Supramolecular regulation of bioorthogonal catalysis in cells using nanoparticle-embedded transition metal catalysts (2024)

1. Patterson, D. M., Nazarova, L. A. & Prescher, J. A. Finding the right (bioorthogonal) chemistry. ACS Chem. Biol. 9, 592–605 (2014).

   Article CAS PubMed Google Scholar

2. Ramil, C. P. & Lin, Q. Bioorthogonal chemistry: strategies and recent developments. Chem. Commun. 49, 11007–11022 (2013).

   Article CAS Google Scholar

3. Bertozzi, C. R. A decade of bioorthogonal chemistry. Acc. Chem. Res. 44, 651–653 (2011).

   Article CAS PubMed PubMed Central Google Scholar

4. Koo, H. et al. Bioorthogonal copper-free click chemistry in vivo for tumor-targeted delivery of nanoparticles. Angew. Chem. Int. Ed. 51, 11836–11840 (2012).

   Article CAS Google Scholar

5. Devaraj, N. K., Thurber, G. M., Keliher, E. J., Marinelli, B. & Weissleder, R. Reactive polymer enables efficient in vivo bioorthogonal chemistry. Proc. Natl Acad. Sci. USA 109, 4762–4767 (2012).

   Article PubMed PubMed Central Google Scholar

6. Komatsu, H., Shindo, Y., Oka, K., Hill, J. P. & Ariga, K. Ubiquinone-Rhodol (UQ-Rh) for fluorescence imaging of NAD(P)H through intracellular activation. Angew. Chem. Int. Ed. 53, 3993–3995 (2014).

   Article CAS Google Scholar

7. Sletten, E. M. & Bertozzi, C. R. From mechanism to mouse: a tale of two bioorthogonal reactions. Acc. Chem. Res. 44, 666–676 (2011).

   Article CAS PubMed PubMed Central Google Scholar

8. Saxon, E. & Bertozzi, C. R. Cell surface engineering by a modified Staudinger reaction. Science 287, 2007–2010 (2000).

   Article CAS PubMed Google Scholar

9. Li, J. & Chen, P. R. Palladium-triggered deprotection chemistry for protein activation in living cells. Nature Chem. 6, 352–361 (2014).

   Article CAS Google Scholar

10. Sasmal, P. K., Streu, C. N. & Meggers, E. Metal complex catalysis in living biological systems. Chem. Commun. 49, 1581–1587 (2013).

    Article CAS Google Scholar

11. Unciti-Broceta, A., Johansson, E. M. V., Yusop, R. M., Sánchez-Martín, R. M. & Bradley, M. Synthesis of polystyrene microspheres and functionalization with Pd(0) nanoparticles to perform bioorthogonal organometallic chemistry in living cells. Nature Protoc. 7, 1207–1218 (2012).

    Article CAS Google Scholar

12. Streu, C. & Meggers, E. Ruthenium-induced allylcarbamate cleavage in living cells. Angew. Chem. Int. Ed. 45, 5645–5648 (2006).

    Article CAS Google Scholar

13. Yusop, R. M., Unciti-Broceta, A., Johansson, E. M. V., Sánchez-Martín, R. M. & Bradley, M. Palladium-mediated intracellular chemistry. Nature Chem. 3, 239–243 (2011).

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    Switching of perpendicular magnetization by spin–orbit torques in the absence of external magnetic fieldsHigh-performance polymer semiconducting heterostructure devices by nitrene-mediated photocrosslinking of alkyl side chains

    Article CAS Google Scholar

14. Sasmal, P. K. et al. Catalytic azide reduction in biological environments. ChemBioChem. 13, 1116–1120 (2012).

    Article CAS PubMed Google Scholar

15. Do, J. H., Kim, H. N., Yoon, J., Kim, J. S. & Kim, H-J. A rationally designed fluorescence turn-on probe for the gold(III) ion. Org. Lett. 12, 932–934 (2010).

    Article CAS PubMed Google Scholar

16. Weiss, J. T. et al. Extracellular palladium-catalysed dealkylation of 5-fluoro-1-propargyl-uracil as a bioorthogonally activated prodrug approach. Nature Commun. 5, 3277 (2014).

    Article CAS Google Scholar

17. Yoon, H. J., Kuwabara, J., Kim, J-H. & Mirkin, C. A. Allosteric supramolecular triple-layer catalysts. Science 330, 66–69 (2010).

