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一种基于分子间键合且具有改善水溶性的新型氨基葡萄糖-大麻二酚复合物。

A Novel Glucosamine-Based Cannabidiol Complex Based on Intermolecular Bonding with Improved Water Solubility.

作者信息

Križman Mitja, Zekič Jure, Šket Primož, Anžlovar Alojz, Zupančič Barbara, Grdadolnik Jože

机构信息

National Institute of Chemistry, Hajdrihova 19, 1000 Ljubljana, Slovenia.

Faculty of Maritime Studies and Transport, University of Ljubljana, Pot pomorščakov 4, 6320 Portorož, Slovenia.

出版信息

Molecules. 2025 Jul 29;30(15):3179. doi: 10.3390/molecules30153179.

DOI:10.3390/molecules30153179
PMID:40807353
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12348863/
Abstract

In this study, a new, patented form of a water-soluble cannabidiol (CBD) complex was synthesised and tested. The formation of the complex is based on the interactions, presumably through hydrogen bonding, between cannabidiol and glucosamine, the latter contributing significantly to the increased hydrophilicity. The complex was characterised by chromatography, thermal analysis, nuclear magnetic resonance, Fourier transform infrared spectroscopy, and permeability tests. This complex has a substantially higher water solubility than normal CBD. Permeability tests indicate that it has almost five times lower permeability through lipophilic membranes and less than half the membrane mass retention of conventional CBD. At the same time, its equilibrium concentration is almost four times higher than that of normal CBD. These results suggest that this new form of CBD is a promising candidate for future biological and clinical studies, as it offers improved bioavailability and biodistribution.

摘要

在本研究中,合成并测试了一种新型的、获得专利的水溶性大麻二酚(CBD)复合物。该复合物的形成基于大麻二酚与葡萄糖胺之间可能通过氢键形成的相互作用,后者对增加亲水性有显著贡献。通过色谱法、热分析、核磁共振、傅里叶变换红外光谱和渗透性测试对该复合物进行了表征。这种复合物的水溶性比普通CBD高得多。渗透性测试表明,它通过亲脂性膜的渗透性几乎低五倍,并且膜质量保留率不到传统CBD的一半。同时,其平衡浓度几乎是普通CBD的四倍。这些结果表明,这种新型CBD是未来生物学和临床研究的有希望的候选物,因为它具有改善的生物利用度和生物分布。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c724/12348863/82d6da338c8f/molecules-30-03179-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c724/12348863/1d7661ea33f7/molecules-30-03179-g0A1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c724/12348863/ef4a23fbc73e/molecules-30-03179-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c724/12348863/f164212bdc7f/molecules-30-03179-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c724/12348863/5a40027fd1b8/molecules-30-03179-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c724/12348863/f53e0466d6f1/molecules-30-03179-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c724/12348863/71f9abf1ae03/molecules-30-03179-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c724/12348863/792f30d3e52c/molecules-30-03179-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c724/12348863/82d6da338c8f/molecules-30-03179-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c724/12348863/1d7661ea33f7/molecules-30-03179-g0A1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c724/12348863/ef4a23fbc73e/molecules-30-03179-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c724/12348863/f164212bdc7f/molecules-30-03179-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c724/12348863/5a40027fd1b8/molecules-30-03179-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c724/12348863/f53e0466d6f1/molecules-30-03179-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c724/12348863/71f9abf1ae03/molecules-30-03179-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c724/12348863/792f30d3e52c/molecules-30-03179-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c724/12348863/82d6da338c8f/molecules-30-03179-g007.jpg

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Pharmaceuticals (Basel). 2025 Mar 21;18(4):446. doi: 10.3390/ph18040446.
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Optimising Cannabidiol Delivery: Improving Water Solubility and Permeability Through Phospholipid Complexation.优化大麻二酚递送:通过磷脂络合提高水溶性和渗透性。
Int J Mol Sci. 2025 Mar 14;26(6):2647. doi: 10.3390/ijms26062647.
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Enhancing Cannabinoid Bioavailability in Pain Management: The Role of Cyclodextrins.增强疼痛管理中大麻素的生物利用度:环糊精的作用。
Molecules. 2024 Nov 13;29(22):5340. doi: 10.3390/molecules29225340.
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Strategies to Improve Cannabidiol Bioavailability and Drug Delivery.提高大麻二酚生物利用度和药物递送的策略。
Pharmaceuticals (Basel). 2024 Feb 13;17(2):244. doi: 10.3390/ph17020244.
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Absorption and Bioavailability of Novel UltraShear Nanoemulsion of Cannabidiol in Rats.新型超剪切纳米乳剂形式的大麻二酚在大鼠体内的吸收与生物利用度
Med Cannabis Cannabinoids. 2023 Nov 7;6(1):148-159. doi: 10.1159/000534473. eCollection 2023 Jan-Dec.
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Co-Dispersion Delivery Systems with Solubilizing Carriers Improving the Solubility and Permeability of Cannabinoids (Cannabidiol, Cannabidiolic Acid, and Cannabichromene) from (Henola Variety) Inflorescences.具有增溶载体的共分散递送系统改善大麻(赫诺拉品种)花序中大麻素(大麻二酚、大麻二酚酸和大麻色烯)的溶解度和渗透性。
Pharmaceutics. 2023 Sep 4;15(9):2280. doi: 10.3390/pharmaceutics15092280.
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Nanoformulations as a strategy to overcome the delivery limitations of cannabinoids.纳米制剂作为克服大麻素传递限制的策略。
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