Bioorthogonal catalytic patch
Source abstract
Abstract
Bioorthogonal catalysis mediated by transition metals has inspired a new subfield of artificial chemistry complementary to enzymatic reactions, enabling the selective labelling of biomolecules or in situ synthesis of bioactive agents via non-natural processes. However, the effective deployment of bioorthogonal catalysis in vivo remains challenging, mired by the safety concerns of metal toxicity or complicated procedures to administer catalysts. Here, we describe a bioorthogonal catalytic device comprising a microneedle array patch integrated with Pd nanoparticles deposited on TiO2 nanosheets. This device is robust and removable, and can mediate the local conversion of caged substrates into their active states in high-level living systems. In particular, we show that such a patch can promote the activation of a prodrug at subcutaneous tumour sites, restoring its parent drug's therapeutic anticancer properties. This in situ applied device potentiates local treatment efficacy and eliminates off-target prodrug activation and dose-dependent side effects in healthy organs or distant tissues.
Source: europepmc · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Click Chemistry and Applications · Monoclonal and Polyclonal Antibodies Research · Chemical Synthesis and Analysis
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (48)
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1. Li, J. & Chen, P. R. Development and application of bond cleavage reactions in bioorthogonal chemistry. Nat. Chem. Biol. 12, 129–137 (2016).10.1038/nchembio.2024 ↗
2. Bai, Y., Chen, J. & Zimmerman, S. C. Designed transition metal catalysts for intracellular organic synthesis. Chem. Soc. Rev. 47, 1811–1821 (2018).10.1039/C7CS00447H ↗
3. Li, J. et al. Palladium-triggered deprotection chemistry for protein activation in living cells. Nat. Chem. 6, 352–361 (2014).10.1038/nchem.1887 ↗
4. Tonga, G. Y. et al. Supramolecular regulation of bioorthogonal catalysis in cells using nanoparticle-embedded transition metal catalysts. Nat. Chem. 7, 597–603 (2015).10.1038/nchem.2284 ↗
5. Jeschek, M. et al. Directed evolution of artificial metalloenzymes for in vivo metathesis. Nature 537, 661–665 (2016).10.1038/nature19114 ↗
6. Sancho-Albero, M. et al. Cancer-derived exosomes loaded with ultrathin palladium nanosheets for targeted bioorthogonal catalysis. Nat. Catal. 2, 864–872 (2019).10.1038/s41929-019-0333-4 ↗
7. Eda, S. et al. Biocompatibility and therapeutic potential of glycosylated albumin artificial metalloenzymes. Nat. Catal. 2, 780–792 (2019).10.1038/s41929-019-0317-4 ↗
8. Coverdale, J. P. C. et al. Asymmetric transfer hydrogenation by synthetic catalysts in cancer cells. Nat. Chem. 10, 347–354 (2018).10.1038/nchem.2918 ↗
9. Vidal, C., Tomás-Gamasa, M., Destito, P., López, F. & Mascareñas, J. L. Concurrent and orthogonal gold(i) and ruthenium(ii) catalysis inside living cells. Nat. Commun. 9, 1913 (2018).10.1038/s41467-018-04314-5 ↗
10. Tomás-Gamasa, M., Martínez-Calvo, M., Couceiro, J. R. & Mascareñas, J. L. Transition metal catalysis in the mitochondria of living cells. Nat. Commun. 7, 12538 (2016).10.1038/ncomms12538 ↗
