The Application of Bio-orthogonality for In Vivo Animal Imaging

Yang, Jun; Zhu, Biyue; Ran, Chongzhao

doi:10.1021/cbmi.3c00033

Cited by 10 publications

(4 citation statements)

References 92 publications

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“…Consequently, it was demonstrated that [ 68 Ga]NOTA-SF-CV could be served as a feasible small-molecule PET tracer for sensitively and specifically monitoring cathepsin B activity in vivo . By combining the advantages of small-molecule probes and nanoprobes, − the successful application of the tracer [ 68 Ga]NOTA-SF-CV also demonstrated the applicability and universality of the SF scaffold designed by our group.…”

Section: Resultsmentioning

confidence: 99%

Cathepsin B-Activated PET Tracer for In Vivo Tumor Imaging

Li,

Liang,

Gao

et al. 2024

Mol. Pharmaceutics

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Cathepsin B, a lysosomal protease, is considered as a crucial biomarker for tumor diagnosis and treatment as it is overexpressed in numerous cancers. A stimulus-responsive SF scaffold has been reported to detect the activity of a variety of tumor-associated enzymes. In this work, a small-molecule PET tracer ([ 68 Ga]NOTA-SF-CV) was developed by combining an SF scaffold with a cathepsin B-specific recognition substrate Cit-Val. Upon activation by cathepsin B, [ 68 Ga]NOTA-SF-CV could form the cyclization product in a reduction environment, resulting in reduced hydrophilicity. This unique property could effectively prevent exocytosis of the tracer in cathepsin B-overexpressing tumor cells, leading to prolonged retention and amplified PET imaging signal. Moreover, [ 68 Ga]NOTA-SF-CV had great targeting specificity to cathepsin B. In vivo microPET imaging results showed that [ 68 Ga]NOTA-SF-CV was able to effectively visualize the expression level of cathepsin B in various tumors. Hence, [ 68 Ga]NOTA-SF-CV may be served as a potential tracer for diagnosing cathepsin B-related diseases.

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Section: Resultsmentioning

confidence: 99%

Cathepsin B-Activated PET Tracer for In Vivo Tumor Imaging

Li,

Liang,

Gao

et al. 2024

Mol. Pharmaceutics

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“…The E-MISA strategy, due to its significant enhancement of functional nanoaggregate accumulation and retention in specific regions of interest, has prompted researchers to consider the potential utility of these accumulated nanoaggregates as “artificial receptors”. Leveraging these nanoaggregates combined with other functional molecules via bioorthogonal reactions, pretargeted imaging and/or theranostics in vivo can be achieved. − Based on this idea and the concept, Rao’s group leveraged the optimized biocompatible intramolecular macrocyclization reaction between pyrimidinecarbonitrile and d -Cys with the inverse-electron-demand Diels–Alder (IEDDA) reaction between tetrazine (Tz) and trans -cyclooctene (TCO) and developed the E-MISA probe 32 for protease activity multimodality imaging in vivo in 2020 . Probe 32 (TCO-C-SNAT 4) contained a TCO handle for rapid reaction with Tz tags ( 33 and 34 ) via the IEDDA reaction, a casp-3/7-responsive DEVD substrate peptide, and a GSH reduction disulfide bond.…”

Section: E-misa Probes For Pretargeted Imaging and Theranostics Of Tu...mentioning

confidence: 99%

Smart Molecular Imaging and Theranostic Probes by Enzymatic Molecular In Situ Self-Assembly

Wen,

Zhang,

Tian

et al. 2024

JACS Au

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Enzymatic molecular in situ self-assembly (E-MISA) that enables the synthesis of high-order nanostructures from synthetic small molecules inside a living subject has emerged as a promising strategy for molecular imaging and theranostics. This strategy leverages the catalytic activity of an enzyme to trigger probe substrate conversion and assembly in situ, permitting prolonging retention and congregating many molecules of probes in the targeted cells or tissues. Enhanced imaging signals or therapeutic functions can be achieved by responding to a specific enzyme. This E-MISA strategy has been successfully applied for the development of enzyme-activated smart molecular imaging or theranostic probes for in vivo applications. In this Perspective, we discuss the general principle of controlling in situ self-assembly of synthetic small molecules by an enzyme and then discuss the applications for the construction of "smart" imaging and theranostic probes against cancers and bacteria. Finally, we discuss the current challenges and perspectives in utilizing the E-MISA strategy for disease diagnoses and therapies, particularly for clinical translation.

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“…Chemical reactions compatible with biological systems have applications in chemical biology, biomedicine, imaging, diagnosis, − and therapy. − Among the many bioorthogonal reactions now available, the inverse electron demand Diels–Alder reaction of 1,2,4,5-tetrazines with strained dienophiles meets the strict criteria for use in living organisms, − including humans . In recent years, researchers have made considerable efforts to fine-tune this bioorthogonal reaction for use in diverse applications. ,,, In addition to other promising synthetic methods, , cross-coupling reactions involving tetrazines provide many opportunities for modifying these heterodienes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of C₃-Substituted N1-tert-Butyl 1,2,4-Triazinium Salts via the Liebeskind–Srogl Reaction for Fluorogenic Labeling of Live Cells

Šlachtová,

Bellová,

Vrabel

2024

J. Org. Chem.

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We recently described the development and application of a new bioorthogonal conjugation, the triazinium ligation. To explore the wider application of this reaction, in this work, we introduce a general method for synthesizing C 3 -substituted triazinium salts based on the Liebeskind−Srogl crosscoupling reaction and catalytic thioether reduction. These methods enabled the synthesis of triazinium derivatives for investigating the effect of different substituents on the ligation kinetics and stability of the compounds under biologically relevant conditions. Finally, we demonstrate that the combination of a coumarin fluorophore attached to position C 3 with a C 5 -(4-methoxyphenyl) substituent yields a fluorogenic triazinium probe suitable for no-wash, live-cell labeling. The developed methodology represents a promising synthetic approach to the late-stage modification of triazinium salts, potentially widening their applications in bioorthogonal reactions.

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The Application of Bio-orthogonality for In Vivo Animal Imaging

Cited by 10 publications

References 92 publications

Cathepsin B-Activated PET Tracer for In Vivo Tumor Imaging

Cathepsin B-Activated PET Tracer for In Vivo Tumor Imaging

Smart Molecular Imaging and Theranostic Probes by Enzymatic Molecular In Situ Self-Assembly

Synthesis of C₃-Substituted N1-tert-Butyl 1,2,4-Triazinium Salts via the Liebeskind–Srogl Reaction for Fluorogenic Labeling of Live Cells

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The Application of Bio-orthogonality for In Vivo Animal Imaging

Cited by 10 publications

References 92 publications

Cathepsin B-Activated PET Tracer for In Vivo Tumor Imaging

Cathepsin B-Activated PET Tracer for In Vivo Tumor Imaging

Smart Molecular Imaging and Theranostic Probes by Enzymatic Molecular In Situ Self-Assembly

Synthesis of C3-Substituted N1-tert-Butyl 1,2,4-Triazinium Salts via the Liebeskind–Srogl Reaction for Fluorogenic Labeling of Live Cells

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Product

Resources

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Synthesis of C₃-Substituted N1-tert-Butyl 1,2,4-Triazinium Salts via the Liebeskind–Srogl Reaction for Fluorogenic Labeling of Live Cells