RSC Communication Template (Version 3.2)
Tuning LCST with thiol-responsiveness of thermoresponsive copolymers containing pendant disulfides Kaiwan Rahimian-Bajgiran,a Nicky Chan,a Qian Zhang,a# Seung Man Noh,b Hyung-il Lee,c Jung Kwon Oh a*Received (in XXX, XXX) Xth XXXXXXXXX 20XX, Accepted Xth XXXXXXXXX 20XXDOI: 10.1039/b000000xA new approach that centers on modulating hydrophobic/hydrophilic balance by conversion of pendant disulfides to thiols, and further to sulfides enables facile tuning of the thermoresponsive properties of thiol-responsive copolymers.32397702631440Scheme 1. A new approach to tune LCST of thiol-responsive thermoresponsive POEOMA copolymers by modulating pendant hydrophobic/hydrophilic balance with disulfide-thiol-sulfide chemistry. 00Scheme 1. A new approach to tune LCST of thiol-responsive thermoresponsive POEOMA copolymers by modulating pendant hydrophobic/hydrophilic balance with disulfide-thiol-sulfide chemistry. Stimuli-responsive polymers undergoing phase transition in response to external stimuli hold a great promise for various applications.PEVuZE5vdGU+PENpdGU+PEF1dGhvcj5BbGV4YW5kZXI8L0F1dGhvcj48WWVhcj4yMDA2PC9ZZWFy
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ADDIN EN.CITE.DATA [1-2] In particular, thermoresponsive polymers possessing lower critical solution temperature (LCST) behaviour are hydrophilic and swell at low temperature, facilitating encapsulation; above LCST, however, they are hydrophobic and shrink, enhancing release.PEVuZE5vdGU+PENpdGU+PEF1dGhvcj5Bb3NoaW1hPC9BdXRob3I+PFllYXI+MjAwODwvWWVhcj48
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ADDIN EN.CITE.DATA [3-4] Poly(N-substituted acrylamide) is representative of the class of thermoresponsive polymers; among these, poly(N-isopropylacrylamide) (PNIPAM) is the most studied polymer due to its near body temperature LCST driven response at 32 C.PEVuZE5vdGU+PENpdGU+PEF1dGhvcj5HaWw8L0F1dGhvcj48WWVhcj4yMDA0PC9ZZWFyPjxSZWNO
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ADDIN EN.CITE.DATA [5-6] However, PNIPAM-based copolymers have been known to be cytotoxic, suggesting that their use for biomedical applications may be limited. ADDIN EN.CITE <EndNote><Cite><Author>Dimitrov</Author><Year>2007</Year><RecNum>77</RecNum><DisplayText><style face="superscript">[7]</style></DisplayText><record><rec-number>77</rec-number><foreign-keys><key app="EN" db-id="5ws5rzwr5fasfqee0zovrt0gpf0ea5d5f02s">77</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>Dimitrov, Ivaylo</author><author>Trzebicka, Barbara</author><author>Mueller, Axel H. E.</author><author>Dworak, Andrzej</author><author>Tsvetanov, Christo B.</author></authors></contributors><auth-address>Institute of Polymers, Bulgarian Academy of Sciences, Sofia, Bulg.</auth-address><titles><title>Thermosensitive water-soluble copolymers with doubly responsive reversibly interacting entities</title><secondary-title>Prog. Polym. Sci.</secondary-title><alt-title>Progress in Polymer Science</alt-title></titles><periodical><full-title>Prog. Polym. Sci.</full-title><abbr-1>Progress in Polymer Science</abbr-1></periodical><alt-periodical><full-title>Prog. Polym. Sci.</full-title><abbr-1>Progress in Polymer Science</abbr-1></alt-periodical><pages>1275-1343</pages><volume>32</volume><number>11</number><keywords><keyword>Heat-sensitive materials (thermosensitive water-sol. copolymers with doubly responsive reversibly interacting entities)</keyword><keyword>Polymers Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (water-sol.</keyword><keyword>thermosensitive water-sol. copolymers with doubly responsive reversibly interacting entities)</keyword><keyword>review thermosensitive water soluble copolymer prepn property</keyword></keywords><dates><year>2007</year></dates><isbn>0079-6700</isbn><accession-num>2007:1131156</accession-num><urls></urls><electronic-resource-num>10.1016/j.progpolymsci.2007.07.001</electronic-resource-num><remote-database-name>CAPLUS</remote-database-name><remote-database-provider>American Chemical Society . All Rights Reserved.</remote-database-provider><language>English</language></record></Cite></EndNote>[7] Polymethacrylates with pendant ethylene oxide (EO) units (i.e. poly(oligo(ethylene oxide) monomethyl ether methacrylate, POEOMA) present a promising alternative. ADDIN EN.CITE <EndNote><Cite><Author>Lutz</Author><Year>2006</Year><RecNum>59</RecNum><DisplayText><style face="superscript">[8]</style></DisplayText><record><rec-number>59</rec-number><foreign-keys><key app="EN" db-id="5ws5rzwr5fasfqee0zovrt0gpf0ea5d5f02s">59</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>Lutz, J. F.</author><author>Akdemir, O.</author><author>Hoth, A.</author></authors></contributors><auth-address>Lutz, J. F.
