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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Netropsin</span></h1>
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<div id="mw-content-text" class="mw-body-content mw-content-ltr" lang="de" dir="ltr"><div class="mw-content-ltr mw-parser-output" lang="de" dir="ltr"><table class="wikitable infobox float-right" id="Vorlage_Infobox_Chemikalie" style="font-size:90%; margin-top:0; width:350px;" summary="Infobox Chemikalie">
<tbody><tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Strukturformel
</th></tr>
<tr>
<td colspan="2" class="hintergrundfarbe-basis skin-invert-image" style="text-align:center;"><span typeof="mw:File"></span>
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<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
</th></tr>
<tr>
<td style="width:33%;">Name
</td>
<td>Netropsin
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>Nt</li>
<li>Congocidin</li>
<li>Sinanomycin</li></ul>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>18</sub>H<sub>26</sub>N<sub>10</sub>O<sub>3</sub> · 2HCl
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>gelber Feststoff<sup id="cite_ref-Sigma_1-0" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Externe Identifikatoren/Datenbanken
</th></tr>
<tr>
<td colspan="2" style="padding:0;">
<table class="mw-collapsible mw-collapsed wikitable" data-expandtext="+" data-collapsetext="−" style="border-top:none; margin:-1px; width:calc(100% + 2px);">
<tbody><tr>
<td style="width:33%;"><a href="CAS-Nummer" title="CAS-Nummer">CAS-Nummer</a>
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=1438-30-8">1438-30-8</a><span class="editoronly" style="display:none;"></span>
</td>
<td style="background:#FFDEAD; color:#202122; border-top:1px solid #FFDEAD; padding:0.2em 0; vertical-align:bottom; width:5%;">
</td></tr>
<tr>
<td><a href="EG-Nummer" title="EG-Nummer">EG-Nummer</a> (<a href="EG-Nummer#Listennummern" title="EG-Nummer">Listennummer</a>)
</td>
<td colspan="2">634-294-2
</td></tr>
<tr>
<td><a href="Europ%C3%A4ische_Chemikalienagentur" title="Europäische Chemikalienagentur">ECHA</a>-InfoCard
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.echa.europa.eu/de/substance-information/-/substanceinfo/100.162.288">100.162.288</a>
</td></tr>
<tr>
<td><a href="PubChem" title="PubChem">PubChem</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/4461">4461</a>
</td></tr>
<tr>
<td><a href="ChemSpider" title="ChemSpider">ChemSpider</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.4306.html">4306</a>
</td></tr>
<tr>
<td style="border-right:1px solid #a2a9b1;"><a href="Wikidata" title="Wikidata">Wikidata</a>
</td>
<td colspan="2"><a href="https://www.wikidata.org/wiki/Q3874969" class="extiw external" title="d:Q3874969">Q3874969</a>
</td></tr></tbody></table>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Eigenschaften
</th></tr>
<tr>
<td><a href="Molare_Masse" title="Molare Masse">Molare Masse</a>
</td>
<td>503,39 g·<a href="Mol" title="Mol">mol</a><sup>−1</sup>
</td></tr>
<tr>
<td><a href="Aggregatzustand" title="Aggregatzustand">Aggregatzustand</a>
</td>
<td>
<p>fest<sup id="cite_ref-Sigma_1-1" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>
<p>>300 <a href="Grad_Celsius" title="Grad Celsius">°C</a><sup id="cite_ref-Sigma_1-2" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Sicherheitshinweise
</th></tr>
<tr>
<td colspan="2">
<table cellspacing="0" cellpadding="2" style="width:100%;">
<tbody><tr>
<td colspan="2" style="text-align:center"><b><a href="Global_harmonisiertes_System_zur_Einstufung_und_Kennzeichnung_von_Chemikalien" title="Global harmonisiertes System zur Einstufung und Kennzeichnung von Chemikalien">GHS-Gefahrstoffkennzeichnung</a></b><sup id="cite_ref-Sigma_1-3" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
