Click Chemistry, A Powerful Tool for Pharmaceutical Sciences

Hein, Christopher D.; Liu, Xin Ming; Wang, Dong

doi:10.1007/s11095-008-9616-1

Cited by 663 publications

(424 citation statements)

References 135 publications

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“…Th e recent development of high-yield 'click' chemistries, such as the azide-alkyne reaction [27], now provides alternative routes to stabilized IONPs. For example, Turro et al [28] described the stabilization of Fe2O3 nanoparticles using alkyne-terminated organophosphate or carboxylic acid groups to exchange with oleic acid on the Fe 2 O 3 surface.…”

Section: Stabilization Of Ionps Using Polymer Chainsmentioning

confidence: 99%

The design and utility of polymer-stabilized iron-oxide nanoparticles for nanomedicine applications

et al. 2010

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Iron-oxide nanoparticles (IONPs) represent a significant class of inorganic nanomaterial that is contributing to the current revolution in nanomedicine [1][2]. Their unique physical properties, including high surface area to volume ratios and superparamagnetism, confer useful attributes for medical applications such as magnetic resonance imaging (MRI), drug and gene delivery, tissue engineering and bioseparation [3].Two distinct classes of superparamagnetic IONP-based materials are currently used for medical applications: superparamagnetic iron-oxide (SPIO) nanoparticles with a mean particle diameter of 50-100 nm, and ultra-small superparamagnetic iron-oxide (USPIO) nanoparticles with a size below 50 nm. Th ese two classes of IONPs have been studied widely for medical applications, particularly as the next (potential) generation of MRI contrast agents. Th ey are also seen as potential vectors for drug and gene delivery. Th e biodistribution of these nanoparticles can be altered by the application of an external magnetic fi eld; they also have potential applications in hyperthermia therapy as some magnetic particles can heat up under the infl uence of a localized high-frequency magnetic fi eld.Th e intent of this review is to present recent advances in the synthesis of IONPs and their subsequent stabilization in biological fluids using polymers, focusing on the current strategies used to graft polymers onto IONPs surfaces (see Figure 1) and the diff erent types of polymers used. Th e additional properties conferred by the polymers, such as targeting, eff ects on biodistribution and pharmacokinetics, are also discussed, and the main applications of IONPs are reviewed. Synthesis and properties of iron-oxide nanoparticlesSPIO and USPIO nanoparticles are the most extensively studied magnetic nanoparticles for biomedical applications as they are both biocompatible and easy to synthesize. Both are composed of ferrite nanocrystallites of magnetite (Fe 3 O 4 ) or maghemite (Fe 2 O 3 , γ). Over the last ten years, there has been an explosion of interest in these materials and this has been reflected in a large number of recent publications describing the synthesis and modifi cation of hybrid IONPs. In this review, we focus on the polymer modifi cation of the nanoparticles, and provide only minimal information on the inorganic synthesis of IONPs. For more detailed information on IONP synthesis, readers are referred to other reviews [3,4]. The design and utility of polymer-stabilized iron-oxide nanoparticles for nanomedicine applicationsCyrille Boyer 1 * , Michael R. Whittaker 1 , Volga Bulmus 2 , Jingquan Liu 1 and Thomas P. Davis 1 * University of New South Wales, AustraliaOver the past decade, the synthesis of superparamagnetic nanoparticles, especially iron-oxide nanoparticles (IONPs), has been researched intensively for many high-technology applications, including enhanced storage media, biosensing and medical applications. In medicine, IONPs are used as contrast agents in magnetic resonance imaging and in hyperthermia...

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Section: Stabilization Of Ionps Using Polymer Chainsmentioning

confidence: 99%

The design and utility of polymer-stabilized iron-oxide nanoparticles for nanomedicine applications

et al. 2010

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“…The concept of "click chemistry" proposed by Kolb, Finn and Sharpless in 2001 [1] has revolutionized molecular engineering including applications to organic and medicinal chemistry [2][3][4][5][6][7][8][9][10][11], polymer science and materials science [12][13][14][15][16][17][18][19][20][21]. Among the various "click" reactions responding to the requirements of this concept, the most generally used one is the copper(I)-catalyzed reaction between terminal alkynes and azides (CuAAC) selectively yielding 1,4-disubstituted 1,2,3-triazoles, that was reported independently by the Sharpless-Fokin [22] and the Meldal groups in 2002 [ 23,24].…”

Section: Introductionmentioning

confidence: 99%

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Changlong

Ikhlef

Kahlal

et al. 2016

Coordination Chemistry Reviews

278

157

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Highlights-The review is focused on the mechanistic aspects and recent trends (since 2012) of the metal-catalyzed azide-alkyne cycloaddition (MAAC) so-called "click" reactions with catalysts based on various metals (Cu, Ru, Ag, Au, Ir, Ni, Zn, Ln), although Cu (I) catalysts are still the most used ones.-These MAAC reactions are by far the most common click reactions relevant to the "green chemistry" concept.-Mechanistic investigations are essential to reaction improvements and subsequent applications, and indeed as shown in this review the proposed mechanisms have been multiple during the last decade based on theoretical computations and experimental search of intermediates.-New trends are also presented here often representing both exciting approaches for various applications and new challenges for further mechanistic investigations.

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“…For example, the amino group can be selectively acylated in the presence of the hydroxy and azido groups; the hydroxy group can be selectively silylated, and organic azides undergo 3 þ 2 cycloaddition reactions with alkynes. The latter reaction has become firmly established as a tool for medicinal chemists [21][22][23][24].…”

Section: Discussionmentioning

confidence: 99%

1,2,4‐Trisubstituted Cyclopentanes as Platforms for Diversity

Guan

Bissantz

Bergstrom

et al. 2012

Archiv der Pharmazie

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Despite their simplicity, relatively few examples of 1,2,4 (1,3,4)-amino-, azido-, and hydroxysubstituted cyclopentanes are reported in the literature. We found that cyclopent-3-en-1-ol can be transformed into a significant variety of compounds of this class by relatively common and efficient synthetic procedures. Stereochemical control of epoxidation of the cyclopentene double bond can be achieved by varying the substitutents at C4. The C4 substituent and epoxide functional group can be converted into a variety of intermediates with differential protection designed for use in applications requiring regiospecific control for further elaboration of the cyclopentane scaffold.

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Click Chemistry, A Powerful Tool for Pharmaceutical Sciences

Cited by 663 publications

References 135 publications

The design and utility of polymer-stabilized iron-oxide nanoparticles for nanomedicine applications

The design and utility of polymer-stabilized iron-oxide nanoparticles for nanomedicine applications

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

1,2,4‐Trisubstituted Cyclopentanes as Platforms for Diversity

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