Fraunhofer Inst Appl Polymer Res, Res Grp Nanotechnol Life Sci, Geiselbergstr 69, D-14476 Golm, Germany
Fraunhofer Inst Appl Polymer Res, Res Grp Nanotechnol Life Sci, D-14476 Golm, Germany</auth-address><titles><title>Point by point comparison of two thermosensitive polymers exhibiting a similar LCST: Is the age of poly(NIPAM) over?</title><secondary-title>J. Am. Chem. Soc.</secondary-title><alt-title>J Am Chem Soc
J Am Chem Soc</alt-title></titles><periodical><full-title>J. Am. Chem. Soc.</full-title><abbr-1>J Am Chem Soc</abbr-1></periodical><pages>13046-13047</pages><volume>128</volume><keywords><keyword>transfer radical polymerization</keyword><keyword>thermal response</keyword><keyword>smart polymers</keyword><keyword>water</keyword><keyword>copolymers</keyword><keyword>chain</keyword><keyword>block</keyword></keywords><dates><year>2006</year><pub-dates><date>OCT 11</date></pub-dates></dates><accession-num>ISI:000241030500009</accession-num><label>Amer Chemical Soc</label><urls><related-urls><url><Go to ISI>://000241030500009</url></related-urls></urls></record></Cite></EndNote>[8] POEOMA-based polymers are analogs of poly(ethylene oxide), a readily used FDA-approved material due to its biocompatibility and low toxicity.PEVuZE5vdGU+PENpdGU+PEF1dGhvcj5CcmFubm9uLVBlcHBhczwvQXV0aG9yPjxZZWFyPjIwMDA8
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ADDIN EN.CITE.DATA [9-10] More importantly, they exhibit tunable LCST between 20 and 90 C by varing the composition of POEOMA with different number of EO units in side chains. ADDIN EN.CITE <EndNote><Cite><Author>Lutz</Author><Year>2008</Year><RecNum>58</RecNum><DisplayText><style face="superscript">[11]</style></DisplayText><record><rec-number>58</rec-number><foreign-keys><key app="EN" db-id="5ws5rzwr5fasfqee0zovrt0gpf0ea5d5f02s">58</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>Lutz, Jean-Francois</author></authors></contributors><titles><title>Polymerization of oligo(ethylene glycol) (meth)acrylates: toward new generations of smart biocompatible materials</title><secondary-title>J. Polym. Sci., Part A: Polym. Chem.</secondary-title></titles><periodical><full-title>J. Polym. Sci., Part A: Polym. Chem.</full-title></periodical><pages>3459-3470</pages><volume>46</volume><number>11</number><keywords><keyword>review polymn oligoethylene glycol methacrylate smart biocompatible</keyword></keywords><dates><year>2008</year></dates><accession-num>An 2008:691402</accession-num><urls></urls></record></Cite></EndNote>[11] These unique properties promote the use of POEOMA-based materials for various biological and biomedical applications.PEVuZE5vdGU+PENpdGU+PEF1dGhvcj5MdXR6PC9BdXRob3I+PFllYXI+MjAxMTwvWWVhcj48UmVj
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ADDIN EN.CITE.DATA [12] -69850462915a Department of Chemistry and Biochemistry, Concordia University, Montreal, Quebec, Canada H4B 1R6; E-mail: john.oh@concordia.cab PPG Industries Korea, Cheonan 330-912 & Department of Chemical and Biological Engineering, Korea University, Seoul 136-713, Republic of Koreac Department of Chemistry, University of Ulsan, Ulsan 680-749, Republic of Korea # Permanent address: Department of Chemistry, School of Sciences, Xi'an University of Technology, Xi'an, Shaanxi Province, China?Electronic Supplementary Information (ESI) available: [details of any supplementary information available should be included here]. See DOI:?10.1039/b000000x/020000a Department of Chemistry and Biochemistry, Concordia University, Montreal, Quebec, Canada H4B 1R6; E-mail: john.oh@concordia.cab PPG Industries Korea, Cheonan 330-912 & Department of Chemical and Biological Engineering, Korea