利用自由基聚合反应合成了聚丙烯酸修饰的富勒烯(C60-PAA),进一步通过酯化反应将核黄素类似物6,7-二甲基-9-(2'-羟乙基)-异咯嗪(DHIX)与C60-PAA共价连接,得到C60-PAA-DHIX.利用傅立叶红外光谱(F-IR)、核磁共振氢谱(1HNMR)、紫外-可见吸收光谱(UV-Vis)、荧光光谱对产物的化学结构进行了表征.循环伏安法表明,C60-PAA-DHIX中富勒烯基团的第一还原电位要高于DHIX基团的第一还原电位.ESR实验表明C60-PAA-DHIX能与N,N-二甲基苯胺发生多步光诱导电子转移反应,即DHIX基团与N,N-二甲基苯胺发生光诱导电子转移生成DHIX负离子自由基(DHIX-·),DHIX-·能进一步将电子传递给富勒烯生成富勒烯负离子自由基.DNA熔解曲线、紫外-可见吸收光谱和荧光光谱结果表明,C60-PAA-DHIX通过沟槽结合与CTDNA作用,而C60-PAA与DNA的作用较弱.无氧条件下,C60-PAA-DHIX具有比C60-PAA更强的DNA光损伤能力.
参考文献
| [1] | Dirk M. Guldi;Beatriz M. Illescas;Carmen M .Fullerene for organic electronics[J].Chemical Society Reviews,2009(6):1587-1597. |
| [2] | Barry C. Thompson;Jean M. J. Fréchet .Polymer-Fullerene Composite Solar Cells[J].Angewandte Chemie,2008(1):58-77. |
| [3] | Eiichi Nakamura;Hiroyuki Isobe .Functionalized Fullerenes in Water.The First 10 Years of Their Chemistry,Biology,and Nanoscience[J].Accounts of Chemical Research,2003(11):807-815. |
| [4] | Tatiana Da Ros;Maurizio Prato .Medicinal chemistry with fullerenes and fullerene derivatives[J].Chemical communications,1999(8):663-669. |
| [5] | C. N. Murthy;K. E. Geckeler .The water-soluble β-cyclodextrin-[60]fullerene complex[J].Chemical communications,2001(13):1194-1195. |
| [6] | 高云燕,刘丽华,欧植泽,李嫕,杨国强,王雪松.胆固醇修饰富勒烯/γ-环糊精包结复合物的生物活性[J].物理化学学报,2010(02):495-501. |
| [7] | Ikeda A;Hatano T;Kawaguchi M.Water-soluble[60]fullerene-cationic homooxacalix[3]arene complex which is applicable to the photoclcavage of DNA[J].Chemical Communications,1999(15):14031404. |
| [8] | Spiotto MT;Banh A;Papandreou .Imaging the unfolded protein response in primary tumors reveals microenvironments with metabolic variations that predict tumor growth.[J].Cancer research,2010(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].Clinical Cancer Research,2008,14(09):2796-2805. |
| [10] | Liu Y;Wang H;Liang P et al.Water-soluble supramolecular fullerene assembly mediated by metallobridged β-cyclodextrins[J].Angewandte Chemie,2004,116(20):2744-2748. |
| [11] | Yoko Yamakoshi;Naoki Umezawa;Akemi Ryu;Kumi Arakane;Naoki Miyata;Yukihiro Goda;Toshiki Masumizu;Tetsuo Nagano .Active Oxygen Species Generated from Photoexcited Fullerene (C_(60)) as Potential Medicines: O_2~(-·) versus ~1O_2[J].Journal of the American Chemical Society,2003(42):12803-12809. |
| [12] | Yamakoshi Y N;Yagami T;Sueyoshi S et al.Acridine adduct of[60]fullerene with enhanced DNA-cleaving activity[J].Journal of Organic Chemistry,1996,61(21):7236-7237. |
| [13] | Yunyan Gao;Zhize Ou;Guoqiang Yang .Efficient photocleavage of DNA utilizing water soluble riboflavin/naphthaleneacetate substituted fullerene complex[J].Journal of Photochemistry and Photobiology, A. Chemistry,2009(2/3):105-111. |
| [14] | Anish Kumar;Mandava V. Rao;Shobhana K. Menon .Photoinduced DNA cleavage by fullerene-lysine conjugate[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2009(47):6526-6530. |
| [15] | Silva E;Edwards A M.Flavins-Photochemistry and Photobiology[M].Cambridge:Royal Society of Chemistry,2006 |
| [16] | Thomas TP;Choi SK;Li MH;Kotlyar A;Baker JR Jr .Design of riboflavin-presenting PAMAM dendrimers as a new nanoplatform for cancer-targeted delivery.[J].Bioorganic and Medicinal Chemistry Letters,2010(17):5191-5194. |
| [17] | Zhi-Ze Ou;Jing-Rong Chen;Xue-Song Wang;Bao-Wen Zhang;Yi Cao .Synthesis of a water-soluble cyclodextrin modified hypocrellin and ESR study of its photodynamic therapy properties[J].New Journal of Chemistry,2002(9):1130-1136. |