<table class="hintergrundfarbe-neutral" style="text-align:center; margin-left:auto; margin-right:auto; display:flex; justify-content:center;">
<tbody><tr>
<td><span typeof="mw:File"><a href="Global_harmonisiertes_System_zur_Einstufung_und_Kennzeichnung_von_Chemikalien#Übersicht:_EU-Gefahrensymbole,_UN/GHS-Gefahrenpiktogramme,_UN/ADR-Gefahrensymbole" title="06 – Giftig oder sehr giftig"></a></span>
</td></tr></tbody></table>
<p>
</p>
</td></tr>
<tr>
<td rowspan="2" width="33%" style="border-top:1px #A7A7A7 dashed; border-right:1px #A7A7A7 dashed;"><a href="H-_und_P-S%C3%A4tze" title="H- und P-Sätze">H- und P-Sätze</a>
</td>
<td style="border-top:1px #A7A7A7 dashed;">H: <span title="Untervorlage eingebunden: H-Sätze"></span><a href="H-_und_P-S%C3%A4tze#H-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Giftig bei Verschlucken.">301</span></span></a>
</td></tr>
<tr>
<td style="border-top:1px #A7A7A7 dashed;">P: <span title="Untervorlage eingebunden: P-Sätze"></span><a href="H-_und_P-S%C3%A4tze#P-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Bei Verschlucken:">301</span></span></a>‐<a href="H-_und_P-S%C3%A4tze#P-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Sofort Giftinformationszentrum, Arzt oder … anrufen.">310</span></span></a><sup id="cite_ref-Sigma_1-4" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</td></tr>
</tbody></table>
</td></tr>
<tr>
<td colspan="2" style="background:#FFDEAD; color:#202122; font-size:80%; text-align:center; line-height:150%; padding:.25em;">Wenn nicht anders vermerkt, gelten die angegebenen Daten bei <a href="Standardbedingungen" title="Standardbedingungen">Standardbedingungen</a> (0 °C, 1000 hPa).
</td></tr></tbody></table><p><span class="editoronly" style="display:none;"></span>
</p><p><b>Netropsin</b> ist ein <a href="Polyamid" class="mw-redirect" title="Polyamid">Polyamid</a>-<a href="Antibiotikum" title="Antibiotikum">Antibiotikum</a>, das an die kleine Furche einer <a href="DNA" class="mw-redirect" title="DNA">DNA</a>-<a href="Doppelhelix" title="Doppelhelix">Doppelhelix</a> bindet.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Es wirkt gegen <a href="Gram-positiv" class="mw-redirect" title="Gram-positiv">Gram-positive</a> und <a href="Gram-negativ" class="mw-redirect" title="Gram-negativ">Gram-negative</a> <a href="Bakterien" title="Bakterien">Bakterien</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p>Netropsin wurde erstmals 1951 durch A. C. Finlay beschrieben, der es aus dem <a href="Actinobacteria" title="Actinobacteria">Actinobakterium</a> <i>Streptomyces netropsis</i> isoliert hatte.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Netropsin gehört zur Klasse <a href="Pyrrol" title="Pyrrol">Pyrrol</a>-<a href="Amidin" class="mw-redirect" title="Amidin">Amidin</a>-Antibiotika und ist ein <a href="Analogon_(Chemie)" title="Analogon (Chemie)">Analogon</a> von <a href="Distamycin" title="Distamycin">Distamycin</a> und den <a href="Lexitropsine" title="Lexitropsine">Lexitropsinen</a>. Es bindet bevorzugt AT-reiche <a href="DNA-Sequenz" class="mw-redirect" title="DNA-Sequenz">DNA-Sequenzen</a> doppelsträngiger DNA und Tetraden aus [TGGGGT]<sub>4</sub>,<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> nicht jedoch an einzelsträngige DNA oder <a href="RNA" class="mw-redirect" title="RNA">RNA</a>. Die Bindung von Netropsin führt zu einer engeren Windung von etwa 9° pro gebundenem Lexitropsin und Basenpaar.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Bei einer positiven <a href="Superspiralisierung" class="mw-redirect" title="Superspiralisierung">Superspiralisierung</a> entspannt es daher die DNA, während es eine negative Superspiralisierung verstärkt.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Der Bindungsmechanismus ist noch nicht vollständig geklärt.