Lidiane Gomes de Araújo , Ashley A.S.S. de Jesus , José Roberto Dantas , Edeltrudes de Oliveira Lima , Boniek Gontijo Vaz , Gabriel Franco dos Santos , Cláudia M. Zaccaron Cristiano , Claudio Gabriel Lima-Junior , Jéssika de Oliveira Viana , Karen C. Weber , Euzébio Guimarães Barbosa , Rodrigo Cristiano
{"title":"2-Styryl-quinoline-4-carboxylic acids: Synthesis, characterization, and investigation of their optical properties and antimicrobial activity","authors":"Lidiane Gomes de Araújo , Ashley A.S.S. de Jesus , José Roberto Dantas , Edeltrudes de Oliveira Lima , Boniek Gontijo Vaz , Gabriel Franco dos Santos , Cláudia M. Zaccaron Cristiano , Claudio Gabriel Lima-Junior , Jéssika de Oliveira Viana , Karen C. Weber , Euzébio Guimarães Barbosa , Rodrigo Cristiano","doi":"10.1016/j.dyepig.2024.112294","DOIUrl":null,"url":null,"abstract":"<div><p>Styrylquinoline-based fluorophores <strong>1–10</strong> were synthesized via Knoevenagel and Pfitzinger reactions. The molecules were fully characterized and studied for the impact of their substitution patterns (<strong>A-D</strong>) on their optical and bioactivity properties. With exception of nitro substituted compounds <strong>9-D</strong> and <strong>10-D</strong>, all compounds were fluorescent in solution with a significant solvatochromic behavior measured in toluene, dioxane, tetrahydrofurane, ethyl acetate, dichloromethane, dimethylformamide, dimethylsulfoxide, acetonitrile, isopropanol, and methanol. The maximum wavelength of their emission ranged from 408 to 539 nm. Additionally, there was a significant variation in the photoluminescence (PL) quantum yield concerning different solvent polarities. The PL quantum yields ranged from small values, such as 1.7 % in methanol for compound <strong>1-A</strong>, to good PL quantum yields, such as 44.4 % in dioxane for <strong>7-C</strong>. For comparison, the quantum yield of <strong>7-C</strong> in methanol was 3.3 %, a total range variation of 41.1 %. <strong>4-B</strong> and <strong>5-B</strong> with <em>O</em>-acetyl groups at <em>ortho</em> and at para position to the C<img>C double bond, respectively, presented an interesting acidochromism with a redshift of about 102 nm in their emission bands along with a visible emitted color change from blue to green. In addition, the antimicrobial activity for all compounds and the theoretical mechanism of action of the more significant bioactive compounds were investigated. In inverse virtual screening studies, the enzymes Dehydrosqualene synthase and Squalene synthase were indicated as putative biological targets for <strong>3-B</strong> and <strong>4-B</strong>. Molecular docking indicated the amino acid residues critical for interaction in bacteria and fungi.</p></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":null,"pages":null},"PeriodicalIF":4.1000,"publicationDate":"2024-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Dyes and Pigments","FirstCategoryId":"88","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0143720824003590","RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
Styrylquinoline-based fluorophores 1–10 were synthesized via Knoevenagel and Pfitzinger reactions. The molecules were fully characterized and studied for the impact of their substitution patterns (A-D) on their optical and bioactivity properties. With exception of nitro substituted compounds 9-D and 10-D, all compounds were fluorescent in solution with a significant solvatochromic behavior measured in toluene, dioxane, tetrahydrofurane, ethyl acetate, dichloromethane, dimethylformamide, dimethylsulfoxide, acetonitrile, isopropanol, and methanol. The maximum wavelength of their emission ranged from 408 to 539 nm. Additionally, there was a significant variation in the photoluminescence (PL) quantum yield concerning different solvent polarities. The PL quantum yields ranged from small values, such as 1.7 % in methanol for compound 1-A, to good PL quantum yields, such as 44.4 % in dioxane for 7-C. For comparison, the quantum yield of 7-C in methanol was 3.3 %, a total range variation of 41.1 %. 4-B and 5-B with O-acetyl groups at ortho and at para position to the CC double bond, respectively, presented an interesting acidochromism with a redshift of about 102 nm in their emission bands along with a visible emitted color change from blue to green. In addition, the antimicrobial activity for all compounds and the theoretical mechanism of action of the more significant bioactive compounds were investigated. In inverse virtual screening studies, the enzymes Dehydrosqualene synthase and Squalene synthase were indicated as putative biological targets for 3-B and 4-B. Molecular docking indicated the amino acid residues critical for interaction in bacteria and fungi.
期刊介绍:
Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied.
Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media.
The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.