Synthesis and bioactivity study of water-soluble C60-dehydroabietylamine derivatives

doi:10.3969/j.jssn.1000-2006.2012.02.007

JOURNAL OF NANJING FORESTRY UNIVERSITY ›› 2012, Vol. 36 ›› Issue (02): 29-34.doi: 10.3969/j.jssn.1000-2006.2012.02.007

Previous Articles Next Articles

Synthesis and bioactivity study of water-soluble C₆₀-dehydroabietylamine derivatives

FAN Xu¹,LIN Zhongxiang^1*,DENG Huimin²,XU Yanmei¹

1.College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037,China; 2.Instrumental Analysis & Research Center, Sun Yat-sen University, Guangzhou 510275,China

Online:2012-04-10 Published:2012-04-10

Abstract

Abstract: Two water-soluble C₆₀-dehydroabietylamine fullerenol derivatives and two water-soluble glycine derivatives were synthesized by different water-borne modification method, with C₆₀-dehydroabietylamine pyrrolidine derivative and nitrene addition derivative as the raw materials. The structures were characterized by TEM, FT-IR, ESI-MS, ¹H NMR and HPLC. The products were confirmed to be mixtures of components with different additional group numbers.These four derivatives were each given a bioactivity test. The results showed that they had different inhibition against both rTaq DNA polymerase and HIV-1 reverse transcriptase, while they showed less inhibition against the Hey 1B ovarian cancer cell line than HIV-1 reverse transcriptase.

CLC Number:

TQ351
O621

FAN Xu,LIN Zhongxiang,DENG Huimin,XU Yanmei. Synthesis and bioactivity study of water-soluble C₆₀-dehydroabietylamine derivatives[J]. JOURNAL OF NANJING FORESTRY UNIVERSITY, 2012, 36(02): 29-34.

