Design of a Clickable Nanoparticle That Target Tumor Cells in Vitro and Vivo 41

In document University of Groningen Application of click chemistry for PET Mirfeizi, Leila (Page 44-50)

Application of click chemistry for PET

Scheme 2.15. Design of a Clickable Nanoparticle That Target Tumor Cells in Vitro and Vivo 41

Scheme 2.15. Design of a Clickable Nanoparticle That Target Tumor Cells in Vitro and Vivo 41

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Cross-linked, fluorescent, superparamagnetic iron oxide nanoparticles were modified to display azido-PEG group. Conjugation of cyclic targeting peptide bearing pendant alkynes to azido-PEG nanoparticles via the copper(l)-catalyzed Huisgen 1,3-dipolar cycloaddition.

The nanoparticles, functionalized by azido-PEG, were subsequently conjugated by copper catalysis to alkyne modified cyclic targeting peptides.

This strategy opens the way to attach different tags, resulting in nanoparticles suitable for multimodality imaging, including MRI, PET and optical imaging.

Conclusions

Click chemistry is a highly valuable approach for biomedical application. One of the unique, important properties of click chemistry is its bio-orthogonal character. Covalent and rapid linkage of two components under environmentally friendly, nontoxic conditions are properties that are completely complementary to the development of novel agents for the development of both imaging and therapeutic products. Of course, there are areas in click chemistry that require further optimization, such as real time usage in living animals, imaging of living cells, and, ultimately, the substitution of the azide group with other less potentially hazardous species. Although these are significant challenges, taking into account the speed and number of applications that click chemistry facilitates for the development of novel biomolecules for preclinical evaluation, it can be anticipated that these requirements will be met in the near future.

Novel labeling methods in 1BF-radiochemistry are highly desired to reduce the scale of effort necessary to obtain 1BF-labeled compounds for their application as imaging agents in nuclear medicine and life science. Great progress is currently made by many groups to find novel produce PET radiopharmaceuticals for various applications. The refinement and/or combination of the above described methods could be a crucial step into this direction.

Application of click chemistry for PET

Ideally, methodologies which are adaptable to a wide range of target molecules and prosthetic groups can be developed. The advantages gained from the intrinsic simplicity of such protocols would be achieved economically, practically and would benefit the fields of nuclear imaging and medicine. Click chemistry may offer the perfect platform for such advances in labelling due to its exquisite selectivity and tolerance to a wide range of conditions.

The introduction of the Cu(I)-catalyzed 1,3-dipolar cycloaddition click reaction has greatly widened the scope of chemoselective (bio )conjugation reactions of carbohydrates and peptides. Moreover, the 1,3-dipolar cycloaddition has opened possibilities for the synthesis of new biomaterials based on peptides and carbohydrates. The number of dipolar cycloadditions, which can be performed under mild conditions, will rapidly expand as is highlighted in this review.

Applications of Cu-free click chemistry include mammalian disease models where the bioavailability and pharmacokinetic properties of the reagents become important. The cyclooctynes that are currently employed for Cu-free click chemistry are not very soluble in aqueous solutions. The hydrophobicity of these cyclooctyne scaffolds could also promote binding to membranes or nonspecific binding to serum proteins, thereby reducing their bioavailable concentrations and increasing the noise in PET-images.

Finally the suitability of azide labeling and Cu-free click chemistry should enable applications in many areas of glycobiology. For example, direct imaging of glycan trafficking under conditions of cell stimulation or pharmacological intervention has been demonstrated already in cells, tissues, or even whole organisms.

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Chapter 3

Ligand acceleration and exploration

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