Carbazole tricationic salt: A novel potential two-photon fluorescent DNA probe for nucleic imaging of cells
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- 作者：Ning Zhao (1)
YuanHong Zhang (1)
Xin Liu (1)
XiaoQiang Yu (1)
MaoFa Ge (2) - 关键词：two ; photon fluorescence microscopy ; two ; photon fluorescent probe ; DNA titration ; DNA staining
- 刊名：Chinese Science Bulletin
- 出版年：2010
- 出版时间：November 2010
- 年：2010
- 卷：55
- 期：32
- 页码：3661-3667
- 全文大小：729KB
- 参考文献：1. Cullander C. Imaging in the far-red with electronic light microscopy: Requirements and limitations. J Microsc, 1994, 176: 281-86
2. Denk W, Strickler J H, Webb W W. Two-photon laser scanning fluorescence microscopy. Science, 1990, 248: 73-6 CrossRef
3. Centonze V E, White J G. Multiphoton excitation provides optical sections from deeper withinscattering specimens than confocal imaging. Biophys J, 1998, 75: 2015-024 CrossRef
4. Feijó J A, Moreno N. Imaging plant cells by two-photon excitation. Protoplasma, 2004, 223: 1-2 CrossRef
5. Feijó J A, Cox G. Visualization of meiotic events in intact living anthers by means of two-photon microscopy. Micron, 2001, 32: 679-84 CrossRef
6. Xu C, Webb W W. Measurement of two-photon excitation cross sections of molecular fluorophores with data from 690 to 1050 nm. J Opt Soc Am B, 1996, 13: 481-91 CrossRef
7. Xu C, Zipfel W, Shear J B, et al. Multiphoton fluorescence excitation: New spectral windows for biological nonlinear microscopy. Pro Natl Acad Sci USA, 1996, 93: 10763-0768 CrossRef
8. Goppert-Mayer M. Uber elementarakte mit zwei quantensprungen. Ann Phys (Leipzig), 1931, 9: 273-94
9. Kaiser W, Garrett C G B. Two-photon excitation in CaF2: Eu2+. Phys Rev Lett, 1961, 7: 229-31 CrossRef
10. So P T C, Dong C Y, Masters B R, et al. Two-photon excitation fluorescence microscopy. Annu Rev Biomed Eng, 2000, 2: 399-29 CrossRef
11. Kim H M, Jeong B H, Hyon J Y, et al. Two-photon fluorescent turn-on probe for lipid rafts in live cell and tissue. J Am Chem Soc, 2008, 130: 4246-247 CrossRef
12. Chen X Y, Shi J, Li Y M, et al. Two-photon fluorescent probes of biological Zn(II) derived from 7-hydroxyquinoline. Org Lett, 2009, 11: 4426-429 CrossRef
13. Kim H M, Kim B R, Hong J H, et al. A two-photon fluorescent probe for calcium waves in living tissue. Angew Chem, 2007, 119: 7589-592 CrossRef
14. Huang C B, Fan J L, Peng X J, et al. Highly selective and sensitive twin-cyano-stilbene-based two-photon fluorescent probe for mercury (ii) in aqueous solution with large two-photon absorption cross-section. J Photochem Photobiol A, 2008, 199: 144-49 CrossRef
15. Kim H M, Yang P R, Seo M S, et al. Magnesium ion delective two-photon fluorescent probe based on a benzo[h]chromene derivative for / in vivo imaging. J Org Chem, 2007, 72: 2088-096 CrossRef
16. Cogn-Laage E, Allemand J F, Ruel O. Diaroyl(methanato)boron difluoride compounds as medium-sensitive two-photon fluorescent probes. Chem Eur J, 2004, 10: 1445-455 CrossRef
17. Kricka L J. Stains, labels and detection strategies for nucleic acids assays. Ann Clin Biochem, 2002, 39: 114-29 CrossRef
18. Gingeras T R, Higuchi R, Kricka L J, et al. Fifty years of molecular (DNA/RNA) diagnostics. Clin Chem, 2005, 51: 661-71 CrossRef
