Intriguing High Z″ Cocrystals of Emtricitabine

Emtricitabine (ECB) afforded dimorphic cocrystals (Forms I, II) of benzoic acid (BA), whereas p-hydroxybenzoic acid (PHBA) and p-aminobenzoic acid (PABA) resulted in high Z″ cocrystals. Intriguingly, the Z″ of cocrystals are trends from 2 to 14 based on the manipulation of functional groups on the p...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Crystal growth & design 2020-08, Vol.20 (8), p.4886-4891
Hauptverfasser: Palanisamy, Vasanthi, Sanphui, Palash, Bolla, Geetha, Narayan, Aditya, Seaton, Colin C, Vangala, Venu R
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 4891
container_issue 8
container_start_page 4886
container_title Crystal growth & design
container_volume 20
creator Palanisamy, Vasanthi
Sanphui, Palash
Bolla, Geetha
Narayan, Aditya
Seaton, Colin C
Vangala, Venu R
description Emtricitabine (ECB) afforded dimorphic cocrystals (Forms I, II) of benzoic acid (BA), whereas p-hydroxybenzoic acid (PHBA) and p-aminobenzoic acid (PABA) resulted in high Z″ cocrystals. Intriguingly, the Z″ of cocrystals are trends from 2 to 14 based on the manipulation of functional groups on the para position of BA (where the H atom is replaced with that of OH or NH2 group). The ECB–PABA cocrystal consists of six molecules each and two water molecules in the asymmetric unit (Z″=14) with 2D planar sheets representing the rare pharmaceutical cocrystal. The findings suggest that the increment of H bond donor(s) systematically via a suitable coformer is in correspondence with attaining high Z″ cocrystals. Further, solid state NMR spectroscopy in conjunction with single crystal X-ray diffraction is demonstrated as a significant tool to enhance the understanding of the number of symmetry independent molecules in the crystalline lattice and provide insights to the mechanistic pathways of crystallization.
doi_str_mv 10.1021/acs.cgd.0c00744
format Article
fullrecord <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_acs_cgd_0c00744</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>c902400503</sourcerecordid><originalsourceid>FETCH-LOGICAL-a277t-6b6e7a9921d1cec51ac5f9a2b98e9ae0f5f814d8f70591eaeab5c7249ac3d79f3</originalsourceid><addsrcrecordid>eNp1j7FOwzAQhi0EEqUws2ZHSW0njuMRRYVWqtQFFhbrcrGDK5ogOx268U68EU-Cq7Zjpzvdff_pPkIeGc0Y5WwGGDLs2owipbIorsiECV6lUlBxfe6LKr8ldyFsaGTKPJ8QuuxH77qd67tk4brP5OPv5zepB_T7MMJXSAabzLcRQTdC43pzT25snJuHU52S95f5W71IV-vXZf28SoFLOaZlUxoJSnHWMjQoGKCwCnijKqPAUCtsxYq2spIKxQwYaARKXijAvJXK5lMyO95FP4TgjdXf3m3B7zWj-iCso7COwvokHBNPx8RhsRl2vo__XaT_AbbOWgc</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Intriguing High Z″ Cocrystals of Emtricitabine</title><source>American Chemical Society Journals</source><creator>Palanisamy, Vasanthi ; Sanphui, Palash ; Bolla, Geetha ; Narayan, Aditya ; Seaton, Colin C ; Vangala, Venu R</creator><creatorcontrib>Palanisamy, Vasanthi ; Sanphui, Palash ; Bolla, Geetha ; Narayan, Aditya ; Seaton, Colin C ; Vangala, Venu R</creatorcontrib><description>Emtricitabine (ECB) afforded dimorphic cocrystals (Forms I, II) of benzoic acid (BA), whereas p-hydroxybenzoic acid (PHBA) and p-aminobenzoic acid (PABA) resulted in high Z″ cocrystals. Intriguingly, the Z″ of cocrystals are trends from 2 to 14 based on the manipulation of functional groups on the para position of BA (where the H atom is replaced with that of OH or NH2 group). The ECB–PABA cocrystal consists of six molecules each and two water molecules in the asymmetric unit (Z″=14) with 2D planar sheets representing the rare pharmaceutical cocrystal. The findings suggest that the increment of H bond donor(s) systematically via a suitable coformer is in correspondence with attaining high Z″ cocrystals. Further, solid state NMR spectroscopy in conjunction with single crystal X-ray diffraction is demonstrated as a significant tool to enhance the understanding of the number of symmetry independent molecules in the crystalline lattice and provide insights to the mechanistic pathways of crystallization.