Assembly of three pharmaceutical salts/cocrystals of tetrahydroberberine with sulfophenyl acids: improving the properties by formation of charge-assisted hydrogen bonds

Liu, Lixin; Zou, Dongyu; Zhang, Yunan; Zhang, Dajun; Zhang, Qiang; Wang, Jian; Zeng, Shaoyu; Wang, Conggang

doi:10.1039/c9nj00131j

Cited by 38 publications

(12 citation statements)

References 42 publications

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“…[ 14,20 ] The building units of CAHONs often possess the acid and base sites, in other words, the acidity and basicity of involved ligands are generally selected as oppositely charged building units for constructing stable CAHONs. [ 21‐23 ] It is well‐known that carboxylic acid can be deprotoned and becomes the anionic building block, while the viologen often possesses the positive charges, which is a good candidate for the cationic building unit. [ 24‐26 ] The combination of the electron‐rich carboxylic acid and the electron‐deficient viologen is an efficient method for probing the novel CAHONs with specific functional properties.…”

Section: Background and Originality Contentmentioning

confidence: 99%

A Photo‐Responsive Charge‐Assisted Hydrogen‐Bonded Organic Network with Ultra‐Stable Viologen Radicals

Shen

Yang

et al. 2021

Chin. J. Chem.

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Comprehensive Summary Hydrogen‐bonded organic networks (HONs) have attracted intense research interest due to their mild synthesis conditions, good solvent processability and strong reproducibility. Most HONs are constructed by electrically neutral organic ligands through intermolecular interactions such as weak hydrogen bonding, π‐π stacking. But there are a few charge‐assisted hydrogen‐bonding networks (CAHONs) constructed by oppositely charged organic components. Under hydrothermal conditions, we successfully synthesized a 3D CAHON (H2CV)(H2BTEC) (1) constructed by H2CV (CV = N,N′‐4,4′‐bipyridine dipropionate) and H4BTEC (H4BTEC = 1,2,4,5‐benzenetetracarboxylic acid) through multiple charge‐assisted hydrogen bonding. Upon soft X‐ray, ultraviolet light or sunlight irradiation under ambient conditions, 1 quickly changes from colorless to blue (1P), and kinetic calculations show that its photochromism meets first‐order dynamics. Interestingly, the colored crystals 1P with long‐lived colored radicals will not fade after being placed for more than two months at room temperature in air, owing to the fact that the photogenerated viologen radicals can be stabilized by the abundant hydrogen bonds, the coplanar pyridinium rings and the slow electron‐hole recombination. Moreover, 1 is a typical direct band gap semiconductor, evidenced by the calculated band gap of 3.24 eV, in agreement with the experimental value of 3.40 eV. In view of its strong colored stability, 1 is designed for distinctive inkless printing.

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Section: Background and Originality Contentmentioning

confidence: 99%

A Photo‐Responsive Charge‐Assisted Hydrogen‐Bonded Organic Network with Ultra‐Stable Viologen Radicals

Shen

Yang

et al. 2021

Chin. J. Chem.

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“…They then act as proton acceptors in the self‐assembly process with coformers containing polar groups (carboxylic groups), thus forming the ideal solid form of fluoroquinolones through CAHBs. [ 30,31 ]…”

Section: Introductionmentioning

confidence: 99%

Improving Solubility and Avoiding Hygroscopicity of Gatifloxacin by Forming Pharmaceutical Salt of Gatifloxacin‐2,3‐Dihydroxybenzoic Acid Based on Charge‐Assisted Hydrogen Bonds

Liu

Zhang

et al. 2022

Crystal Research and Technology

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To improve the solubility of the fluoroquinolone drug gatifloxacin (GAT), a pharmaceutical salt of GAT with 2,3‐dihydroxybenzoic acid (2,3‐HBA) is designed, synthesized, and characterized. This work is based on previous research into the synthesis of the pharmaceutical salts/cocrystals of fluoroquinolones. A comprehensive assessment of the crystal structure and the molecular electrostatic potential, as well as a Hirshfeld surface analysis, revealed that the H protons of the carboxylic groups in 2,3‐HBA are transferred to the N of the GAT piperazine ring. This results in the ionization of GAT to form charge‐assisted hydrogen bonds (CAHBs) and the construction of a crystal structure. It is precisely the conversion of GAT from a neutral state to an ionic state that results in a significant increase in the solubility of GAT‐2,3‐HBA. Surprisingly, in the process of increasing its solubility, the hygroscopic stability and the antibacterial activities in vitro of GAT‐2,3‐HBA is also superior to GAT. In this study, a pharmaceutical salt of gatifloxacin with targeted structures and desired properties, based on CAHBs is successfully designed and synthesized. These encouraging results suggest that CAHBs play a crucial role in adjusting molecular packing through a co‐crystallization strategy, thus improving the physicochemical properties of fluoroquinolones.

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“…Cocrystalization is an effective and widely employed approach to modify the physicochemical properties of active pharmaceutical ingredients without changing their bioactivities. − For example, pharmaceutical salts/cocrystals were used to simultaneously improve the aqueous dissolution of tetrahydroberberine by 8-20-fold and decrease its hygroscopicity . Two drug–drug cocrystals of BCl with myricetin and dihydromyricetin were prepared to improve the physical stability of BCl against high humidity, but the dissolution was also inadvertently reduced .…”

Section: Introductionmentioning

confidence: 99%

Novel Salt-Cocrystals of Berberine Hydrochloride with Aliphatic Dicarboxylic Acids: Odd–Even Alternation in Physicochemical Properties

et al. 2021

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In this study, various structurally similar aliphatic dicarboxylic acids, namely, succinic acid, glutaric acid, adipic acid, and pimelic acid, were employed as coformers to obtain phase pure cocrystals with berberine chloride (BCl) by a slow solvent evaporation method. The structures of the four novel salt-cocrystals of BCl were determined by single crystal X-ray diffraction analysis and their solid-state properties were characterized. Compared with BCl•2H 2 O, all the cocrystals showed a higher melting point, improved powder dissolution and intrinsic dissolution rate (IDR), and lower hygroscopicity. It is noteworthy that the melting points and IDRs of these cocrystals exhibit an odd-even alternation with the carbon chain length of the acids.

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Assembly of three pharmaceutical salts/cocrystals of tetrahydroberberine with sulfophenyl acids: improving the properties by formation of charge-assisted hydrogen bonds

Abstract: The self-recognition of CAHBs could stabilize crystal packing of pharmaceutical salts/cocrystals of THB and improve physicochemical properties of THB.

Cited by 38 publications

References 42 publications

A Photo‐Responsive Charge‐Assisted Hydrogen‐Bonded Organic Network with Ultra‐Stable Viologen Radicals

A Photo‐Responsive Charge‐Assisted Hydrogen‐Bonded Organic Network with Ultra‐Stable Viologen Radicals

Improving Solubility and Avoiding Hygroscopicity of Gatifloxacin by Forming Pharmaceutical Salt of Gatifloxacin‐2,3‐Dihydroxybenzoic Acid Based on Charge‐Assisted Hydrogen Bonds

Novel Salt-Cocrystals of Berberine Hydrochloride with Aliphatic Dicarboxylic Acids: Odd–Even Alternation in Physicochemical Properties

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