    Article CAS PubMed Google Scholar

18. De, M., Ghosh, P. S. & Rotello, V. M. Applications of nanoparticles in biology. Adv. Mater. 20, 4225–4241 (2008).

    Article CAS Google Scholar

19. Murphy, C. J. et al. Gold nanoparticles in biology: beyond toxicity to cellular imaging. Acc. Chem. Res. 41, 1721–1730 (2008).

    Article CAS PubMed Google Scholar

20. Boisselier, E. & Astruc, D. Gold nanoparticles in nanomedicine: preparations, imaging, diagnostics, therapies and toxicity. Chem. Soc. Rev. 38, 1759–1782 (2009).

    Article CAS PubMed Google Scholar

21. Tonga, G. Y., Saha, K. & Rotello, V. M. Interfacing nanoparticles and biology new strategies for biomedicine. Adv. Mater. 26, 359–370 (2014).

    Article CAS PubMed Google Scholar

22. Mout, R. & Rotello, V. M. Bio and nano working together: engineering the protein–nanoparticle interface. Isr. J. Chem. 53, 521–529 (2013).

    Article CAS Google Scholar

23. Kim, B. et al. Tuning payload delivery in tumour cylindroids using gold nanoparticles. Nature Nanotech. 5, 465–472 (2010).

    Article CAS Google Scholar

24. Ghosh, P. et al. Intracellular delivery of a membrane-impermeable enzyme in active form using functionalized gold nanoparticles. J. Am. Chem. Soc. 132, 2642–2645 (2010).

    Article CAS PubMed PubMed Central Google Scholar

25. Kim, C. K. et al. Entrapment of hydrophobic drugs in nanoparticle monolayers with efficient release into cancer cells. J. Am. Chem. Soc. 131, 1360–1361 (2009).

    Article CAS PubMed PubMed Central Google Scholar

26. Manea, F., Houillon, F. B., Pasquato, L. & Scrimin, P. Nanozymes: gold-nanoparticles-based transphosphorylation catalysts. Angew. Chem. Int. Ed. 43, 6165–6169 (2004).

    Article CAS Google Scholar

27. Wang, Z. et al. Nanoparticle-based artificial RNA silencing machinery for antiviral therapy. Proc. Natl Acad. Sci. USA 109, 12387–12392 (2012).

    Article PubMed PubMed Central Google Scholar

28. Pengo, P., Baltzer, L., Pasquato, L. & Scrimin, P. Substrate modulation of the activity of an artificial nanoesterase made of peptide-functionalized gold nanoparticles. Angew. Chem. Int. Ed. 46, 400–404 (2007).

    Article CAS Google Scholar

29. Wei, H. & Wang, E. Nanomaterials with enzyme-like characteristics (nanozymes): next-generation artificial enzymes. Chem. Soc. Rev. 42, 6060–6093 (2013).

    Article CAS PubMed Google Scholar

30. Natalio, F. et al. Vanadium pentoxide nanoparticles mimic vanadium haloperoxidases and thwart biofilm formation. Nature Nanotech. 7, 530–535 (2012).

    Article CAS Google Scholar

31. Hastings, C. J., Backlund, M. P., Bergman, R. G. & Raymond, K. N. Enzyme-like control of carbocation deprotonation regioselectivity in supramolecular catalysis of the Nazarov cyclization. Angew. Chem. Int. Ed. 50, 10570–10573 (2011).

    Article CAS Google Scholar

32. Ghosh, S. & Isaacs, L. Biological catalysis regulated by cucurbit[7]uril molecular containers. J. Am. Chem. Soc. 132, 4445–4454 (2010).

    Article CAS PubMed Google Scholar

33. Masson, E., Ling, X., Joseph, R., Kyeremeh-Mensah, L. & Lu, X. Cucurbituril chemistry: a tale of supramolecular success. RSC Adv. 2, 1213–1247 (2012).

    Article CAS Google Scholar

34. Lee, J. W., Samal, S., Selvapalam, N., Kim, H-J. & Kim, K. Cucurbituril hom*ologues and derivatives: new opportunities in supramolecular chemistry. Acc. Chem. Res. 36, 621–630 (2003).

    Article CAS PubMed Google Scholar

35. Kim, K. et al. Functionalized cucurbiturils and their applications. Chem. Soc. Rev. 36, 267–279 (2007).

    Article CAS PubMed Google Scholar

36. Ambrogio, M. W., Thomas, C. R., Zhao, Y-L., Zink, J. I. & Stoddart, J. F. Mechanized silica nanoparticles: a new frontier in theranostic nanomedicine. Acc. Chem. Res. 44, 903–913 (2011).

