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聚酰胺-胺-杯芳烃树枝状大分子:第二代合成、荧光性质及儿茶酚胺结合

PAMAM-Calix-Dendrimers: Second Generation Synthesis, Fluorescent Properties and Catecholamines Binding.

作者信息

Mostovaya Olga, Shiabiev Igor, Pysin Dmitry, Stanavaya Alesia, Abashkin Viktar, Shcharbin Dzmitry, Padnya Pavel, Stoikov Ivan

机构信息

A.M. Butlerov Chemical Institute, Kazan Federal University, 18 Kremlevskaya Street, Kazan 420008, Russia.

Institute of Biophysics and Cell Engineering of NASB, 27 Akademicheskaya Street, 220072 Minsk, Belarus.

出版信息

Pharmaceutics. 2022 Dec 8;14(12):2748. doi: 10.3390/pharmaceutics14122748.

Abstract

A convenient method for the synthesis of the second generation of PAMAM dendrimers based on a -butylthiacalix[4]arene core in , and conformations was developed. Unusual fluorescence of the obtained PAMAM-calix-dendrimers has been found and explained. The binding ability of the synthesized dendrimers toward catecholamines (dopamine, -adrenaline and -noradrenaline) was shown by UV-Vis, fluorescence, 1D and 2D NMR spectroscopy and the binding constants (logK 3.85-4.74) calculated. As was shown, the PAMAM-calix-dendrimers bind catecholamines by the internal cavities. All the studied hormones were most efficiently bound by the dendrimers bearing a macrocyclic core in conformation. The size of the formed supramolecular systems of dendrimer/catecholamine was established by the DLS method. A decrease in hemolytic activity of the PAMAM-calix-dendrimers with an increase in the generation number of a dendrimer was shown for the dendrimers with a core in conformation. The prospects for the use of the synthesized dendrimers with the macrocyclic core as drug delivery agents were discussed.

摘要

开发了一种基于α-丁基硫杂杯[4]芳烃核,以椅式、船式和扭船式构象合成第二代PAMAM树枝状大分子的简便方法。已发现并解释了所得PAMAM-杯芳烃树枝状大分子异常的荧光现象。通过紫外-可见光谱、荧光光谱、一维和二维核磁共振光谱显示了合成树枝状大分子对儿茶酚胺(多巴胺、α-肾上腺素和β-去甲肾上腺素)的结合能力,并计算了结合常数(logK 3.85-4.74)。结果表明,PAMAM-杯芳烃树枝状大分子通过内腔结合儿茶酚胺。所有研究的激素都能被具有船式构象大环核的树枝状大分子最有效地结合。通过动态光散射法确定了树枝状大分子/儿茶酚胺形成的超分子体系的大小。对于具有椅式构象核心的树枝状大分子,随着树枝状大分子代数的增加,PAMAM-杯芳烃树枝状大分子的溶血活性降低。讨论了使用具有大环核的合成树枝状大分子作为药物递送剂的前景。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1b37/9781744/337907d043b6/pharmaceutics-14-02748-sch001.jpg

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