University, Seoul 136-713, Republic of Koreac Department of Chemistry, University of Ulsan, Ulsan 680-749, Republic of Korea # Permanent address: Department of Chemistry, School of Sciences, Xi'an University of Technology, Xi'an, Shaanxi Province, China?Electronic Supplementary Information (ESI) available: [details of any supplementary information available should be included here]. See DOI:?10.1039/b000000x/Stimuli-responsive degradation (SRD) is a promising property that enables enhancing the release of encapsulated guest molecules as well as tuning the morphologies of self-assembled nanostructures.PEVuZE5vdGU+PENpdGU+PEF1dGhvcj5SaWpja2VuPC9BdXRob3I+PFllYXI+MjAwNzwvWWVhcj48
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ADDIN EN.CITE.DATA [13-14] Particularly, disulfide linkages can be incorporated into designer nanomaterials, and then cleaved to the corresponding thiols in a reducing environment or through a disulfide-thiol exchange. ADDIN EN.CITE <EndNote><Cite><Author>Tsarevsky</Author><Year>2002</Year><RecNum>847</RecNum><DisplayText><style face="superscript">[15]</style></DisplayText><record><rec-number>847</rec-number><foreign-keys><key app="EN" db-id="9ee9va2psrw2e8evea8xe0soxd925s0tf5ep">847</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>Tsarevsky, Nicolay V.</author><author>Matyjaszewski, Krzysztof</author></authors></contributors><titles><title>Reversible Redox Cleavage/Coupling of Polystyrene with Disulfide or Thiol Groups Prepared by Atom Transfer Radical Polymerization</title><secondary-title>Macromolecules</secondary-title></titles><pages>9009-9014</pages><volume>35</volume><number>24</number><keywords><keyword>atom transfer radical polymn styrene bishydroxyethyl disulfide bromopropionate initiator</keyword><keyword>mercapto terminal group oxidn internal disulfide group formation polystyrene</keyword></keywords><dates><year>2002</year></dates><accession-num>An 2002:799321</accession-num><urls></urls></record></Cite></EndNote>[15] In biological systems, glutathione (GSH) is found at millimolar concentrations in normal cells, and at further elevated levels in cancer cells. ADDIN EN.CITE <EndNote><Cite><Author>Saito</Author><Year>2003</Year><RecNum>893</RecNum><DisplayText><style face="superscript">[16]</style></DisplayText><record><rec-number>893</rec-number><foreign-keys><key app="EN" db-id="9ee9va2psrw2e8evea8xe0soxd925s0tf5ep">893</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>Saito, Go</author><author>Swanson, Joel A.</author><author>Lee, Kyung-Dall</author></authors></contributors><auth-address>College of Pharmacy, Department of Pharmaceutical Sciences, University of Michigan, Ann Arbor, MI, USA.</auth-address><titles><title>Drug delivery strategy utilizing conjugation via reversible disulfide linkages: role and site of cellular reducing activities</title><secondary-title>Adv. Drug Delivery Rev.</secondary-title><alt-title>Advanced Drug Delivery Reviews</alt-title></titles><pages>199-215</pages><volume>55</volume><number>2</number><keywords><keyword>Disulfide group</keyword><keyword>Drug delivery systems</keyword><keyword>Human (drug delivery strategy utilizing conjugation via reversible disulfide linkages and role and site of cellular reducing activities)</keyword><keyword>review drug delivery strategy disulfide linkage</keyword></keywords><dates><year>2003</year></dates><isbn>0169-409X</isbn><accession-num>2003:64518</accession-num><urls></urls><electronic-resource-num>10.1016/s0169-409x(02)00179-5</electronic-resource-num><remote-database-name>CAPLUS</remote-database-name><remote-database-provider>American Chemical Society . All Rights Reserved.</remote-database-provider><language>English</language></record></Cite></EndNote>[16] The thiol-disulfide degradation property offers an advantageous SRD platform in constructing thiol-responsive degradable nanomaterials desirable for various biomedical applications; these include micelles,PEVuZE5vdGU+PENpdGU+PEF1dGhvcj5aaGFuZzwvQXV0aG9yPjxZZWFyPjIwMTI8L1llYXI+PFJl