    Article CAS PubMed PubMed Central Google Scholar

37. Kim, H. et al. Glutathione-induced intracellular release of guests from mesoporous silica nanocontainers with cyclodextrin gatekeepers. Adv. Mater. 22, 4280–4283 (2010).

    Article CAS PubMed Google Scholar

38. Liu, S. et al. The cucurbit[n]uril family: prime components for self-sorting systems. J. Am. Chem. Soc. 127, 15959–15967 (2005).

    Article CAS PubMed Google Scholar

39. Khashab, N. M. et al. pH-responsive mechanised nanoparticles gated by semirotaxanes. Chem. Commun. 5371–5373 (2009).

40. Hong, R. et al. Control of protein structure and function through surface recognition by tailored nanoparticle scaffolds. J. Am. Chem. Soc. 126, 739–743 (2004).

    Article CAS PubMed Google Scholar

41. Kim, C., Agasti, S. S., Zhu, Z., Isaacs, L. & Rotello, V. M. Recognition-mediated activation of therapeutic gold nanoparticles inside living cells. Nature Chem. 2, 962–966 (2010).

    Article CAS Google Scholar

42. Angelos, S. et al. pH clock-operated mechanized nanoparticles. J. Am. Chem. Soc. 131, 12912–12914 (2009).

    Article CAS PubMed Google Scholar

43. Alcaide, B., Almendros, P. & Alonso, J. M. A practical ruthenium-catalyzed cleavage of the allyl protecting group in amides, lactams, imides, and congeners. Chem. Eur. J. 12, 2874–2879 (2006).

    Article CAS PubMed Google Scholar

44. Sasmal, P. K., Carregal-Romero, S., Parak, W. J. & Meggers, E. Light-triggered ruthenium-catalyzed allylcarbamate cleavage in biological environments. Organometallics 31, 5968–5970 (2012).

    Article CAS Google Scholar

45. Zhu, Z-J. et al. Determination of the intracellular stability of gold nanoparticle monolayers using mass spectrometry. Anal. Chem. 84, 4321–4326 (2012).

    Article CAS PubMed PubMed Central Google Scholar

46. Jeon, W. S. et al. Complexation of ferrocene derivatives by the cucurbit[7]uril host: a comparative study of the cucurbituril and cyclodextrin host families. J. Am. Chem. Soc. 127, 12984–12989 (2005).

    Article CAS PubMed Google Scholar

47. Lineweaver, H. & Burk, D. The determination of enzyme dissociation constants. J. Am. Chem. Soc. 56, 658–666 (1934).

    Article CAS Google Scholar

48. Miller, D. J., Surfraz, M. B-U., Akhtar, M., Gani, D. & Allemann, R. K. Removal of the phosphate group in mechanism-based inhibitors of inositol monophosphatase leads to unusual inhibitory activity. Org. Biomol. Chem. 2, 671–688 (2004).

    Article CAS PubMed Google Scholar

49. Verma, A. et al. Surface-structure-regulated cell-membrane penetration by monolayer-protected nanoparticles. Nature Mater. 7, 588–595 (2008).

    Article CAS Google Scholar

50. Gu, Z., Biswas, A., Zhao, M. & Tang, Y. Tailoring nanocarriers for intracellular protein delivery. Chem. Soc. Rev. 40, 3638–3655 (2011).

    Article CAS PubMed Google Scholar

51. Cai, S. X. et al. Design and synthesis of rhodamine 110 derivative and caspase-3 substrate for enzyme and cell-based fluorescent assay. Bioorg. Med. Chem. Lett. 11, 39–42 (2001).

    Article CAS PubMed Google Scholar

52. Saif, M. W., Choma, A., Salamone, S. J. & Chu, E. Pharmaco*kinetically guided dose adjustment of 5-fluorouracil: a rational approach to improving therapeutic outcomes. J. Natl Cancer Inst. 101, 1543–1552 (2009).

    Article CAS PubMed Google Scholar

53. Longley, D. B., Harkin, D. P. & Johnston, P. G. 5-Fluorouracil: mechanisms of action and clinical strategies. Nature Rev. 3, 330–338 (2003).

    CAS Google Scholar

54. Wang, Z. J., Clary, K. N., Bergman, R. G., Raymond, K. N. & Toste, F. D. A supramolecular approach to combining enzymatic and transition metal catalysis. Nature Chem. 5, 100–103 (2013).

    Article CAS Google Scholar

55. Marr, A. C. & Liu, S. Combining bio- and chemo-catalysis: from enzymes to cells, from petroleum to biomass. Trends Biotechnol. 29, 199–204 (2011).

    Article CAS PubMed Google Scholar

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