Synthesis of isoalloxazine modified C60-polypropylene acid and its interaction with DNA

Yingxiang Kexue yu Guanghuaxue/Imaging Science and Photochemistry

Volumn 29, Issue 3, 2011, Pages 181-193

  Wang, Zhong Li ^a   Gao, Yun Yan ^a   Ou, Zhi Ze ^a   Guo, Chuang Long ^a   Li, Hai Xia ^a   Jin, He Lin ^a  

^a NORTHWESTERN POLYTECHNICAL UNIVERSITY   (China)

Author keywords

DNA photocleavage; Fullerene polymer; Groove binding; Isoalloxazine; Photoinduced electron transfer

Indexed keywords

EID: 79959508628     PISSN: 16740475     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (38)

1. Guldi D M, Illescas B M, Atienza C M, et al. Fullerene for organic electronics [J]. Chem. Soc. Rev., 2009, 40 (37): 1587-1597.
2. Thompson B C, Frechet J M. Polymer-fullerene composite solar cells [J]. J. Angew. Chem. Int. Edit., 2008, 47 (1): 58-77.
3. Nakamura E, Isobe H. Functionalized fullerenes in water. the first 10 years of their chemistry, biology, and nanoscience [J]. Acc. Chem. Res., 2003, 36 (11): 807-815.
4. Ros T D, Prato M. Medicinal chemistry with fullerenes and fullerene derivatives [J]. Chem. Commun., 1999, (8): 663-669.
5. Murthy C N, Geckeler K E. The water-soluble β-cyclodextrin-[60]fullerene complex [J]. Chem. Commun., 2001, (13): 1194-1195.
6. Gao Y, Liu L, Ou Z, et al. Biological activity of a cholesterol modified fullerene/γ-cyclodextrin inclusion complex [J]. Acta Phys.-Chim. Sin., 2010, 26 (2): 495-501.
7. Ikeda A, Hatano T, Kawaguchi M, et al. Water-soluble [60]fullerene-cationic homooxacalix [3]arene complex which is applicable to the photocleavage of DNA [J]. Chem. Commun., 1999, (15): 1403-1404.
8. Spiotto M T, Banh A, Papandreou I, et al. Visualization of the unfolded protein response in primary tumors reveals unique microenvironments that reflect metabolic variations and predict for tumor growth [J]. Cancer Res., 2010, 70 (1): 78-88.
9. Seshadri M, Bellnier D A, Vaughan L A, et al. Light delivery over extended time periods enhances the effectiveness of photodynamic therapy [J]. Clin. Cancer Res., 2008, 14 (9): 2796-2805.
10. Liu Y, Wang H, Liang P, et al. Water-soluble supramolecular fullerene assembly mediated by metallobridged β-cyclodextrins [J]. Angew. Chem., 2004, 116 (20): 2744-2748.
11. 2 [J]. J. Am. Chem. Soc., 2003, 125 (42): 12803-12809.
12. Yamakoshi Y N, Yagami T, Sueyoshi S, et al. Acridine adduct of [60]fullerene with enhanced DNA-cleaving activity [J]. J. Org. Chem., 1996, 61 (21): 7236-7237.
13. Gao Y, Ou Z, Yang G, et al. Efficient photocleavage of DNA utilizing water soluble riboflavin/naphthaleneacetate substituted fullerene complex [J], J. Photochem. Photobiol. A: Chem., 2009, 203 (2-3): 105-111.
14. Kumar A, Rao M V, Menon S K. Photoinduced DNA cleavage by fullerene lysine conjugate [J]. Tetrahedron Lett., 2009, 50 (47): 6526-6530.
15. Silva E, Edwards A M. Flavins-Photochemistry and Photobiology [M]. Cambridge: Royal Society of Chemistry, 2006.
16. Thomas T P, Choi S K, Li M H, et al. Design of riboflavin-presenting PAMAM dendrimers as a new nanoplatform for cancer-targeted delivery [J]. Bioorg. Med. Chem., 2010, 20 (17): 5191-5194.
17. Ou Z, Chen J, Wang X, et al. Synthesis of a water-soluble cyclodextrin modified hypocrellin and ESR study of its photodynamic therapy properties [J]. New J. Chem., 2002, 26 (9): 1130-1136.