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ADDIN EN.CITE.DATA [17-19] nanocapsules, ADDIN EN.CITE <EndNote><Cite><Author>Li</Author><Year>2010</Year><RecNum>854</RecNum><DisplayText><style face="superscript">[20]</style></DisplayText><record><rec-number>854</rec-number><foreign-keys><key app="EN" db-id="9ee9va2psrw2e8evea8xe0soxd925s0tf5ep">854</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>Li, Wenwen</author><author>Yoon, Jeong Ae</author><author>Matyjaszewski, Krzysztof</author></authors></contributors><auth-address>Department of Chemistry, Carnegie Mellon University, Pittsburgh, PA, USA.</auth-address><titles><title>Dual-Reactive Surfactant Used for Synthesis of Functional Nanocapsules in Miniemulsion</title><secondary-title>J. Am. Chem. Soc.</secondary-title><alt-title>Journal of the American Chemical Society</alt-title></titles><pages>7823-7825</pages><volume>132</volume><number>23</number><keywords><keyword>Polymerization</keyword><keyword>Polymerization catalysts (atom transfer, radical</keyword><keyword>dual-reactive surfactant used for synthesis of functional nanocapsules in miniemulsion)</keyword><keyword>Amphiphiles</keyword><keyword>Fluorescence</keyword><keyword>Nanocapsules</keyword><keyword>Particle size</keyword><keyword>Polymer morphology</keyword><keyword>Surfactants (dual-reactive surfactant used for synthesis of functional nanocapsules in miniemulsion)</keyword><keyword>Polyoxyalkylenes Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (dual-reactive surfactant used for synthesis of functional nanocapsules in miniemulsion)</keyword><keyword>amphiphile ATRP chloroisobutyrate ethylene oxide polymer nanocapsule</keyword></keywords><dates><year>2010</year></dates><isbn>0002-7863</isbn><accession-num>2010:645143</accession-num><urls></urls><electronic-resource-num>10.1021/ja100685s</electronic-resource-num><remote-database-name>CAPLUS</remote-database-name><remote-database-provider>American Chemical Society . All Rights Reserved.</remote-database-provider><language>English</language></record></Cite></EndNote>[20] nanogels, ADDIN EN.CITE <EndNote><Cite><Author>Miyata</Author><Year>2004</Year><RecNum>846</RecNum><DisplayText><style face="superscript">[21-22]</style></DisplayText><record><rec-number>846</rec-number><foreign-keys><key app="EN" db-id="9ee9va2psrw2e8evea8xe0soxd925s0tf5ep">846</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>Miyata, Kanjiro</author><author>Kakizawa, Yoshinori</author><author>Nishiyama, Nobuhiro</author><author>Harada, Atsushi</author><author>Yamasaki, Yuichi</author><author>Koyama, Hiroyuki</author><author>Kataoka, Kazunori</author></authors></contributors><titles><title>Block catiomer polyplexes with regulated densities of charge and disulfide cross-linking directed to enhance gene expression</title><secondary-title>J. Am. Chem. Soc. </secondary-title></titles><pages>2355-2361</pages><volume>126</volume><number>8</number><keywords><keyword>PEG lysine block copolymer disulfide crosslinked gene expression</keyword></keywords><dates><year>2004</year></dates><accession-num>An 2004:102775</accession-num><urls></urls></record></Cite><Cite><Author>Petros</Author><Year>2008</Year><RecNum>882</RecNum><record><rec-number>882</rec-number><foreign-keys><key app="EN" db-id="9ee9va2psrw2e8evea8xe0soxd925s0tf5ep">882</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>Petros, Robby A.