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Abstract No.: ThP-219
Session: Polymer Characterization
Presentation date: Thu, Aug 31, 2006
Presentation time: 09:50 – 11:20

Characterization of Enzymatic Degradation Products of 2,2-bis(2-oxazoline) Linked poly-e-caprolactone by Electrospray Ionization Mass Spectrometry

Joni Juhani Palmgren1, Mika Pulkkinen1, Minna Malin1, Jukka Seppala1, Tiina Jarvinen1, Seppo Auriola1

1 University of Kuopio, Kuopio, Finland

Correspondence address: Joni Juhani Palmgren, University of Kuopio, Department of pharmaceutical chemistry, Harjulantie 2, Kuopio, B.O. 1627 70211 Kuopio Finland.

Keywords: Electrospray Ionization (ESI); Mass Spectrometry; MS/MS, Liquid Chromatography; Polymer.

Novel aspect: Characterization of degradation products of novel polymer.


Aliphatic polyesters, such as poly(e-caprolactone, PCL) are promising candidates for biodegradable medical and pharmaceutical applications. In the absence of enzymes, slow degradation of PCL occurs by ester bond cleavage. Various co-polymers of PCL have been synthesized to enhance their enzyme-induced degradation. Earlier report showed that the novel 2,2-bis(2-oxazoline) linked poly-e-caprolactone (PCL-O) was degraded by pancreatin enzyme and decreased molecular weight was observed. In this study, the aim was to characterize the enzymatic degradation products of PCL-O and to develop the new liquid chromatography mass spectrometry method.

The samples were filtered with size-exclusion filter (Mw10000) prior to analysis. The chromatographic separation was performed by Xterra column (2.1×150 mm, 3.5 mm, C8). Gradient (5 mM ammonium acetate and 90 % ACN in 37 min) flow (200 ml/min) was used for separation. Finnigan LTQ mass spectrometer equipped with electrospray ionization source (Thermo, San Jose, CA) was operated in positive full scan mode (m/z 200-2000) and tandem mass spectra (MS/MS) were also measured.

Degradation products were separated effectively by reversed phase column. Typically, they eluted within 25 min run time. We found that molecular ions of the degradation products ranged between m/z 300 and 800 and there were differences of 100 or 114 (m/z) in the structures. The molecular structures of the degradation products were confirmed by MS/MS spectrums.

Tarvainen et al. J. Control. Rel. 86, 213 (2003).