18. Karlsson H J, Eriksson M, Perzon E, et al. Groove-binding unsymmetrical cyanine dyes for staining of DNA: syntheses and characterization of the DNA-binding [J]. Nucleic. Acids. Res., 2003, 31 (21): 6227-6234.
19. Fall H H, Peterin H G. Metabolite inhibitors. i. 6, 7-dimethyl-9-formylmethylisoalloxazine, 6, 7-dimethyl-9-(2'-hydroxyethyl)-isoalloxazine and derivatives [J]. J. Am. Chem. Soc., 1956, 78 (2): 377-380.
20. Yao W, Wu B Y, Gao L H, et al. DNA-binding properties of a fluorenyl-containing ru (ii) complex [J]. Acta Phys.-Chim. Sin., 2007, 23 (2): 237-241.
21. Zeng Y, Montrichok A, Zocchi G. Bubble nucleation and cooperativity in DNA melting [J]. J. Mol. Biol., 2004, 339 (1): 67-75.
22. Giacalone F, Martin N. Fullerene polymers: synthesis and properties [J]. Chem. Rev., 2006, 106 (12): 5136-5190.
23. Li G, Glusac K D. Light-triggered proton and electron transfer in flavin cofactors [J]. J. Phys. Chem. A., 2008, 112 (20): 4573-4583.
24. Mansoorabadi S O, Thibodeaux C J, Liu H. The diverse roles of flavin coenzymesnature's most versatile thespians [J]. J. Org. Chem., 2007, 72 (17): 6329-6342.
25. 60/70) with acrylic acid [J]. Chim. Jour. Chin. Univer., 1998, 19 (3): 492-493.
26. Wang Z Y, Kuang L, Meng, X S, et al. New route to incorporation of [60] fullerene into polymers via the benzocyclobutenone group [J]. Macromolecules, 1998, 31 (16): 5556-5558.
27. Hermann D T, Schindler A C, Polborn K, et al. Synthesis, spectroscopy, and semiempirical study of a novel porphyrin flavin dyad [J]. Chem. Eur. J., 1999, 5 (11): 3208-3220.
28. Yuan Z, Zeng Y, Chen J P, et al. Investigation of the microenvironment of novel amphiphilic dendrimers with nile red as a probe [J]. Imaging Science and Photochemistry, 2010, 28 (5): 343-353.
29. 60 [J]. New J. Chem., 2008, 32 (9): 1555-1560.
30. Sun Y P, Bunker C E, Ma B. Quantitative studies of ground and excited state charge transfer complexes of fullerenes with N, N-dimethylaniline and N, N-diethylaniline [J]. J. Am. Chem. Soc., 1994, 116 (21): 9692-9699.
31. Kowalczyk R M, Schleicher E, Bittl R, et al. The photoinduced triplet of flavins and its protonation states [J]. J. Am. Chem. Soc., 2004, 126 (36): 11393-11399.
32. Kumar C V, Turener R S, Asuncion E H. Groove binding of a styrylcyanine dye to the DNA double helix: the salt effect [J]. J. Photochem. Photobiol. A, 1993, 74 (2): 231-238.
33. Hianik T, Wang X, Tashlitsky V, et al. Thompson M. Interaction of cationic surfactants with DNA detected by spectroscopic and acoustic wave techniques [J]. Analyst, 2010, 135 (5): 980-986.
34. Rosa M, Dias R, Miguel M G, et al. DNA-cationic surfactant interactions are different for doubleand single-stranded DNA [J]. Biomacromolecules, 2005, 6 (4): 2164-2171.
35. Mikhailenko I, Shlyakhtenko L. A study of DNA melting in concentrated water-alcohol solutions [J]. J. Biomol. Struct. Dyn., 1984, 1 (6): 1501-1510.
36. McFarland G D, Borer P N. Separation of oligo-RNA by reverse-phase HPLC [J]. Nucleic Acids Res., 1979, 7 (6): 1067-1080.
37. Qiao C, Bi S, Sun Y, et al. Study of interactions of anthraquinones with DNA using ethidium bromide as a fluorescence probe [J]. Spectrochim. Acta, Part A, 2008, 70 (1): 136-143.
38. 2+on DNA binding affinity [J]. J. Inorg. Biochem., 1999, 76 (1): 47-53.