Platinum precursor of anticancer drug: a structure fixed by long intermolecular N–H···I and C–H···I hydrogen bonds
Identifieur interne : 000C66 ( Istex/Corpus ); précédent : 000C65; suivant : 000C67Platinum precursor of anticancer drug: a structure fixed by long intermolecular N–H···I and C–H···I hydrogen bonds
Auteurs : Richard Pažout ; Jitka Housková ; Michal Dušek ; Jaroslav Maixner ; Petr Ka ErSource :
- Structural Chemistry [ 1040-0400 ] ; 2011-12-01.
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Abstract
Abstract: The title compound 1, cis-[diiodo(1R,2R)-1,2-diaminocyclohexane-κN,κN′]platinum(II), a precursor of a novel platinum-based anticancer complex, was synthesized. High purity (>99%) was determined by HPLC–UV/VIS and its structure was characterized by LC–ESI–MS, FT-IR and X-ray single-crystal diffraction. The molecules of the title compound interact via N–H···I and C–H···I intermolecular (ultra)-long hydrogen–iodine (acceptor) bonds (distances up to 3.1 Å). The crystal structure of the title compound 1 was compared to the structure calculated on the basis of density function theory (DFT). The calculated and measured data varied by a maximum of 0.09 Å in bond lengths and the maximum deviation between the compared angles were less than 2°. Experimentally measured bond lengths in the crystal were observed to be reduced when compared to the theoretical calculation. This was caused by both steric requirements of individual structural units and the presence of hydrogen bonds in real sample, which were confirmed by FT-IR (new bands as well as the band shifts to lower wavelengths).
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DOI: 10.1007/s11224-011-9826-8
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http://www.springer-ny.com</publisher><pubPlace>Boston</pubPlace><date type="published" when="2011-12-01">2011-12-01</date><biblScope unit="volume">22</biblScope><biblScope unit="issue">6</biblScope><biblScope unit="page" from="1325">1325</biblScope><biblScope unit="page" to="1330">1330</biblScope></imprint><idno type="ISSN">1040-0400</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">1040-0400</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Cytostatics</term><term>DFT</term><term>Intermolecular long hydrogen bond</term><term>Platinum-based anticancer complex</term><term>Single crystal/structure</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Abstract: The title compound 1, cis-[diiodo(1R,2R)-1,2-diaminocyclohexane-κN,κN′]platinum(II), a precursor of a novel platinum-based anticancer complex, was synthesized. High purity (>99%) was determined by HPLC–UV/VIS and its structure was characterized by LC–ESI–MS, FT-IR and X-ray single-crystal diffraction. The molecules of the title compound interact via N–H···I and C–H···I intermolecular (ultra)-long hydrogen–iodine (acceptor) bonds (distances up to 3.1 Å). The crystal structure of the title compound 1 was compared to the structure calculated on the basis of density function theory (DFT). The calculated and measured data varied by a maximum of 0.09 Å in bond lengths and the maximum deviation between the compared angles were less than 2°. Experimentally measured bond lengths in the crystal were observed to be reduced when compared to the theoretical calculation. This was caused by both steric requirements of individual structural units and the presence of hydrogen bonds in real sample, which were confirmed by FT-IR (new bands as well as the band shifts to lower wavelengths).</div></front></TEI><istex><corpusName>springer-journals</corpusName><author><json:item><name>Richard Pažout</name><affiliations><json:string>Central Laboratories, Institute of Chemical Technology, Technická 5, 166 28, Prague, Czech Republic</json:string><json:string>E-mail: richard.pazout@vscht.cz</json:string></affiliations></json:item><json:item><name>Jitka Housková</name><affiliations><json:string>Department of Organic Technology, Institute of Chemical Technology, Technická 5, 166 28, Prague, Czech Republic</json:string></affiliations></json:item><json:item><name>Michal Dušek</name><affiliations><json:string>Institute of Physics of the AS CR, Na Slovance 2, 182 21, Praha 8, Czech Republic</json:string></affiliations></json:item><json:item><name>Jaroslav Maixner</name><affiliations><json:string>Central Laboratories, Institute of Chemical Technology, Technická 5, 166 28, Prague, Czech Republic</json:string></affiliations></json:item><json:item><name>Petr