11. Wang, X. et al. Copper-triggered bioorthogonal cleavage reactions for reversible protein and cell surface modifications. J. Am. Chem. Soc. 141, 17133–17141 (2019).10.1021/jacs.9b05833 ↗
12. Liu, Y. et al. Catalytically active single-chain polymeric nanoparticles: exploring their functions in complex biological media. J. Am. Chem. Soc. 140, 3423–3433 (2018).10.1021/jacs.8b00122 ↗
13. Streu, C. & Meggers, E. Ruthenium-induced allylcarbamate cleavage in living cells. Angew. Chem. Int. Ed. 45, 5645–5648 (2006).10.1002/anie.200601752 ↗
14. Spicer, C. D., Triemer, T. & Davis, B. G. Palladium-mediated cell-surface labeling. J. Am. Chem. Soc. 134, 800–803 (2012).10.1021/ja209352s ↗
15. Li, J. et al. Ligand-free palladium-mediated site-specific protein labeling inside gram-negative bacterial pathogens. J. Am. Chem. Soc. 135, 7330–7338 (2013).10.1021/ja402424j ↗
16. Völker, T., Dempwolff, F., Graumann, P. L. & Meggers, E. Progress towards bioorthogonal catalysis with organometallic compounds. Angew. Chem. Int. Ed. 53, 10536–10540 (2014).10.1002/anie.201404547 ↗
17. Tsubokura, K. et al. In vivo gold complex catalysis within live mice. Angew. Chem. Int. Ed. 56, 3579–3584 (2017).10.1002/anie.201610273 ↗
18. Yusop, R. M., Unciti-Broceta, A., Johansson, E. M. V., Sánchez-Martín, R. M. & Bradley, M. Palladium-mediated intracellular chemistry. Nat. Chem. 3, 239–243 (2011).10.1038/nchem.981 ↗
19. Wang, F., Zhang, Y., Du, Z., Ren, J. & Qu, X. Designed heterogeneous palladium catalysts for reversible light-controlled bioorthogonal catalysis in living cells. Nat. Commun. 9, 1209 (2018).10.1038/s41467-018-03617-x ↗
20. Weiss, J. T. et al. Extracellular palladium-catalysed dealkylation of 5-fluoro-1-propargyl-uracil as a bioorthogonally activated prodrug approach. Nat. Commun. 5, 3277 (2014).10.1038/ncomms4277 ↗
21. Pérez-López, A. M. et al. Gold-triggered uncaging chemistry in living systems. Angew. Chem. Int. Ed. 56, 12548–12552 (2017).10.1002/anie.201705609 ↗
22. Clavadetscher, J. et al. Copper catalysis in living systems and in situ drug synthesis. Angew. Chem. Int. Ed. 55, 15662–15666 (2016).10.1002/anie.201609837 ↗
23. Bray, T. L. et al. Bright insights into palladium-triggered local chemotherapy. Chem. Sci. 9, 7354–7361 (2018).10.1039/C8SC02291G ↗
24. Wang, F. et al. A biocompatible heterogeneous MOF–Cu catalyst for in vivo drug synthesis in targeted subcellular organelles. Angew. Chem. Int. Ed. 58, 6987–6992 (2019).10.1002/anie.201901760 ↗
25. Miller, M. A. et al. Nano-palladium is a cellular catalyst for in vivo chemistry. Nat. Commun. 8, 15906 (2017).10.1038/ncomms15906 ↗
26. Prausnitz, M. R. & Langer, R. Transdermal drug delivery. Nat. Biotechnol. 26, 1261–1268 (2008).10.1038/nbt.1504 ↗
27. Lee, K. et al. Non-transdermal microneedles for advanced drug delivery. Adv. Drug Deliv. Rev. 165-166, 41–59 (2020).10.1016/j.addr.2019.11.010 ↗
28. Chen, Z., Hu, Q. & Gu, Z. Leveraging engineering of cells for drug delivery. Acc. Chem. Res. 51, 668–677 (2018).10.1021/acs.accounts.7b00526 ↗
29. Li, W. et al. Rapidly separable microneedle patch for the sustained release of a contraceptive. Nat. Biomed. Eng. 3, 220–229 (2019).10.1038/s41551-018-0337-4 ↗
