Design and synthesis of water-soluble bioconjugatable trans-AB-porphyrins

Tetrahedron

Volumn 64, Issue 50, 2008, Pages 11440-11448

  Muresan, Ana Z ^a   Lindsey, Jonathan S ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

Bioconjugation; Facial encumbrance; Hydrocarbon; Porphyrin; Water; Water soluble

Indexed keywords

PHENYLQUINONE; PORPHYRIN;

ABSORPTION SPECTROSCOPY; ARTICLE; CONJUGATION; PRIORITY JOURNAL; ROOM TEMPERATURE; SOLUBILITY; SYNTHESIS;

EID: 55049133697     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.08.096     Document Type: Article

References (62)

1. Licha K. Top. Curr. Chem. 222 (2002) 1-29
2. Berg K., Selbo P.K., Weyergang A., Dietze A., Prasmickaite L., Bonsted A., Engesaeter B., ØAngell-Petersen E., Warloe T., Frandsen N., and Høgset A. J. Microsc. 218 (2005) 133-147
3. Kee H.L., Nothdurft R., Muthiah C., Diers J.R., Fan D., Ptaszek M., Bocian D.F., Lindsey J.S., Culver J.P., and Holten D. Photochem. Photobiol. 84 (2008) 1061-1072
4. De Rosa S.C., Brenchley J.M., and Roederer M. Nat. Med. 9 (2003) 112-117
5. Perfetto S.P., Chattopadhyay P.K., and Roederer M. Nature Rev. Immunol. 4 (2004) 648-655
6. Chattopadhyay P.K., Price D.A., Harper T.F., Betts M.R., Yu J., Gostick E., Perfetto S.P., Goepfert P., Koup R.A., De Rosa S.C., Bruchez M.P., and Roederer M. Nat. Med. 12 (2006) 972-977
7. Borbas K.E., Mroz P., Hamblin M.R., and Lindsey J.S. Bioconjugate Chem. 17 (2006) 638-653
8. Wainright M. J. Antimicrob. Chemother. 42 (1998) 13-28
9. Maisch T., Szeimies R.-M., Jori G., and Abels C. Photochem. Photobiol. Sci. 3 (2004) 907-917
10. Hamblin M.R., and Hasan T. Photochem. Photobiol. Sci. 3 (2004) 436-450
11. Sternberg E.D., Dolphin D., and Brückner C. Tetrahedron 54 (1998) 4151-4202
12. Pandey R.K., and Zheng G. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook Vol. 6 (2000), Academic, San Diego, CA pp 157-230
13. Bonnett R. Chemical Aspects of Photodynamic Therapy (2000), Gordon and Breach Science, Amsterdam
14. Detty M.R., Gibson S.L., and Wagner S.J. J. Med. Chem. 47 (2004) 3897-3915
15. Nyman E.S., and Hynninen P.H. J. Photochem. Photobiol., B 73 (2004) 1-28
16. Da Ros T., and Prato M. J. Org. Chem. 61 (1996) 9070-9072
17. Hirsch A. Tetrahedron Lett. 39 (1998) 2731-2734
18. Georgakilas V., Tagmatarchis N., Pantarotto D., Bianco A., Briand J.-P., and Prato M. Chem. Commun. (2002) 3050-3051
19. Zhao B., Hu H., and Haddon R.C. Adv. Funct. Mater. 14 (2004) 71-76
20. Guldi D.M., Rahman G.M.A., Jux N., Balbinot D., Hartnagel U., Tagmatarchis N., and Prato M. J. Am. Chem. Soc. 127 (2005) 9830-9838
21. Sutton J.M., Clarke O.J., Fernandez N., and Boyle R.W. Bioconjugate Chem. 13 (2002) 249-263
22. Mauzerall D. J. Am. Chem. Soc. 84 (1962) 2437-2445
23. Mauzerall D. J. Phys. Chem. 66 (1962) 2531-2533
24. Mauzerall D. Biochemistry 4 (1965) 1801-1810
25. Carapellucci P.A., and Mauzerall D. Ann. N.Y. Acad. Sci. 244 (1975) 214-238
26. Feitelson J., and Mauzerall D. J. Phys. Chem. B 106 (2002) 9674-9678
27. Hambright P. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook Vol. 3 (2000), Academic, San Diego, CA pp 129-210
28. Lindsey J.S. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook Vol. 1 (2000), Academic, San Diego, CA pp 45-118