References

[1] Zhu Z W, Schuster D I, Tuckerman M E. Molecular dynamics study of the connection between flap closing and binding of fullerene-based inhibitors of the HIV-1 protease[J]. Biochemistry, 2003, 42(5): 1326-1333.
[2] Marcheesan S, Da Ros T, Spalluto G, et al. Anti-HIV properties of cationic fullerene derivatives[J]. Bioorg Med Chem Lett, 2005, 15(15): 3615-3618.
[3] Mashino T, Shimotohno K, Ikegami N, et al. Human immunodeficiency virus-reverse transcriptase inhibition and hepatitis C virus RNA-dependent RNA polymerase inhibition activities of fullerene derivatives[J]. Bioorg Med Chem Lett, 2005, 15(4):1107-1109.
[4] Lee V S, Nimmanpipug P, Aruksakunwong O, et al. Structural analysis of lead fullerene-based inhibitor bound to human immunodeficiency virus type 1 protease in solution from molecular dynamics simulations[J]. J Mol Graphics Modell, 2007,26(2): 558-570.
[5] Yang X L, Fan C H, Zhu H S. Photo-induced cytotoxicity of malonic acid [C₆₀]fullerene derivatives and its mechanism[J]. Toxicol In Vitro, 2002, 16(1): 41-46.
[6] 熊垚,林中祥,范旭,邓慧敏,等.C₆₀与N-羧甲基脱氢枞胺的1,3-偶极环加成反应研究[J].化学通报, 2009, 72(5):474-477.
[7] 高健,林中祥,邓慧敏,等. 微波辐射下
[60]富勒烯与脱氢枞胺的加成反应[J]. 现代化工, 2007, 27(Z1): 266-268.
[8] Vileno B, Marcoux P R, Lekka M, et al. Spectroscopic and photophysical properties of a highly deivatized C₆₀ fullerol[J]. Adv Funct Mater, 2006, 16(1): 120-128.
[9] Arrais A, Diana E. Highly Water Soluble C₆₀ derivatives: A new synthesis[J]. Fuller Nanotub Carbon Nanostruct, 2003, 11(1): 35-46.
[10] Xing G, Zhang J, Zhao Y, et al. Influences of structural properties on stavility of fullerenols[J]. J Phys Chem B, 2004,108(31): 11473-11479.
[11] Wang S, He P, Zhang J M, et al. Noveland efficient synthesis of water-soluble
[60]Fullerenol by solvent-free reaction[J]. Synth Commun, 2005, 36(44): 1803-1807.
[12] 张云怀,黄宗卿,欧忠文.在相转移剂TABH存在下水溶性C₆₀(OH)_n的合成[J].化学研究与应用, 1998, 10(5): 507-509.
[13] 官文超, 许铭飞, 廖立琼. 多羟基富勒烯衍生物的合成与表征[J].华中科技大学学报:自然科学版, 2004, 32(11): 111-113.
[14] Chiang L Y, Upasani R B, Swirczewski J W, et al. Evidence of hemiketals incorporated in the structure of fullerols derived from aqueous acid chemistry[J]. J Am Chem Soc, 1993, 24(13): 5453-5457.
[15] 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,2005,25(6):741-744.
[16] 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,2005,33(8):24-26.
[17] 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,2005,19(8):135-138.
[18] Sun T, Xu Z. Radical scavenging activites of α-alanine C₆₀adduct[J]. Bioorg Med Chem Lett, 2006, 16(14): 3731-3734.
[19] Wang F, Xiao Z, Yao Z, et al. Lewis acid promoted preparation of isomerically pure fullerenols from fullerene peroxides C₆₀(OOt-Bu)₆ and C₆₀(O)(OOt-Bu)₆[J]. J Org Chem, 2006, 71(12): 4374-4382.
[20] 孙大勇,刘子阳,郭兴华,等.C₆₀(OH)_x的简便合成及性质[J].高等学校化学学报,1996,17(1):19-20.
[21] Irngartinger H, Weber A. Ring opening of the heterocycle in
[60] fullereno
[1,2-d]isoxazole[J].Tetrahedron Lett, 1997, 38(12): 2075-2076.
[22] Huang S, Xiao Z, Wang F, et al. Preparation of
[5,6]-and
[6,6]-oxahomofullerene derivatives and their interconversion by lewis acid assisted reactions of fullerene mixed peroxides[J]. Chemistry, 2005, 11(18): 5449-5456.
[23] Al-Matar H, Abdul-Sada A K, Avent A G, et al. Isolation and characterization of symmetrical C₆₀Me₆, C₆₀Me₅Cl and C₆₀Me₅O₂OH, together with unsymmetrical C₆₀Me₅O₃H, C₆₀Me₅OOH, C₆₀Me₄PhO₂OH, and C₆₀Me₁₂[J]. Chem Soc, Perkin Trans, 2002, 2(1): 53-58.
[24] Gan L, Zhou D, Luo C, et al. Synthesis of fullerene amino acid derivatives by direct interaction of amino acid ester with C₆₀[J]. J Org Chem, 1996, 61(6): 1954-1961.
[25] Gan L B, Luo C P, Xu L B, et al. Water-soluble fullerene derivatives synthesis and characterization of β-alanine C₆₀ addult [J]. Chin Chem Lett, 1994, 5(4):275-279.
[26] Miller G P, Millar J M, Liang B, et al. The absence of “globetrotting” hydrogen on the surfaces of aminated fullerenes: 3-D hydrogen bonding between aminated fullerenes and water revealed[J].J Chem Soc, Chem Commun, 1993(11):897-899.
[27] Maggini M, Scorrano G, Prato M. Chemlnforin abstiact:Addition of azomethine ylides to C₆₀: synthesis, characterization, and functionalization of fullerene pyrrolidines[J]. J Am Chem Soc, 1994,25(5): 9798-9799.
[28] Nishimura T, Maeda K, Chsawa S, et al. Helical arrays of aendant fullerenes on optically active poly(phenylacetylene)s[J]. Chem Eur J, 2005, 11(4): 1181-1190.
[29] Zhang X J, Willems M, Foote C S. 1,3-Dipolar cycloaddition of N-benzyl azomethine ylide to C₆₀:formation of a C₆₀-fused N-benzylpyrrolidine[J]. Tetrahedron Letters, 1993, 34(51): 8187-8188.
[30] Maria D L, Marcorin G L, Pirri G, et al. Synthesis of novel 60 ullerene-flavonoid dyads[J]. Tetrahedron Letters, 2002, 43(9): 1689-1691.

