Phenylboronic acids-based diagnostic and therapeutic applications

Analytical Sciences

Volumn 30, Issue 1, 2014, Pages 111-117

  Sanjoh, Mai ^a   Miyahara, Yuji ^a   Kataoka, Kazunori ^b   Matsumoto, Akira ^a  

^a TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

Diagnosis; Drug delivery system; Phenylboronic acid; Sialic acid

Indexed keywords

CARBOXYLIC ACIDS; CHEMICAL ANALYSIS; CHEMICAL SENSORS; DIAGNOSIS; TARGETED DRUG DELIVERY;

DRUG DELIVERY APPLICATIONS; DRUG DELIVERY SYSTEM; MOLECULAR BASIS; MOLECULAR TARGETS; PHENYLBORONIC ACIDS; RESEARCH EFFORTS; SIALIC ACIDS; THERAPEUTIC APPLICATION;

CONTROLLED DRUG DELIVERY;

BENZENEBORONIC ACID; BORONIC ACID DERIVATIVE; DIAGNOSTIC AGENT; N ACETYLNEURAMINIC ACID;

ANIMAL; ARTICLE; CHEMISTRY; DRUG DELIVERY SYSTEM; HUMAN;

ANIMALS; BORONIC ACIDS; DRUG DELIVERY SYSTEMS; HUMANS; N-ACETYLNEURAMINIC ACID;

EID: 84892460336     PISSN: 09106340     EISSN: 13482246     Source Type: Journal    
DOI: 10.2116/analsci.30.111     Document Type: Article

References (63)