</author><author>Ropp, Patricia A.</author><author>DeSimone, Joseph M.</author></authors></contributors><titles><title>Reductively Labile PRINT Particles for the Delivery of Doxorubicin to HeLa Cells</title><secondary-title>J. Am. Chem. Soc.</secondary-title></titles><pages>5008-5009</pages><volume>130</volume><number>15</number><keywords><keyword>nanoparticle doxorubicin targeting crosslinking disulfide crosslinker HeLa cell</keyword></keywords><dates><year>2008</year></dates><accession-num>An 2008:347500</accession-num><urls></urls></record></Cite></EndNote>[21-22] hydrogels,PEVuZE5vdGU+PENpdGU+PEF1dGhvcj5BbGl5YXI8L0F1dGhvcj48WWVhcj4yMDA1PC9ZZWFyPjxS
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ADDIN EN.CITE.DATA [25-27] Recently, this property has also been utilized to adjust thermoresponsive properties of thiol-responsive polydisulfides of multisegmented POEOMA ADDIN EN.CITE <EndNote><Cite><Author>Zhang</Author><Year>2012</Year><RecNum>72</RecNum><DisplayText><style face="superscript">[28]</style></DisplayText><record><rec-number>72</rec-number><foreign-keys><key app="EN" db-id="5ws5rzwr5fasfqee0zovrt0gpf0ea5d5f02s">72</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>Zhang, Qian</author><author>Noh, Seung Man</author><author>Nam, Joon Hyun</author><author>Jung, Hyun Wook</author><author>Park, Jong Myung</author><author>Oh, Jung Kwon</author></authors></contributors><auth-address>Department of Chemistry and Biochemistry and Center for Nanoscience Research (CENR), Concordia University, Montreal, QC, Can.</auth-address><titles><title>Dual Temperature and Thiol-Responsive POEOMA-Multisegmented Polydisulfides: Synthesis and Thermoresponsive Properties</title><secondary-title>Macromol. Rapid Commun.</secondary-title><alt-title>Macromolecular Rapid Communications</alt-title></titles><periodical><full-title>Macromol. Rapid Commun.</full-title><abbr-1>Macromolecular Rapid Communications</abbr-1></periodical><alt-periodical><full-title>Macromol. Rapid Commun.</full-title><abbr-1>Macromolecular Rapid Communications</abbr-1></alt-periodical><pages>1528-1534</pages><volume>33</volume><number>18</number><dates><year>2012</year></dates><isbn>1022-1336</isbn><accession-num>2012:891962</accession-num><urls></urls><electronic-resource-num>10.1002/marc.201200289</electronic-resource-num><remote-database-name>CAPLUS</remote-database-name><remote-database-provider>American Chemical Society . All Rights Reserved.</remote-database-provider><language>English</language></record></Cite></EndNote>[28] and PNIPAMPEVuZE5vdGU+PENpdGU+PEF1dGhvcj5QaGlsbGlwczwvQXV0aG9yPjxZZWFyPjIwMTI8L1llYXI+
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ADDIN EN.CITE.DATA [31-32] decreasing hydrophilicity, and thus decreasing the LCST. Our approach is promising in that the further modification of pendant thiols through thiol-ene Michael addition or thiol-disulfide exchange reaction will allow for the incorporation of additional reactive moieties or the conjugation of designed therapeutics for biological applications. 32315151305560Fig 1. 1H-NMR (a) and temperature dependence of normalized light scattering intensity by DLS (b) of ssCP-6 with pendant disulfide linkages, shCP-6 with pendant thiols formed by cleavage of pendant disulfides in response to DTT, and sCP-6 with pendant sulfides converted by thiol-ene reactions with tBA. 00Fig 1. 