Related Articles 15

[1]	LI Shu-ping，YANG Ping，DAI Zhao-hua，YUAN Zheng. Economical and Technical Feasibility of the Residence Whole-decoration Industrialization [J]. JOURNAL OF NANJING FORESTRY UNIVERSITY, 2006, 30(S1): 89-91.
[2]	YANG Yi-qin, LI Zhong-zheng. Syntheses and Properties of Cationic Lignin Surfactant [J]. JOURNAL OF NANJING FORESTRY UNIVERSITY, 2006, 30(06): 47-50.
[3]	HUANG Jin tian, ZHANG Chen-xia, GAO Guan-hui. Liquefaction of Salix, Caragana and Populus in the Presence of Phenol [J]. JOURNAL OF NANJING FORESTRY UNIVERSITY, 2006, 30(05): 67-70.
[4]	TIAN Jie1,2, SHANG Gao-gao2, ZHOU Li rain1. Motion Simulation of Tail-lift Lifting Mechanism for Vehicle Based on Pro/E [J]. JOURNAL OF NANJING FORESTRY UNIVERSITY, 2006, 30(05): 76-78.
[5]	WANG Chun-jing1, ZHOU Shou-biao1*, YANG Hal jun2, LI Jin-hua1, WANG Gui-jun1, CHEN Nai-dong1. Diversity of Aquatic Vascular Plants in Anhui Province [J]. JOURNAL OF NANJING FORESTRY UNIVERSITY, 2006, 30(05): 87-90.
[6]	ZHANG Sen-lin. Development Prospect of Forest Industry in China [J]. JOURNAL OF NANJING FORESTRY UNIVERSITY, 2006, 30(02): 1-5.
[7]	BAI Hechao, JIANG Lu, WANG Bucheng, YONG Qiang,YU Shiyuan. Effect of periodic harvest of enzyme on cellulase production by Trichoderma reesei [J]. JOURNAL OF NANJING FORESTRY UNIVERSITY, 2016, 40(01): 87-91.
[8]	XU Xu,CAO Xiaoqin,XING Yingying,WANG Shifa. Synthesis and properties investigation of waterborne polyurethane modified with IBOMA by copolymerization [J]. JOURNAL OF NANJING FORESTRY UNIVERSITY, 2016, 40(01): 104-110.
[9]	LIU Bing,PENG Han,XU Xu,WANG Shifa. Preparation of longifolene with high purity [J]. JOURNAL OF NANJING FORESTRY UNIVERSITY, 2015, 39(02): 116-120.
[10]	LU Qiang,GAO Feifei,LUO Jinyue,YANG Fan,FENG Hongjun,LIU Zuguang. Synthesis of 5,5-dimethyl-5,6,7,8-tetrahydroanthracene-1,4-dione [J]. JOURNAL OF NANJING FORESTRY UNIVERSITY, 2015, 39(02): 127-131.
[11]	XU Xu,XU Xiaowei,XING Yingying,WANG Shifa. Preparation and properties of waterborne polyurethane modified by IBOMA [J]. JOURNAL OF NANJING FORESTRY UNIVERSITY, 2014, 38(05): 123-128.
[12]	MENG Xin, TAN Xu, ZHANG Quan, JIN Yongcan. Effects of green liquor pretreatment on chemical composition and enzymatic hydrolysis of moso bamboo [J]. JOURNAL OF NANJING FORESTRY UNIVERSITY, 2014, 38(04): 118-122.
[13]	XIE Yinfeng, LI Bo,TAO Gongsheng,ZHANG Qianqian,ZHANG Chunxia. Effects of nano-silicon dioxide on photosynthetic fluorescence characteristics ofIndocalamus barbatus McClure [J]. JOURNAL OF NANJING FORESTRY UNIVERSITY, 2012, 36(02): 59-63.
[14]	XU Yong, HUA Fengfei,ZHU Junjun, YONG Qiang, YU Shiyuan. Selective synthesis of pectinase from Trichoderma reesei through liquid fermentation [J]. JOURNAL OF NANJING FORESTRY UNIVERSITY, 2012, 36(01): 93-96.
[15]	LI Zhongzheng. Research on renewable biomass resource—lignin [J]. JOURNAL OF NANJING FORESTRY UNIVERSITY, 2012, 36(01): 1-7.

Metrics

Comments

www.nldxb.njfu.edu.cn

Edited ＆ Published by Editorial Department of Nanjing Forestry University(Natural Sciences Edition)
Address： No.159 Longpan Road,Nanjing 210037 Jiangsu,P.R.China
E-mail ：xuebao@njfu.edu.cn , xuebao@njfu.com.cn
Telephone +86-25-85428247,85427076
Distributed by China International Book Trading Corporation P.O. Box 399, Beijing ,P.R. China

Synthesis and bioactivity study of water-soluble C₆₀-dehydroabietylamine derivatives

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

Author

Reader

Reviewer