Near infrared dipyrrin-based fluorogenic chelators for metal ions

Progress in Biomedical Optics and Imaging - Proceedings of SPIE

Volumn 7910, Issue , 2011, Pages

  Thyagarajan, Sujatha ^a   Ghosh, Brahma ^b   Filatov, Mikhail A ^c   Moore, Anna V ^b   Cheprakov, Andrei V ^c   Vinogradov, Sergei A ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b MASSACHUSETTS GENERAL HOSPITAL   (United States)

^c MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

BODIPY; Dendrimer; Dipyrrin; Dipyrromethenes; Fluorescence; Near infrared; Zinc

Indexed keywords

AROMATIC FRAGMENTS; BINDING AFFINITIES; BODIPY; DIPYRRIN; DIPYRROMETHENES; EXCITON COUPLING; FLUORESCENT SENSORS; FLUOROGENICS; HIGH SELECTIVITY; INFRARED RANGE; METAL COORDINATION; NEAR INFRARED; SPECTRAL PROPERTIES; SPECTROSCOPIC DATA;

BINDING ENERGY; COORDINATION REACTIONS; DENDRIMERS; INFRARED DEVICES; METAL IONS; METALS; NANOPARTICLES; PROBES; ZINC;

FLUORESCENCE;

EID: 79955155464     PISSN: 16057422     EISSN: None     Source Type: Conference Proceeding    
DOI: 10.1117/12.873654     Document Type: Conference Paper

References (51)