Kačer</name><affiliations><json:string>Department of Organic Technology, Institute of Chemical Technology, Technická 5, 166 28, Prague, Czech Republic</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>Cytostatics</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>DFT</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Intermolecular long hydrogen bond</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Platinum-based anticancer complex</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Single crystal/structure</value></json:item></subject><articleId><json:string>9826</json:string><json:string>s11224-011-9826-8</json:string></articleId><arkIstex>ark:/67375/VQC-MV52C866-P</arkIstex><language><json:string>eng</json:string></language><originalGenre><json:string>OriginalPaper</json:string></originalGenre><abstract>Abstract: The title compound 1, cis-[diiodo(1R,2R)-1,2-diaminocyclohexane-κN,κN′]platinum(II), a precursor of a novel platinum-based anticancer complex, was synthesized. High purity (>99%) was determined by HPLC–UV/VIS and its structure was characterized by LC–ESI–MS, FT-IR and X-ray single-crystal diffraction. The molecules of the title compound interact via N–H···I and C–H···I intermolecular (ultra)-long hydrogen–iodine (acceptor) bonds (distances up to 3.1 Å). The crystal structure of the title compound 1 was compared to the structure calculated on the basis of density function theory (DFT). The calculated and measured data varied by a maximum of 0.09 Å in bond lengths and the maximum deviation between the compared angles were less than 2°. Experimentally measured bond lengths in the crystal were observed to be reduced when compared to the theoretical calculation. 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High purity (>99%) was determined by HPLC–UV/VIS and its structure was characterized by LC–ESI–MS, FT-IR and X-ray single-crystal diffraction. The molecules of the title compound interact via N–H···I and C–H···I intermolecular (ultra)-long hydrogen–iodine (acceptor) bonds (distances up to 3.1 Å). The crystal structure of the title compound 1 was compared to the structure calculated on the basis of density function theory (DFT). The calculated and measured data varied by a maximum of 0.09 Å in bond lengths and the maximum deviation between the compared angles were less than 2°. Experimentally measured bond lengths in the crystal were observed to be reduced when compared to the theoretical calculation. 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N–H···I and C–H···I hydrogen bonds</ArticleTitle><ArticleCategory>Original Research</ArticleCategory><ArticleFirstPage>1325</ArticleFirstPage><ArticleLastPage>1330</ArticleLastPage><ArticleHistory><RegistrationDate><Year>2011</Year><Month>6</Month><Day>14</Day></RegistrationDate><Received><Year>2011</Year><Month>3</Month><Day>16</Day></Received><Accepted><Year>2011</Year><Month>6</Month><Day>14</Day></Accepted><OnlineDate><Year>2011</Year><Month>7</Month><Day>8</Day></OnlineDate></ArticleHistory><ArticleCopyright><CopyrightHolderName>Springer Science+Business Media, LLC</CopyrightHolderName><CopyrightYear>2011</CopyrightYear></ArticleCopyright><ArticleGrants Type="Regular"><MetadataGrant Grant="OpenAccess"></MetadataGrant><AbstractGrant Grant="OpenAccess"></AbstractGrant><BodyPDFGrant Grant="Restricted"></BodyPDFGrant><BodyHTMLGrant Grant="Restricted"></BodyHTMLGrant><BibliographyGrant Grant="Restricted"></BibliographyGrant><ESMGrant Grant="Restricted"></ESMGrant></ArticleGrants></ArticleInfo><ArticleHeader><AuthorGroup><Author AffiliationIDS="Aff1" CorrespondingAffiliationID="Aff1"><AuthorName DisplayOrder="Western"><GivenName>Richard</GivenName><FamilyName>Pažout</FamilyName></AuthorName><Contact><Phone>+00420-22044-4080</Phone><Email>richard.pazout@vscht.cz</Email></Contact></Author><Author AffiliationIDS="Aff2"><AuthorName DisplayOrder="Western"><GivenName>Jitka</GivenName><FamilyName>Housková</FamilyName></AuthorName></Author><Author AffiliationIDS="Aff3"><AuthorName DisplayOrder="Western"><GivenName>Michal</GivenName><FamilyName>Dušek</FamilyName></AuthorName></Author><Author AffiliationIDS="Aff1"><AuthorName DisplayOrder="Western"><GivenName>Jaroslav</GivenName><FamilyName>Maixner</FamilyName></AuthorName></Author><Author AffiliationIDS="Aff2"><AuthorName DisplayOrder="Western"><GivenName>Petr</GivenName><FamilyName>Kačer</FamilyName></AuthorName></Author><Affiliation