{"title":"利福平作为无环葫芦[n]脲包合物的溶解度和稳定性提高","authors":"Hui Liu, Zu-Zheng He, Lei Yu, Jun Ma, Xue-Pin Jin","doi":"10.1007/s10847-021-01093-3","DOIUrl":null,"url":null,"abstract":"<div><p>The poor solubility and low stability of rifampicin limited its therapeutic efficacy. One of the common strategies is to form an inclusion complex to address the problems. In this study, acyclic cucurbit[n]uril was used for encapsulation of rifampicin to form an inclusion complex. The inclusion complex was prepared by the kneading method and characterized by DSC, SEM, FT-IR, NMR, PXRD, and UV-Vis spectroscopy. The results confirmed the formation of 1:1 inclusion complex. The drug content was calculated to be 27.35 ± 0.54%. The aqueous solubility of rifampicin was increased 20-fold by complexation with acyclic cucurbit[n]uril. Moreover, the thermo-stability and photo-stability of free rifampicin and inclusion complex were investigated by HPLC. Rifampicin was stabilized by encapsulating the piperazine ring in the cavity of acyclic cucurbit[n]uril. In addition, the MIC of free RIF and RIF‧ACB were determined by using in vitro experiments. It was found that rifampicin complexed by acyclic cucurbit[n]uril exhibited similar antibacterial activities against strain H37Rv to rifampicin alone.</p><h3>Graphic abstract</h3>\n <figure><div><div><div><picture><source><img></source></picture></div></div></div></figure>\n <dl><dt><dfn>•:</dfn></dt><dd>\n <p>Acyclic cucurbit[n]uril was used to encapsulate rifampicin to form an inclusion complex.</p>\n </dd><dt><dfn>•:</dfn></dt><dd>\n <p>The aqueous solubility of rifampicin was increased 20-fold by encapsulation with acyclic\ncucurbit[n]uril.</p>\n </dd><dt><dfn>•:</dfn></dt><dd>\n <p>The thermo-stability and photo-stability of rifampicin was improved by formation of\ninclusion complex.</p>\n </dd><dt><dfn>•:</dfn></dt><dd>\n <p>The antibiotic potency of rifampicin complexed by acyclic cucurbit[n]uril was close to that\nof rifampicin alone.</p>\n </dd></dl>\n </div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3000,"publicationDate":"2021-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s10847-021-01093-3","citationCount":"4","resultStr":"{\"title\":\"Improved solubility and stability of rifampicin as an inclusion complex of acyclic cucurbit[n]uril\",\"authors\":\"Hui Liu, Zu-Zheng He, Lei Yu, Jun Ma, Xue-Pin Jin\",\"doi\":\"10.1007/s10847-021-01093-3\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>The poor solubility and low stability of rifampicin limited its therapeutic efficacy. One of the common strategies is to form an inclusion complex to address the problems. In this study, acyclic cucurbit[n]uril was used for encapsulation of rifampicin to form an inclusion complex. The inclusion complex was prepared by the kneading method and characterized by DSC, SEM, FT-IR, NMR, PXRD, and UV-Vis spectroscopy. The results confirmed the formation of 1:1 inclusion complex. The drug content was calculated to be 27.35 ± 0.54%. The aqueous solubility of rifampicin was increased 20-fold by complexation with acyclic cucurbit[n]uril. Moreover, the thermo-stability and photo-stability of free rifampicin and inclusion complex were investigated by HPLC. Rifampicin was stabilized by encapsulating the piperazine ring in the cavity of acyclic cucurbit[n]uril. In addition, the MIC of free RIF and RIF‧ACB were determined by using in vitro experiments. It was found that rifampicin complexed by acyclic cucurbit[n]uril exhibited similar antibacterial activities against strain H37Rv to rifampicin alone.</p><h3>Graphic abstract</h3>\\n <figure><div><div><div><picture><source><img></source></picture></div></div></div></figure>\\n <dl><dt><dfn>•:</dfn></dt><dd>\\n <p>Acyclic cucurbit[n]uril was used to encapsulate rifampicin to form an inclusion complex.</p>\\n </dd><dt><dfn>•:</dfn></dt><dd>\\n <p>The aqueous solubility of rifampicin was increased 20-fold by encapsulation with acyclic\\ncucurbit[n]uril.</p>\\n </dd><dt><dfn>•:</dfn></dt><dd>\\n <p>The thermo-stability and photo-stability of rifampicin was improved by formation of\\ninclusion complex.</p>\\n </dd><dt><dfn>•:</dfn></dt><dd>\\n <p>The antibiotic potency of rifampicin complexed by acyclic cucurbit[n]uril was close to that\\nof rifampicin alone.</p>\\n </dd></dl>\\n </div>\",\"PeriodicalId\":638,\"journal\":{\"name\":\"Journal of Inclusion Phenomena and Macrocyclic Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.3000,\"publicationDate\":\"2021-06-30\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1007/s10847-021-01093-3\",\"citationCount\":\"4\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Inclusion Phenomena and Macrocyclic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s10847-021-01093-3\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"Agricultural and Biological Sciences\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s10847-021-01093-3","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Agricultural and Biological Sciences","Score":null,"Total":0}
Improved solubility and stability of rifampicin as an inclusion complex of acyclic cucurbit[n]uril
The poor solubility and low stability of rifampicin limited its therapeutic efficacy. One of the common strategies is to form an inclusion complex to address the problems. In this study, acyclic cucurbit[n]uril was used for encapsulation of rifampicin to form an inclusion complex. The inclusion complex was prepared by the kneading method and characterized by DSC, SEM, FT-IR, NMR, PXRD, and UV-Vis spectroscopy. The results confirmed the formation of 1:1 inclusion complex. The drug content was calculated to be 27.35 ± 0.54%. The aqueous solubility of rifampicin was increased 20-fold by complexation with acyclic cucurbit[n]uril. Moreover, the thermo-stability and photo-stability of free rifampicin and inclusion complex were investigated by HPLC. Rifampicin was stabilized by encapsulating the piperazine ring in the cavity of acyclic cucurbit[n]uril. In addition, the MIC of free RIF and RIF‧ACB were determined by using in vitro experiments. It was found that rifampicin complexed by acyclic cucurbit[n]uril exhibited similar antibacterial activities against strain H37Rv to rifampicin alone.
Graphic abstract
•:
Acyclic cucurbit[n]uril was used to encapsulate rifampicin to form an inclusion complex.
•:
The aqueous solubility of rifampicin was increased 20-fold by encapsulation with acyclic
cucurbit[n]uril.
•:
The thermo-stability and photo-stability of rifampicin was improved by formation of
inclusion complex.
•:
The antibiotic potency of rifampicin complexed by acyclic cucurbit[n]uril was close to that
of rifampicin alone.
期刊介绍：
The Journal of Inclusion Phenomena and Macrocyclic Chemistry is the premier interdisciplinary publication reporting on original research into all aspects of host-guest systems. Examples of specific areas of interest are: the preparation and characterization of new hosts and new host-guest systems, especially those involving macrocyclic ligands; crystallographic, spectroscopic, thermodynamic and theoretical studies; applications in chromatography and inclusion polymerization; enzyme modelling; molecular recognition and catalysis by inclusion compounds; intercalates in biological and non-biological systems, cyclodextrin complexes and their applications in the agriculture, flavoring, food and pharmaceutical industries; synthesis, characterization and applications of zeolites.
The journal publishes primarily reports of original research and preliminary communications, provided the latter represent a significant advance in the understanding of inclusion science. Critical reviews dealing with recent advances in the field are a periodic feature of the journal.
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