A New Two‐Photon‐Sensitive Block Copolymer Nanocarrier

Babin, Jérôme; Pelletier, Maxime; Lepage, Martin; Allard, Jean François; Morris, Denis; Zhao, Yue

doi:10.1002/anie.200900255

Cited by 295 publications

(248 citation statements)

References 32 publications

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“…Beside azobenzene, 5 o-nitrobenzyl alcohol 6 photosensitive derivatives are today the most studied in polymer science, among all others photochromics groups like coumarin, 7,8 spiropyran, 9 pyrene, 10 or cinnamic derivatives. 11 For instance, o-nitrobenzyl esters have been used as photocleavable junction between blocks in copolymer 12,13 or as polymer-drug linkage in bioconjugates.…”

Section: Introductionmentioning

confidence: 99%

o -nitrobenzyl acrylate is polymerizable by single electron transfer-living radical polymerization

Soliman

Nouvel

Babin

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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Polymers containing o-nitrobenzyl esters are promising for preparation of light sensitive materials. o-Nitrobenzyl methacrylate has already been polymerized by controlled ATRP or RAFT. Unfortunately, the radical polymerization of o-nitrobenzyl acrylate (NBA) was not controlled until now due to inhibition and retardation effects coming from the nitro-aromatic groups. Recent developments in the Single Electron TransferLiving Radical Polymerization (SET-LRP) provide us an access to control this NBA polymerization and living character of this NBA SET-LRP is demonstrated. Effects of CuBr 2 and ligand concentrations, as well as Cu(0) wire length on SET-LRP kinetics are shown presently. A first-order kinetics with respect to the NBA concentration is observed after one induction period. SET-LRP proceeds with a linear evolution of molecular weight and a narrow distribution. High initiation efficiency close to 1 and high chain-end functionality (93%) are reached. Chain extension of poly(o-nitrobenzyl acrylate) is realized with methyl acrylate (MA) to obtain well defined poly(o-nitrobenzyl acrylate)-b-poly(methyl acrylate) (PNBA-b-PMA). Finally, lightsensitive properties of PNBA are checked upon UV irradiation.

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Section: Introductionmentioning

confidence: 99%

o -nitrobenzyl acrylate is polymerizable by single electron transfer-living radical polymerization

Soliman

Nouvel

Babin

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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“…9 But better penetration to the deeper part of cells 10 can be afforded using chromophores having significant twophoton absorption (TPA) character in the near-IR region. 11,12 Chromophores with TPA character have attracted much attention because of their application in physiology. Caged compounds with TPA character enable greater spatial control of the release of bioactive substances.…”

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confidence: 99%

Design, Synthesis, and Reaction of π-Extended Coumarin-based New Caged Compounds with Two-photon Absorption Character in the Near-IR Region

Chitose¹,

Abe²,

Furukawa³

et al. 2016

Chem. Lett.

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Novel π-extended coumarin-based chromophores were designed with two-photon absorption (TPA) character in the near-IR region. Caged benzoates with a TP-responsive chromophore were synthesized, and their TP-uncaging reactions were conducted under near-IR light. The 6,7-dimethoxy-substituted derivative had a high TPA cross-section of 69 GM at 740 nm. The 7-methoxysubstituted derivative showed a high TPA uncaging efficiency with a TPA efficiency of 3.4 GM at 710 nm.Keywords: Caged compounds | Two-photon absorption | Donor-π-AcceptorCaged compounds, 1 the inactive forms of bioactive molecules formed using a photolabile protecting group (PPG), 2 are now used to elucidate the mechanism of bioactivity of substances in various life processes and phenomena. For instance, caged compounds contribute to the development of new medicines. The PPG is removed photochemically under neutral conditions without chemical reagents, thus rapidly releasing the bioactive compound. This efficient uncaging is biologically useful because the timing, location, and amplitude of photoirradiation can be controlled. Thus, the photoinduced release of bioactive molecules has been utilized in various fields such as neuroscience, cell patterning, or biomedical science. 35 Coumarin derivatives have been used to study various functions of biomolecules and for cellular imaging.6 The advantages of coumarin as a chromophore include its inherent fast response to photolysis, thermal stability, high molar extinction coefficient, and good fluorescent property for monitoring its reactions in vivo.7 However, the recent concern for physiological application of coumarin-based compounds is mainly its short absorption wavelength. Coumarin itself possesses an absorption wavelength maximum of 274 nm in methanol.8 Due to this short wavelength, cell damages cannot be avoided using one-photon absorption (OPA).9 But better penetration to the deeper part of cells 10 can be afforded using chromophores having significant twophoton absorption (TPA) character in the near-IR region. 11,12Chromophores with TPA character have attracted much attention because of their application in physiology. Caged compounds with TPA character enable greater spatial control of the release of bioactive substances. 13 For practical applications, a higher uncaging efficiency is necessary to conduct biological studies. The uncaging efficiency for OP excitation is defined as the uncaging quantum yield (Φ u ) multiplied by the excitation probability (¾: molar extinction coefficient). Similarly, the efficiency ¤ u of a TP excitation process is expressed using the TPA cross-section (· 2 ): ¤ u = Φ u · 2 . The minimum threshold value of TP efficiency for in vivo studies was reported as 3 GM.14 In 1999, Furuta et al. In this study, a coumarin containing a stilbene skeleton (12 GM at 514 nm) 18 with a p-nitrophenyl group as the electronwithdrawing group was designed to increase the TPA crosssections due to its dipolar character (Figure 1). 19 The cyclic structure should prevent cistrans isomerization ...

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“…[17][18][19] They synthesized polymers containing one hydrophilic poly(ethylene oxide) (PEO) sequence linked to a hydrophophic polymethacrylate (PMA) block bearing photolabile side groups ( Figure 2). The block copolymers were prepared by the ATRP of the photosensitive monomers initiated by a PEO macroinitiator.…”

Section: Irreversible Micelles Disruptionmentioning

confidence: 99%

Light‐Responsive Block Copolymers

Schumers

Fustin

Gohy

2010

Macromol. Rapid Commun.

307

255

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Stimuli-responsive polymers are the subject of intense research because they are able to show responses to various environmental changes. Among those stimuli, light has attracted much attention since it can be localized in time and space and it can also be triggered from outside of the system. In this paper, we review light-responsive block copolymers (LRBCs) that combine characteristic features of block copolymers, e.g., self-assembly behavior, and light-responsive systems. The different photo-responsive moieties that have been incorporated so far in block copolymers as well as the proposed applications are discussed.

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A New Two‐Photon‐Sensitive Block Copolymer Nanocarrier

Cited by 295 publications

References 32 publications

o -nitrobenzyl acrylate is polymerizable by single electron transfer-living radical polymerization

o -nitrobenzyl acrylate is polymerizable by single electron transfer-living radical polymerization

Design, Synthesis, and Reaction of π-Extended Coumarin-based New Caged Compounds with Two-photon Absorption Character in the Near-IR Region

Light‐Responsive Block Copolymers

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