A Comparison of Triazole‐forming Bioconjugation Techniques for Constructing Comb‐Shaped Peptide–Polymer Bioconjugates

Canalle, Luiz Alberto; Knaap, Matthijs van der; Overhand, Mark; Hest, Jan C. M. van

doi:10.1002/marc.201000507

Cited by 22 publications

(20 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…257 In order to avoid the use of toxic copper catalysts in these reactions, various copper-free click chemistry reactions have also been developed and many studies are now underway that demonstrate the versatility of this type of bioconjugation technique. 258–261 A further bioorthogonal [4+2] cycloaddition reaction was recently described by Devaraj et al . and was applied to the labelling of cancer cells, peptides and small molecules.…”

Section: Preparation Of Targeted Polymeric Npsmentioning

confidence: 99%

Targeted polymeric therapeutic nanoparticles: design, development and clinical translation

et al. 2012

View full text Add to dashboard Cite

Polymeric materials have been used in a range of pharmaceutical and biotechnology products for more than 40 years. These materials have evolved from their earlier use as biodegradable products such as resorbable sutures, orthopaedic implants, macroscale and microscale drug delivery systems such as microparticles and wafers used as controlled drug release depots, to multifunctional nanoparticles (NPs) capable of targeting, and controlled release of therapeutic and diagnostic agents. These newer generations of targeted and controlled release polymeric NPs are now engineered to navigate the complex in vivo environment, and incorporate functionalities for achieving target specificity, control of drug concentration and exposure kinetics at the tissue, cell, and subcellular levels. Indeed this optimization of drug pharmacology as aided by careful design of multifunctional NPs can lead to improved drug safety and efficacy, and may be complimentary to drug enhancements that are traditionally achieved by medicinal chemistry. In this regard, polymeric NPs have the potential to result in a highly differentiated new class of therapeutics, distinct from the original active drugs used in their composition, and distinct from first generation NPs that largely facilitated drug formulation. A greater flexibility in the design of drug molecules themselves may also be facilitated following their incorporation into NPs, as drug properties (solubility, metabolism, plasma binding, biodistribution, target tissue accumulation) will no longer be constrained to the same extent by drug chemical composition, but also become in-part the function of the physicochemical properties of the NP. The combination of optimally designed drugs with optimally engineered polymeric NPs opens up the possibility of improved clinical outcomes that may not be achievable with the administration of drugs in their conventional form. In this critical review, we aim to provide insights into the design and development of targeted polymeric NPs and to highlight the challenges associated with the engineering of this novel class of therapeutics, including considerations of NP design optimization, development and biophysicochemical properties. Additionally, we highlight some recent examples from the literature, which demonstrate current trends and novel concepts in both the design and utility of targeted polymeric NPs (444 references).

show abstract

Section: Preparation Of Targeted Polymeric Npsmentioning

confidence: 99%

Targeted polymeric therapeutic nanoparticles: design, development and clinical translation

et al. 2012

View full text Add to dashboard Cite

show abstract

“…Complex syntheses and unfavourable kinetics with bulky dipoles can limit the preference for cyclooctynes of enhanced reactivity (e.g., diaryl or fluorinated variants) as azide click partners. Recently it has been remarked that the steric requirement of the conjugating moiety limits the extent of peptide polymer conjugation 82 . Simple unactivated monocyclic octynes with reduced lipophilicity and limited steric bulk could therefore be valuable.…”

Section: Strain‐promoted Cycloadditions Of Nitrile Oxides (Nitronementioning

confidence: 99%

Nitrile Oxide/Alkyne Cycloadditions – A Credible Platform for Synthesis of Bioinspired Molecules by Metal‐Free Molecular Clicking

Heaney

2012

Eur J Org Chem

104

View full text Add to dashboard Cite

The need for precise and flexible synthetic methodology to underpin modern research in chemical biology and materials science has fuelled a resurgence of interest in Huisgen 1,3‐dipolar cycloaddition chemistry. Of late, the in vogue chemistry for the assembly of complex biological molecules and specialist materials has been the copper‐catalysed azide alkyne cycloaddition (CuAAC) reaction. However, in certain circumstances aversion to the copper catalyst flaws this approach and alternatives have been sought. Click chemistry has developed beyond the original triazole‐forming trick and azides are no longer the only dipoles pursued as click cycloaddition partners. This article reviews some of the complications of the CuAAC reaction and evaluates the potential of nitrile oxide/alkyne cycloaddition (NOAC) as a covalent conjugation tool. With a focus on applications in nucleic acid chemistry and materials science it presents the case for a prominent position for nitrile oxides in the catalyst‐free bioconjugation toolbox.

show abstract

“…Comb‐shape copolymers are a special class of graft copolymers with the following structural characteristics: 1) same length of side chains, 2) shorter side chain than main chain, and 3) one or two grafting chains in each repeat unit . Compared with linear polymers, grafting chains of comb‐shape copolymers exhibit size exclusion and electrical repulsion so that main chain is very difficult to curl . The macromolecular chains with an extended conformation and big hydrodynamic radius form a comb shape in solution .…”

Section: Introductionmentioning

confidence: 99%

“…[ 17,18 ] Compared with linear polymers, grafting chains of comb-shape copolymers exhibit size exclusion and electrical repulsion so that main chain is very diffi cult to curl. [ 19 ] The macromolecular chains with an extended conformation and big hydrodynamic radius form a comb shape in solution. [ 20 ] These structural characteristics make comb-shape copolymers good tackifying, antisalt, antishear, and antiaging properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Amphiphilic Comb-Shape Copolymers Via Ring-Opening Polymerization of a Macromonomer

Zhang

et al. 2015

Macromol. Chem. Phys.

View full text Add to dashboard Cite

Amphiphilic comb‐shape copolymers PCL‐co‐P(MTC‐mPEG16) (where PCL, MTC, and mPEG refer to poly(ε‐caprolactone), 2‐methyltrimethylene carbonate, and methoxy poly(ethylene glycol), respectively) are synthesized by ring‐opening polymerization of ε‐caprolactone and cyclic carbonate‐terminated PEG macromonomer (MTC‐mPEG16) with benzyl alcohol as an initiator and Sn(Oct)2 as a catalyst. Amphiphilic copolymers PCL‐co‐P(MTC‐mPEG16) can form micelles in aqueous solution by self‐assembly. The diameters of PCL‐co‐P(MTC‐mPEG16) micelles characterized by dynamic light scattering area few dozens of nanometers with a narrow size distribution and the morphology of the micelles observed through transmission electron microscopy are nanosized spheres. The in vitro drug release of comb‐shape copolymer PCL‐co‐P(MTC‐mPEG16) micelles is more stable and sustained than that of linear block copolymers mPEG‐b‐PCL.

show abstract

A Comparison of Triazole‐forming Bioconjugation Techniques for Constructing Comb‐Shaped Peptide–Polymer Bioconjugates

Cited by 22 publications

References 35 publications

Targeted polymeric therapeutic nanoparticles: design, development and clinical translation

Targeted polymeric therapeutic nanoparticles: design, development and clinical translation

Nitrile Oxide/Alkyne Cycloadditions – A Credible Platform for Synthesis of Bioinspired Molecules by Metal‐Free Molecular Clicking

Synthesis of Amphiphilic Comb-Shape Copolymers Via Ring-Opening Polymerization of a Macromonomer

Contact Info

Product

Resources

About