</description><identifier>ISSN: 1528-7483</identifier><identifier>EISSN: 1528-7505</identifier><identifier>DOI: 10.1021/acs.cgd.0c00744</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Crystal growth &amp; design, 2020-08, Vol.20 (8), p.4886-4891</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a277t-6b6e7a9921d1cec51ac5f9a2b98e9ae0f5f814d8f70591eaeab5c7249ac3d79f3</citedby><cites>FETCH-LOGICAL-a277t-6b6e7a9921d1cec51ac5f9a2b98e9ae0f5f814d8f70591eaeab5c7249ac3d79f3</cites><orcidid>0000-0003-4094-720X ; 0000-0002-0836-2052 ; 0000-0002-2726-8352</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.cgd.0c00744$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.cgd.0c00744$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids></links><search><creatorcontrib>Palanisamy, Vasanthi</creatorcontrib><creatorcontrib>Sanphui, Palash</creatorcontrib><creatorcontrib>Bolla, Geetha</creatorcontrib><creatorcontrib>Narayan, Aditya</creatorcontrib><creatorcontrib>Seaton, Colin C</creatorcontrib><creatorcontrib>Vangala, Venu R</creatorcontrib><title>Intriguing High Z″ Cocrystals of Emtricitabine</title><title>Crystal growth &amp; design</title><addtitle>Cryst. Growth Des</addtitle><description>Emtricitabine (ECB) afforded dimorphic cocrystals (Forms I, II) of benzoic acid (BA), whereas p-hydroxybenzoic acid (PHBA) and p-aminobenzoic acid (PABA) resulted in high Z″ cocrystals. Intriguingly, the Z″ of cocrystals are trends from 2 to 14 based on the manipulation of functional groups on the para position of BA (where the H atom is replaced with that of OH or NH2 group). The ECB–PABA cocrystal consists of six molecules each and two water molecules in the asymmetric unit (Z″=14) with 2D planar sheets representing the rare pharmaceutical cocrystal. The findings suggest that the increment of H bond donor(s) systematically via a suitable coformer is in correspondence with attaining high Z″ cocrystals. Further, solid state NMR spectroscopy in conjunction with single crystal X-ray diffraction is demonstrated as a significant tool to enhance the understanding of the number of symmetry independent molecules in the crystalline lattice and provide insights to the mechanistic pathways of crystallization.</description><issn>1528-7483</issn><issn>1528-7505</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp1j7FOwzAQhi0EEqUws2ZHSW0njuMRRYVWqtQFFhbrcrGDK5ogOx268U68EU-Cq7Zjpzvdff_pPkIeGc0Y5WwGGDLs2owipbIorsiECV6lUlBxfe6LKr8ldyFsaGTKPJ8QuuxH77qd67tk4brP5OPv5zepB_T7MMJXSAabzLcRQTdC43pzT25snJuHU52S95f5W71IV-vXZf28SoFLOaZlUxoJSnHWMjQoGKCwCnijKqPAUCtsxYq2spIKxQwYaARKXijAvJXK5lMyO95FP4TgjdXf3m3B7zWj-iCso7COwvokHBNPx8RhsRl2vo__XaT_AbbOWgc</recordid><startdate>20200805</startdate><enddate>20200805</enddate><creator>Palanisamy, Vasanthi</creator><creator>Sanphui, Palash</creator><creator>Bolla, Geetha</creator><creator>Narayan, Aditya</creator><creator>Seaton, Colin C</creator><creator>Vangala, Venu