1. Wood, T. E., and Thompson, A., "Advances in the chemistry of dipyrrins and their complexes, " Chem. Rev., 107(5), 1831-1861 (2007). (Pubitemid 46864973)
2. Ulrich, G., Ziessel, R., and Harriman, A., "The chemistry of fluorescent bodipy dyes: Versatility unsurpassed, " Angew. Chem. Int. Ed., 47(7), 1184-1201 (2008).
3. Loudet, A., and Burgess, K., "BODIPY dyes and their derivatives: Syntheses and spectroscopic properties, " Chem. Rev., 107(11), 4891-4932 (2007). (Pubitemid 350225866)
4. Fischer, H., Ber. Dtsch. Ges., 57, 610 (1924).
5. Bruckner, C., Karunaratne, V., Rettig, S. J. et al., "Synthesis of meso-phenyl-4, 6-dipyrrins, preparation of their Cu(II), Ni(II), and Zn(II) chelates, and structural characterization of bis meso-phenyl-4, 6-dipyrrinato Ni(II), " Can. J. Chem., 74(11), 2182-2193 (1996).
6. Yu, L. H., Muthukumaran, K., Sazanovich, I. V. et al., "Excited-state energy-transfer dynamics in self-assembled triads composed of two porphyrins and an intervening bis(dipyrrinato)metal complex, " Inorg. Chem., 42(21), 6629-6647 (2003).
7. Zhang, Y. J., Thompson, A., Rettig, S. J. et al., "The use of dipyrromethene ligands in supramolecular chemistry, " J. Am. Chem. Soc., 120(51), 13537-13538 (1998). (Pubitemid 29025229)
8. Sazanovich, I. V., Kirmaier, C., Hindin, E. et al., "Structural control of the excited-state dynamics of bis(dipyrrinato)zinc complexes: Self-assembling chromophores for light-harvesting architectures, " J. Am. Chem. Soc., 126(9), 2664-2665 (2004). (Pubitemid 38314250)
9. Ikeda, C., Ueda, S., and Nabeshima, T., "Aluminium complexes of N2O2-type dipyrrins: the first heteromultinuclear complexes of metallo-dipyrrins with high fluorescence quantum yields, " Chem. Commun. (18), 2544- 2546 (2009).
10. Kobayashi, J., Kushida, T., and Kawashima, T., "Synthesis and reversible control of the fluorescent properties of a divalent tin dipyrromethene, " J. Am. Chem. Soc., 131(31), 10836 (2009).
11. Cooke, M. W., Chartrand, D., and Hanan, G. S., "Self-assembly of discrete metallosupramolecular luminophores, " Coord. Chem. Rev., 252(8-9), 903-921 (2008).
12. Germain, M. E., and Knapp, M. J., "Discrimination of nitroaromatics and explosives mimics by a fluorescent Zn(salicylaidimine) sensor array, " J. Am. Chem. Soc., 130(16), 5422 (2008).
13. Filatov, M. A., Lebedev, A. Y., Mukhin, S. N. et al., " Π-Extended dipyrrins capable of highly fluorogenic complexation with metal ions, " J. Am. Chem. Soc., 132(28), 9552-9554 (2010).
14. Kasha, M., Rawls, H. R., and El-Bayoumi, M. A., "The exciton model in molecular spectroscopy, " Pure and Applied Chemistry, 11, 371-592 (1965).
15. Finikova, O. S., Cheprakov, A. V., Carroll, P. J. et al., "Novel route to functionalized tetraaryltetra [2, 3]naphthaloporphyrins via oxidative aromatization, " J. Org. Chem., 68(19), 7517-7520 (2003). (Pubitemid 37122509)
16. Finikova, O. S., Aleshchenkov, S. E., Brinas, R. P. et al., "Synthesis of symmetrical tetraaryltetranaphtho [2, 3]porphyrins, " J. Org. Chem., 70(12), 4617-4628 (2005).
17. Filatov, M. A., Cheprakov, A. V., and Beletskaya, I. P., "A facile and reliable method for the synthesis of tetrabenzoporphyrin from 4, 7-dihydroisoindole, " Eur. J. Org. Chem. (21), 3468-3475 (2007).
18. Filatov, M. A., Lebedev, A. Y., Vinogradov, S. A. et al., "Synthesis of 5, 15-diaryltetrabenzoporphyrins, " J. Org. Chem., 73(11), 4175-4185 (2008).
19. Finikova, O. S., Cheprakov, A. V., Beletskaya, I. P. et al., "Novel versatile synthesis of substituted tetrabenzoporphyrins, " J. Org. Chem., 69(2), 522-535 (2004). (Pubitemid 38101738)
20. Amiri, A., Comeau, I. M., and Thompson, A., "Heteroleptic zinc dipyrromethene complexes, " J. Heter. Chem., 43(2), 431-435 (2006).
21. Cipot-Wechsler, J., Ali, A. A. S., Chapman, E. E. et al., "Synthesis and reactivity of a dipyrrinatolithium complex, " Inorg. Chem., 46(26), 10947-10949 (2007).
22. Yadav, M., Singh, A. K., and Pandey, D. S., "First examples of heteroleptic dipyrrin/eta(5)- pentamethylcyclopentadienyl rhodium/Iridium(III) complexes and their catalytic activity, " Organometallics, 28(16), 4713-4723 (2009).
23. Motekaitis, R. J., and Martell, A. E., "Halogenated symmetrical dipyrromethene chelates, " Inorg. Chem., 9(8), 1832 (1970).
24. Clarke, E. T., Squattrito, P. J., Rudolf, P. R. et al., "Structural investigations of the dipyrromethene complexes of calcium(II), nickel(II) and copper(II), " Inorg. Chim. Acta, 166(2), 221-231 (1989).
25. Bergstrom, F., Mikhalyov, I., Hagglof, P. et al., "Dimers of dipyrrometheneboron difluoride (BODIPY) with light spectroscopic applications in chemistry and biology, " J. Am. Chem. Soc., 124(2), 196-204 (2002). (Pubitemid 34065297)
