Synthesis of pyridine acrylates and acrylamides and their corresponding pyridinium ions as versatile cross-linkers for tunable hydrogels

• Verfasst von: Mateescu, Markus [VerfasserIn]
• Verfasst von: Nuss, Isabell [VerfasserIn]
• Verfasst von: Southan, Alexander [VerfasserIn]
• Verfasst von: Messenger, Hayley [VerfasserIn]
• Verfasst von: Wegner, Seraphine V. [VerfasserIn]
• Verfasst von: Kupka, Julia [VerfasserIn]
• Verfasst von: Bach, Monika [VerfasserIn]
• Verfasst von: Tovar, Günter E. M. [VerfasserIn]
• Verfasst von: Böhm, Heike [VerfasserIn]
• Verfasst von: Laschat, Sabine [VerfasserIn]
• Titel: Synthesis of pyridine acrylates and acrylamides and their corresponding pyridinium ions as versatile cross-linkers for tunable hydrogels
• Verf.angabe: Markus Mateescu, Isabell Nuss, Alexander Southan, Hayley Messenger, Seraphine V. Wegner, Julia Kupka, Monika Bach, Günter E. M. Tovar, Heike Boehm, Sabine Laschat
• E-Jahr: 2014
• Jahr: 06. März 2014
• Umfang: 11 S.
• Fussnoten: Gesehen am 01.09.2020
• Titel Quelle: Enthalten in: Synthesis
• Ort Quelle: Stuttgart [u.a.] : Thieme, 1969
• Jahr Quelle: 2014
• Band/Heft Quelle: 46(2014), 9, Seite 1243-1253
• ISSN Quelle: 1437-210X
• DOI: doi:10.1055/s-0033-1338614
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 172851553X

Abstract

<p>A small library of cross-linkers for hydrogels was synthesized. The cross-linkers consisted of 2,6- and 3,5-diacylpyridine or 2,4,6-triacylpyridine as the core unit, which were tethered via ethylene glycol, amino ethanol, and 1,n-diamine spacers to terminal acrylate or acrylamide moieties. Esterification and amide formation of the terminal acryl units were found to be dependent on the ratio of NH/O in the spacer, the constitution pattern of the pyridine ring, and the total number of acryl groups. Thus, esters generally gave higher yields than amides decreasing with increasing number of NH in the spacer and with increasing number of acryl units. In the case of 3,5-diacylpyridine derivatives, these trends were less prominent as compared to the 2,6-diacylpyridine series, indicating that steric hindrance and unfavorable hydrogen bonding interaction of the spacers might influence the observed reactivity differences. The 3,5-diacylpyridines were converted to the <i>N</i>-methylpyridinium salts and selected members of both neutral and cationic 3,5-diacylpyridinium derivatives were submitted to hydrogelations with synthetic polymer poly(1-glycidylpiperazine) via aza-Michael addition and thiolated natural hyaluronan via thio-Michael reaction, respectively. Rheological properties of the resulting hydrogels were studied, revealing that both spacer type as well as charge affected elastic moduli and degree of swelling.</p>