R</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-4094-720X</orcidid><orcidid>https://orcid.org/0000-0002-0836-2052</orcidid><orcidid>https://orcid.org/0000-0002-2726-8352</orcidid></search><sort><creationdate>20200805</creationdate><title>Intriguing High Z″ Cocrystals of Emtricitabine</title><author>Palanisamy, Vasanthi ; Sanphui, Palash ; Bolla, Geetha ; Narayan, Aditya ; Seaton, Colin C ; Vangala, Venu R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a277t-6b6e7a9921d1cec51ac5f9a2b98e9ae0f5f814d8f70591eaeab5c7249ac3d79f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Palanisamy, Vasanthi</creatorcontrib><creatorcontrib>Sanphui, Palash</creatorcontrib><creatorcontrib>Bolla, Geetha</creatorcontrib><creatorcontrib>Narayan, Aditya</creatorcontrib><creatorcontrib>Seaton, Colin C</creatorcontrib><creatorcontrib>Vangala, Venu R</creatorcontrib><collection>CrossRef</collection><jtitle>Crystal growth &amp; design</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Palanisamy, Vasanthi</au><au>Sanphui, Palash</au><au>Bolla, Geetha</au><au>Narayan, Aditya</au><au>Seaton, Colin C</au><au>Vangala, Venu R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Intriguing High Z″ Cocrystals of Emtricitabine</atitle><jtitle>Crystal growth &amp; design</jtitle><addtitle>Cryst. Growth Des</addtitle><date>2020-08-05</date><risdate>2020</risdate><volume>20</volume><issue>8</issue><spage>4886</spage><epage>4891</epage><pages>4886-4891</pages><issn>1528-7483</issn><eissn>1528-7505</eissn><abstract>Emtricitabine (ECB) afforded dimorphic cocrystals (Forms I, II) of benzoic acid (BA), whereas p-hydroxybenzoic acid (PHBA) and p-aminobenzoic acid (PABA) resulted in high Z″ cocrystals. Intriguingly, the Z″ of cocrystals are trends from 2 to 14 based on the manipulation of functional groups on the para position of BA (where the H atom is replaced with that of OH or NH2 group). The ECB–PABA cocrystal consists of six molecules each and two water molecules in the asymmetric unit (Z″=14) with 2D planar sheets representing the rare pharmaceutical cocrystal. The findings suggest that the increment of H bond donor(s) systematically via a suitable coformer is in correspondence with attaining high Z″ cocrystals. Further, solid state NMR spectroscopy in conjunction with single crystal X-ray diffraction is demonstrated as a significant tool to enhance the understanding of the number of symmetry independent molecules in the crystalline lattice and provide insights to the mechanistic pathways of crystallization.</abstract><pub>American Chemical Society</pub><doi>10.1021/acs.cgd.0c00744</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-4094-720X</orcidid><orcidid>https://orcid.org/0000-0002-0836-2052</orcidid><orcidid>https://orcid.org/0000-0002-2726-8352</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1528-7483
ispartof Crystal growth & design, 2020-08, Vol.20 (8), p.4886-4891
issn 1528-7483
1528-7505
language eng
recordid cdi_crossref_primary_10_1021_acs_cgd_0c00744
source American Chemical Society Journals
title Intriguing High Z″ Cocrystals of Emtricitabine
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-24T14%3A29%3A43IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Intriguing%20High%20Z%E2%80%B3%20Cocrystals%20of%20Emtricitabine&rft.jtitle=Crystal%20growth%20&%20design&rft.au=Palanisamy,%20Vasanthi&rft.date=2020-08-05&rft.volume=20&rft.issue=8&rft.spage=4886&rft.epage=4891&rft.pages=4886-4891&rft.issn=1528-7483&rft.eissn=1528-7505&rft_id=info:doi/10.1021/acs.cgd.0c00744&rft_dat=%3Cacs_cross%3Ec902400503%3C/acs_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true