| [18] | H. Jonas Karlsson;Maja Eriksson;Erik Perzon;Bjorn Akerman;Per Lincoln;Gunnar Westman .Groove-binding unsymmetrical cyanine dyes for staining of DNA: syntheses and characterization of the DNA-binding[J].Nucleic Acids Research,2003(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].Journal of the American Chemical Society,1956,78(02):377-380. |
| [20] | 姚威,吴宝燕,高丽华,王科志.一种含芴基的钌（Ⅱ）配合物的合成及DNA键合性质[J].物理化学学报,2007(02):237-241. |
| [21] | Zeng Y;Montrichok A;Zocchi G .Bubble nucleation and cooperativity in DNA melting.[J].Journal of Molecular Biology,2004(1):67-75. |
| [22] | Francesco Giacalone;Nazario Martin .Fullerene Polymers:Synthesis and Properties[J].Chemical Reviews,2006(12):5136-5190. |
| [23] | Guifeng Li;Ksenija D.Glusac .Light-Triggered Proton and Electron Transfer in Flavin Cofactors[J].The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory,2008(20):4573-4583. |
| [24] | Steven O.Mansoorabadi;Christopher J.Thibodeaux;Hung-wen Liu .The Diverse Roles of Flavin Coenzymes-Nature's Most Versatile Thespians[J].The Journal of Organic Chemistry,2007(17):6329-6342. |
| [25] | 官文超,段标,余俊.富勒烯（C60/70）-丙烯酸的自由基共聚[J].高等学校化学学报,1998(03):492-493. |
| [26] | Wang ZY.;Meng XS.;Gao JP.;Kuang L. .New route to incorporation of [60]fullerene into polymers via the benzocyclobutenone group[J].Macromolecules,1998(16):5556-5558. |
| [27] | Dominik T. Hermann;Anne Christina Schindler;Kurt Polborn;Rudolf Gompper;Susanne Stark;Andreas B. J. Parusel;Gottfried Grabner;Gottfried Kohler .Synthesis, Spectroscopy, and Semiempirical Study of a Novel Porphyrin-Flavin Dyad[J].Chemistry: A European journal,1999(11):3208-3220. |
| [28] | 袁钊,曾毅,陈金平,李迎迎,韩永滨,李嫕.以尼罗红为探针对新型两亲性树枝形聚合物微环境的研究[J].影像科学与光化学,2010(05):343-353. |
| [29] | Yunyan Gao;Zhize Ou;Jingrong Chen .Photodynamic properties of supramolecular assembly constructed by magnesium complex of hypocrellin A and fullerene C_(60)[J].New Journal of Chemistry,2008(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].Journal of the American Chemical Society,1994,116(21):9692-9699. |
| [31] | Kowalczyk, RM;Schleicher, E;Bittl, R;Weber, S .The photoinduced triplet of flavins and its protonation states[J].Journal of the American Chemical Society,2004(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].Journal of Photochemistry and Photobiology A: Chemistry,1993,74(02):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(05):980-986. |
| [34] | Monica Rosa;Rita Dias;Maria da Graga Miguel;Bjorn Lindman .DNA-Cationic Surfactant Interactions Are Different for Double-and Single-Stranded DNA[J].Biomacromolecules,2005(4):2164-2171. |
| [35] | Mikhailenko I;Shlyakhtenko L .A study of DNA melting in concentrated water-alcohol solutions[J].Journal of Biomolecular Structure and Dynamics,1984,1(06):1501-1510. |
| [36] | McFarland G D;Borer P N .Separation of oligo-RNA by reverse-phase HPLC[J].Nucleic Acids Research,1979,7(06):1067-1080. |
| [37] | Qiao CY;Bi SY;Sun Y;Song DQ;Zhang HQ;Zhou WH .Study of interactions of anthraquinones with DNA using ethidium bromide as a fluorescence probe[J].Spectrochimica acta, Part A. Molecular and biomolecular spectroscopy,2008(1):136-143. |
| [38] | Qi-Xiong Zhen;Bao-Hui Ye;Qian-Ling Zhang;Jin-Gang Liu;Hong Li;Liang-Nian Ji;Lei Wang .Synthesis, characterization and the effect of ligand planarity of [Ru(bpy)_2L]~(2+) on DNA binding affinity[J].Journal of Inorganic Biochemistry: An Interdisciplinary Journal,1999(1):47-53. |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分：
-
10%
-
20%
-
30%
-
40%
-
50%