Synthesis of Poly(2-(methylsulfinyl)ethyl methacrylate) via Oxidation of Poly(2-(methylthio)ethyl methacrylate): Evaluation of the Sulfoxide Side Chain on Cryopreservation
Conventional cryopreservation solutions rely on the addition of organic solvents such as DMSO or glycerol, but these do not give full recovery for all cell types, and innovative cryoprotectants may address damage pathways which these solvents do not protect against. Macromolecular cryoprotectants ar...
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Published in | ACS polymers Au Vol. 2; no. 6; pp. 449 - 457 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
United States
American Chemical Society
14.12.2022
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Abstract | Conventional cryopreservation solutions rely on the addition of organic solvents such as DMSO or glycerol, but these do not give full recovery for all cell types, and innovative cryoprotectants may address damage pathways which these solvents do not protect against. Macromolecular cryoprotectants are emerging, but there is a need to understand their structure–property relationships and mechanisms of action. Here we synthesized and investigated the cryoprotective behavior of sulfoxide (i.e., “DMSO-like”) side-chain polymers, which have been reported to be cryoprotective using poly(ethylene glycol)-based polymers. We also wanted to determine if the polarized sulfoxide bond (S+O– character) introduces cryoprotective effects, as this has been seen for mixed-charge cryoprotective polyampholytes, whose mechanism of action is not yet understood. Poly(2-(methylsulfinyl)ethyl methacrylate) was synthesized by RAFT polymerization of 2-(methylthio)ethyl methacrylate and subsequent oxidation to sulfoxide. A corresponding N-oxide polymer was also prepared and characterized: (poly(2-(dimethylamineoxide)ethyl methacrylate). Ice recrystallization inhibition assays and differential scanning calorimetry analysis show that the sulfoxide side chains do not modulate the frozen components during cryopreservation. In cytotoxicity assays, it was found that long-term (24 h) exposure of the polymers was not tolerated by cells, but shorter (30 min) incubation times, which are relevant for cryopreservation, were tolerated. It was also observed that overoxidation to the sulfone significantly increased the cytotoxicity, and hence, these materials require a precision oxidation step to be deployed. In suspension cell cryopreservation investigations, the polysulfoxides did not increase cell recovery 24 h post-thaw. These results show that unlike hydrophilic backboned polysulfides, which can aid cryopreservation, the installation of the sulfoxide group onto a polymer does not necessarily bring cryoprotective properties, highlighting the challenges of developing and discovering macromolecular cryoprotectants. |
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AbstractList | Conventional cryopreservation solutions rely on the addition
of
organic solvents such as DMSO or glycerol, but these do not give full
recovery for all cell types, and innovative cryoprotectants may address
damage pathways which these solvents do not protect against. Macromolecular
cryoprotectants are emerging, but there is a need to understand their
structure–property relationships and mechanisms of action.
Here we synthesized and investigated the cryoprotective behavior of
sulfoxide (i.e., “DMSO-like”) side-chain polymers, which
have been reported to be cryoprotective using poly(ethylene glycol)-based
polymers. We also wanted to determine if the polarized sulfoxide bond
(S
+
O
–
character) introduces cryoprotective
effects, as this has been seen for mixed-charge cryoprotective polyampholytes,
whose mechanism of action is not yet understood. Poly(2-(methylsulfinyl)ethyl
methacrylate) was synthesized by RAFT polymerization of 2-(methylthio)ethyl
methacrylate and subsequent oxidation to sulfoxide. A corresponding
N
-oxide polymer was also prepared and characterized: (poly(2-(dimethylamineoxide)ethyl
methacrylate). Ice recrystallization inhibition assays and differential
scanning calorimetry analysis show that the sulfoxide side chains
do not modulate the frozen components during cryopreservation. In
cytotoxicity assays, it was found that long-term (24 h) exposure of
the polymers was not tolerated by cells, but shorter (30 min) incubation
times, which are relevant for cryopreservation, were tolerated. It
was also observed that overoxidation to the sulfone significantly
increased the cytotoxicity, and hence, these materials require a precision
oxidation step to be deployed. In suspension cell cryopreservation
investigations, the polysulfoxides did not increase cell recovery
24 h post-thaw. These results show that unlike hydrophilic backboned
polysulfides, which can aid cryopreservation, the installation of
the sulfoxide group onto a polymer does not necessarily bring cryoprotective
properties, highlighting the challenges of developing and discovering