19. Abbotto A, Baldinib G, Beverinaa L, et al. Dimethyl-pepep: A DNA probe in two-photon excitation cellular imaging. Biophys Chem, 2005, 114: 35-1 CrossRef
20. Ohulchanskyy T Y, Pudavar H E, Yarmoluk S M, et al. A monomethine cyanine dye cyan 40 for fluorescence detection of nucleic acids and their visualization in live cells. Photochem Photobiol, 2003, 77: 138-45 CrossRef
21. Allain C, Schmidt F, Lartia R, et al. Vinyl-pyridinium triphenylamines: Novel far-red emitterswith high photostability and two-photon absorption properties for staining DNA. Chem Bio Chem, 2007, 8: 424-33
22. Bordeau G, Faurel E, Allain C, et al. New triarylamine-based far-red DNA stainers with high two-photon absorption properties. Nucleic Acids Symp Ser, 2008, 52: 155-56 CrossRef
23. Albota M A, Xu C, Webb W W. Two-photon fluorescence excitation cross sections of biomolecular probes from 690 to 960 nm. Appl Opt, 1998, 37: 7352-356 CrossRef
24. Amit N, Debabrata G. Solvent effect on two-photon absorption and fluorescence of rhodamine dyes. J Photochem Photobiol A: Chem, 2009, 206: 188-97 CrossRef
25. Kevin D B, Mykhailo V B, Oleksiy D K, et al. Solvent effect on the steady-state fluorescence anisotropy of two-photon absorbing fluorene derivatives. J Lumin, 2007, 126: 14-0 CrossRef
26. Yu Z S, Dong M L, Xiu N S, et al. Solvent effects on two-photon absorption cross sections of a newly synthesized polymerization initiator. THEOCHEM, 2006, 772: 75-9 CrossRef
27. Zale?ny R, Bartkowiak W, Styrcz S, et al. Solvent effects on conformationally induced enhancement of the two-photon absorption cross section of a pyridinium- / N-phenolate betaine dye. A Quantum Chemical Study. J Phys Chem A, 2002, 106: 4032-037
28. Chauhan M, Arjmand F. Chiral and achiral macrocyclic copper(II) complexes: Synthesis, characterization, and comparative binding studies with Calf-Thymus DNA. Chem Biodivers, 2006, 3: 660-76 CrossRef
29. Xu Z D, Liu H, Xiao S L, et al. Synthesis, crystal structure, antitumor activity and DNA-binding study on the Mn(II) complex of 2H-5-hydroxy-1,2,5-oxadiazo[3,4-f]1,10-phenanthroline. J Inorg Biochem, 2002, 90: 79-4 CrossRef
30. Zhong W Y, Yu J S, Huang W L, et al. Spectroscopic studies of interaction of chlorobenzylidine with DNA. Biopolymers, 2001, 62: 315-23 CrossRef
31. Vaidyanathan V G, Nair B U. Synthesis, characterization, and DNA binding studies of a chromium(III) complex containing a tridentate ligand. Eur J Inorg Chem, 2003: 3633-638
32. Jiang X, Shang L, Wang Z X, et al. Spectrometric and voltammetric investigation of interaction of neutral red with calf thymus DNA: Ph effect. Biophys Chem, 2005, 118: 42-0 CrossRef
33. Huang W M, Han X J, Tang J L, et al. Liposome-mediated conformation transition of DNA detected by molecular probe: Methyl green. Bioelectrochem, 2003, 59: 21-7 CrossRef
34. Wang Y M, Song Y, Kong D, et al. Interaction between poly(amidoamine) dendrimers and DNA studied by spectroscopic methods. Chinese Sci Bull, 2005, 50: 2161-165
35. Wang B D, Yang Z Y, Li T R. Synthesis, characterization, and DNA-binding properties of the Ln(III) complexes with 6-hydroxy chromone-3-carbaldehyde-(2-hydroxy) benzoyl hydrazone. Bioorg Med Chem, 2006, 14: 6012-021 CrossRef
