富勒烯具有独特的物理化学性质,是药物设计的理想基体.将富勒烯与各种生物分子进行连接,能改善富勒烯在极性溶剂中的溶解度,得到的新化合物具有富勒烯与生物分子的双重特性,因而具备生物分子的原有功能或产生一些新的生物活性,近年来引起越来越多的关注.综述了富勒烯与氨基酸、肽、寡糖、卟啉等生物分子的最新合成及生物学方面的研究进展.展望了富勒烯生物分子的研究方向和应用前景.
参考文献
[1] | Kroto H W;Heath J R;O'Brien S C et al.C60:Buckminsterfullerene[J].Nature,1985,318:162. |
[2] | Taylor R;Walton D R M .The chemistry of fullerenes[J].Nature,1993,363(6431):685. |
[3] | Kr(a)tschmer W;Lamb L D;Fostiropoulos K et al.Solid C60:A new form of carbon[J].Nature,1990,347(27):354. |
[4] | Maeda-Mamiya R;Noiri E;Isobe H et al.From the cover:In vivo gene delivery by cationic tetraamino fullerene[J].Proceedings of the National Academy of Sciences(USA),2010,107(12):5339. |
[5] | Francesco Giacalone;Nazario Martin .Fullerene Polymers:Synthesis and Properties[J].Chemical Reviews,2006(12):5136-5190. |
[6] | Prylutska S V;Grynyuk I I;Palyvoda K O et al.Photoinduced cytotoxic effect of fullerenes C60 on trarisformed Tlymphocytes[J].Experimental Oncology,2010,32(01):29. |
[7] | Constantin C;Neagu M;Ion RM;Gherghiceanu M;Stavaru C .Fullerene-porphyrin nanostructures in photodynamic therapy.[J].Nanomedicine,2010(2):307-317. |
[8] | Dirk M. Guldi .Fullerenes: three dimensional electron acceptor materials[J].Chemical communications,2000(5):321-327. |
[9] | Diederich F;Thilgen C .Covalent fullerene chemistry[J].Science,1996,271(5247):317. |
[10] | 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. |
[11] | Iwamoto Y;Yamakoshi Y .A highly water-soluble C-60-NVP copolymer: a potential material for photodynamic therapy[J].Chemical communications,2006(46):4805-4807. |
[12] | Jared M. Ashcroft;Dmitri A. Tsyboulski;Keith B. Hartman;Tatiana Y. Zakharian;John W. Marks;R. Bruce Weisman;Michael G. Rosenblum;Lon J. Wilson .Fullerene (C_(60)) immunoconjugates: interaction of water-soluble C_(60) derivatives with the murine anti-gp240 melanoma antibody[J].Chemical communications,2006(28):3004-3006. |
[13] | Tagmatarchis N.;Prato M. .The addition of azomethine ylides to [60]fullerene leading to fulleropyrrolidines [Review][J].Synlett,2003(6):768-779. |
[14] | MAURIZIO PRATO;MICHELE MAGGINI .Fulleropyrrolidines: A Family of Full-Fledged Fullerene Dreivatives[J].Accounts of Chemical Research,1998(9):519-526. |
[15] | Enes RF;Tome AC;Cavaleiro JAS .Synthesis of [60]fullerene-based alpha-amino acid derivatives[J].Tetrahedron,2005(6):1423-1431. |
[16] | Jing Zhang,Yan Xia Wang,Feng Kang,Ying Ya Shao,Zong Jie Li,Xin Lin Yang.Synthesis of novel fullerene α-amino acid conjugates[J].中国化学快报(英文版),2008(10):1159-1162. |
[17] | 张静,王艳霞,康峰,彭琦云,杨新林.新型富勒烯α-氨基酸的合成及其纳米颗粒水悬液的制备[J].高等学校化学学报,2008(10):1986-1989. |
[18] | 宋高广,姚璐,黄成,解馨,谭信,杨新林.富勒烯膦酸衍生物纳米水悬液对DNA限制性内切酶的抑制作用及其机理[J].中国科学B辑,2009(01):61-67. |
[19] | Yang JZ;Barron AR .A new route to fullerene substituted phenylalanine derivatives[J].Chemical communications,2004(24):2884-2885. |
[20] | Jianzhong Yang;Lawrence B.Alemany;Jonathan Driver .Fullerene-Derivatized Amino Acids:Synthesis,Characterization,Antioxidant Properties,and Solid-Phase Peptide Synthesis[J].Chemistry: A European journal,2007(9):2530-2545. |