1H-NMR (a) and temperature dependence of normalized light scattering intensity by DLS (b) of ssCP-6 with pendant disulfide linkages, shCP-6 with pendant thiols formed by cleavage of pendant disulfides in response to DTT, and sCP-6 with pendant sulfides converted by thiol-ene reactions with tBA. A new methacrylate functionalized with a pendant disulfide linkage, HMssEt, was synthesized (Scheme S1), and characterized using 1H-, 13C-NMR, and high resolution mass spectroscopies, as described in our previous publication. ADDIN EN.CITE <EndNote><Cite><Author>Zhang</Author><Year>2012</Year><RecNum>79</RecNum><DisplayText><style face="superscript">[33]</style></DisplayText><record><rec-number>79</rec-number><foreign-keys><key app="EN" db-id="5ws5rzwr5fasfqee0zovrt0gpf0ea5d5f02s">79</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>Zhang, Qian</author><author>Aleksanian, Samuel</author><author>Noh, Seung Man</author><author>Oh, Jung Kwon</author></authors></contributors><titles><secondary-title>Polym. Chem.</secondary-title></titles><periodical><full-title>Polym. Chem.</full-title></periodical><dates><year>2012</year></dates><urls></urls></record></Cite></EndNote>[33] Scheme S2 (supporting information) illustrates the synthesis of well-defined P(OEOMA-co-HMssEt) copolymers (ssCPs) using atom transfer radical polymerization (ATRP), ADDIN EN.CITE <EndNote><Cite><Author>Matyjaszewski</Author><Year>2001</Year><RecNum>810</RecNum><DisplayText><style face="superscript">[34]</style></DisplayText><record><rec-number>810</rec-number><foreign-keys><key app="EN" db-id="9ee9va2psrw2e8evea8xe0soxd925s0tf5ep">810</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>Matyjaszewski, Krzysztof</author><author>Xia, Jianhui</author></authors></contributors><titles><title>Atom Transfer Radical Polymerization</title><secondary-title>Chem. Rev. </secondary-title></titles><pages>2921-2990</pages><volume>101</volume><number>9</number><keywords><keyword>review atom transfer radical polymn</keyword></keywords><dates><year>2001</year></dates><urls></urls></record></Cite></EndNote>[34] a successful CRP method. A series of ATRP was catalyzed with CuBr/PMDETA (N,N,N′,N′′,N′′-pentamethyldiethylenetriamine) complexes in the presence ethyl -bromoisobutyrate initiator in acetone at 47 C. The amounts of HMssEt were varied at 0 – 10 mol% in monomer mixtures. Table 1 summarizes the characteristics of ssCP copolymers. Table 1. Characteristics of ssCP copolymers prepared by ATRP.assCPHMssEt (mol%)Convb Mnc (g/mol)Mw/MncLCSTd (°C)00?0.2910,2001.2848.522?0.3711,3001.2842.32H20.64?17,4001.3138.3440.3011,7001.2433.6660.29?11,3001.2729.210100.3112,4001.22-a. Conditions: [monomers]0/[EBiB]0/[CuBr/PMDETA]0 = 120/1/0.5, [OEOMA]0/[DEGMA]0 = 0.38/1, monomers/anisole = 1/1 wt/wt.b. Determined by 1H-NMRc. Determined by GPC using DMF as an eluent with poly(methyl methacrylate) standards.d. Determined by DLSFor kinetic studies, aliquots were taken to determine monomer conversion using 1H-NMR and molecular weight and molecular weight distribution using gel permeation chromatography (GPC). As seen in Fig. S1a, all polymerizations had first-order kinetics, suggesting constant concentration of active centers. Monomer conversion reached over 60% in 4 hrs, suggesting no significant effect of the amount of HMssEt on the rate of polymerization. Molecular weight increased linearly with conversion and molecular weight distribution remained relatively narrow with Mw/Mn < 1.4 (Fig S1b). Furthermore, GPC traces evolved to the high molecular weight region over the course of the polymerization (Fig S2). These results suggest that ATRP of mixtures of OEOMA and HMssEt proceeded in a living fashion.The purified ssCPs are thermoresponsive and dynamic light scattering (DLS) technique was used to examine thermoresponsive behavior of these ssCPs with different amounts of HMssEt units. Light scattering (LS) intensity