Improving hygroscopic stability of palmatine by replacing Clˉ and preparing single crystal of palmatine-salicylic acid

Zhang, Yunan; Sun, Jiuyi; Liu, Lixin; Chang, Liang; Ji, Yuanyuan; Sun, Weitong; Li, Jinjing; Feng, Yanru; Geng, Yiding; Cheng, Guangdong; Gong, Yixia; Guo, Yingxue; Wu, Lili; Wang, Chaoxing; Liu, Yingli

doi:10.1016/j.molstruc.2022.132521

Cited by 8 publications

(2 citation statements)

References 54 publications

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“…The extraction of PLTCl and synthesis of PLT-SA and PLT-SSA were performed following the reported papers. , …”

Section: Methodsmentioning

confidence: 99%

“…Natural alkaloids, as secondary metabolites in plants, are widely found in nature with novel molecular structures and fluorescent properties. − The main sources of yellow alkaloids are plants, and some of them exhibit coloring properties and are used mainly as traditional Chinese medicines, e.g., derivatives of protoberberine. Alkaloids are also recognized as the largest group of nitrogen-containing secondary metabolites. − Palmatine (PLT) is a natural isoquinoline alkaloid as well as a close analogue of berberine (BB), sharing many performances and activities of BB. , Recently, PLT was widely used as a potential fluorescent dye in the application of bioimaging , as well as in sensing and developing of functional dyes. − PLT as a class of protoberberines is bright yellow in color that has been utilized for centuries in Chinese and other traditional medicines and also as dyes for textiles and paper. , PLT chloride (PLTCl) is the most commonly used salt form of PLT in commercial tablets, exhibiting a series of biochemical and pharmacological effects and coloring properties. , Some papers have suggested a new approach to design and produce single crystals of PLT-organic acid salt by replacing anions, offering insights into improving the physicochemical properties of active pharmaceutical ingredients. − Similarly, the supramolecular salt of PLT-sulfosalicylic acid (PLT-SSA) was designed and synthesized by replacing the Cl – of PLTCl, and the physicochemical and biological properties were obviously improved . Given that sulfosalicylic acid is a strong organic acid with rich functional groups such as hydroxyl, carboxylic acid, and sulfonic acid, it is likely to form new crystal supramolecular structures. − …”

Section: Introductionmentioning

confidence: 99%

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Significant Effect of Guest Ions on the Fluorescence Behaviors of Palmatine-Based Supramolecular Systems

Du,

Huang,

Wang

et al. 2024

Crystal Growth & Design

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Palmatine as a natural isoquinoline alkaloid possesses biological activity, low toxicity, biodegradability, fluorescence, and antibacterial properties; however, the low fluorescent intensity and poor stability hindered its practical applications, especially in bioimaging, detection of probes, and functional dyes as the fluorophore. Serial aromatic carboxylic acids as guest ions were introduced by replacing anions of the host Palmatine to fabricate new crystalline Palmatine-based supramolecular salts or cocrystals. The structures and fluorescent properties of the prepared supramolecules were examined by single-crystal X-ray diffraction, thermogravimetry, ultraviolet spectrophotometry, fluorescence spectrometry, and infrared spectrometry. It was found that the fluorescence performance could be tuned by introducing guest molecules based on salicylic acid with different push−pull electronic groups to affect the π−π conjugation system. The introduction of −NO 2 in salicylic acid can result in a decrease in fluorescence on account of withdrawing electrons from the benzene ring, thereby reducing the probability of electron transition. Surprisingly, the fluorescence intensity of Palmatine-aminosalicylic acid (−NH 2 ) exhibited a 10-fold increase due to the decline of the energy gap between the highest occupied molecular orbital and the lowest unoccupied molecular orbital. These findings provided a theoretical basis for further regulating the fluorescence performance of Palmatine and other natural dyes through the introduction of guest molecules to form the supramolecular systems.

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“…The extraction of PLTCl and synthesis of PLT-SA and PLT-SSA were performed following the reported papers. , …”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Significant Effect of Guest Ions on the Fluorescence Behaviors of Palmatine-Based Supramolecular Systems

Du,

Huang,

Wang

et al. 2024

Crystal Growth & Design

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Improving Solubility and Avoiding Hygroscopicity of Tetrahydropalmatine by Forming a Pharmaceutical Salt Cocrystal via CAHBs

Zhang

Shi

Liu

et al. 2022

Cryst. Res. Technol.

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In order to improve the solubility of tetrahydropalmatine (THP), an unreported THP‐sulfosalicylic acid (THP‐SSA) pharmaceutical salt cocrystal is designed and synthesized. Structural analysis shows that the building unit of THP‐SSA is composed of two THP cations, two SSA anions and one ethyl acetate molecule. Meanwhile, 1D chain, 2D layered structure, 3D hydrogen bond network, and Supramolecular motif R1110(48) of THP‐SSA are connected by stable charge‐assisted hydrogen bonds (CAHBs) N+‐H···O‐, π–π packing, and hydrogen bond. As expected, the maximum solubility of THP‐SSA in water is about 60 times that of THP, probably due to the protonation of the N atom on the piperidine ring in THP forms a pharmaceutical salt cocrystal, which greatly improves the solubility of THP. However, to the surprise, the hygroscopicity of THP‐SSA is also effectively reduced compared with THP, probably because the hydrogen bonds between THP and SSA have been formed, preventing the entry of water molecules. In addition, THP‐SSA also has higher antibacterial activity than THP. This suggests that forming a pharmaceutical salt cocrystal by cocrystal technology can not only improve the solubility of THP and avoid the hygroscopic property, but also improve the antibacterial activity of THP in vitro.

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Studies on crystal structures, optical, dyeing and biological properties of protoberberine alkaloids and their supramolecular salts

Hao

Wang

et al. 2023

Bioorganic Chemistry

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Improving hygroscopic stability of palmatine by replacing Clˉ and preparing single crystal of palmatine-salicylic acid

Cited by 8 publications

References 54 publications

Significant Effect of Guest Ions on the Fluorescence Behaviors of Palmatine-Based Supramolecular Systems

Significant Effect of Guest Ions on the Fluorescence Behaviors of Palmatine-Based Supramolecular Systems

Improving Solubility and Avoiding Hygroscopicity of Tetrahydropalmatine by Forming a Pharmaceutical Salt Cocrystal via CAHBs

Studies on crystal structures, optical, dyeing and biological properties of protoberberine alkaloids and their supramolecular salts

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