---
title: "Organelle‑Resolved Tetrazine–trans‑Cyclooctene Click Chemistry for Targeted Cargo Delivery and Rel"
id: "pubmed-42225547"
canonical_url: "https://medichelpline.com/clinical-feed/pubmed-42225547"
content_type: "clinical_feed_article"
specialty: "Pharmacology"
source_name: "PubMed / NCBI"
source_url: "https://pubmed.ncbi.nlm.nih.gov/42225547/"
doi: "10.1002/chem.71198"
published_at: "2026-09-19T00:00:00.000Z"
evidence_level: "Journal Article"
license: "CC-BY-NC-4.0 / Informational Use"
---
# Organelle‑Resolved Tetrazine–trans‑Cyclooctene Click Chemistry for Targeted Cargo Delivery and Rel
## Provenance & Clinical Metadata
- **Canonical URL:** https://medichelpline.com/clinical-feed/pubmed-42225547
- **Specialty:** [Pharmacology](https://medichelpline.com/clinical-feed/pharmacology.md)
- **Primary Source:** PubMed / NCBI
- **Source URL:** [Original Journal Publication](https://pubmed.ncbi.nlm.nih.gov/42225547/)
- **DOI:** [10.1002/chem.71198](https://doi.org/10.1002%2Fchem.71198)
- **Published At:** 2026-09-19T00:00:00.000Z
- **Evidence Rating:** Journal Article
## Executive GIST (TL;DR)
- The study evaluates a modular strategy combining organelle‑targeting groups with **tetrazine‑trans‑cyclooctene** bioorthogonal **click chemistry** to direct small molecules to specific subcellular compartments. - Researchers demonstrated that probes bearing **tetrazine** or **trans‑cyclooctene** undergo inverse‑electron‑demand Diels–Alder (IEDDA) reactions inside multiple organelles, including the **plasma membrane**, **mitochondria**, **nucleus**, **endoplasmic reticulum**, and **lysosomes**. - The method was used to localize both fluorescent dyes and the chemotherapeutic **doxorubicin** to defined organelles in living cells. - **Doxorubicin** prodrugs modified with tetrazine or trans‑cyclooctene could be reactivated inside cells by click‑to‑release chemistry, restoring cytotoxic activity. - Direct comparisons of different probe architectures showed that **organelle targeting** and reaction efficiency depend strongly on structural context, cargo identity, and the subcellular environment, and cannot be predicted solely from targeting motifs. - The authors present a framework for comparing organelle‑targeted bioorthogonal chemistries and offer practical guidance for designing probes and prodrugs to achieve spatiotemporal control of small‑molecule activity. - The abstract does not provide experimental protocols, quantitative yields, kinetics, cell types used, or toxicity data; those details were not reported in the abstract and must be consulted in the full text for implementation.
## Clinical Analysis & Structured Key Points
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Epub 2026 Jun 1. # Organelle-Resolved Tetrazine-trans-Cyclooctene Click Chemistry for Cargo Delivery and Release [Oleh Durydivka](https://pubmed.ncbi.nlm.nih.gov/?term=Durydivka+O&cauthor_id=42225547)[ 1 ](https://pubmed.ncbi.nlm.nih.gov/42225547/#full-view-affiliation-1 "Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Prague, Czech Republic."), [Marek Chovanec](https://pubmed.ncbi.nlm.nih.gov/?term=Chovanec+M&cauthor_id=42225547)[ 1 ](https://pubmed.ncbi.nlm.nih.gov/42225547/#full-view-affiliation-1 "Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Prague, Czech Republic."), [Rastislav Dzijak](https://pubmed.ncbi.nlm.nih.gov/?term=Dzijak+R&cauthor_id=42225547)[ 1 ](https://pubmed.ncbi.nlm.nih.gov/42225547/#full-view-affiliation-1 "Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Prague, Czech Republic."), [Michal Rahm](https://pubmed.ncbi.nlm.nih.gov/?term=Rahm+M&cauthor_id=42225547)[ 1 ](https://pubmed.ncbi.nlm.nih.gov/42225547/#full-view-affiliation-1 "Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Prague, Czech Republic."), [Jachym Hrusak](https://pubmed.ncbi.nlm.nih.gov/?term=Hrusak+J&cauthor_id=42225547)[ 1 ](https://pubmed.ncbi.nlm.nih.gov/42225547/#full-view-affiliation-1 "Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Prague, Czech Republic."), [Paul E Reyes-Gutierrez](https://pubmed.ncbi.nlm.nih.gov/?term=Reyes-Gutierrez+PE&cauthor_id=42225547)[ 1 ](https://pubmed.ncbi.nlm.nih.gov/42225547/#full-view-affiliation-1 "Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Prague, Czech Republic."), [Milan Vrabel](https://pubmed.ncbi.nlm.nih.gov/?term=Vrabel+M&cauthor_id=42225547)[ 1 ](https://pubmed.ncbi.nlm.nih.gov/42225547/#full-view-affiliation-1 "Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Prague, Czech Republic.") Affiliations Expand ### Affiliation * 1 Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Prague, Czech Republic. * PMID: **42225547** * DOI: [ 10.1002/chem.71198 ](https://doi.org/10.1002/chem.71198) Item in Clipboard # Organelle-Resolved Tetrazine-trans-Cyclooctene Click Chemistry for Cargo Delivery and Release Oleh Durydivka et al. Chemistry. 2026. Show details Display options Display options Format Abstract PubMed PMID Chemistry Actions * [ Search in PubMed ](https://pubmed.ncbi.nlm.nih.gov/?term=%22Chemistry%22%5Bjour%5D&sort=date&sort_order=desc) * [ Search in NLM Catalog ](https://www.ncbi.nlm.nih.gov/nlmcatalog?term=%22Chemistry%22%5BTitle+Abbreviation%5D) * [ Add to Search ](https://pubmed.ncbi.nlm.nih.gov/42225547/) . 2026 Sep 19;32(35):e71198. doi: 10.1002/chem.71198. Epub 2026 Jun 1. ### Authors [Oleh Durydivka](https://pubmed.ncbi.nlm.nih.gov/?term=Durydivka+O&cauthor_id=42225547)[ 1 ](https://pubmed.ncbi.nlm.nih.gov/42225547/#short-view-affiliation-1 "Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Prague, Czech Republic."), [Marek Chovanec](https://pubmed.ncbi.nlm.nih.gov/?term=Chovanec+M&cauthor_id=42225547)[ 1 ](https://pubmed.ncbi.nlm.nih.gov/42225547/#short-view-affiliation-1 "Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Prague, Czech Republic."), [Rastislav Dzijak](https://pubmed.ncbi.nlm.nih.gov/?term=Dzijak+R&cauthor_id=42225547)[ 1 ](https://pubmed.ncbi.nlm.nih.gov/42225547/#short-view-affiliation-1 "Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Prague, Czech Republic."), [Michal Rahm](https://pubmed.ncbi.nlm.nih.gov/?term=Rahm+M&cauthor_id=42225547)[ 1 ](https://pubmed.ncbi.nlm.nih.gov/42225547/#short-view-affiliation-1 "Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Prague, Czech Republic."), [Jachym Hrusak](https://pubmed.ncbi.nlm.nih.gov/?term=Hrusak+J&cauthor_id=42225547)[ 1 ](https://pubmed.ncbi.nlm.nih.gov/42225547/#short-view-affiliation-1 "Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Prague, Czech Republic."), [Paul E Reyes-Gutierrez](https://pubmed.ncbi.nlm.nih.gov/?term=Reyes-Gutierrez+PE&cauthor_id=42225547)[ 1 ](https://pubmed.ncbi.nlm.nih.gov/42225547/#short-view-affiliation-1 "Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Prague, Czech Republic."), [Milan Vrabel](https://pubmed.ncbi.nlm.nih.gov/?term=Vrabel+M&cauthor_id=42225547)[ 1 ](https://pubmed.ncbi.nlm.nih.gov/42225547/#short-view-affiliation-1 "Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Prague, Czech Republic.") ### Affiliation * 1 Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Prague, Czech Republic. * PMID: **42225547** * DOI: [ 10.1002/chem.71198 ](https://doi.org/10.1002/chem.71198) Item in Clipboard Full text links Cite Display options Display options Format Abstract PubMed PMID ## Abstract Accurate delivery of small molecules to specific cell compartments or organelles offers great potential for bioimaging and targeted therapy but remains challenging to predict and control. In this study, we evaluate a modular strategy for organelle-directed delivery based on organelle-targeting groups combined with tetrazine-trans-cyclooctene bioorthogonal chemistry. We demonstrate that organelle-targeting probes bearing tetrazine or trans-cyclooctene can efficiently undergo inverse-electron-demand Diels-Alder reactions within various cellular compartments, including the plasma