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Verschiedene Distamycin-Derivate wurden entwickelt, um als <a href="Alkylanzien" title="Alkylanzien">Alkylanzien</a> gegen <a href="Tumor" title="Tumor">Tumoren</a> eingesetzt zu werden oder zur <a href="Fluoreszenzmarkierung" title="Fluoreszenzmarkierung">Fluoreszenzmarkierung</a> von doppelsträngiger DNA.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-Sigma-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Sigma_1-0">a</a></sup> <sup><a href="#cite_ref-Sigma_1-1">b</a></sup> <sup><a href="#cite_ref-Sigma_1-2">c</a></sup> <sup><a href="#cite_ref-Sigma_1-3">d</a></sup> <sup><a href="#cite_ref-Sigma_1-4">e</a></sup></span> <span class="reference-text">Datenblatt <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/catalog/product/SIGMA/N9653">Netropsin dihydrochloride</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 24. November 2013 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/SIGMA/N9653?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-2"><span class="mw-cite-backlink"><a href="#cite_ref-2">↑</a></span> <span class="reference-text">M. P. Barrett, C. G. Gemmell, C. J. Suckling: <i>Minor groove binders as anti-infective agents.</i> In: <i><a href="Pharmacology_%26_Therapeutics" title="Pharmacology & Therapeutics">Pharmacology & Therapeutics</a>.</i> Band 139, Nummer 1, Juli 2013, S. 12–23, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1016/j.pharmthera.2013.03.002">10.1016/j.pharmthera.2013.03.002</a></span>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/23507040?dopt=Abstract">PMID 23507040</a>.</span>
</li>
<li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text">C. Zimmer, U. Wähnert: <i>Nonintercalating DNA-binding ligands: specificity of the interaction and their use as tools in biophysical, biochemical and biological investigations of the genetic material.</i> In: <i>Progress in biophysics and molecular biology.</i> Band 47, Nummer 1, 1986, S. 31–112, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/2422697?dopt=Abstract">PMID 2422697</a>.</span>
</li>
<li id="cite_note-4"><span class="mw-cite-backlink"><a href="#cite_ref-4">↑</a></span> <span class="reference-text">A.C. Finlay, F. A. Hochstein, B. A. Sobin, and F. X. Murphy, <i><a href="J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a></i> <b>73</b> 341–343 (1951). <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1021/ja01145a113">10.1021/ja01145a113</a></span>.</span>
</li>
<li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text">M. L. Kopka, C. Yoon, D. Goodsell, P. Pjura, and R.E. Dickerson, <i><a href="J._Mol._Biol." class="mw-redirect" title="J. Mol. Biol.">J. Mol. Biol.</a></i> <b>183</b> 553–563 (1985)</span>
</li>
<li id="cite_note-6"><span class="mw-cite-backlink"><a href="#cite_ref-6">↑</a></span> <span class="reference-text">M. L. Kopka, C. Yoon, D. Goodsell, P. Pjura, R. E. Dickerson: <i>The molecular origin of DNA-drug specificity in netropsin and distamycin.</i> In: <i><a href="Proceedings_of_the_National_Academy_of_Sciences_of_the_United_States_of_America" title="Proceedings of the National Academy of Sciences of the United States of America">Proceedings of the National Academy of Sciences of the United States of America</a>.</i> Band 82, Nummer 5, März 1985, S. 1376–1380, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/2983343?dopt=Abstract">PMID 2983343</a>. <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC397264/">PMC 397264</a> (freier Volltext).</span>
</li>
<li id="cite_note-7"><span class="mw-cite-backlink"><a href="#cite_ref-7">↑</a></span> <span class="reference-text">B. Pagano, I. Fotticchia, S. De Tito, C. A. Mattia, L. Mayol, E. Novellino, A. Randazzo, C. Giancola: <i>Selective Binding of Distamycin A Derivative to G-Quadruplex Structure [d(TGGGGT)](4).</i> In: <i>Journal of nucleic acids.</i> Band 2010, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.4061/2010%2F247137">10.4061/2010/247137</a></span>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/20725616?dopt=Abstract">PMID 20725616</a>. <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2915651/">PMC 2915651</a> (freier Volltext).</span>
