Enhancing the solubility of natural compound xanthotoxin by modulating stability via cocrystallization engineering
[Display omitted] •Two cocrystals of xanthotoxin were obtained. Crystal structures of the two cocrystals were elucidated.•Energy framework calculation was performed to confirm hydrogen bond and π···π interactions generated in cocrystals are stronger than that in xanthotoxin.•Superior solubility and...
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| Veröffentlicht in: | International journal of pharmaceutics 2019-12, Vol.572, p.118776-118776, Article 118776 |
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| container_title | International journal of pharmaceutics |
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| creator | Chen, Jin-Yao Wu, Hao Guo, Chun-Yang Zhu, Bin Ren, Guo-Bin |
| description | [Display omitted]
•Two cocrystals of xanthotoxin were obtained. Crystal structures of the two cocrystals were elucidated.•Energy framework calculation was performed to confirm hydrogen bond and π···π interactions generated in cocrystals are stronger than that in xanthotoxin.•Superior solubility and stability of xanthotoxin-oxalic acid cocrystal were demonstrated. The cocrystallization engineering can prolong the enhanced apparent solubility via modulating the stability.
A comprehensive cocrystal study for the insoluble natural pharmaceutical compound xanthotoxin (XT) was conducted, in which xanthotoxin-para aminobenzoic acid (XT-PABA) and xanthotoxin-oxalic acid (XT-OA) cocrystals were obtained. The xanthotoxin cocrystals were characterized by powder X-ray diffraction, thermal analysis, and FT-IR spectra, and the crystal structures were determined by single-crystal X-ray diffraction. Crystal structures and thermal analysis showed that XT-OA was more stable than XT-PABA. Energy framework calculation indicated that H-bond and π···π interactions generated in XT-OA were stronger than that in XT-PABA and xanthotoxin. The powder dissolution experiments of xanthotoxin and its cocrystals suggested the XT-OA cocrystal might be applied as an alternative formulation of API, on account of its enhanced solubility and stability in the hydrochloric acid buffer solution (pH 1.2). The cocrystallization engineering can prolong the enhanced apparent solubility via modulating the stability. |
| doi_str_mv | 10.1016/j.ijpharm.2019.118776 |
| format | Article |
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•Two cocrystals of xanthotoxin were obtained. Crystal structures of the two cocrystals were elucidated.•Energy framework calculation was performed to confirm hydrogen bond and π···π interactions generated in cocrystals are stronger than that in xanthotoxin.•Superior solubility and stability of xanthotoxin-oxalic acid cocrystal were demonstrated. The cocrystallization engineering can prolong the enhanced apparent solubility via modulating the stability.
A comprehensive cocrystal study for the insoluble natural pharmaceutical compound xanthotoxin (XT) was conducted, in which xanthotoxin-para aminobenzoic acid (XT-PABA) and xanthotoxin-oxalic acid (XT-OA) cocrystals were obtained. The xanthotoxin cocrystals were characterized by powder X-ray diffraction, thermal analysis, and FT-IR spectra, and the crystal structures were determined by single-crystal X-ray diffraction. Crystal structures and thermal analysis showed that XT-OA was more stable than XT-PABA. Energy framework calculation indicated that H-bond and π···π interactions generated in XT-OA were stronger than that in XT-PABA and xanthotoxin. The powder dissolution experiments of xanthotoxin and its cocrystals suggested the XT-OA cocrystal might be applied as an alternative formulation of API, on account of its enhanced solubility and stability in the hydrochloric acid buffer solution (pH 1.2). The cocrystallization engineering can prolong the enhanced apparent solubility via modulating the stability.