Functional Hyperbranched Polymers: Toward Targeted <i>in Vivo</i> <sup>19</sup>F Magnetic Resonance Imaging Using Designed Macromolecules

Thurecht, Kristofer J.; Blakey, Idriss; Peng, Hui; Squires, Oliver; Hsu, Steven; Alexander, Cameron; Whittaker, Andrew K.

doi:10.1021/ja100252y

Cited by 185 publications

(243 citation statements)

References 13 publications

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“…[267] Pressley et al [611] have reported on an improved methodology for conducting click reactions to form block and cyclic polymers. [227] PFPMA/LMA Ph AIBN 25 70 100 [225] BA Ph AIBN 30 80 ,25 [194] HA Ph ACPA 5 70 100 [240] HA Ph AHPN 5 70 100 [240] BA/NA Ph AIBN 20 80 100 [202] BA C 4 H 9 S AIBN 30 80 ,25 [194] BA C 4 H 9 S AIBN þ BPO 20 þ 2 E 80 100 [194] HPA [596] tBA Poly(tBA)S AIBN -80 100 [597] NIPAm Poly(tBA-b-NIPAm)S AIBN -80 100 [597] tBA/TBBPMA Ph AIBN (20) (80) 100 [598] DAMEA/TFEA C 12 H 25 S AIBN 20 65 100 [599] HADA [194] St Ph AIBN þ BPO 20 þ 2 E 80 100 [194] St C 4 H 9 S AIBN 30 À 100 80 ,60 [194] St C 12 H 25 S AIBN 10 95 92 [393] A Monomer unit adjacent to thiocarbonylthio group. The process makes use of commercially available copper nanoparticles and is performed with microwave irradiation.…”

Section: Click Reactionsmentioning

confidence: 99%

Living Radical Polymerization by the RAFT Process – A Third Update

2012

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This paper provides a third update to the review of reversible deactivation radical polymerization (RDRP) achieved with thiocarbonylthio compounds (ZC(¼S)SR) by a mechanism of reversible addition-fragmentation chain transfer ( Chem. 2009Chem. , 62, 1402. This review cites over 700 publications that appeared during the period mid 2009 to early 2012 covering various aspects of RAFT polymerization which include reagent synthesis and properties, kinetics and mechanism of polymerization, novel polymer syntheses, and a diverse range of applications. This period has witnessed further significant developments, particularly in the areas of novel RAFT agents, techniques for end-group transformation, the production of micro/nanoparticles and modified surfaces, and biopolymer conjugates both for therapeutic and diagnostic applications.

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Section: Click Reactionsmentioning

confidence: 99%

Living Radical Polymerization by the RAFT Process – A Third Update

2012

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“…Recently, RAFT has been applied in synthesis of classic hyperbranched or core cross-linked star polymer nanocontrast agents, which has demonstrated good control of polymer structure. [36][37][38]44,45 The novel dimethacrylate cross-linker 6 employed incorporates the DO3A macrocycles simultaneously during the branching process ensuring the DO3A macrocycles are …”

Section: Synthesis Of Branched Copolymer Nanoparticles Via Raft Polymmentioning

confidence: 99%

Synthesis and in vivo magnetic resonance imaging evaluation of biocompatible branched copolymer nanocontrast agents

Jackson¹,

Chandrasekharan²,

Shi³

et al. 2015

IJN

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Branched copolymer nanoparticles ( D h =20–35 nm) possessing 1,4,7, 10-tetraazacyclododecane- N , N ′, N ″, N ‴-tetraacetic acid macrocycles within their cores have been synthesized and applied as magnetic resonance imaging (MRI) nanosized contrast agents in vivo. These nanoparticles have been generated from novel functional monomers via reversible addition–fragmentation chain transfer polymerization. The process is very robust and synthetically straightforward. Chelation with gadolinium and preliminary in vivo experiments have demonstrated promising characteristics as MRI contrast agents with prolonged blood retention time, good biocompatibility, and an intravascular distribution. The ability of these nanoparticles to perfuse and passively target tumor cells through the enhanced permeability and retention effect is also demonstrated. These novel highly functional nanoparticle platforms have succinimidyl ester-activated benzoate functionalities within their corona, which make them suitable for future peptide conjugation and subsequent active cell-targeted MRI or the conjugation of fluorophores for bimodal imaging. We have also demonstrated that these branched copolymer nanoparticles are able to noncovalently encapsulate hydrophobic guest molecules, which could allow simultaneous bioimaging and drug delivery.

