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Immobilization of alkyl-pterin photosensitizer on silicon surfaces through in situ SN2 reaction as suitable approach for photodynamic inactivation of Staphylococcus aureus
Colloids and Surfaces B: Biointerfaces ( IF 5.8 ) Pub Date : 2020-11-08 , DOI: 10.1016/j.colsurfb.2020.111456
María Noel Urrutia 1 , María José Sosa 1 , Diego E Pissinis 1 , Antonela Cánneva 2 , Alejandro G Miñán 1 , Mariana Vignoni 1 , Alejandra Calvo 2 , Andrés H Thomas 1 , Patricia L Schilardi 1
Affiliation  

The tuning of surface properties through functionalization is an important field of research with a broad spectrum of applications. Self-assembled monolayers (SAMs) allow the surface tailoring through the adsorption of molecular layers having the appropriate functional group or precursor group enabling in situ chemical reactions and thus to the incorporation of new functionalities. The latter approach is particularly advantageous when the incorporation of huge groups is needed.

In this study, we report the immobilization of pterin moieties on 11-bromoundecyltrichlorosilane-modified silicon substrates based on the in situ replacement of the bromine groups by pterin (Ptr), the parent derivative of pterins, by means of a nucleophilic substitution reaction. The modified surface was structurally characterized through a multi-technique approach, including high-resolution XPS analysis, contact angle measurements, and AFM. The designed synthesis method leads to the functionalization of the silicon surface with two compounds, O-undecyl-Ptr and N-undecyl-Ptr, with a higher proportion of the N-derivative (1:8 ratio). The alkyl-pterins immobilized via the proposed strategy, retain their photochemical properties, being able to inhibit Staphylococcus aureus growth under irradiation (84.3 ± 15.6 % reduction in viable cells). Our results open the possibility for the modification of several materials, such as glass and metal, through the formation of SAMs having the proper head group, thus allowing the design of photosensitive surfaces with potential microbiological self-cleaning properties.



中文翻译:

通过原位S N 2反应将烷基蝶呤光敏剂固定在硅表面作为金黄色葡萄球菌光动力学失活的合适方法

通过功能化来调节表面性质是具有广泛应用的重要研究领域。自组装单分子层(SAM)允许通过吸附具有适当功能基团或前体基团的分子层进行表面修整,从而实现原位化学反应,从而引入新的功能。当需要合并庞大的组时,后一种方法特别有利。

在这项研究中,我们报告了蝶呤部分在11-溴三乙基三氯硅烷改性的硅基板上的固定化,这通过蝶呤(Ptr)(蝶呤的母体衍生物)通过亲核取代反应原位取代溴基而实现的。通过多种技术方法对改性表面进行结构表征,包括高分辨率XPS分析,接触角测量和AFM。设计的合成方法导致硅表面被两种化合物O-十一烷基-Ptr和N-十一烷基-Ptr官能化,其中N-衍生物的比例更高(比例为1:8)。通过固定的烷基蝶呤建议的策略,保留其光化学特性,能够抑制辐射下的金黄色葡萄球菌生长(活细胞减少84.3±15.6%)。我们的结果为通过形成具有适当头基的SAM修饰几种材料(例如玻璃和金属)提供了可能性,从而允许设计具有潜在微生物自清洁特性的光敏表面。

更新日期:2020-11-09
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