antimicrobial micellar systems based on mono- and dicationic Dabco-surfactants and furazolidone: Structure-solubilization properties relationships

Pashirova

Burilova

Лукашенко

et al. 2019

Journal of Molecular Liquids

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Self-assembly and solubilization properties of amphiphilic mono-and bisquaternized derivatives of 1,4diazabicyclo[2.2.2]octane (mono-CS-n and di-CS-n, where CScationic surfactant, n = 12, 14, 16, 18) was investigated by nuclear magnetic resonance with magnetic field pulse gradient. The influence of Dabco-surfactant structure (head group and length of alkyl chains) on critical micelle concentration and aggregation number of micelles was studied. The CMC of mono-CS-n are lower than CMC of di-CS-n. The aggregation numbers of mono-CS-n micelles are higher than for di-CS-n micelles. The solubilization capacity of mono-CS-n is higher than di-CS-n. The solubilization capacity of mono-CS-16 is 2.5 times higher than CTAB in the case of Orange OT as a solute, and it is close to CTAB in the case of Sudan I. The solubility of a poorly water-soluble antibacterial drug furazolidone was improved by micellar solubilization based on mono-and di-Dabco-surfactants. Mono-CSn is the best solubilizing agents toward furazolidone. The use of mixed composition mono-Dabco-16-furazolidone provides a significant increase in antimicrobial activity (by 2 times against bacteria and 8 times against fungi) and reduces by 2 times the dose of each of the components in combination formulation and causes b2% haemolysis of human red blood cells at the active dose.

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Chemistry of pyrimidinophanes: synthesis and applications: a review from 1990 until recently

Cited by 10 publications

References 89 publications

Cationic Surfactants: Self-Assembly, Structure-Activity Correlation and Their Biological Applications

Cationic Surfactants: Self-Assembly, Structure-Activity Correlation and Their Biological Applications

5-Deazaflavinas: síntesis química

Nontoxic antimicrobial micellar systems based on mono- and dicationic Dabco-surfactants and furazolidone: Structure-solubilization properties relationships

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