29. Fan D., Taniguchi M., Yao Z., Dhanalekshmi S., and Lindsey J.S. Tetrahedron 61 (2005) 10291-10302
30. Taniguchi M., Balakumar A., Fan D., McDowell B.E., and Lindsey J.S. J. Porphyrins Phthalocyanines 9 (2005) 554-574
31. Hornung R., Fehr M.K., Walt H., Wyss P., Berns M.W., and Tadir Y. Photochem. Photobiol. 72 (2000) 696-700
32. Zingg A., Felber B., Gramlich V., Fu L., Collman J.P., and Diederich F. Helv. Chim. Acta 85 (2002) 333-351
33. Lamarche F., Sol V., Huang Y.-M., Granet R., Guilloton M., and Krausz P. J. Porphyrins Phthalocyanines 6 (2002) 130-134
34. Subbarayan M., Shetty S.J., Srivastava T.S., Noronha O.P.D., Samuel A.M., and Mukhtar H. Biochem. Biophys. Res. Commun. 281 (2001) 32-36
35. Lindsey J.S., Prathapan S., Johnson T.E., and Wagner R.W. Tetrahedron 50 (1994) 8941-8968
36. Loewe R.S., Tomizaki K.-Y., Youngblood W.J., Bo Z., and Lindsey J.S. J. Mater. Chem. 12 (2002) 3438-3451
37. Borbas K.E., Kee H.L., Holten D., and Lindsey J.S. Org. Biomol. Chem. 6 (2008) 187-194
38. Bhaumik J., Yao Z., Borbas K.E., Taniguchi M., and Lindsey J.S. J. Org. Chem. 71 (2006) 8807-8817
39. Borbas K.E., Chandrashaker V., Muthiah C., Kee H.L., Holten D., and Lindsey J.S. J. Org. Chem. 73 (2008) 3145-3158
40. Jux N. Org. Lett. 2 (2000) 2129-2132
41. Guldi D.M., Zilbermann I., Anderson G., Li A., Balbinot D., Jux N., Hatzimarinaki M., Hirsch A., and Prato M. Chem. Commun. (2004) 726-727
42. Jee J.-E., Eigler S., Hampel F., Jux N., Wolak M., Zahl A., Stochel G., and van Eldik R. Inorg. Chem. 44 (2005) 7717-7731
43. Jee J.-E., Eigler S., Jux N., Zahl A., and van Eldik R. Inorg. Chem. 46 (2007) 3336-3352
44. Hermanson G.T. Bioconjugate Techniques (1996), Academic, San Diego, CA
45. Lindsey J.S., and Mauzerall D.C. J. Am. Chem. Soc. 104 (1982) 4498-4500
46. Lindsey J.S., Delaney J.K., Mauzerall D.C., and Linschitz H. J. Am. Chem. Soc. 110 (1988) 3610-3621
47. Fan D., Taniguchi M., and Lindsey J.S. J. Org. Chem. 72 (2007) 5350-5357
48. Ruzié C., Krayer M., Balasubramanian T., and Lindsey J.S. J. Org. Chem. 73 (2008) 5806-5820
49. Lindsey J.S., and Wagner R.W. J. Org. Chem. 54 (1989) 828-836
50. Wagner R.W., Breakwell B.V., Ruffing J., and Lindsey J.S. Tetrahedron Lett. 32 (1991) 1703-1706
51. Wagner R.W., Lindsey J.S., Turowska-Tyrk I., and Scheidt W.R. Tetrahedron 50 (1994) 11097-11112
52. Wagner R.W., Johnson T.E., and Lindsey J.S. Tetrahedron 53 (1997) 6755-6790
53. Laha J.K., Dhanalekshmi S., Taniguchi M., Ambroise A., and Lindsey J.S. Org. Process Res. Dev. 7 (2003) 799-812
54. Srinivasan N., Haney C.A., Lindsey J.S., Zhang W., and Chait B.T. J. Porphyrins Phthalocyanines 3 (1999) 283-291
55. Lindsey J.S., Brown P.A., and Siesel D.A. Tetrahedron 45 (1989) 4845-4866
56. Schmidt I., Jiao J., Thamyongkit P., Sharada D.S., Bocian D.F., and Lindsey J.S. J. Org. Chem. 71 (2006) 3033-3050
57. Manka J.S., and Lawrence D.S. Tetrahedron Lett. 30 (1989) 6989-6992
58. Balakumar A., Muthukumaran K., and Lindsey J.S. J. Org. Chem. 69 (2004) 5112-5115
59. Yao Z., Bhaumik J., Dhanalekshmi S., Ptaszek M., Rodriguez P.A., and Lindsey J.S. Tetrahedron 63 (2007) 10657-10670
60. Wagner R.W., and Lindsey J.S. Pure Appl. Chem. 68 (1996) 1373-1380
61. Corrigendum:. Wagner R.W., and Lindsey J.S. Pure Appl. Chem. 70 (1998) i
62. Yao Z., Borbas K.E., and Lindsey J.S. New J. Chem. 32 (2008) 436-451