Microfluidic Mixing of Polyamine with Acrolein Enables the Detection of the [4+4] Polymerization of Intermediary Unsaturated Imines

The Properties of a Cytotoxic 1,5-Diazacyclooctane Hydrogel

Ambara R. Pradipta, Ayumi Tsutsui, Akihiro Ogura, Shinya Hanashima, Yoshiki Yamaguchi, Almira Kurbangalieva, Katsunori Tanaka

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The [4+4] polymerization of an unsaturated imine, generated from the condensation of a polyamine and excess acrolein, was investigated. The polyamine was added by micropipet to acrolein, immediately yielding a mixture of the immiscible polymeric material. Microfluidic mixing was used to gradually form the soluble diazacyclooctane polymers. The polymerization reaction ultimately gave an insoluble cationic hydrogel that adhered strongly to anionic compounds on cell surfaces, including sialoglycan, and displayed a high cytotoxicity.

Original languageEnglish
Article numberst-2014-u0541-l
Pages (from-to)2442-2446
Number of pages5
JournalSynlett
Volume25
Issue number17
DOIs
Publication statusPublished - 2014 Oct 22
Externally publishedYes

Fingerprint

Acrolein
Imines
Hydrogel
Polyamines
Microfluidics
Polymerization
Cytotoxicity
Condensation
Polymers

Keywords

  • 1 5-diazacyclooctane
  • acrolein
  • cytotoxicity
  • hydrogel
  • microreactor
  • N -alkyl unsaturated imine
  • polyamine
  • sialoglycan
  • [4+4] polymerization

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Microfluidic Mixing of Polyamine with Acrolein Enables the Detection of the [4+4] Polymerization of Intermediary Unsaturated Imines : The Properties of a Cytotoxic 1,5-Diazacyclooctane Hydrogel. / Pradipta, Ambara R.; Tsutsui, Ayumi; Ogura, Akihiro; Hanashima, Shinya; Yamaguchi, Yoshiki; Kurbangalieva, Almira; Tanaka, Katsunori.

In: Synlett, Vol. 25, No. 17, st-2014-u0541-l, 22.10.2014, p. 2442-2446.

Research output: Contribution to journalArticle

Pradipta, Ambara R. ; Tsutsui, Ayumi ; Ogura, Akihiro ; Hanashima, Shinya ; Yamaguchi, Yoshiki ; Kurbangalieva, Almira ; Tanaka, Katsunori. / Microfluidic Mixing of Polyamine with Acrolein Enables the Detection of the [4+4] Polymerization of Intermediary Unsaturated Imines : The Properties of a Cytotoxic 1,5-Diazacyclooctane Hydrogel. In: Synlett. 2014 ; Vol. 25, No. 17. pp. 2442-2446.
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