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氟喹诺酮类药物与α,ω-二羧酸形成的盐及分子离子共晶体

Formation of Salts and Molecular Ionic Cocrystals of Fluoroquinolones and α,ω-Dicarboxylic Acids.

作者信息

O'Malley Ciaran, McArdle Patrick, Erxleben Andrea

机构信息

School of Chemistry, National University of Ireland, Galway H91TK33, Ireland.

Synthesis and Solid State Pharmaceutical Centre (SSPC), Limerick V94T9PX, Ireland.

出版信息

Cryst Growth Des. 2022 May 4;22(5):3060-3071. doi: 10.1021/acs.cgd.1c01509. Epub 2022 Apr 11.

DOI:10.1021/acs.cgd.1c01509
PMID:35529070
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9073931/
Abstract

The cocrystallization of the fluoroquinolones ciprofloxacin (cip), norfloxacin (nor), and enrofloxacin (enro) with the α,ω-dicarboxylic acids glutaric acid (glu), adipic acid (adi), pimelic acid (pim), suberic acid (sub), azeliac acid (az), and sebacic acid (seb) resulted in 27 new molecular salts and ternary molecular ionic cocrystals of compositions AB, A B, A BB, and ABA. Depending on the solvent, different stoichiomorphs, solvates, or polymorphs were obtained. All salts and cocrystals contain the robust RNH OOC or RNHOOC synthon but have different supramolecular ring motifs. Moderate solubility enhancements over the parent fluoroquinolones were observed. Salts in the ratio of 1:1 and 2:1 were also prepared by ball-milling. The milled sample nor/az (1:1) was shown to gel the GRAS (generally recognized as safe) solvent propylene glycol, and enro/sub (1:1) was shown to gel both propylene glycol and water. Dynamic rheology measurements confirmed that nor/az and enro/sub behave like viscoelastic materials and supramolecular gels.

摘要

氟喹诺酮类药物环丙沙星（cip）、诺氟沙星（nor）和恩诺沙星（enro）与α,ω - 二羧酸戊二酸（glu）、己二酸（adi）、庚二酸（pim）、辛二酸（sub）、壬二酸（az）和癸二酸（seb）的共结晶产生了27种新的分子盐以及组成分别为AB、A B、A BB和ABA的三元分子离子共晶体。根据溶剂的不同，可得到不同的化学计量变体、溶剂化物或多晶型物。所有的盐和共晶体都包含稳定的RNH OOC或RNHOOC合成子，但具有不同的超分子环基序。相对于母体氟喹诺酮类药物，观察到了适度的溶解度增强。通过球磨还制备了比例为1:1和2:1的盐。研磨后的样品nor/az（1:1）被证明能使公认为安全的溶剂丙二醇凝胶化，而enro/sub（1:1）被证明能使丙二醇和水都凝胶化。动态流变学测量证实，nor/az和enro/sub表现得像粘弹性材料和超分子凝胶。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/8f657b0de267/cg1c01509_0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/f01351686f85/cg1c01509_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/20d53a2ff0f3/cg1c01509_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/fd72bfadf454/cg1c01509_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/2b29ab78cd0c/cg1c01509_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/09c521205b6b/cg1c01509_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/1be19a77a2a2/cg1c01509_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/97230e3d7497/cg1c01509_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/1305139a6bb1/cg1c01509_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/a6cd6e0dc067/cg1c01509_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/8f657b0de267/cg1c01509_0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/f01351686f85/cg1c01509_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/20d53a2ff0f3/cg1c01509_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/fd72bfadf454/cg1c01509_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/2b29ab78cd0c/cg1c01509_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/09c521205b6b/cg1c01509_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/1be19a77a2a2/cg1c01509_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/97230e3d7497/cg1c01509_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/1305139a6bb1/cg1c01509_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/a6cd6e0dc067/cg1c01509_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91aa/9073931/8f657b0de267/cg1c01509_0011.jpg

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