26. Mikhalyov, I., Gretskaya, N., Bergstrom, F. et al., "Electronic ground and excited state properties of dipyrrometheneboron difluoride (BODIPY): Dimers with application to biosciences, " Phys. Chem. Chem. Phys., 4(22), 5663-5670 (2002).
27. Tleugabulova, D., Zhang, Z., and Brennan, J. D., "Characterization of bodipy dimers formed in a molecularly confined environment, " J. Phys. Chem. B, 106(51), 13133-13138 (2002).
28. Strickler, S. J., and Berg, R. A., "Relation between absorption intensity and fluorescence lifetime of molecules, " J. Chem. Phys., 37, 814-822 (1962).
29. Tomat, E., and Lippard, S. J., "Imaging mobile zinc in biology, " Curr. Opin. Chem. Biol., 14(2), 225-230 (2010).
30. Ahn, Y.-H., Kim, Y.-H., Hong, S.-H. et al., "Depletion of intracellular zinc induces protein synthesis-dependent neuronal apoptosis in mouse cortical culture, " Experimental Neurology, 154(1), 47-56 (1998). (Pubitemid 28553566)
31. Frederickson, C. J., and Bush, A. I., "Synaptically released zinc: Physiological functions and pathological effects, " Biometals, 14(3-4), 353-366 (2001).
32. Grummt, F., Weinmanndorsch, C., Schneiderschaulies, J. et al., "Zinc as a 2nd Messenger of Mitogenic Induction - Effects on Diadenosine Tetraphosphate (Ap4a) and DNA-Synthesis, " Experimental Cell Research, 163(1), 191-200 (1986). (Pubitemid 16050637)
33. Huang, E. P., "Metal ions and synaptic transmission: Thick zinc, " Proc. Nat. Acad. Sci. USA, 94(25), 13386-13387 (1997). (Pubitemid 28009589)
34. Manzerra, P., Behrens, M. M., Canzoniero, L. M. T. et al., "Zinc induces a Src family kinase-mediated upregulation of NMDA receptor activity and excitotoxicity, " Proc. Nat. Acad. Sci. USA, 98(20), 11055-11061 (2001). (Pubitemid 32928682)
35. Takeda, A., "Zinc homeostasis and functions of zinc in the brain, " Biometals, 14(3-4), 343-351 (2001). (Pubitemid 34066637)
36. Frederickson, C. J., "Neurobiology of zinc and zinc-containing neurons, " International Review of Neurobiology, Volume 31, 145-238 (1989).
37. Zalewski, P. D., Forbes, I. J., Giannakis, C. et al., "Synergy between zinc and phorbol ester in translocation of protein kinase C to cytoskeleton, " FEBS Letters, 273(1-2), 131-134 (1990). (Pubitemid 20362449)
38. Maret, W., Jacob, C., Vallee, B. L. et al., "Inhibitory sites in enzymes: Zinc removal and reactivation by thionein, " Proc. Nat. Acad. Sci. USA, 96(5), 1936-1940 (1999). (Pubitemid 29117846)
39. Martin, S. J., Mazdai, G., Strain, J. J. et al., "Programmed cell death (apoptosis) in lymphoid and myeloid cell cines during zinc deficiency, " Clinical and Experimental Immunology, 83(2), 338-343 (1991).
40. Zalewski, P. D., Forbes, I. J., and Giannakis, C., "Physiological role for zinc in prevention of apoptosis (genedirected death), " Biochemistry International, 24(6), 1093-1101 (1991).
41. Truong-Tran, A. Q., Carter, J., Ruffin, R. E. et al., "The role of zinc in caspase activation and apoptotic cell death, " Biometals, 14(3-4), 315-330 (2001). (Pubitemid 34066635)
42. Epner, D. E., and Herschman, H. R., "Heavy metals induce expression of the Tpa-inducible sequence (Tis) genes, " J. Cell. Physiol., 148(1), 68-74 (1991). (Pubitemid 21910128)
43. Cousins, R. J., and Leeambrose, L. M., "Nuclear zinc uptake, interactions and metallothionein gene-expression are influenced by dietary zinc in rats, " J. Nutr., 122(1), 56-64 (1992).
44. Falchuk, K. H., "The molecular basis for the role of zinc in developmental biology, " Mol. Cell. Biochem., 188(1- 2), 41-48 (1998). (Pubitemid 28493316)
45. Liuzzi, J. P., and Cousins, R. J., "Mammalian zinc transporters, " Ann. Rev. Nutr., 24, 151-172 (2004). (Pubitemid 38949814)
46. Valente, T., and Auladell, C., "Developmental expression of ZnT3 in mouse brain: Correlation between the vesicular zinc transporter protein and chelatable vesicular zinc (CVZ) cells. Glial and neuronal CVZ cells interact, " Mol. Cell. Neurosci., 21(2), 189-204 (2002). (Pubitemid 35333812)
47. 2+, " Chem. Soc. Rev., 39(6), 1996-2006 (2010).
48. Brinas, R. P., Troxler, T., Hochstrasser, R. M. et al., "Phosphorescent oxygen sensor with dendritic protection and two-photon absorbing antenna, " J. Am. Chem. Soc., 127(33), 11851-11862 (2005). (Pubitemid 41208771)
49. Lebedev, A. Y., Cheprakov, A. V., Sakadzic, S. et al., "Dendritic phosphorescent probes for oxygen imaging in biological systems, " ACS Applied Materials & Interfaces, 1(6), 1292-1304 (2009).
50. Nolan, E. M., Jaworski, J., Okamoto, K. I. et al., "QZ1 and QZ2: Rapid, reversible quinoline-derivatized fluoresceins for sensing biological Zn(II), " J. Am. Chem. Soc., 127(48), 16812-16823 (2005). (Pubitemid 41772842)
51. Finikova, O. S., Cheprakov, A. V., Carroll, P. J. et al., "Influence of nonplanarity and extended conjugation on porphyrin basicity, " Inorg. Chem., 41(26), 6944-6946 (2002).