[21] | Evaggelia Ioannou;Andreas Hirsch;Yiannis Elemes .Sulfur-containing dihydro-pyrrolo [60]fullerene derivatives via 1,3-dipolar cycloadditions of glycine imine esters to C_60[J].Tetrahedron,2007(30):7070-7076. |
[22] | Bianco A .Efficient solid-phase synthesis of fullero-peptides using Merrifield strategy[J].Chemical Communications,2005,25:3174. |
[23] | Can L B;Zhou D J;Luo C P et al.Synthesis of fullerene amino acid derivatives by direct interaction of amino add ester with C60[J].Journal of Organic Chemistry,1996,61(06):1954. |
[24] | 江贵长,郑启新.富勒烯-甘氨酸衍生物的制备[J].化工新型材料,2005(08):24-26,30. |
[25] | 江贵长,郑启新.富勒烯-赖氨酸衍生物的合成及其体外抗癌活性研究[J].材料导报,2005(08):135-138. |
[26] | 刘绪峰,官文超,程珍贤.6-氨基己酸及2-氨基乙磺酸C60加成物的合成及溶解性[J].有机化学,2005(06):741-744. |
[27] | Zhen Hu;Wenchao Guan;Wei Wang;Lizhen Huang;Haiping Xing;Zhou Zhu .Synthesis of β-alanine C_(60) derivative and its protective effect on hydrogen peroxide-induced apoptosis in rat pheochromocytoma cells[J].Cell biology international,2007(8):798-804. |
[28] | Hu Z;Guan W;Wang W;Huang L;Xing H;Zhu Z .Protective effect of a novel cystine C(60) derivative on hydrogen peroxide-induced apoptosis in rat pheochromocytoma PC12 cells.[J].Chemico-biological interactions,2007(2):135-144. |
[29] | Wolff DJ.;Mialkowski K.;Richardson CF.;Schuster DI. Wilson SR.;Papoiu ADP. .Inhibition of nitric oxide synthase isoforms by tris-malonyl-C-60-fullerene adducts[J].Archives of Biochemistry and Biophysics,2000(2):216-223. |
[30] | Kotelnikova RA.;Bogdanov GN.;Romanova VS.;Kuleshova EF. Parnes ZN.;Volpin ME.;Kotelnikov AI. .MEMBRANOTROPIC PROPERTIES OF THE WATER SOLUBLE AMINO ACID AND PEPTIDE DERIVATIVES OF FULLERENE C-60[J].FEBS Letters,1996(2):111-114. |
[31] | Rajagopalan P;Wudl F;Schinazi R F et al.Pharmacokinetics of a water-soluble fullerene in rats antimicrob[J].Antimicrobial Agents and Chemotherapy,1996,40(10):2262. |
[32] | Prato M;Bianco A;Maggini M et al.Synthesis and characterization of the first fullerene-peptide[J].Journal of Organic Chemistry,1993,58(21):5578. |
[33] | Toniolo C;Bianco A;Maggini M et al.A bioactive fullerene peptide[J].Journal of Medicinal Chemistry,1994,37(26):4558. |
[34] | Chen BX;Wilson SR;Das M;Coughlin DJ;Erlanger BF .Antigenicity of fullerenes: antibodies specific for fullerenes and their characteristics.[J].Proceedings of the National Academy of Sciences of the United States of America,1998(18):10809-10813. |
[35] | Sofou P.;Elemes Y.;Panou-Pomonis E.;Stavrakoudis A.;Tsikaris V. Sakarellos C.;Sakarellos-Daitsiotis M.;Maggini M.;Formaggio F.;Toniolo C. .Synthesis of a proline-rich [60]fullerene peptide with potential biological activity[J].Tetrahedron,2004(12):2823-2828. |
[36] | Yang J Z;Wang K;Driver J et al.The use of fullcrene substituted phenylalanine amino acid as a passport for petides through cell membranes[J].Organic and Biological Chemistry,2007,5:260. |
[37] | Louis A.Watanabe;Mohammed P.I.Bhuiyan;Binoy Jose .Synthesis of novel fullerene amino acids and their multifullerene peptides[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2004(38):7137-7140. |
[38] | 王乃兴.水溶性五加成二甘肽C60衍生物的合成[J].合成化学,2002(03):251-252. |
