Synthesis of Well-Defined Dihydroxy Telechelics by (Co)polymerization of Morpholine-2,5-Diones Catalyzed by Sn(IV) Alkoxide
- Well-defined dihydroxy telechelic oligodepsipeptides (oDPs), which have a high application potential as building blocks for scaffold materials for tissue engineering applications or particulate carrier systems for drug delivery applications are synthesized by ring-opening polymerization (ROP) of morpholine-2,5-diones (MDs) catalyzed by 1,1,6,6-tetra-n-butyl-1,6-distanna-2,5,7,10-tetraoxacyclodecane (Sn(IV) alkoxide). In contrast to ROP catalyzed by Sn(Oct)(2), the usage of Sn(IV) alkoxide leads to oDPs, with less side products and well-defined end groups, which is crucial for potential pharmaceutical applications. A slightly faster reaction of the ROP catalyzed by Sn(IV) alkoxide compared to the ROP initiated by Sn(Oct)(2)/EG is found. Copolymerization of different MDs resulted in amorphous copolymers with T(g)s between 44 and 54 degrees C depending on the molar comonomer ratios in the range from 25% to 75%. Based on the well-defined telechelic character of the Sn(IV) alkoxide synthesized oDPs as determined by matrix-assisted laserWell-defined dihydroxy telechelic oligodepsipeptides (oDPs), which have a high application potential as building blocks for scaffold materials for tissue engineering applications or particulate carrier systems for drug delivery applications are synthesized by ring-opening polymerization (ROP) of morpholine-2,5-diones (MDs) catalyzed by 1,1,6,6-tetra-n-butyl-1,6-distanna-2,5,7,10-tetraoxacyclodecane (Sn(IV) alkoxide). In contrast to ROP catalyzed by Sn(Oct)(2), the usage of Sn(IV) alkoxide leads to oDPs, with less side products and well-defined end groups, which is crucial for potential pharmaceutical applications. A slightly faster reaction of the ROP catalyzed by Sn(IV) alkoxide compared to the ROP initiated by Sn(Oct)(2)/EG is found. Copolymerization of different MDs resulted in amorphous copolymers with T(g)s between 44 and 54 degrees C depending on the molar comonomer ratios in the range from 25% to 75%. Based on the well-defined telechelic character of the Sn(IV) alkoxide synthesized oDPs as determined by matrix-assisted laser desorption/ionization time of flight measurements, they resemble interesting building blocks for subsequent postfunctionalization or multifunctional materials based on multiblock copolymer systems whereas the amorphous oDP-based copolymers are interesting building blocks for matrices of drug delivery systems.…
Author details: | Xingzhou PengORCiDGND, Marc BehlORCiDGND, Pengfei Zhang, Magdalena Mazurek-BudzynskaORCiD, Yakai FengORCiDGND, Andreas LendleinORCiDGND |
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DOI: | https://doi.org/10.1002/mabi.201800257 |
ISSN: | 1616-5187 |
ISSN: | 1616-5195 |
Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/30318738 |
Title of parent work (English): | Macromolecular bioscience |
Publisher: | Wiley-VCH |
Place of publishing: | Weinheim |
Publication type: | Article |
Language: | English |
Date of first publication: | 2018/10/14 |
Publication year: | 2018 |
Release date: | 2021/06/22 |
Tag: | Sn(IV) alkoxide; oligodepsipeptides; ring-opening polymerization; telechelics; tin(II) 2-ethylhexanoate |
Volume: | 18 |
Issue: | 12 |
Number of pages: | 11 |
Funding institution: | Helmholtz AssociationHelmholtz Association; Tianjin University-Helmholtz-Zentrum Geesthacht Joint Laboratory for Biomaterials and Regenerative Medicine - German Federal Ministry of Education and Research (BMBF) [0315496]; Chinese Ministry of Science and Technology (MOST)Ministry of Science and Technology, China [2013DFG52040]; Deutsche Forschungsgemeinschaft (DFG) through the Collaborative Research Centre 1112 "Nanocarriers"; China Scholarship Council (CSC)China Scholarship Council [201206250098] |
Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
DDC classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Peer review: | Referiert |