ID="Aff1"><OrgName>Central Laboratories, Institute of Chemical Technology</OrgName><OrgAddress><Street>Technická 5</Street><Postcode>166 28</Postcode><City>Prague</City><Country Code="CZ">Czech Republic</Country></OrgAddress></Affiliation><Affiliation ID="Aff2"><OrgDivision>Department of Organic Technology</OrgDivision><OrgName>Institute of Chemical Technology</OrgName><OrgAddress><Street>Technická 5</Street><Postcode>166 28</Postcode><City>Prague</City><Country Code="CZ">Czech Republic</Country></OrgAddress></Affiliation><Affiliation ID="Aff3"><OrgName>Institute of Physics of the AS CR</OrgName><OrgAddress><Street>Na Slovance 2</Street><Postcode>182 21</Postcode><City>Praha 8</City><Country Code="CZ">Czech Republic</Country></OrgAddress></Affiliation></AuthorGroup><Abstract ID="Abs1" Language="En" OutputMedium="All"><Heading>Abstract</Heading><Para TextBreak="No">The title compound <Emphasis Type="Bold">1</Emphasis>, <Emphasis Type="Italic">cis</Emphasis>-[diiodo(1<Emphasis Type="Italic">R</Emphasis>,2<Emphasis Type="Italic">R</Emphasis>)-1,2-diaminocyclohexane-κ<Emphasis Type="Italic">N</Emphasis>,κ<Emphasis Type="Italic">N</Emphasis>′]platinum(II), a precursor of a novel platinum-based anticancer complex, was synthesized. High purity (>99%) was determined by HPLC–UV/VIS and its structure was characterized by LC–ESI–MS, FT-IR and X-ray single-crystal diffraction. The molecules of the title compound interact via N–H···I and C–H···I intermolecular (ultra)-long hydrogen–iodine (acceptor) bonds (distances up to 3.1 Å). The crystal structure of the title compound <Emphasis Type="Bold">1</Emphasis> was compared to the structure calculated on the basis of density function theory (DFT). The calculated and measured data varied by a maximum of 0.09 Å in bond lengths and the maximum deviation between the compared angles were less than 2°. Experimentally measured bond lengths in the crystal were observed to be reduced when compared to the theoretical calculation. This was caused by both steric requirements of individual structural units and the presence of hydrogen bonds in real sample, which were confirmed by FT-IR (new bands as well as the band shifts to lower wavelengths).</Para></Abstract><KeywordGroup Language="En" OutputMedium="All"><Heading>Keywords</Heading><Keyword>Cytostatics</Keyword><Keyword>DFT</Keyword><Keyword>Intermolecular long hydrogen bond</Keyword><Keyword>Platinum-based anticancer complex</Keyword><Keyword>Single crystal/structure</Keyword></KeywordGroup><ArticleNote Type="Misc"><SimplePara>Systematic name: <Emphasis Type="Italic">cis</Emphasis>-[diiodo(1<Emphasis Type="Italic">R</Emphasis>,2<Emphasis Type="Italic">R</Emphasis>)-1,2-diaminocyclohexane-κ<Emphasis Type="Italic">N</Emphasis>,κ<Emphasis Type="Italic">N</Emphasis>′]platinum(II), Other name: <Emphasis Type="Italic">cis</Emphasis>-[Pt(C<Subscript>6</Subscript>H<Subscript>14</Subscript>N<Subscript>2</Subscript>)I<Subscript>2</Subscript>] or <Emphasis Type="Italic">cis</Emphasis>-[Pt(DACH)I<Subscript>2</Subscript>].</SimplePara></ArticleNote></ArticleHeader><NoBody></NoBody></Article></Issue></Volume></Journal></Publisher></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Platinum precursor of anticancer drug: a structure fixed by long intermolecular N–H···I and C–H···I hydrogen bonds</title></titleInfo><titleInfo type="alternative" contentType="CDATA"><title>Platinum precursor of anticancer drug: a structure fixed by long intermolecular N–H···I and C–H···I hydrogen bonds</title></titleInfo><name type="personal" displayLabel="corresp"><namePart type="given">Richard</namePart><namePart type="family">Pažout</namePart><affiliation>Central Laboratories, Institute of Chemical Technology, Technická 5, 166 28, Prague, Czech Republic</affiliation><affiliation>E-mail: richard.pazout@vscht.cz</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Jitka</namePart><namePart type="family">Housková</namePart><affiliation>Department of Organic Technology, Institute of Chemical Technology, Technická 5, 166 28, Prague, Czech Republic</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Michal</namePart><namePart type="family">Dušek</namePart><affiliation>Institute of Physics of the AS CR, Na Slovance 2, 182 21, Praha 8, Czech Republic</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Jaroslav</namePart><namePart type="family">Maixner</namePart><affiliation>Central Laboratories, Institute of Chemical