[39] | Romanova V S;Tsyryaphin V A et al.Addition of amino acids and dipeptides to fullerene G60 giving rise to monoadducts[J].Russian Chemical Bulletin,1994,43(06):1154. |
[40] | Vol'pin M E;Belavtseva E M;Romanova V S et al.Selfassembling of associates of amino acids and dipeptide derivatives of[60]fullerene in aqueous solution cA study by scaning electron microscopy[J].Mendeleev Communications,1995,5(04):129. |
[41] | Klemenkova Z S,Romanova V S,Tsyryapkin V A,et al.Infrared spectra of amino acid and peptide monoderivatives of[Q]. |
[42] | Klemenkova Z S;Romanova V S;Tsyryapkin V A et al.Infrared spectra of amino acid and peptide monoderivatives of fullerene and their methyl esters[J].Mendeleev Communications,1996,6(02):60. |
[43] | Rancan F;Helmreich M;M(o)lich A et al.Synthesis and invitro testing of a pyropheophorbide-α-fullerene hexakis adduct immunoconjugate for photodynamic therapy[J].Bioconjugate Chemistry,2007,18(04):1078. |
[44] | Bianco A;Pantarotto D;Hoebeke J et al.Solid-phase synthesis and characterization of a novel fullerene-peptide derived from histone H3[J].Organic and Biological Chemistry,2003,1:4141. |
[45] | Federica Pellarini;Davide Pantarotto;Tatiana Da Ros;Anna Giangaspero;Alessandro Tossi;Maurizio Prato .A novel [60]fullerene amino acid for use in solid-phase peptide synthesis[J].Organic letters,2001(12):1845-1848. |
[46] | Keisuke Kobata;Junya Ogawa;Shyam S. Pandey;Hidetoshi Oshima;Toru Arai;Tamaki Kato;Norikazu Nishino .Synthesis and characterization of dendritic poly(l-lysine) containing porphyrin–fullerene moieties[J].Synthetic Metals,2007(6/7):311-317. |
[47] | Higashi N;Shosu T;Koga T;Niwa M;Tanigawa T .pH-responsive, self-assembling nanoparticle from a fullerene-tagged poly(L-glutamic acid) and its superoxide dismutase mimetic property[J].Journal of Colloid and Interface Science,2006(1):118-123. |
[48] | Toru Arai;Junya Ogawa;Emiko Mouri;Mohammed P.I.Bhuiyan;Norikazu Nishino .Formation of Submicron Scale Particles of Narrow Size Distribution from a Water-Soluble Dendrimer with Links to Porphyrins and a Fullerene[J].Macromolecules,2006(4):1607-1613. |
[49] | Tokuyama H;Yarnago S;Nakamura E et al.Photoinduced biochemical activity of fullerene carboxylic acid[J].Journal of the American Chemical Society,1993,115(17):7918. |
[50] | Boutorine A S;Tokuyama H;Takasugi M et al.Fullereneoligonucleotide conjugates:Photoinduced sequence-specific DNA cleavage[J].Angewandte Chemie International Edition in English,1994,33:2462. |
[51] | An YZ.;Anderson JL.;Sigman DS.;Foote CS.;Rubin Y.;Chen CHB. .SEQUENCE-SPECIFIC MODIFICATION OF GUANOSINE IN DNA BY A C-60-LINKED DEOXYOLIGONUCLEOTIDE - EVIDENCE FOR A NON-SINGLET OXYGEN MECHANISM[J].Tetrahedron,1996(14):5179-5189. |
[52] | Bergamin M;da Ros T;Spalluto G et al.Synthesis of a hybrid fullerene-trirnethoxyindole-oligonucleotide conjugate[J].Chemical Communications,2001,217:17. |
[53] | Da Ros T;Bergamin M;Spalluto G et al.Synthesis and molecular modeling and studies of fullerene-5,6,7-trimetboxyindole-oligonucleotide conjugates as possible probe for studing photochemical reactions in DNA triple helices[J].European Journal of Organic Chemistry,2002,2002(03):405. |
