Harnessing nature's insights: Synthetic small molecules with peroxidase-mimicking DNAzyme properties

Chemistry - A European Journal

Volumn 17, Issue 39, 2011, Pages 10857-10862

  Stefan, Loic ^a   Xu, Hai Jun ^a   Gros, Claude P ^a   Denat, Franck ^a   Monchaud, David ^a  

^a UNIVERSITÉ DE BOURGOGNE   (France)

Author keywords

biomimetics; bioorganic chemistry; catalysis; DNAzymes; hemin

Indexed keywords

BIOORGANIC CHEMISTRY; DNAZYME; DNAZYMES; ENZYMATIC PROPERTIES; HEMIN; IRON PORPHYRIN; SMALL MOLECULES;

BIOMIMETICS; CATALYSIS; IRON COMPOUNDS; PORPHYRINS;

BIOCHEMISTRY;

1,4,7,10-TETRAAZACYCLODODECANE- 1,4,7,10-TETRAACETIC ACID; BIOMIMETIC MATERIAL; DEOXYRIBOZYME; HEMIN; PEROXIDASE; SINGLE HETEROCYCLIC RINGS; TETRAXETAN;

ARTICLE; BIOMIMETICS; CATALYSIS; CHEMISTRY; METABOLISM; METHODOLOGY;

BIOMIMETIC MATERIALS; BIOMIMETICS; CATALYSIS; DNA, CATALYTIC; HEMIN; HETEROCYCLIC COMPOUNDS, 1-RING; PEROXIDASES;

EID: 80052835660     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101337     Document Type: Article

References (61)