</description><identifier>ISSN: 0378-5173</identifier><identifier>EISSN: 1873-3476</identifier><identifier>DOI: 10.1016/j.ijpharm.2019.118776</identifier><identifier>PMID: 31678374</identifier><language>eng</language><publisher>Netherlands: Elsevier B.V</publisher><subject>4-Aminobenzoic Acid - chemistry ; Cocrystals ; Crystal structure ; Crystallization - methods ; Crystallography, X-Ray - methods ; Drug Stability ; Hydrogen Bonding ; Methoxsalen - chemistry ; Oxalic Acid - chemistry ; Powder Diffraction - methods ; Powders - chemistry ; Solubility ; Solubility - drug effects ; Stability ; X-Ray Diffraction - methods ; Xanthotoxin</subject><ispartof>International journal of pharmaceutics, 2019-12, Vol.572, p.118776-118776, Article 118776</ispartof><rights>2019 Elsevier B.V.</rights><rights>Copyright © 2019 Elsevier B.V. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c365t-78e2a8559e085ce38c7bb9c123941463487dfa91aa92b8087d028057f50bd3233</citedby><cites>FETCH-LOGICAL-c365t-78e2a8559e085ce38c7bb9c123941463487dfa91aa92b8087d028057f50bd3233</cites><orcidid>0000-0003-1085-1231</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ijpharm.2019.118776$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27922,27923,45993</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31678374$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chen, Jin-Yao</creatorcontrib><creatorcontrib>Wu, Hao</creatorcontrib><creatorcontrib>Guo, Chun-Yang</creatorcontrib><creatorcontrib>Zhu, Bin</creatorcontrib><creatorcontrib>Ren, Guo-Bin</creatorcontrib><title>Enhancing the solubility of natural compound xanthotoxin by modulating stability via cocrystallization engineering</title><title>International journal of pharmaceutics</title><addtitle>Int J Pharm</addtitle><description>[Display omitted]
•Two cocrystals of xanthotoxin were obtained. Crystal structures of the two cocrystals were elucidated.•Energy framework calculation was performed to confirm hydrogen bond and π···π interactions generated in cocrystals are stronger than that in xanthotoxin.•Superior solubility and stability of xanthotoxin-oxalic acid cocrystal were demonstrated. The cocrystallization engineering can prolong the enhanced apparent solubility via modulating the stability.
A comprehensive cocrystal study for the insoluble natural pharmaceutical compound xanthotoxin (XT) was conducted, in which xanthotoxin-para aminobenzoic acid (XT-PABA) and xanthotoxin-oxalic acid (XT-OA) cocrystals were obtained. The xanthotoxin cocrystals were characterized by powder X-ray diffraction, thermal analysis, and FT-IR spectra, and the crystal structures were determined by single-crystal X-ray diffraction. Crystal structures and thermal analysis showed that XT-OA was more stable than XT-PABA. Energy framework calculation indicated that H-bond and π···π interactions generated in XT-OA were stronger than that in XT-PABA and xanthotoxin. The powder dissolution experiments of xanthotoxin and its cocrystals suggested the XT-OA cocrystal might be applied as an alternative formulation of API, on account of its enhanced solubility and stability in the hydrochloric acid buffer solution (pH 1.2). The cocrystallization engineering can prolong the enhanced apparent solubility via modulating the stability.</description><subject>4-Aminobenzoic Acid - chemistry</subject><subject>Cocrystals</subject><subject>Crystal structure</subject><subject>Crystallization - methods</subject><subject>Crystallography, X-Ray - methods</subject><subject>Drug Stability</subject><subject>Hydrogen Bonding</subject><subject>Methoxsalen - chemistry</subject><subject>Oxalic Acid - chemistry</subject><subject>Powder Diffraction - methods</subject><subject>Powders - chemistry</subject><subject>Solubility</subject><subject>Solubility - drug effects</subject><subject>Stability</subject><subject>X-Ray Diffraction - methods</subject><subject>Xanthotoxin</subject><issn>0378-5173</issn><issn>1873-3476</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1v3CAQhlGVqtmk_QmNOObiLR824FNVRWkbKVIv7RlhPM6ywrABHGXz68Nqt7nmNBrmeRjNi9BXStaUUPFtu3bb3cakec0I7deUKinFB7SqlTe8leIMrQiXqumo5OfoIuctIUQwyj-hc06FVFy2K5Ruw8YE68IDLhvAOfplcN6VPY4TDqYsyXhs47yLSxjxswllE0t8dgEPezzHcfGmHORczMl7cqYKNu3rk_fupc5jwBAeXABIlf2MPk7GZ_hyqpfo38_bvze_m_s_v-5uftw3louuNFIBM6rreiCqs8CVlcPQW8p439JW8FbJcTI9NaZngyK1I0yRTk4dGUbOOL9E18d_dyk-LpCLnl224L0JEJesGae0Z4ITUdHuiNoUc04w6V1ys0l7TYk-xK23-hS3PsStj3FX7-q0YhlmGN-s__lW4PsRgHrok4Oks3UQLIwugS16jO6dFa8fOJYr</recordid><startdate>20191215</startdate><enddate>20191215</enddate><creator>Chen, Jin-Yao</creator><creator>Wu, Hao</creator><creator>Guo, Chun-Yang</creator><creator>Zhu, Bin</creator><creator>Ren, Guo-Bin</creator><general>Elsevier