[54] | Yang X L;Meng X M;Li B et al.Inhibition of DNA restrictive endonucleases by aqueous nanoparticle suspension of methanophosphonate fullerene derivatives and its mechanisms[J].Biologicals,2008,36:223. |
[55] | Huang,ST;Liao,JS;Fang,HW;Lin,CM .Synthesis and anti-inflammation evaluation of new C60 fulleropyrrolidines bearing biologically active xanthine.[J].Bioorganic and Medicinal Chemistry Letters,2008(1):99-103. |
[56] | Ishi-i, Tsutomu;Shinkai, Seiji;Ikeda, Atsushi;Nakashima, Kazuaki .Saccharide libraries as potential templates for regio- and chiroselective introduction of two functional groups into [60]fullerene[J].The Journal of Organic Chemistry,1999(3):984-990. |
[57] | Kato H;Yashiro A;Mizuno A;Nishida Y;Kobayashi K;Shinohara H .Syntheses and biological evaluations of alpha-D-mannosyl (60)fullerenols.[J].Bioorganic and Medicinal Chemistry Letters,2001(22):2935-2939. |
[58] | Rancan F;Rosan S;Boehm K et al.Cytotoxicity and photocytotoxicity of a dendritic C(60) mono-adduct and a malonic acid C(60) tris-aclduct on Jurkat cells[J].Journal of Photochemistry and Photobiology B:Biology,2002,67(03):157. |
[59] | Hiroyuki Isobe;Hiroko Mashima;Hideki Yorimitsu;Eiichi Nakamura .Synthesis of Fullerene Glycoconjugates through Sulfide Connection in Aqueous Media[J].Organic letters,2003(23):4461-4463. |
[60] | Abe S;Moriyama H;Niikura K;Fei F;Monde K;Nishimura S .Versatile synthesis of oligosaccharide-containing fullerenes[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2005(1):15-19. |
[61] | Samai S;Geckeler K E .Cyclodextrin-fullerenes:A new class of water-soluble fuilerenes[J].Journal of The Chemical Society,chemical Communications,2000,13:1101. |
[62] | Filippone S;Heimann F;Rassat A.A highly water-soluble 2:1 β-cyclodextrin-fullerene eonjugate[J].Chemical Communications,2002(14):1508. |
[63] | Jiang Dong Lin et al.Bioinspired molecular design of functional dendrimers[J].Progress in Polymer Science,2005,30(3-4):403. |
[64] | Jean-Francois Nierengarten;Jean-Francois Eckert;Yannick Rio .Amphiphilic Diblock Dendrimers: Synthesis and Incorporation in Langmuir and Langmuir-Blodgett Films[J].Journal of the American Chemical Society,2001(40):9743-9748. |
[65] | Zhang S.;Rio Y.;Cardinali F.;Bourgogne C.;Gallani JL.;Nierengarten JF. .Amphiphilic diblock dendrimers with a fullerene core[J].The Journal of Organic Chemistry,2003(25):9787-9797. |
[66] | Jensen AW;Maru BS;Zhang X;Mohanty DK;Fahlman BD;Swanson DR;Tomalia DA .Preparation of fullerene-shell dendrimer-core nanoconjugates[J].Nano letters,2005(6):1171-1173. |
[67] | Yannick Rio;jean-Francois Nierengarten .Water soluble supramolecular cyclotriveratrylene-[60]fullerene complexes with potential for biological applications[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2002(24):4321-4324. |
[68] | Yutaka Takaguchi;Yuuki Sako;Yasushi Yanagimoto;Sadao Tsuboi;Jiro Motoyoshiya;Hiromu Aoyama;Takatsugu Wakahara;Takeshi Akasaka .Facile and reversible synthesis of an acidic water-soluble poly(amidoamine) fullerodendrimer[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2003(31):5777-5780. |
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%