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用于药物递送应用的哌啶基生物活性薄膜制备中丙腈哌啶的合成与晶体结构

Synthesis and crystal structure of piperidinyl propanenitrile towards the preparation of piperidine based bioactive films for drug delivery applications.

作者信息

Mohamed-Ezzat Reham A, Hasanin Mohamed S, Kariuki Benson M, Dacrory Sawsan

机构信息

Chemistry of Natural and Microbial Products Department, Pharmaceutical and Drug Industries Research Institute, National Research Centre, Cairo, 12622, Egypt.

Cellulose and Paper Department, National Research Centre, Cairo, 12622, Egypt.

出版信息

Sci Rep. 2025 Jan 3;15(1):705. doi: 10.1038/s41598-024-81996-6.


DOI:10.1038/s41598-024-81996-6
PMID:39753604
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11698915/
Abstract

Compounds containing the piperidine group are highly attractive as building blocks for designing new drugs. Functionalized piperidines are of significant interest due to their prevalence in the pharmaceutical field. Herein, 3-oxo-3-(piperidin-1-yl) propanenitrile has been synthesized, and piperidine-based sodium alginate/poly(vinyl alcohol) films have been prepared. The polymeric films display potency and potential for application to fight against microbial infections. The films could also help maintain interaction with tissue to ensure the controlled release of therapeutic molecules. Thus, they are promising in developing drug delivery systems essential in the pharmaceutical industry. The structure of the 3-oxo-3-(piperidin-1-yl)propanenitrile was confirmed via spectroscopic and single crystal x-ray diffraction techniques. A homogenous solution of sodium alginate (SA) was used to prepare the film by the casting method in the presence of poly(vinyl alcohol) (PVA) and 3-oxo-3-(piperidin-1-yl)propanenitrile (PPN). The prepared films were characterized physiochemically via FTIR, XRD, and TGA. The film morphology was studied using SEM. The antimicrobial potency of the prepared films was assessed against various species of microorganisms. The physicochemical analysis indicated that the films were bound by chemical and physical bond formation between the cyano group of 3-oxo-3-(piperidin-1-yl)propanenitrile, methylene group of PVA, and the hydroxyl group of SA. The films showed smooth, homogenous surfaces and good mechanical properties. The results revealed that the films are bioactive, as indicated by promising antimicrobial potency against P. aeruginosa, S. aureus, E. coli, B. subtilis, and C. albicans, with high potency as well as moderate activity against A. niger. Polymeric films have promising potential to be utilized in drug delivery applications.

摘要

含哌啶基团的化合物作为设计新药的结构单元极具吸引力。功能化哌啶因其在制药领域的广泛存在而备受关注。本文合成了3-氧代-3-(哌啶-1-基)丙腈,并制备了基于哌啶的海藻酸钠/聚乙烯醇薄膜。这些聚合物薄膜显示出对抗微生物感染的效力和应用潜力。这些薄膜还可有助于维持与组织的相互作用,以确保治疗分子的控释。因此,它们在开发制药行业必需的药物递送系统方面很有前景。通过光谱和单晶X射线衍射技术确定了3-氧代-3-(哌啶-1-基)丙腈的结构。在聚乙烯醇(PVA)和3-氧代-3-(哌啶-1-基)丙腈(PPN)存在下,采用流延法,用海藻酸钠(SA)的均相溶液制备薄膜。通过傅里叶变换红外光谱(FTIR)、X射线衍射(XRD)和热重分析(TGA)对制备的薄膜进行了物理化学表征。使用扫描电子显微镜(SEM)研究了薄膜的形态。评估了制备薄膜对各种微生物的抗菌效力。物理化学分析表明,薄膜是通过3-氧代-3-(哌啶-1-基)丙腈的氰基、PVA的亚甲基和SA的羟基之间形成化学和物理键而结合的。薄膜表面光滑、均匀,具有良好的机械性能。结果表明,这些薄膜具有生物活性,对铜绿假单胞菌、金黄色葡萄球菌、大肠杆菌、枯草芽孢杆菌和白色念珠菌具有良好的抗菌效力,对黑曲霉也有高效力和中等活性。聚合物薄膜在药物递送应用中具有广阔的应用潜力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e10/11698915/83e8278efc9a/41598_2024_81996_Fig8_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e10/11698915/98e914e5c18a/41598_2024_81996_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e10/11698915/c5da4aabebe6/41598_2024_81996_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e10/11698915/8384a0b440a4/41598_2024_81996_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e10/11698915/da1d91f16a71/41598_2024_81996_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e10/11698915/fa3174ba3379/41598_2024_81996_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e10/11698915/d21d622e22d0/41598_2024_81996_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e10/11698915/c7059ba428ec/41598_2024_81996_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e10/11698915/83e8278efc9a/41598_2024_81996_Fig8_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e10/11698915/98e914e5c18a/41598_2024_81996_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e10/11698915/c5da4aabebe6/41598_2024_81996_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e10/11698915/8384a0b440a4/41598_2024_81996_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e10/11698915/da1d91f16a71/41598_2024_81996_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e10/11698915/fa3174ba3379/41598_2024_81996_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e10/11698915/d21d622e22d0/41598_2024_81996_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e10/11698915/c7059ba428ec/41598_2024_81996_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e10/11698915/83e8278efc9a/41598_2024_81996_Fig8_HTML.jpg

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[2]
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[3]
The Construction of Highly Substituted Piperidines via Dearomative Functionalization Reaction.

Angew Chem Int Ed Engl. 2023-12-4

[4]
Curcumin-Sodium Alginate and Curcumin-Chitosan Conjugates as Drug Delivery Systems: An Interesting Rheological Behaviour.

Molecules. 2023-8-5

[5]
Synthetic strategy towards novel composite based on substituted pyrido[2,1-b][1,3,4]oxadiazine-dialdehyde chitosan conjugate with antimicrobial and anticancer activities.

BMC Chem. 2023-7-26

[6]
Making a new bromo-containing cellulosic dye with antibacterial properties for use on various fabrics using computational research.

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[7]
Antimicrobial finishing of textiles using nanomaterials.

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[8]
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[9]
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[10]
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