B.V</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-1085-1231</orcidid></search><sort><creationdate>20191215</creationdate><title>Enhancing the solubility of natural compound xanthotoxin by modulating stability via cocrystallization engineering</title><author>Chen, Jin-Yao ; Wu, Hao ; Guo, Chun-Yang ; Zhu, Bin ; Ren, Guo-Bin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c365t-78e2a8559e085ce38c7bb9c123941463487dfa91aa92b8087d028057f50bd3233</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>4-Aminobenzoic Acid - chemistry</topic><topic>Cocrystals</topic><topic>Crystal structure</topic><topic>Crystallization - methods</topic><topic>Crystallography, X-Ray - methods</topic><topic>Drug Stability</topic><topic>Hydrogen Bonding</topic><topic>Methoxsalen - chemistry</topic><topic>Oxalic Acid - chemistry</topic><topic>Powder Diffraction - methods</topic><topic>Powders - chemistry</topic><topic>Solubility</topic><topic>Solubility - drug effects</topic><topic>Stability</topic><topic>X-Ray Diffraction - methods</topic><topic>Xanthotoxin</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Jin-Yao</creatorcontrib><creatorcontrib>Wu, Hao</creatorcontrib><creatorcontrib>Guo, Chun-Yang</creatorcontrib><creatorcontrib>Zhu, Bin</creatorcontrib><creatorcontrib>Ren, Guo-Bin</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>International journal of pharmaceutics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Jin-Yao</au><au>Wu, Hao</au><au>Guo, Chun-Yang</au><au>Zhu, Bin</au><au>Ren, Guo-Bin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enhancing the solubility of natural compound xanthotoxin by modulating stability via cocrystallization engineering</atitle><jtitle>International journal of pharmaceutics</jtitle><addtitle>Int J Pharm</addtitle><date>2019-12-15</date><risdate>2019</risdate><volume>572</volume><spage>118776</spage><epage>118776</epage><pages>118776-118776</pages><artnum>118776</artnum><issn>0378-5173</issn><eissn>1873-3476</eissn><abstract>[Display omitted]
•Two cocrystals of xanthotoxin were obtained. Crystal structures of the two cocrystals were elucidated.•Energy framework calculation was performed to confirm hydrogen bond and π···π interactions generated in cocrystals are stronger than that in xanthotoxin.•Superior solubility and stability of xanthotoxin-oxalic acid cocrystal were demonstrated. The cocrystallization engineering can prolong the enhanced apparent solubility via modulating the stability.
A comprehensive cocrystal study for the insoluble natural pharmaceutical compound xanthotoxin (XT) was conducted, in which xanthotoxin-para aminobenzoic acid (XT-PABA) and xanthotoxin-oxalic acid (XT-OA) cocrystals were obtained. The xanthotoxin cocrystals were characterized by powder X-ray diffraction, thermal analysis, and FT-IR spectra, and the crystal structures were determined by single-crystal X-ray diffraction. Crystal structures and thermal analysis showed that XT-OA was more stable than XT-PABA. Energy framework calculation indicated that H-bond and π···π interactions generated in XT-OA were stronger than that in XT-PABA and xanthotoxin. The powder dissolution experiments of xanthotoxin and its cocrystals suggested the XT-OA cocrystal might be applied as an alternative formulation of API, on account of its enhanced solubility and stability in the hydrochloric acid buffer solution (pH 1.2). The cocrystallization engineering can prolong the enhanced apparent solubility via modulating the stability.</abstract><cop>Netherlands</cop><pub>Elsevier B.V</pub><pmid>31678374</pmid><doi>10.1016/j.ijpharm.2019.118776</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0003-1085-1231</orcidid></addata></record> |
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| subjects | 4-Aminobenzoic Acid - chemistry Cocrystals Crystal structure Crystallization - methods Crystallography, X-Ray - methods Drug Stability Hydrogen Bonding Methoxsalen - chemistry Oxalic Acid - chemistry Powder Diffraction - methods Powders - chemistry Solubility Solubility - drug effects Stability X-Ray Diffraction - methods Xanthotoxin |
| title | Enhancing the solubility of natural compound xanthotoxin by modulating stability via cocrystallization engineering |
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