1. P. Travascio, Y. Li, D. Sen, Chem. Biol. 1998, 5, 505
2. P. Travascio, A. J. Bennet, D. Y. Wang, D. Sen, Chem. Biol. 1999, 6, 779.
3. S. Neidle, Curr. Opin. Struct. Biol. 2009, 19, 239
4. D. Yang, K. Okamoto, Future Med. Chem. 2010, 2, 619.
5. For three authoritative reviews on "DNA enzymology", see: S. K. Silverman, Angew. Chem. 2010, 122, 7336
6. Angew. Chem. Int. Ed. 2010, 49, 7180
7. C. Teller, I. Willner, Curr. Opin. Biotechnol. 2010, 21, 376
8. Y. Krishnan, F. Simmel, Angew. Chem. 2011, 123, 3180
9. Angew. Chem. Int. Ed. 2011, 50, 3124.
10. 2+
11. 2+
12. +
13. +
14. D.-M. Kong, L.-L. Cai, H.-X. Shen, Analyst 2010, 135, 1253.
15. For detection of nucleolin, see: T. Li, L. Shi, E. Wang, S. Dong, Chem. Eur. J. 2009, 15, 1036; lysozyme
16. D. Li, B. Shlyahovsky, J. Elbaz, I. Willner, J. Am. Chem. Soc. 2007, 129, 5804; thrombin
17. J. Zhu, T. Li, J. Hu, E. Wang, Anal. Bioanal. Chem. 2010, 397, 2923.
18. For detection of telomerase activity, see: V. Pavlov, Y. Xiao, R. Gill, A. Dishon, M. Kotler, I. Willner, Anal. Chem. 2004, 76, 2152
19. Y. Xiao, V. Pavlov, T. Niazov, A. Dishon, M. Kotler, I. Willner, J. Am. Chem. Soc. 2004, 126, 7430
20. R. Freeman, E. Sharon, C. Teller, A. Henning, Y. Tzfati, I. Willner, ChemBioChem 2010, 11, 2362; methyltransferase activity
21. W. Li, Z. Liu, H. Lin, J. Chen, X. Xu, S. Yao, Anal. Chem. 2010, 82, 1935.
22. For detection of single-stranded DNA, see: Y. Weizmann, M. K. Beissenhirtz, Z. Cheglakov, R. Nowarski, M. Kotler, I. Willner, Angew. Chem. 2006, 118, 7544
23. Angew. Chem. Int. Ed. 2006, 45, 7384; DNA/RNA analytes
24. S. Nakayama, H. O. Sintim, J. Am. Chem. Soc. 2009, 131, 10320; adenosine
25. C. Sun, X. Liu, K. Feng, J. Jiang, G. Shen, R. Yu, Anal. Chim. Acta 2010, 669, 87.
26. For detection of SNP, see: M. Deng, D. Zhang, Y. Zhou, X. Zhou, J. Am. Chem. Soc. 2008, 130, 13095; single-base mutations
27. I. Willner, Z. Cheglakov, Y. Weizmann, E. Sharon, Analyst 2008, 133, 923.
28. X. Zhu, Y. Cao, Z. Liang, G. Li, Protein Cell 2010, 1, 842.
29. For G-quadruplex ligand assays, see: D.-M. Kong, J. Wu, Y.-E. Ma, H.-X. Shen, Analyst 2008, 133, 1158
30. X. Cheng, X. Liu, T. Bing, Z. Cao, D. Shangguan, Biochemistry 2009, 48, 7817; antioxidant assay
31. M. Wang, Y. Han, Z. Nie, C. Lei, Y. Huang, M. Guo, S. Yao, Biosens. Bioel. 2010, 26, 523.
32. D. Thirstrup, G. S. Baird, Anal. Chem. 2010, 82, 2498.
33. T. Li, E. Wang, S. Dong, J. Am. Chem. Soc. 2009, 131, 15082
34. B. Shlyahovsky, Y. Li, O. Lioubashevski, J. Elbaz, I. Willner, ACS Nano 2009, 3, 1831.
35. N. Nikan, J. C. Sherman, Angew. Chem. 2008, 120, 4978
36. Angew. Chem. Int. Ed. 2008, 47, 4900
37. N. Nikan, J. C. Sherman, J. Org. Chem. 2009, 74, 5211
38. M. Nikan, G. A. L. Bare, J. C. Sherman, Tetrahedron Lett. 2011, 52, 1791.
39. L. Stefan, A. Guédin, S. Amrane, N. Smith, F. Denat, J.-L. Mergny, D. Monchaud, Chem. Commun. 2011, 47, 4992.
40. For a recent review, see:, S. Balasubramanian, L. H. Hurley, S. Neidle, Nat. Rev. Drug Discovery 2011, 10, 261.
41. Y. He, Y. Tian, C. Mao, Mol. Biosyst. 2009, 5, 238
42. Q. Yang, Y. Nie, X. Zhu, X. Liu, G. Li, Electrochim. Acta 2009, 55, 276.
43. S. Nakayama, J. Wang, H. O. Sintim, Chem. Eur. J. 2011, 17, 5691.
44. T. Li, S. Dong, E. Wang, Chem. Asian J. 2009, 4, 918.
45. S. B. Brown, P. Jones, A. Suggett, Trans. Faraday Soc. 1968, 64, 986
46. S. B. Brown, P. Jones, Trans. Faraday Soc. 1968, 64, 994.
47. B. Li, Y. Du, T. Li, S. Dong, Anal. Chim. Acta 2009, 651, 234.
48. L. A. Marquez, H. B. Dunford, Biochemistry 1997, 36, 9349.
49. For the seminal article, see: Y. Li, C. R. Geyer, D. Sen, Biochemistry 1996, 35, 6911; for a recent application, see
50. J. S. Smith, Q. Chen, L. A. Yatsunyk, J. M. Nicoludis, M. S. Garcia, R. Kranaster, S. Balasubramanian, D. Monchaud, M.-P. Teulade-Fichou, L. Abramowitz, D. C. Schultz, F. B. Johnson, Nat. Struct. Mol. Biol. 2011, 18, 478.
51. H. Yaku, T. Murashima, D. Miyoshi, N. Sugimoto, Chem. Commun. 2010, 46, 5740.
52. For recent reviews, see: D. Monchaud, M.-P. Teulade-Fichou, Org. Biomol. Chem. 2008, 6, 627
53. S. Balasubramanian, S. Neidle, Curr. Opin. Chem. Biol. 2009, 13, 345
54. S. Neidle, FEBS J. 2010, 277, 1118.
55. For a seminal article, see: G. Labat, J.-L. Seris, B. Meunier, Angew. Chem. 1990, 102, 1488
56. Angew. Chem. Int. Ed. Engl. 1990, 29, 1471; for a more recent study, see
57. G. Lente, J. H. Espenson, New J. Chem. 2004, 28, 847.
58. A. A. El-Awady, P. C. Wilkins, R. G. Wilkins, Inorg. Chem. 1985, 24, 2053
59. V. E. Yushmanov, Inorg. Chem. 1999, 38, 1713.
60. K. Kano, H. Kitagishi, S. Tamura, A. Yamada, J. Am. Chem. Soc. 2004, 126, 15202.
61. T. T. Tominaga, V. E. Yushmanov, I. E. Borissevitch, H. Imasato, M. Tabak, J. Inorg. Biochem. 1997, 65, 235.