30. Chen, G. et al. Transdermal cold atmospheric plasma-mediated immune checkpoint blockade therapy. Proc. Natl Acad. Sci. USA 117, 3687–3692 (2020).10.1073/pnas.1917891117 ↗
31. Yang, S. Y. et al. A bio-inspired swellable microneedle adhesive for mechanical interlocking with tissue. Nat. Commun. 4, 1702 (2013).10.1038/ncomms2715 ↗
32. Yu, J. et al. Microneedle-array patches loaded with hypoxia-sensitive vesicles provide fast glucose-responsive insulin delivery. Proc. Natl Acad. Sci. USA 112, 8260–8265 (2015).10.1073/pnas.1505405112 ↗
33. Yu, J. et al. Glucose-responsive insulin patch for the regulation of blood glucose in mice and minipigs. Nat. Biomed. Eng. 4, 499–506 (2020).10.1038/s41551-019-0508-y ↗
34. Wang, Z. et al. Dual self-regulated delivery of insulin and glucagon by a hybrid patch. Proc. Natl Acad. Sci. USA 117, 29512–29517 (2020).10.1073/pnas.2011099117 ↗
35. Ye, Y. et al. A melanin-mediated cancer immunotherapy patch. Sci. Immunol. 2, eaan5692 (2017).10.1126/sciimmunol.aan5692 ↗
36. Sullivan, S. P. et al. Dissolving polymer microneedle patches for influenza vaccination. Nat. Med. 16, 915–920 (2010).10.1038/nm.2182 ↗
37. DeMuth, P. C., Garcia-Beltran, W. F., Ai-Ling, M. L., Hammond, P. T. & Irvine, D. J. Composite dissolving microneedles for coordinated control of antigen and adjuvant delivery kinetics in transcutaneous vaccination. Adv. Funct. Mater. 23, 161–172 (2013).10.1002/adfm.201201512 ↗
38. Liu, P. et al. Photochemical route for synthesizing atomically dispersed palladium catalysts. Science 352, 797–800 (2016).10.1126/science.aaf5251 ↗
39. Fasolino, A., Los, J. H. & Katsnelson, M. I. Intrinsic ripples in graphene. Nat. Mater. 6, 858–861 (2007).10.1038/nmat2011 ↗
40. Hassan, C. M. & Peppas, N. A. Structure and morphology of freeze/thawed PVA hydrogels. Macromolecules 33, 2472–2479 (2000).10.1021/ma9907587 ↗
41. Yang, S. et al. Phase-transition microneedle patches for efficient and accurate transdermal delivery of insulin. Adv. Funct. Mater. 25, 4633–4641 (2015).10.1002/adfm.201500554 ↗
42. Samant, P. P. & Prausnitz, M. R. Mechanisms of sampling interstitial fluid from skin using a microneedle patch. Proc. Natl Acad. Sci. USA 115, 4583–4588 (2018).10.1073/pnas.1716772115 ↗
43. Rautio, J., Meanwell, N. A., Di, L. & Hageman, M. J. The expanding role of prodrugs in contemporary drug design and development. Nat. Rev. Drug Discov. 17, 559–587 (2018).10.1038/nrd.2018.46 ↗
44. Nitiss, J. L. Targeting DNA topoisomerase II in cancer chemotherapy. Nat. Rev. Cancer 9, 338–350 (2009).10.1038/nrc2607 ↗
45. Qu, X. & Chaires, J. B. in Methods in Enzymology Vol. 321 353–369 (Academic Press, 2000).10.1016/S0076-6879(00)21202-0 ↗
46. Melber, C., Keller, D. & Mangelsdorf, I. Environmental Health Criteria 226: Palladium (World Health Organization, 2002).
47. Li, J. & Mooney, D. J. Designing hydrogels for controlled drug delivery. Nat. Rev. Mater. 1, 16071 (2016).10.1038/natrevmats.2016.71 ↗
48. Li, Y., Boone, E. & El-Sayed, M. A. Size effects of PVP−Pd nanoparticles on the catalytic Suzuki reactions in aqueous solution. Langmuir 18, 4921–4925 (2002).10.1021/la011469q ↗