1. J. P. Lorand and J. O. Edwards, J. Org. Chem., 1959, 24, 769.
2. M. Van Duin, J. A. Peters, A. P. G. Kieboom, and H.van Bekkum, Tetrahedron, 1984, 40, 2901.
3. H. Miyazaki, T. Okano, Y. Sakurai, and K. Kataoka, Biochem. Biophys. Res. Commun., 1993, 195, 829.
4. E. Uchimura, H. Otsuka, T. Okano, Y. Sakurai, and K. Kataoka, Biotechnol. Bioeng., 2001, 72, 307.
5. C. W. Gehrke, K. C. Kuo, G. E. Davis, R. D. Suits, T. P. Waalkes, and E. Borek, J. Chromatogr., 1978, 150, 455.
6. S. Hase, K. Hatanaka, K. Ochiai, and H. Shimizu, Biosci., Biotechnol., Biochem., 1992, 56, 1676.
7. M. Rosenberg, J. L. Wiebers, and P. T. Gilham, Biochemistry, 1972, 11, 3623.
8. R. Tuytten, F. Lemiere, W. Van Dongen, E. Witters, E. L. Esmans, R. P. Newton, and E. Dudley, Anal. Chem., 2008, 80, 1263.
9. R. Tuytten, F. Lemiere, E. L. Esmans, W. A. Herrebout, B. J. Van Der Veken, B. U. W. Maes, E. Witters, R. P. Newton, and E. Dudley, Anal. Chem., 2007, 79, 6662.
10. K. Tsukagoshi, F. Ueno, R. Nakajima, and K. Araki, Anal. Sci., 2007, 23, 227.
11. I. Suzuki, A. Yamauchi, Y. Sakashita, K. Hirose, T. Miura, and T. Hayashita, Anal. Sci., 2007, 23, 1167.
12. M. Kumai, S. Kozuka, M. Samizo, T. Hashimoto, I. Suzuki, and T. Hayashita, Anal. Sci., 2012, 23,121.
13. T. D. James, K. R. A. S. Sandanayake, R. Iguchi, and S. Shinkai, J. Am. Chem. Soc., 1995, 117, 8982.
14. N. Kanayama and H. Kitano, Langmuir, 2000, 16, 577.
15. Z. Xing, H. Wang, Y. Cheng, C. Zhu, T. D. James, and J. Zhao, Eur. J. Org. Chem., 2012, 6, 1223.
16. T. D. James, K. R. A. S. Sandanayake, and S. Shinkai, Angew. Chem., Int. Ed. Engl., 1996, 35, 1910.
17. T. D. James, K. R. A. S. Sandanayake, and S. Shinkai, Nature, 1994, 374, 345.
18. M. Melendez, O. Rosario, B. Zayas, and J. F. Rodriguez, J. Pharm. Biomed. Anal., 2009, 49, 1233.
19. Q. Peng, F. Chen, Z. Zhong, and R. Zhuo, Chem. Commun., 2010, 46, 5888.
20. X. Chen, S. Scgauder, N. Potier, A. V. Dorsselaer, I. Pelczer, B. L. Bassler, and F. M. Hughson, Nature, 2002, 415, 545.
21. G. Pasparakis, A. Cockayne, and C. Alexander, J. Am. Chem. Soc., 2007, 129, 11014.
22. S. Saito, T. Maeda, H. Nakazumi, and C. L. Colyer, Anal. Sci., 2013, 29, 157.
23. H. Otsuka, T. Ikeya, T. Okano, and K. Kataoka, Eur. Cells Mater., 2006, 12, 36.
24. G. A. Ellis, M. J. Palte, and R. T. Raines, J. Am. Chem. Soc., 2012, 134, 3631.
25. Q. Peng, F. Chen, Z. Zhong, and R. Zhuo, Chem. Commun., 2010, 46, 5888.
26. J. Su, F. Chen, V. L. Cryns, and P. B. Messersmith, J. Am. Chem. Soc., 2011, 133, 11850.
27. M. Fukuda, Cancer Res., 1996, 56, 2237.
28. C. R. Bertozzi and L. L. Kiessling, Science, 2001, 291, 2357.
29. R. Raman, S. Raguram, G. Venkataraman, J. C. Paulson, and R. Sasisekharan, Nat. Methods, 2005, 2, 817.
30. W. P. Van Beek, L. A. Smets, and P. Emmelot, Cancer Res., 1973, 33, 2913.
31. M. M. Fuster1 and J. D. Esko, Nat. Rev. Cancer, 2005, 5, 526.
32. E. Severi, D. W. Hood, and G. H. Thomas, Microbiology, 2007, 153, 2817.
33. R. Kannagi, K. Sakuma, K. Miyazaki, K. T. Lim, A. Yusa, J. Yin, and M. Izawa, Cancer Sci., 2010, 101, 586.
34. R. Kannagi, M. Izawa, T. Koike, K. Miyazaki, and N. Kimura, Cancer Sci., 2004, 95, 377.
35. M. Takeuchi, M. Yamamoto, and S. Shinkai, Chem. Commun., 1997, 18, 1731.
36. S. Patterson, B. D. Smith, and R. E. Taylor, Tetrahedron Lett., 1998, 39, 3111.
37. S. M. Levonis, M. J. Kiefel, and T. A. Houston, Chem. Commun., 2009, 2278.
38. A. Matsumoto, N. Sato, K. Kataoka, and Y. Miyahara, J. Am. Chem. Soc., 2009, 131, 12022.
39. H. Otsuka, E. Uchimura, H. Koshino, T. Okano, and K. Kataoka, J. Am. Chem. Soc., 2003, 125, 3493.
40. C. S. Lee, S. K. Kim, and M. Kim, Sensors, 2009, 9, 7111.
41. M. J. Schoning and A. Poghossian, Electroanalysis, 2006, 18, 1893.
42. A. Matsumoto, H. Cabral, N. Sato, K. Kataoka, and Y. Miyahara, Angew. Chem., Int. Ed., 2010, 49, 5494.
43. D. H. Dube and C. R. Bertozzi, Nat. Rev. Drug Discovery, 2005, 4, 477.
44. Y. Xu, A. Sette, J. Sidney, S. J. Gendler, and A. Franco, Immunol. Cell Biol., 2005, 83, 440.
45. J. L. A. Shih and R. M. Brugger, Med. Phys., 1992, 19, 733.
46. L. Frullano, J. Rohovec, S. Aime, T. Maschmeyer, M. I. Prata, J. J. Lima, C. F. Geraldes, and J. A. Peters, Contrast Media Mol. Imaging, 2007, 2, 35.
47. S. G. Crich, D. Alberti, I. Szabo, S. Aime, and K. Djanashvili, Angew. Chem., Int. Ed., 2013, 52, 1161.
48. J. Gong, M. Chen, Y. Zheng, S. Wang, and Y. Wang, J. Controlled Release, 2012, 159, 312.
49. Y. Matsumura and K. Kataoka, Cancer Sci., 2009, 100, 572.
50. Y. Matsumura and H. Maeda, Cancer Res., 1986, 46, 6387.
51. H. Cabral, M. Murakami, H. Hojo, Y. Terada, M. R. Kano, U. Chung, N. Nishiyama, and K. Kataoka, Proc. Natl. Acad. Sci. U. S. A., 2013, 110, 11397.
52. S. Deshayes, H. Cabral, T. Ishii, Y. Miura, S. Kobayashi, T. Yamashita, A. Matsumoto, Y. Miyahara, N. Nishiyama, and K. Kataoka, J. Am. Chem. Soc., 2013, 135, 15501.
53. S. M. Elbashir, J. Harborth, W. Lendeckel, A. Yalcin, K. Weber, and T. Tuschl, Nature, 2001, 411, 494.
54. K. A. Whitehead, R. Langer, and D. G. Anderson, Nat. Rev. Drug Discovery, 2009, 8, 129.
55. S. Matsumoto, R. J. Christie, N. Nishiyama, K. Miyata, A. Ishii, M. Oba, H. Koyama, Y. Yamasaki, and K. Kataoka, Biomacromolecules, 2009, 10, 119.
56. M. Naito, T. Ishii, A. Matsumoto, K. Miyata, Y. Miyahara, and K. Kataoka, Angew. Chem., Int. Ed., 2012, 51, 10751.
57. T. Miyata, T. Uragami, and K. Nakamae, Adv. Drug Delivery Rev., 2002, 54, 79.
58. A. Matsumoto, T. Kurata, D. Shiino, and K. Kataoka, Macromolecules, 2004, 37, 1502.
59. K. Kataoka, H. Miyazaki, M. Bunya, T. Okana, and Y. Sakurai, J. Am. Chem. Soc., 1998, 120, 12694.
60. A. Matsumoto, S. Ikeda, A. Harada, and K. Kataoka, Biomacromolecules, 2003, 4, 1410.
61. A. Matsumoto, R. Yoshida, and K. Kataoka, Biomacromolecules, 2004, 5, 1038.
62. A. Matsumoto, K. Yamamoto, R. Yoshida, K. Kataoka, T. Aoyagi, and Y. Miyahara, Chem. Commun., 2010, 46, 2203.
63. A. Matsumoto, T. Ishii, J. Nishida, H. Matsumoto, K. Kataoka, and Y. Miyahara, Angew. Chem., Int. Ed., 2012, 51, 2124.