36. Tanious F A, Veal J M, Buczak H, et al. DAPI (4,6-diamidino-2-phenylindole) binds differently to DNA and RNA: Minor-groove binding at AT sites and intercalation at AU sites. Biochemistry, 1992, 31: 3103-112 CrossRef
37. Wilson W D, Tanious F A, Barton H J, et al. DNA sequence dependent binding modes of 4-6-diamidino-2-phenylindole ( DAPI). Biochemistry, 1990, 29: 8452-461 CrossRef
38. Woo H Y, Korystov D, Mikhailovsky A, et al. Two-photon absorption in aqueous micellar solutions. J Am Chem Soc, 2005, 127: 13794-3795 CrossRef
39. Chang C C, Chu J F, Kuo H H, et al. Solvent effect on photophysical properties of a fluorescence probe: BMVC. J Lumin, 2006, 119: 84-0 CrossRef
40. Woo H Y, Hong J W, Liu B, et al. Water-soluble [2.2] paracyc-lophane chromophores with large two-photon action cross sections. J Am Chem Soc, 2005, 127: 820-21 CrossRef
41. Strehmel B, Sarker A M, Malpert J H, et al. Effect of aromatic ring substitution on the optical properties, emission dynamics, and solid-state behavior of fluorinated oligophenylenevinylenes. J Am Chem Soc, 1999, 121: 1226-236 CrossRef
42. Castex M C, Olivero C, Pichler G, et al. Photoluminescence of donor-acceptor carbazole chromophores. Synth Me, 2001, 122: 59-1 CrossRef
43. Ade’s D, Boucard V, Cloutet E, et al. Photoluminescence of donor-acceptor carbazole-based molecules in amorphous and powder forms. J Appl Phys, 2000, 87: 7290-293 CrossRef
44. Rotkiewicz K, Grellman K H, Grabowski Z R. Reinterpretation of the anomalous fluorescence of p-n,n-dimethylamino-benzonitrile. Chem Phys Lett, 1973, 19: 315-18 CrossRef
45. Rettig W. Charge separation in excited states of decoupled systems-TICT compounds and implications regarding the development of new laser dyes and the primary process of vision and photosynthesis. Angew Chem Int Ed, 1986, 25: 971-88 CrossRef
46. Nag A, Bhattacharyya K. Role of twisted intramolecular charge transfer in the fluorescence sensitivity of biological probes: Diethyl-aminocoumarin laser dyes. Chem Phys Lett, 1990, 169: 12-6 CrossRef - 作者单位：Ning Zhao (1)
YuanHong Zhang (1)
Xin Liu (1)
XiaoQiang Yu (1)
MaoFa Ge (2)
1. State Key Laboratory of Crystal Materials, Shandong University, Jinan, 250100, China
2. Beijing National Laboratory for Molecular Sciences (BNLM), Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China - ISSN：1861-9541
文摘
A new carbazole tricationic salt, 4,4-(1E,1′E)-2,2-(9-(2-(1-(2-hydroxyethyl)pyridinium-4-yl)ethyl)-9H-carbazole-3,6-diyl) bis(ethane-2,1-diyl) bis(1-(2-hydroxyethyl)pyridinium) iodide (THEPC) was synthesized. Photophysical experiments have shown that THEPC has large two-photon excited fluorescence action cross-sections (33 GM in the presence of DNA), which ranks THEPC as a good biological fluorophore. The results from electronic absorption, circle dichroism and single-/two-photon fluorescence emission spectra suggest that THEPC can strongly bind to DNA, with an intrinsic binding constant of 5.79 × 106 L mol?. THEPC has better photostability under one- or two-photon excitation conditions. Finally, the staining photos from two-photon fluorescence microscopy (TPM) show that THEPC can exclusively label the nucleus with high contrast and without image distortion. These remarkable properties and optimized imaging ability make THEPC an attractive DNA probe in TPM.