Not so innocent: Impact of fluorophore chemistry on the in vivo properties of bioconjugates

Usama, Syed Muhammad; Thapaliya, Ek Raj; Luciano, Michael; Schnermann, Martin J.

doi:10.1016/j.cbpa.2021.01.009

Cited by 33 publications

(32 citation statements)

References 88 publications

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“…The fact that this linker could therefore also be used for tracking purposes—avoiding an extra fluorophore for this purpose—is noteworthy because incorporation of too many fluorophores can drastically alter the behavior and chemical properties of biomolecules. [39] …”

Section: Resultsmentioning

confidence: 99%

Controlling Coagulation in Blood with Red Light

et al. 2021

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Precise control of blood clotting and rapid reversal of anticoagulation are essential in many clinical situations. We were successful in modifying a thrombin‐binding aptamer with a red‐light photocleavable linker derived from Cy7 by Cu‐catalyzed Click chemistry. We were able to show that we can successfully deactivate the modified aptamer with red light (660 nm) even in human blood—restoring the blood's natural coagulation capability.

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Section: Resultsmentioning

confidence: 99%

Controlling Coagulation in Blood with Red Light

et al. 2021

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“…Thef act that this linker could therefore also be used for tracking purposes-avoiding an extra fluorophore for this purpose-is noteworthy because incorporation of too many fluorophores can drastically alter the behavior and chemical properties of biomolecules. [39] One has to keep in mind that the spatial requirements for this linker are necessarily different from the ones of the previous optimization. Hence,w eh ad to take the previous results with H as optimal compound with agrain of salt for the steps,w hich were to follow,a nd designed TBA-derivatives I and J (Figure 3c).…”

Section: Resultsmentioning

confidence: 99%

“…Interestingly, the fluorescence of the Cy7‐chromophore could still be detected in a 96‐well plate in the presence of human blood (Supporting Information). The fact that this linker could therefore also be used for tracking purposes—avoiding an extra fluorophore for this purpose—is noteworthy because incorporation of too many fluorophores can drastically alter the behavior and chemical properties of biomolecules [39] …”

Section: Resultsmentioning

confidence: 99%

Controlling Coagulation in Blood with Red Light

et al. 2021

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“…Another issue is competitive clearance pathways, in which net-neutral charged fluorophores are suggested to avoid this rapid clearance issue. [164] Finally, the probe needs to have a high affinity to the receptor, to overcome non-selective binding, which is affected upon fluorophore coupling. Noninvasive probes utilising near-infrared and BODIPY dyes have the potential for in vivo imaging due to a negation of bioluminescence, although membrane permeability could still prove to be problematic.…”

Section: Conclusion and Future Perspectivesmentioning

confidence: 99%

Imaging Cannabinoid Receptors: A Brief Collection of Covalent and Fluorescent Probes for CB

Hamilton¹,

Payne²,

Mocerino³

et al. 2021

Aust. J. Chem.

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There has been an expanding public interest towards the notion that modulation of the sophisticated endocannabinoid system can lead to various therapeutic benefits that are yet to be fully explored. In recent years, the drug discovery paradigm in this field has been largely based on the development of selective CB 2 receptor agonists, avoiding the unwanted CB 1 receptor-mediated psychoactive side effects. Mechanistically, target engagement studies are crucial for confirming the ligand-receptor interaction and the subsequent biological cascades that lead to the observed therapeutic effects. Concurrently, imaging techniques for visualisation of cannabinoid receptors are increasingly reported in the literature. Small molecule imaging tools ranging from phytocannabinoids such as tetrahydrocannabinol (THC) and cannabidiol (CBD) to the endocannabinoids as well as the purely synthetic cannabimimetics, have been explored to date with varying degrees of success. This Review will cover currently known photoactivatable, electrophilic, and fluorescent ligands for both the CB 1 and CB 2 receptors. Structural insights from techniques such as ligand-assisted protein structure (LAPS) and the discovery of novel allosteric modulators are significant additions for better understanding of the endocannabinoid system. There has also been a plethora of fluorescent conjugates that have been assessed for their binding to cannabinoid receptors as well as their potential for cellular imaging. More recently, bifunctional probes containing either fluorophores or electrophilic tags are becoming more prevalent in the literature. Collectively, these molecular tools are invaluable in demonstrating target engagement within the human endocannabinoid system.

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Not so innocent: Impact of fluorophore chemistry on the in vivo properties of bioconjugates

Cited by 33 publications

References 88 publications

Controlling Coagulation in Blood with Red Light

Controlling Coagulation in Blood with Red Light

Controlling Coagulation in Blood with Red Light

Imaging Cannabinoid Receptors: A Brief Collection of Covalent and Fluorescent Probes for CB

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