Technology, Technická 5, 166 28, Prague, Czech Republic</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Petr</namePart><namePart type="family">Kačer</namePart><affiliation>Department of Organic Technology, Institute of Chemical Technology, Technická 5, 166 28, Prague, Czech Republic</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="research-article" displayLabel="OriginalPaper" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-1JC4F85T-7">research-article</genre><originInfo><publisher>Springer US; http://www.springer-ny.com</publisher><place><placeTerm type="text">Boston</placeTerm></place><dateCreated encoding="w3cdtf">2011-03-16</dateCreated><dateIssued encoding="w3cdtf">2011-12-01</dateIssued><copyrightDate encoding="w3cdtf">2011</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><abstract lang="en">Abstract: The title compound 1, cis-[diiodo(1R,2R)-1,2-diaminocyclohexane-κN,κN′]platinum(II), a precursor of a novel platinum-based anticancer complex, was synthesized. High purity (>99%) was determined by HPLC–UV/VIS and its structure was characterized by LC–ESI–MS, FT-IR and X-ray single-crystal diffraction. The molecules of the title compound interact via N–H···I and C–H···I intermolecular (ultra)-long hydrogen–iodine (acceptor) bonds (distances up to 3.1 Å). The crystal structure of the title compound 1 was compared to the structure calculated on the basis of density function theory (DFT). The calculated and measured data varied by a maximum of 0.09 Å in bond lengths and the maximum deviation between the compared angles were less than 2°. Experimentally measured bond lengths in the crystal were observed to be reduced when compared to the theoretical calculation. This was caused by both steric requirements of individual structural units and the presence of hydrogen bonds in real sample, which were confirmed by FT-IR (new bands as well as the band shifts to lower wavelengths).</abstract><note>Original Research</note><subject lang="en"><genre>Keywords</genre><topic>Cytostatics</topic><topic>DFT</topic><topic>Intermolecular long hydrogen bond</topic><topic>Platinum-based anticancer complex</topic><topic>Single crystal/structure</topic></subject><relatedItem type="host"><titleInfo><title>Structural Chemistry</title><subTitle>Computational and Experimental Studies of Chemical and Biological Systems</subTitle></titleInfo><titleInfo type="abbreviated"><title>Struct Chem</title></titleInfo><genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre><originInfo><publisher>Springer</publisher><dateIssued encoding="w3cdtf">2011-10-30</dateIssued><copyrightDate encoding="w3cdtf">2011</copyrightDate></originInfo><subject><genre>Chemistry</genre><topic>Theoretical and Computational Chemistry</topic><topic>Physical Chemistry</topic><topic>Computer Applications in Chemistry</topic></subject><identifier type="ISSN">1040-0400</identifier><identifier type="eISSN">1572-9001</identifier><identifier type="JournalID">11224</identifier><identifier type="IssueArticleCount">25</identifier><identifier type="VolumeIssueCount">6</identifier><part><date>2011</date><detail type="volume"><number>22</number><caption>vol.</caption></detail><detail type="issue"><number>6</number><caption>no.</caption></detail><extent unit="pages"><start>1325</start><end>1330</end></extent></part><recordInfo><recordOrigin>Springer Science+Business Media, LLC, 2011</recordOrigin></recordInfo></relatedItem><identifier type="istex">6CA457279CE6080C61446CA7958F7D9C1C0EFB66</identifier><identifier type="ark">ark:/67375/VQC-MV52C866-P</identifier><identifier type="DOI">10.1007/s11224-011-9826-8</identifier><identifier type="ArticleID">9826</identifier><identifier type="ArticleID">s11224-011-9826-8</identifier><accessCondition type="use and reproduction" contentType="copyright">Springer Science+Business Media, LLC, 2011</accessCondition><recordInfo><recordContentSource authority="ISTEX" authorityURI="https://loaded-corpus.data.istex.fr" valueURI="https://loaded-corpus.data.istex.fr/ark:/67375/XBH-3XSW68JL-F">springer</recordContentSource><recordOrigin>Springer Science+Business Media, LLC, 2011</recordOrigin></recordInfo></mods><json:item><extension>json</extension><original>false</original><mimetype>application/json</mimetype><uri>https://api.istex.fr/ark:/67375/VQC-MV52C866-P/record.json</uri></json:item></metadata><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
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