macromolecular cryoprotectants. Conventional cryopreservation solutions rely on the addition of organic solvents such as DMSO or glycerol, but these do not give full recovery for all cell types, and innovative cryoprotectants may address damage pathways which these solvents do not protect against. Macromolecular cryoprotectants are emerging, but there is a need to understand their structure-property relationships and mechanisms of action. Here we synthesized and investigated the cryoprotective behavior of sulfoxide (i.e., "DMSO-like") side-chain polymers, which have been reported to be cryoprotective using poly(ethylene glycol)-based polymers. We also wanted to determine if the polarized sulfoxide bond (S O character) introduces cryoprotective effects, as this has been seen for mixed-charge cryoprotective polyampholytes, whose mechanism of action is not yet understood. Poly(2-(methylsulfinyl)ethyl methacrylate) was synthesized by RAFT polymerization of 2-(methylthio)ethyl methacrylate and subsequent oxidation to sulfoxide. A corresponding -oxide polymer was also prepared and characterized: (poly(2-(dimethylamineoxide)ethyl methacrylate). Ice recrystallization inhibition assays and differential scanning calorimetry analysis show that the sulfoxide side chains do not modulate the frozen components during cryopreservation. In cytotoxicity assays, it was found that long-term (24 h) exposure of the polymers was not tolerated by cells, but shorter (30 min) incubation times, which are relevant for cryopreservation, were tolerated. It was also observed that overoxidation to the sulfone significantly increased the cytotoxicity, and hence, these materials require a precision oxidation step to be deployed. In suspension cell cryopreservation investigations, the polysulfoxides did not increase cell recovery 24 h post-thaw. These results show that unlike hydrophilic backboned polysulfides, which can aid cryopreservation, the installation of the sulfoxide group onto a polymer does not necessarily bring cryoprotective properties, highlighting the challenges of developing and discovering macromolecular cryoprotectants. Conventional cryopreservation solutions rely on the addition of organic solvents such as DMSO or glycerol, but these do not give full recovery for all cell types, and innovative cryoprotectants may address damage pathways which these solvents do not protect against. Macromolecular cryoprotectants are emerging, but there is a need to understand their structure–property relationships and mechanisms of action. Here we synthesized and investigated the cryoprotective behavior of sulfoxide (i.e., “DMSO-like”) side-chain polymers, which have been reported to be cryoprotective using poly(ethylene glycol)-based polymers. We also wanted to determine if the polarized sulfoxide bond (S+O– character) introduces cryoprotective effects, as this has been seen for mixed-charge cryoprotective polyampholytes, whose mechanism of action is not yet understood. Poly(2-(methylsulfinyl)ethyl methacrylate) was synthesized by RAFT polymerization of 2-(methylthio)ethyl methacrylate and subsequent oxidation to sulfoxide. A corresponding N-oxide polymer was also prepared and characterized: (poly(2-(dimethylamineoxide)ethyl methacrylate). Ice recrystallization inhibition assays and differential scanning calorimetry analysis show that the sulfoxide side chains do not modulate the frozen components during cryopreservation. In cytotoxicity assays, it was found that long-term (24 h) exposure of the polymers was not tolerated by cells, but shorter (30 min) incubation times, which are relevant for cryopreservation, were tolerated. It was also observed that overoxidation to the sulfone significantly increased the cytotoxicity, and hence, these materials require a precision oxidation step to be deployed. In suspension cell cryopreservation investigations, the polysulfoxides did not increase cell recovery 24 h post-thaw. These results show that unlike hydrophilic backboned polysulfides, which can aid cryopreservation, the installation of the sulfoxide group onto a polymer does not necessarily bring cryoprotective properties, highlighting the challenges of developing and discovering macromolecular cryoprotectants. |
Author | Gibson, Matthew I. Georgiou, Panagiotis G. Gonzalez-Martinez, Natalia Ishibe, Toru Murray, Kathryn A. |
AuthorAffiliation | Department of Chemistry Division of Biomedical Sciences, Warwick Medical School |
AuthorAffiliation_xml | – name: Department of Chemistry – name: Division of Biomedical Sciences, Warwick Medical School |
Author_xml | – sequence: 1 givenname: Toru surname: Ishibe fullname: Ishibe, Toru organization: Department of Chemistry – sequence: 2 givenname: Natalia orcidid: 0000-0003-1038-5306 surname: Gonzalez-Martinez fullname: Gonzalez-Martinez, Natalia organization: Department of Chemistry – sequence: 3 givenname: Panagiotis G. orcidid: 0000-0001-8968-1057 surname: Georgiou fullname: Georgiou, Panagiotis G. organization: Department of Chemistry – sequence: 4 givenname: Kathryn A. orcidid: 0000-0002-8465-7143 surname: Murray fullname: Murray, Kathryn A. organization: Division of Biomedical Sciences, Warwick Medical School – sequence: 5 givenname: Matthew I. orcidid: 0000-0002-8297-1278 surname: Gibson fullname: Gibson, Matthew I. email: m.i.gibson@warwick.ac.uk organization: Division of Biomedical Sciences, Warwick Medical School |
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CitedBy_id | crossref_primary_10_1016_j_eurpolymj_2023_112258 crossref_primary_10_1039_D3CC04092E crossref_primary_10_1021_acs_biomac_2c01488 crossref_primary_10_1039_D3TB02432F |
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Keywords | macromolecular cryoprotectant polymers RAFT DMSO cryopreservation |
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Snippet | Conventional cryopreservation solutions rely on the addition of organic solvents such as DMSO or glycerol, but these do not give full recovery for all cell... Conventional cryopreservation solutions rely on the addition of organic solvents such as DMSO or glycerol, but these do not give full recovery for all cell... |
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Title | Synthesis of Poly(2-(methylsulfinyl)ethyl methacrylate) via Oxidation of Poly(2-(methylthio)ethyl methacrylate): Evaluation of the Sulfoxide Side Chain on Cryopreservation |
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