of the aqueous copolymer solutions at 0.1 mg/mL (0.1 wt%) was measured with temperatures varying from 20 to 85 C at increments of 1 C. The effect of the amount of hydrophobic HMssEt units in ssCPs was first examined. Note that molecular weights of five copolymers (ssCP-0, 2, 4, 6, and 10 in Table 1) ranged from Mn = 10-12 kg/mol. As seen in Table 1, LCST decreased from 48.5 C to 29.2 C with an increasing amount of hydrophobic HMssEt units from 0 to 6 mol%. Such significant decrease in LCST is attributed to increasing hydrophobicity of ssCPs. Note that ssCP-10 with 10 mol% HMssEt formed aggregates in aqueous solutions. The effect of molecular weight was also examined. For copolymers with 2 mol% HMssEt, DLS results show that the LCST decreased from 42.3 to 38.3 C when molecular weight increased from Mn = 11.3 kg/mol (ssCP-2) to 17.4 kg/mol (ssCP-2H) (Fig S3). Similar molecular weight dependent results are reported elsewhere.PEVuZE5vdGU+PENpdGU+PEF1dGhvcj5ZYW1hbW90bzwvQXV0aG9yPjxZZWFyPjIwMDg8L1llYXI+
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ADDIN EN.CITE.DATA [35] Next, pendant disulfide linkages of ssCPs were cleaved in the presence of D,L-dithiothreitol (DTT), a well-known amphiphilic thiol, in DMF. 1H-NMR was used to monitor the cleavage of disulfide linkages. As seen in 1H-NMR spectrum of ssCP-6 as a typical example (Fig 1a, upper), the peaks at 2.9 ppm correspond to two methylene protons adjacent to disulfides (c and d) and peaks at 2.7-2.8 ppm correspond to two methylene protons adjacent to carbonyl (-C=O) groups (b and e). Upon the cleavage of disulfides to corresponding thiols (Fig 1a, middle), peaks (d and e) disappeared (due to the removal of small thiol moieties during precipitation) and peak (c) was shifted to 2.7 ppm (c) (due to the conversion of disulfide to thiol). In addition, a new triplet at 1.5 ppm corresponding to thiol (-SH) proton (g) appeared. These results confirm the pronounced cleavage of pendant disulfide linkages of ssCPs to form the corresponding P(OEOMA-co-HMSH) copolymers having pendant thiol (-SH) groups (shCPs).Fig 1b shows a typical example of thermal properties of ssCP-6 with 6 mol% HMssEt, showing an increase in LCST from 29.2 to 38.3 C before and after cleavage of pendant disulfide linkages. For ssCP-4 with 4 mol% HMssEt, its LCST also increased from 33.2 to 42.3 C after the cleavage of pendant disulfide linkages. This considerable increase in LCST by ca. 10 C can be attributed to the cleavage of pendant disulfides to thiols, changing the hydrophilic/hydrophobic balance in the pendant chains of ssCPs. Note that no significant effect of residual DTT on thermal properties of shCPs is observed (Fig S4). Further, the resulting hydrophilic thiols were reacted with t-butyl acrylate (tBA) in the presence of n-butyl amine. After purification to remove excess tBA, 1H-NMR (Fig 1a, lower) shows a typical peak at 1.5 ppm corresponding to nine tertiary methyl protons (h) and peaks at 2.5 ppm corresponding to two methylene protons adjacent to sulfide linkage (j), suggesting the formation of P(OEOMA-co-HMstBA) (sCP-6). The conversion of thiols to sulfide linkages was determined to be 38% (see supporting information and Fig S5). As seen in Fig 1b, the DLS results indicate the LCST decreasing from 38.2 to 35.3 C as a result from conversion of hydrophilic thiols to hydrophobic sulfides (decreasing hydrophilicity). In conclusion, we demonstrated a new approach to tuning thermoresponsive properties of thiol-responsive POEOMA copolymers by modulating the pendant hydrophobic/hydrophilic balance with disulfide-thiol-sulfide conversions. The LCST decreased with increasing incorporation of