Mechanistic applications of click chemistry for pharmaceutical drug discovery and drug delivery

Meghani, Nilesh M.; Amin, Hardik H.; Lee, Beom‐Jin

doi:10.1016/j.drudis.2017.07.007

Cited by 73 publications

(35 citation statements)

References 134 publications

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“…Unlinked peptides were rapidly released within the first two to three days when physically mixed with collagen, which is consistent with the short peptide half-lives reported previously in the literature (Fig. 2) 20 . By comparison, cross-linked peptides demonstrated prolonged release lasting for periods longer than 15 days.…”

Section: Resultssupporting

confidence: 92%

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Prolonged survival of transplanted stem cells after ischaemic injury via the slow release of pro-survival peptides from a collagen matrix

et al. 2018

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Stem-cell-based therapies hold considerable promise for regenerative medicine. However, acute donor-cell death within several weeks after cell delivery remains a critical hurdle for clinical translation. Co-transplantation of stem cells with pro-survival factors can improve cell engraftment, but this strategy has been hampered by the typically short half-lives of the factors and by the use of Matrigel and other scaffolds that are not chemically defined. Here, we report a collagen–dendrimer biomaterial crosslinked with pro-survival peptide analogues that adheres to the extracellular matrix and slowly releases the peptides, significantly prolonging stem cell survival in mouse models of ischaemic injury. The biomaterial can serve as a generic delivery system to improve functional outcomes in cell-replacement therapy.

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Section: Resultssupporting

confidence: 92%

“…1d) 20 . Crosslinking occurred in the range 7–19 nmol peptide/collagen by weight, resulting in an average crosslinking efficiency of 33 ± 12% s.d.…”

Section: Resultsmentioning

confidence: 99%

Prolonged survival of transplanted stem cells after ischaemic injury via the slow release of pro-survival peptides from a collagen matrix

et al. 2018

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“…There are a few limitations that need to be considered (Table 1). The most significant is that copper, as a catalyst in the reaction, is cytotoxic in vivo and in vitro, due in part to its capacity for sensitizing oxidative damage to proteins and nucleic acids (Hein et al, 2008;Meghani et al, 2017). Therefore, copper-free click reactions are ideal reactions for viral tracking and virus-based delivery systems in live cells or in vivo.…”

Section: Advantages and Disadvantages Of Click Chemistry For Virusrelmentioning

confidence: 99%

Recent trends in click chemistry as a promising technology for virus-related research

et al. 2018

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Click chemistry involves reactions that were originally introduced and used in organic chemistry to generate substances by joining small units together with heteroatom linkages (C-X-C). Over the last few decades, click chemistry has been widely used in virus-related research. Using click chemistry, the virus particle as well as viral protein and nucleic acids can be labeled. Subsequently, the labeled virions or molecules can be tracked in real time. Here, we reviewed the recent applications of click reactions in virus-related research, including viral tracking, the design of antiviral agents, the diagnosis of viral infection, and virus-based delivery systems. This review provides an overview of the general principles and applications of click chemistry in virus-related research.

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“…Their tissue specificity is first confined to the cells of the reticuloendothelial system which recognizes them as foreign microparticles and transports them to liver and spleen . Among the alternatives to overcome these inconveniences, the inclusion of drugs in polymeric micelles and the synthesis of polymer–drug conjugates by click chemistry are the most attractive options nowadays …”

Section: Introductionmentioning

confidence: 99%

Different drug incorporation routes in ethylene oxide based copolymers

Carrero

Borreguero

Rodrı́guez

et al. 2020

Polymer International

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Coumarin is successfully incorporated in poly(ethylene oxide)‐poly(propylene oxide) block copolymers functionalized with terminal alkynes, PEO‐b‐PPO‐b‐GPE, by click reactions at atmospheric pressure and in CO2 supercritical conditions (scCO2). The presence of glycidyl propargyl ether (GPE), an alkynyl‐terminated monomer, in the copolymer chain allows the covalent attachment of the coumarin by click chemistry, obtaining polymer–drug conjugates. First, the most suitable synthesis procedure for the above‐mentioned copolymers was established. Then, the click reactions were carried out confirming the coumarin attachment by Fourier transform IR and 1H NMR analyses, achieving good yields in both cases with a coumarin content of about 9.3 wt% and avoiding the use of toxic solvents in the case of scCO2. In addition, thanks to the amphiphilic character of the copolymer due to the presence of hydrophilic (PEO) and hydrophobic (PPO) segments, micelle formation is also possible and was confirmed by dynamic light scattering and high resolution SEM. Finally, coumarin incorporation was achieved by micelle formation using the direct dissolution method in order to compare the polymer–drug system properties. This second route allows a drug entrapment efficiency of 14 wt% to be reached. In both cases, the size of the polymeric micelles obtained is in a suitable range to enable permeability. However, an interesting point is the reduction in the size of the micelles with increase in the GPE percentage and with the covalent attachment of the coumarin to the copolymer, which is supposed to improve their permeability. © 2019 Society of Chemical Industry

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Mechanistic applications of click chemistry for pharmaceutical drug discovery and drug delivery

Cited by 73 publications

References 134 publications

Prolonged survival of transplanted stem cells after ischaemic injury via the slow release of pro-survival peptides from a collagen matrix

Prolonged survival of transplanted stem cells after ischaemic injury via the slow release of pro-survival peptides from a collagen matrix

Recent trends in click chemistry as a promising technology for virus-related research

Different drug incorporation routes in ethylene oxide based copolymers

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