membrane, mitochondria, nucleus, endoplasmic reticulum, and lysosomes. Using this method, we localize fluorophores and the cytotoxic drug doxorubicin to specific organelles in living cells. We further show that tetrazine- or trans-cyclooctene-modified doxorubicin prodrugs restore cytotoxic activity upon click-to-release activation inside cells. However, direct comparisons of different probe architectures revealed that organelle targeting and reaction efficiency are highly sensitive to structural context, cargo type, and subcellular environment, and cannot be predicted solely from targeting motifs. Overall, these findings establish a framework for comparing organelle-targeted bioorthogonal chemistry and offer practical guidance for designing probes and prodrugs that enable precise spatiotemporal control of small-molecule activity in living cells. **Keywords:** click chemistry; doxorubicin; drug delivery; inverse‐electron‐demand Diels‐Alder reaction; live‐cell imaging; organelle targeting. © 2026 The Author(s). Chemistry ‐ A European Journal published by Wiley‐VCH GmbH. [PubMed Disclaimer](https://pubmed.ncbi.nlm.nih.gov/disclaimer/) ## Similar articles * [ Tetrazine-trans-cyclooctene ligation: Unveiling the chemistry and applications within the human body. ](https://pubmed.ncbi.nlm.nih.gov/38905885/) Tomarchio EG, Turnaturi R, Saccullo E, Patamia V, Floresta G, Zagni C, Rescifina A.Tomarchio EG, et al.Bioorg Chem. 2024 Sep;150:107573. doi: 10.1016/j.bioorg.2024.107573. Epub 2024 Jun 18.Bioorg Chem. 2024.PMID: 38905885Review. * [ A Lysosome-Targeted Tetrazine for Organelle-Specific Click-to-Release Chemistry in Antigen Presenting Cells. ](https://pubmed.ncbi.nlm.nih.gov/37269296/) Ligthart NAM, de Geus MAR, van de Plassche MAT, Torres García D, Isendoorn MME, Reinalda L, Ofman D, van Leeuwen T, van Kasteren SI.Ligthart NAM, et al.J Am Chem Soc. 2023 Jun 14;145(23):12630-12640. doi: 10.1021/jacs.3c02139. Epub 2023 Jun 3.J Am Chem Soc. 2023.PMID: 37269296Free PMC article. * [ Tetrazine-based bioorthogonal reactions to image hypoxia in cancer cells. ](https://pubmed.ncbi.nlm.nih.gov/42699542/) Boumya S, Boero C, De Luigi E, Foglietta F, Ferreira-Alves G, Mancardi D, Lupo B, Spyrakis F, Lazzarato L, Serafini M.Boumya S, et al.iScience. 2026 Aug 25;29(9):117290. doi: 10.1016/j.isci.2026.117290. eCollection 2026 Sep 18.iScience. 2026.PMID: 42699542Free PMC article. * [ Reactive oxygen species-activated bioorthogonal chemistry in living systems enabled by boronate-caged dihydrotetrazines. ](https://pubmed.ncbi.nlm.nih.gov/41667439/) Ming D, Zhang J, Mu B, Peng D, Wang Y, Kong Y, Wang W, Chu L, Wang R, Liu L.Ming D, et al.Nat Commun. 2026 Feb 10;17(1):2568. doi: 10.1038/s41467-026-68771-z.Nat Commun. 2026.PMID: 41667439Free PMC article. * [ Tetrazine-Mediated Bioorthogonally Activated Therapeutic (TBAT) Platforms. ](https://pubmed.ncbi.nlm.nih.gov/41771012/) Kim J, Debnath S, Kim E, Yoon C, Seo J, Hua S, Kim JS.Kim J, et al.J Am Chem Soc. 2026 Mar 11;148(9):9169-9184. doi: 10.1021/jacs.5c23084. Epub 2026 Mar 2.J Am Chem Soc. 2026.PMID: 41771012Review. [ See all similar articles ](https://pubmed.ncbi.nlm.nih.gov/?linkname=pubmed_pubmed&from_uid=42225547) ## References 1. 1. D. K. Banfield and W. Prinz, “Editorial Overview: Cell Organelles,” Current Opinion in Cell Biology 29 (2014): v–vi, . 2. 1. D. C. Wallace, “A Mitochondrial Paradigm of Metabolic and Degenerative Diseases, Aging, and Cancer: A Dawn for Evolutionary Medicine,” Annual Review of Genetics 39 (2005): 359–407, . 3. 1. S. DiMauro and E. A. Schon, “Mechanisms of Disease: Mitochondrial Respiratory‐Chain Diseases,” New England Journal of Medicine 348 (2003): 2656–2668, . 4. 1. G. S. Gorman, P. F. Chinnery, S. DiMauro, et al., “Mitochondrial Diseases,” Nature Reviews Disease Primers 2 (2016): 1–22, . 5. 1. B. D. Roussel, A. J. Kruppa, E. Miranda, D. C. Crowther, D. A. Lomas, and S. J. 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