hydrophobic HMssEt monomer functionalized with pendant disulfide linkage. The LCST could then be increased by thiol-responsive cleavage of pendant disulfide linkages to the corresponding thiols; and further decreased by thiol-ene reactions to convert sulfides. These results suggest that the new approach will be useful in constructing novel nanomaterials requiring tunable LCST behaviour for biological and biomedical applications. This research was supported by the NSERC Canada, Canada Research Chair (CRC) Award, and partially Advanced Technology Center program (10032218) in the Korean Ministry of Knowledge Economy. KRB thanks for NSERC Undergraduate Summer Research Award (USRA).Notes and references ADDIN EN.REFLIST [1]C. Alexander, K. M. Shakesheff, Adv. Mater. 2006, 18, 3321.[2]D. Roy, J. N. Cambre, B. S. Sumerlin, Prog. Polym. Sci. 2010, 35, 278.[3]S. Aoshima, S. Kanaoka, Adv. Polym. Sci. 2008, 210, 169.[4]H. G. Schild, Prog. Polym. Sci. 1992, 17, 163.[5]E. S. Gil, S. M. Hudson, Prog. Polym. Sci. 2004, 29, 1173.[6]H.-i. Lee, J. Pietrasik, S. S. Sheiko, K. Matyjaszewski, Prog. Polym. Sci. 2010, 35, 24.[7]I. Dimitrov, B. Trzebicka, A. H. E. Mueller, A. Dworak, C. B. Tsvetanov, Prog. Polym. Sci. 2007, 32, 1275.[8]J. F. Lutz, O. Akdemir, A. Hoth, J. Am. Chem. Soc. 2006, 128, 13046.[9]L. Brannon-Peppas, J. Control. Release 2000, 66, 321.[10]K. Knop, R. Hoogenboom, D. Fischer, U. S. Schubert, Angew. Chem., Int. Ed. 2010, 49, 6288.[11]J.-F. Lutz, J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 3459.[12]J.-F. Lutz, Adv. Mater. 2011, 23, 2237.[13]C. J. F. Rijcken, O. Soga, W. E. Hennink, C. F. van Nostrum, J. Controlled Release 2007, 120, 131.[14]Y. Wang, H. Xu, X. Zhang, Adv. Mater. 2009, 21, 2849.[15]N. V. Tsarevsky, K. Matyjaszewski, Macromolecules 2002, 35, 9009.[16]G. Saito, J. A. Swanson, K.-D. Lee, Adv. Drug Delivery Rev. 2003, 55, 199.[17]Q. Zhang, N. R. Ko, J. K. Oh, Chem. Commun. 2012, 48, 7542.[18]R. Cheng, F. Feng, F. Meng, C. Deng, J. Feijen, Z. Zhong, J. Controlled Release 2011, 152, 2.[19]F. Meng, W. E. Hennink, Z. Zhong, Biomaterials 2009, 30, 2180.[20]W. Li, J. A. Yoon, K. Matyjaszewski, J. Am. Chem. Soc. 2010, 132, 7823.[21]K. Miyata, Y. Kakizawa, N. Nishiyama, A. Harada, Y. Yamasaki, H. Koyama, K. Kataoka, J. Am. Chem. Soc. 2004, 126, 2355.[22]R. A. Petros, P. A. Ropp, J. M. DeSimone, J. Am. Chem. Soc. 2008, 130, 5008.[23]H. A. Aliyar, P. D. Hamilton, N. Ravi, Biomacromolecules 2005, 6, 204.[24]J. A. Yoon, S. A. Bencherif, B. Aksak, E. K. Kim, T. Kowalewski, J. K. Oh, K. Matyjaszewski, Chem.--Asian J. 2011, 6, 128.[25]D. Bontempo, L. Heredia Karina, A. Fish Benjamin, D. Maynard Heather, J Am Chem Soc 2004, 126, 15372.[26]C. Boyer, J. Liu, L. Wong, M. Tippett, V. Bulmus, T. P. Davis, J. Polym. Sci., Part A Polym. Chem. 2008, 46, 7207.[27]C. Boyer, V. Bulmus, J. Liu, T. P. Davis, M. H. Stenzel, C. Barner-Kowollik, J. Am. Chem. Soc. 2007, 129, 7145.[28]Q. Zhang, S. M. Noh, J. H. Nam, H. W. Jung, J. M. Park, J. K. Oh, Macromol. Rapid Commun. 2012, 33, 1528.[29]D. J. Phillips, M. I. Gibson, Chem. Commun. 2012, 48, 1054.[30]K. Matyjaszewski, T. P. Davis, John Wiley & Sons Inc., 2002.[31]C. E. Hoyle, A. B. Lowe, C. N. Bowman, Chem. Soc. Rev. 2010, 39, 1355.[32]G.-Z. Li, R. K. Randev, A. H. Soeriyadi, G. Rees, C. Boyer, Z. Tong, T. P. Davis, C. R. Becer, D. M. Haddleton, Polym. Chem. 2010, 1, 1196.[33]Q. Zhang, S. Aleksanian, S. M. Noh, J. K. Oh, Polym. Chem. 2012.[34]K. Matyjaszewski, J. Xia, Chem. Rev. 2001, 101, 2921.[35]S. I. Yamamoto, J. Pietrasik, K. Matyjaszewski, J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 194. ................
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