One-Pot Conversion of RAFT-Generated Multifunctional Block Copolymers of HPMA to Doxorubicin Conjugated Acid- and Reductant-Sensitive Crosslinked Micelles

Jia, Zhongfan; Wong, Ling Jiun; Davis, Thomas P.; Bulmuş, Volga

doi:10.1021/bm800657e

Cited by 154 publications

(157 citation statements)

References 60 publications

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“…BMA [139] MAA [140] MMA [64,141] AEMA [90,142] DEGMA [141] DMAEMA [143] DPAEMA [144] MAA [145] PEGMA [144,[146][147][148] 383 [149] DMAM [150] NIPAM [151] 274 [152,153] 325 [154] 326 [154] APMAM-b-NIPAM [89,152] AEMAM [153] St [155] 274 [153] 275 [153] 285 [156] 286 [156] 289 [157] 292 [158] 304 [140] 305 [140] 331 [159] 329 [140] 327 [157] 380 [160] 391 [161,162] 389 [104] (390) [104] 416 [163,164] MAA-b-280 [145] BMA-b-MPC [139] PEGMA/ 320 [165] PEGMA/344 [165] DEGMA-b-384 [141] MMA-b-384 …”

Section: Choice Of Raft Agentsmentioning

confidence: 99%

“…[465] These active ester groups undergo facile reaction with, in particular, substrates with primary amine groups. Other monomers with reactive functionality that have been successfully (co)polymerized include 391 (with thiol reactive functionality) [161,162] and 392 (with protected aldehyde functionality) (Table 26). [97,98] Copolymers of monomers with reactive functionality, such as 371-392 (Tables 24-26), have potential application as scaffolds for bioconjugation.…”

Section: Raft Polymer Synthesesmentioning

confidence: 99%

“…We found that with this method, while successful for removing the chain ends of polymers with a terminal MA unit, it was not possible to obtain complete removal of dithiobenzoate or butyl trithiocarbonate Table 26. Monomers with masked reactive functionality amenable to RAFT (co)polymerization 391 [161,162] O O S S N 392 [97,98] O O O O [94] BA C 12 H 25 S (159) EPHP [94] tBA C 12 H 25 S (135) EPHP [328] MMA C 12 H 25 S (121) EPHP [94] St Ph (22) EPHP [94] 358 Ph (22) B u 3 SnH [244] VAc C 2 H 5 O (227) B u 3 SnH [395] A Monomer unit adjacent to thiocarbonylthio group. B ((CH 3 ) 3 Si) 3 SiH -tris(trimethylsilyl)silane, EPHP -N-ethylpiperidine hypophosphite, Bu 3 SnH -tri-n-butylstannane.…”

Section: Radical-induced Reductionmentioning

confidence: 99%

“…[161] The production of such scaffolds by RAFT and other RDRP processes for post polymerization modification has recently been reviewed. [540] The general approach has wide application and has, for example, been used in the synthesis of photochromic polymers by coupling of spiropyran moieties to RAFT-synthesized P(BMA-co-HEMA).…”

Section: Grafting-to Processesmentioning

confidence: 99%

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Living Radical Polymerization by the RAFT Process - A Second Update

Moad¹,

Rizzardo²,

Thang³

2009

Aust. J. Chem.

906

720

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This paper provides a second update to the review of reversible deactivation radical polymerization achieved with thiocarbonylthio compounds (ZC(=S)SR) by a mechanism of reversible addition-fragmentation chain transfer (RAFT) that was published in June 2005 (Aust. J. Chem. 2005, 58, 379-410). The first update was published in November 2006 (Aust. J. Chem. 2006, 59, 669-692). This review cites over 500 papers that appeared during the period mid-2006 to mid-2009 covering various aspects of RAFT polymerization ranging from reagent synthesis and properties, kinetics and mechanism of polymerization, novel polymer syntheses and a diverse range of applications. Significant developments have occurred, particularly in the areas of novel RAFT agents, techniques for end-group removal and transformation, the production of micro/nanoparticles and modified surfaces, and biopolymer conjugates both for therapeutic and diagnostic applications.

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Section: Choice Of Raft Agentsmentioning

confidence: 99%

Section: Raft Polymer Synthesesmentioning

confidence: 99%

Section: Radical-induced Reductionmentioning

confidence: 99%

Section: Grafting-to Processesmentioning

confidence: 99%

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Living Radical Polymerization by the RAFT Process - A Second Update

Moad¹,

Rizzardo²,

Thang³

2009

Aust. J. Chem.

906

720

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“…29 As a synthetic technique, RAFT offers a convenient platform for molecular engineering of polymeric systems for drug delivery, biotechnology, nanotechnology and nanomedicine applications. [30][31][32][33][34][35][36][37] It has already been used to synthesise a range of polymeric structures for siRNA delivery, [38][39][40][41][42][43][44][45][46] with certain RAFT generated polymers found to have low levels of cytotoxicity. 47,48 In this study a novel polycationic system that is capable of selfassembly in aqueous solutions and of forming small, stable nanoparticles when complexed to siRNAs has been synthesized, imbuing nonviral carrier characteristics such as gene protection, phase transition and buffering capacity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, self-assembly and stimuli responsive properties of cholesterol conjugated polymers

et al. 2012

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Reversible addition-fragmentation chain transfer (RAFT) polymerization was used to generate welldefined pH-responsive biofunctional polymers as potential 'smart' gene delivery systems. A series of five poly(dimethylamino ethyl methacrylate-co-cholesteryl methacrylate) P(DMAEMA-co-CMA) statistical copolymers, with similar molecular weights and varying cholesterol content, were prepared. The syntheses, compositions and molecular weight distributions for P(DMAEMA-co-CMA) were monitored by nuclear magnetic resonance (NMR), solid-state NMR and gel permeation chromatography (GPC) evidencing well-defined polymeric structures with narrow polydispersities. Aqueous solution properties of the copolymers were investigated using turbidimetry and light scattering to determine hydrodynamic diameters and zeta potentials associated with the phase transition behaviour of P(DMAEMA-co-CMA) copolymers. UV-Visible spectroscopy was used to investigate the pH-responsive behaviour of copolymers. Hydrodynamic radii were measured in the range 10-30 nm (pH, temperature dependent) by dynamic light scattering (DLS). Charge studies indicated that P(DMAEMA-co-CMA) polymers have an overall cationic charge, mediated by pH. Potentiometric studies revealed that the buffering capacity and pK a values of polymers were dependent on cholesterol content as well as on cationic charge. The buffering capacity increased with increasing charge ratio, overall demonstrating transitions in the pH endosomal region for all five copolymeric structures. Cell viability assay showed that the copolymers displayed increasing cytotoxicity with decreasing number of cholesterol moieties. These preliminary results show the potential of these welldefined P(DMAEMA-co-CMA) polymers as in vitro siRNA delivery agents.

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