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“…More recently, there has been an increase in literature reports of experimental studies which have exploited these properties of hyperbranched polymers in a vast array of medical applications, 2 including gene delivery, [18][19] drug delivery, 20 bio-surfaces modification, 21 and molecular imaging. [22][23] In the field of biomedical polymers, polyesters are a class of material which find particular utility. This is because of their good thermal and mechanical properties, acceptable levels of chemical resistance, ease of synthesis, availability of monomer feed stocks and many are defined to be biodegradable.…”

Section: Introductionmentioning

confidence: 99%

Facile one-spot synthesis of highly branched polycaprolactone

et al. 2014

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Reported is the first solvent-free (bulk) synthesis of degradable/bioresorbable, highly branched polymers via tin octanoate Sn(Oct 2 ) catalysed controlled ring opening copolymerisation (ROP) of mono and di-functional lactone monomers that proceed to near quantitative conversion. The successful isolation of solvent soluble, highly branched structures was shown to be dependent on both the concentration of the di-functional monomer and the overall reaction time. Comparison with analogous systems utilising controlled radical polymerisation (CRP) to form the highly/hyper branched polymers suggested significant experimental differences between the two chain growth methods. The maximum proportion of di-functional monomer without gelation ensuing was found to be 0.6 equivalents w.r.t. mono-functional monomer (c.f. 1 with CRP) and the onset of significant levels of branching occurred at approximately 90% conversion (c.f. ~70% with CRP). These differences and significant disparity in reaction times were attributed to (a) the coordination and insertion (C+I) propagation mechanism adopted by the Sn catalyst and (b) the presence of additional trans-esterification reactions at high conversion. Evidence is presented to support the conclusion that there are two mechanisms contributing to the overall branching process in the ROP system at high conversion. First, the C+I mechanism promotes growth of linear polymer until approximately 90% conversion, after which both the C+I and transesterification processes contribute to the interchain branching process. The branched nature of the molecular structures was supported by confirmation plots generated from static light scattering. This data demonstrated that the polymers synthesised exhibit varying degrees of branching, consistent with the di-functional monomer (4, concentration in the feed. The degree of branching was calculated using 3 different methods 2 and the results were shown to be independent of method. Finally, DSC analysis of the polymers demonstrated correlation between the degree of branching achieved and the observed T m for the material where increased branching leads to a drop in the recorded T m .

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Functional Hyperbranched Polymers: Toward Targeted in Vivo ¹⁹F Magnetic Resonance Imaging Using Designed Macromolecules

Cited by 185 publications

References 13 publications

Living Radical Polymerization by the RAFT Process – A Third Update

Living Radical Polymerization by the RAFT Process – A Third Update

Synthesis and in vivo magnetic resonance imaging evaluation of biocompatible branched copolymer nanocontrast agents

Facile one-spot synthesis of highly branched polycaprolactone

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Functional Hyperbranched Polymers: Toward Targeted in Vivo 19F Magnetic Resonance Imaging Using Designed Macromolecules

Cited by 185 publications

References 13 publications

Living Radical Polymerization by the RAFT Process – A Third Update

Living Radical Polymerization by the RAFT Process – A Third Update

Synthesis and in vivo magnetic resonance imaging evaluation of biocompatible branched copolymer nanocontrast agents

Facile one-spot synthesis of highly branched polycaprolactone

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Product

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Functional Hyperbranched Polymers: Toward Targeted in Vivo ¹⁹F Magnetic Resonance Imaging Using Designed Macromolecules