</li>
<li id="cite_note-8"><span class="mw-cite-backlink"><a href="#cite_ref-8">↑</a></span> <span class="reference-text">G. Snounou and A. D. B. Malcolm, <i>J. Mol. Biol.</i> <b>167</b> 211–216 (1983)</span>
</li>
<li id="cite_note-9"><span class="mw-cite-backlink"><a href="#cite_ref-9">↑</a></span> <span class="reference-text">H. Triebel, H. Bär, R. Geuther, and G. Burckhardt, <i>Progr. Colloid. Polym. Sci.</i> <b>99</b> 45–54 (1995).</span>
</li>
<li id="cite_note-10"><span class="mw-cite-backlink"><a href="#cite_ref-10">↑</a></span> <span class="reference-text">J. Lipfert, S. Klijnhout, N. H. Dekker: <i>Torsional sensing of small-molecule binding using magnetic tweezers.</i> In: <i><a href="Nucleic_Acids_Research" title="Nucleic Acids Research">Nucleic Acids Research</a>.</i> Band 38, Nummer 20, November 2010, S. 7122–7132, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1093/nar%2Fgkq598">10.1093/nar/gkq598</a></span>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/20624816?dopt=Abstract">PMID 20624816</a>. <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2978369/">PMC 2978369</a> (freier Volltext).</span>
</li>
<li id="cite_note-11"><span class="mw-cite-backlink"><a href="#cite_ref-11">↑</a></span> <span class="reference-text">Y. Y. Fang, V. R. Morris, G. M. Lingani, E. C. Long, W. M. Southerland: <i>Genome-Targeted Drug Design: Understanding the Netropsin-DNA Interaction.</i> In: <i>The open conference proceedings journal.</i> Band 1, 2010, S. 157–163, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/21297883?dopt=Abstract">PMID 21297883</a>. <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3032215/">PMC 3032215</a> (freier Volltext).</span>
</li>
<li id="cite_note-12"><span class="mw-cite-backlink"><a href="#cite_ref-12">↑</a></span> <span class="reference-text">G. S. Khan, A. Shah, Zia-ur-Rehman, D. Ba: <i>Chemistry of DNA minor groove binding agents.</i> In: <i>Journal of photochemistry and photobiology. B, Biology.</i> Band 115, Oktober 2012, S. 105–118, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1016/j.jphotobiol.2012.07.003">10.1016/j.jphotobiol.2012.07.003</a></span>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/22857824?dopt=Abstract">PMID 22857824</a>.</span>
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<li id="cite_note-13"><span class="mw-cite-backlink"><a href="#cite_ref-13">↑</a></span> <span class="reference-text">C. Bailly, J. B. Chaires: <i>Sequence-specific DNA minor groove binders. Design and synthesis of netropsin and distamycin analogues.</i> In: <i><a href="Bioconjugate_Chemistry" title="Bioconjugate Chemistry">Bioconjugate Chemistry</a>.</i> Band 9, Nummer 5, 1998 Sep-Oct, S. 513–538, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1021/bc980008m">10.1021/bc980008m</a></span>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/9736486?dopt=Abstract">PMID 9736486</a>.</span>
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<li id="cite_note-14"><span class="mw-cite-backlink"><a href="#cite_ref-14">↑</a></span> <span class="reference-text">T. Vaijayanthi, T. Bando, G. N. Pandian, H. Sugiyama: <i>Progress and prospects of pyrrole-imidazole polyamide-fluorophore conjugates as sequence-selective DNA probes.</i> In: <i><a href="ChemBioChem" title="ChemBioChem">ChemBioChem</a></i> Band 13, Nummer 15, Oktober 2012, S. 2170–2185, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1002/cbic.201200451">10.1002/cbic.201200451</a></span>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/23023993?dopt=Abstract">PMID 23023993</a>.</span>
</li>
</ol>
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