Recent Advances in Bioorthogonal Click Chemistry for Efficient Synthesis of Radiotracers and Radiopharmaceuticals

Mushtaq, Sajid; Yun, Seong-Jae; Jeon, Jongho

doi:10.3390/molecules24193567

Cited by 55 publications

(55 citation statements)

References 137 publications

(138 reference statements)

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“…Bioorthogonal click chemistry is an alternative conjugation method widely used nowadays for in situ conjugation. Trans-cyclooctene/tetrazine bioorthogonal click reaction is extremely fast and widely used for pretargeting conjugation compared to other reactions in this category such as, copper-free azide-cyclooctyne click chemistry and Staudinger ligation (8,9). Specific interaction between peptide nucleic acids, which are non-natural DNA/RNA analogs, can also be used for pretargeting approach (10).…”

Section: In Situ Conjugation Methods In Pretargeting Theranosticsmentioning

confidence: 99%

Theranostic Pretargeting Drug Delivery and Imaging Platforms in Cancer Precision Medicine

Hapuarachchige

Artemov

2020

Front. Oncol.

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Theranostics are nano-size or molecular-level agents serving for both diagnosis and therapy. Structurally, they are drug delivery systems integrated with molecular or targeted imaging agents. Theranostics are becoming popular because they are targeted therapeutics and can be used with no or minimal changes for diagnostic imaging to aid in precision medicine. Thus, there is a close relation between theranostics and image-guided therapy (IGT), and theranostics are actually a subclass of IGT in which both therapeutic and imaging functionalities are attributed to a single platform. An important theranostics strategy is biological pretargeting. In pretargeted IGT, first, the target is identified by a target-specific natural or synthetic bioligand followed by a nano-scale or molecular drug delivery component, which form therapeutic clusters by in situ conjugation reactions. If pretargeted drug delivery platforms are labeled with multimodal imaging probes, they can be used as theranostics for both diagnostic imaging and therapy. Optical and nuclear imaging techniques have mostly been used in proof-of-concept studies with pretargeted theranostics. The concept of pretargeting in theranostics is comparatively novel and generally requires a confirmed overexpression of surface receptors on targeted cells/tissue. In addition, the receptors should have natural or synthetic bioligands to be used as pretargeting components. Therefore, applications of pretargeting theranostics are still limited to several cancer types, which overexpress cell-surface markers on the target cancer cells. In this review, recent discoveries of pretargeting theranostics in breast, ovarian, prostate, and colorectal cancers are discussed to highlight main strengths and potential limitations the strategy.

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Section: In Situ Conjugation Methods In Pretargeting Theranosticsmentioning

confidence: 99%

Theranostic Pretargeting Drug Delivery and Imaging Platforms in Cancer Precision Medicine

Hapuarachchige

Artemov

2020

Front. Oncol.

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“…Biomolecules are often functionalized through a primary amine, which provides an ideal conjugation site for a coupling reaction, most often with peptide or thiourea type links. Other links based on thioether, triazole, oxime, or more recently via a copper-free click-chemistry with tetrazine/cyclooctyne may prove to be interesting, in particular, because they have very good stability in vivo [ 51 , 54 , 61 ].…”

Section: Targeting Of Somatostatin Receptors With Radiopharmaceutimentioning

confidence: 99%

“…Many somatostatin analogs have already been labeled with various radioelements, whether for imaging, with probes used today in clinical applications, or for therapy, with many compounds in clinical studies [ 17 , 61 , 62 , 63 ]. These analogs were obtained from modifications in the sequence of amino acids that make up the peptide.…”

Section: Targeting Of Somatostatin Receptors With Radiopharmaceutimentioning

confidence: 99%

Overview of Radiolabeled Somatostatin Analogs for Cancer Imaging and Therapy

et al. 2020

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Identified in 1973, somatostatin (SST) is a cyclic hormone peptide with a short biological half-life. Somatostatin receptors (SSTRs) are widely expressed in the whole body, with five subtypes described. The interaction between SST and its receptors leads to the internalization of the ligand–receptor complex and triggers different cellular signaling pathways. Interestingly, the expression of SSTRs is significantly enhanced in many solid tumors, especially gastro-entero-pancreatic neuroendocrine tumors (GEP-NET). Thus, somatostatin analogs (SSAs) have been developed to improve the stability of the endogenous ligand and so extend its half-life. Radiolabeled analogs have been developed with several radioelements such as indium-111, technetium-99 m, and recently gallium-68, fluorine-18, and copper-64, to visualize the distribution of receptor overexpression in tumors. Internal metabolic radiotherapy is also used as a therapeutic strategy (e.g., using yttrium-90, lutetium-177, and actinium-225). With some radiopharmaceuticals now used in clinical practice, somatostatin analogs developed for imaging and therapy are an example of the concept of personalized medicine with a theranostic approach. Here, we review the development of these analogs, from the well-established and authorized ones to the most recently developed radiotracers, which have better pharmacokinetic properties and demonstrate increased efficacy and safety, as well as the search for new clinical indications.

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“…Strained hydrocarbons have traditionally represented a playground for basic researchers interested in testing the limits of creativity, imagination and synthetic skills. Fascinating and the exponentially growing area of bioorthogonal and bio-conjugation chemistry, for which a number of excellent specialized reviews are available, [1][2][3] but to present and discuss molecular properties, synthesis and reactivity -unavoidably including some examples of bioorthogonal chemistry -of highly strained unsaturated carbocyclic rings. Because of space limits, strained cumulene rings, such as cyclic allenes, have not been included.…”

Section: Introductionmentioning

confidence: 99%

Highly Strained Unsaturated Carbocycles

et al. 2020

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Highly strained unsaturated carbocyclic rings are high‐energy compounds which are attracting increasing interest – not just for their peculiar structural and reactivity features – but also as modern chemical tools for bioorthogonal and in vivo chemistry, especially via inverse‐electron demand Diels–Alder (iEDDA) and strain‐promoted azide‐alkyne cycloaddition (SPAAC) reactions. This mini‐review covers two main classes of compounds: 3 to 10 membered‐ring cycloalkynes and trans‐cycloalkenes, including some examples of cyclic enynes, dienes and bridgehead alkenes. Their molecular properties, synthesis and reactivity are presented and discussed, with an emphasis on their functionalization and reactivity.

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Recent Advances in Bioorthogonal Click Chemistry for Efficient Synthesis of Radiotracers and Radiopharmaceuticals

Cited by 55 publications

References 137 publications

Theranostic Pretargeting Drug Delivery and Imaging Platforms in Cancer Precision Medicine

Theranostic Pretargeting Drug Delivery and Imaging Platforms in Cancer Precision Medicine

Overview of Radiolabeled Somatostatin Analogs for Cancer Imaging and Therapy

Highly Strained Unsaturated Carbocycles

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