Synthesis and characterization of fluorescent oligo(3,4,5-triethoxycarbonyl-2-pyrazoline)

被引:12
作者
Jia, Xiangxiang [1 ]
Li, Yan [1 ]
Xiao, Longqiang [1 ]
Liu, Lijian [1 ]
机构
[1] Wuhan Univ, Coll Chem & Mol Sci, Minist Educ, Key Lab Biomed Polymers, Wuhan 430072, Peoples R China
基金
中国国家自然科学基金;
关键词
CONJUGATED POLYMERS; CRYSTAL-STRUCTURE; PROTEIN; 2-PYRAZOLINES; DECOMPOSITION; PYRAZOLINES; DERIVATIVES; DEVICES; SENSOR; AGENT;
D O I
10.1039/c4py00315b
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Pseudopeptide oligomers as newly developing fluorescent macromolecules are of significant importance and fairly attractive in bioimaging of living cells. We report that a type of efficient fluorescent pseudopeptide oligo(3,4,5-triethoxycarbonyl-2-pyrazoline) is prepared by the novel cyclo-polycondensation of 3,4,5-triethoxycarbonyl-2-pyrazoline that is a weakly-fluorescent chromophore. The pseudopeptide oligomer exhibits a strong red-shift and remarkable fluorescence enhancement compared with the monomer 2-pyrazoline and images living cells in good quality, even though it only consists of fewer than 70 glycine residues whereas for the famous green fluorescent protein (GFP) the amount of the various natural amino acid residues is 238. Oligo(3,4,5-triethoxycarbonyl-2-pyrazoline) is a GFP-mimetic but structurally-simplified fluorescent pseudopeptide with simple chemistry, generated from the only natural resource of glycine.
引用
收藏
页码:4781 / 4789
页数:9
相关论文
共 35 条
[1]   Fluorescence Enhancement at Docking Sites of DNA-Directed Self-Assembled Nanoantennas [J].
Acuna, G. P. ;
Moeller, F. M. ;
Holzmeister, P. ;
Beater, S. ;
Lalkens, B. ;
Tinnefeld, P. .
SCIENCE, 2012, 338 (6106) :506-510
[2]   Recent Advances in Conjugated Polymers for Light Emitting Devices [J].
AlSalhi, Mohamad Saleh ;
Alam, Javed ;
Dass, Lawrence Arockiasamy ;
Raja, Mohan .
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2011, 12 (03) :2036-2054
[3]   On the development of sensor molecules that display FeIII-amplified fluorescence [J].
Bricks, JL ;
Kovalchuk, A ;
Trieflinger, C ;
Nofz, M ;
Büschel, M ;
Tolmachev, AI ;
Daub, J ;
Rurack, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (39) :13522-13529
[4]   LIGHT-EMITTING-DIODES BASED ON CONJUGATED POLYMERS [J].
BURROUGHES, JH ;
BRADLEY, DDC ;
BROWN, AR ;
MARKS, RN ;
MACKAY, K ;
FRIEND, RH ;
BURN, PL ;
HOLMES, AB .
NATURE, 1990, 347 (6293) :539-541
[5]   GREEN FLUORESCENT PROTEIN AS A MARKER FOR GENE-EXPRESSION [J].
CHALFIE, M ;
TU, Y ;
EUSKIRCHEN, G ;
WARD, WW ;
PRASHER, DC .
SCIENCE, 1994, 263 (5148) :802-805
[6]   GFP: Lighting up life [J].
Chalfie, Martin .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2009, 106 (25) :10073-10080
[7]   Fluorescent Proteins and Their Applications in Imaging Living Cells and Tissues [J].
Chudakov, Dmitriy M. ;
Matz, Mikhail V. ;
Lukyanov, Sergey ;
Lukyanov, Konstantin A. .
PHYSIOLOGICAL REVIEWS, 2010, 90 (03) :1103-1163
[8]   Process research, development, and pilot-plant preparation of clofencet, a novel wheat hybridizing agent: Lewis acid-catalyzed reaction of ethyl diazoacetate with 4-chlorophenyl hydrazonoacetaldehyde [J].
Clark, JD ;
Heise, JD ;
Shah, AS ;
Peterson, JC ;
Chou, SK ;
Levine, J ;
Karakas, AM ;
Ma, Y ;
Ng, KY ;
Patelis, L ;
Springer, JR ;
Stano, DR ;
Wettach, RH ;
Dutra, GA .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2004, 8 (02) :176-185
[9]   Trapping Reactive Metal-Carbene Complexes by a Bis-Pocket Porphyrin: X-ray Crystal Structures of Ru=CHCO2Et and trans-[Ru(CHR)(CO)] Species and Highly Selective Carbenoid Transfer Reactions [J].
Deng, Qing-Hai ;
Chen, Jian ;
Huang, Jie-Sheng ;
Chui, Stephen Sin-Yin ;
Zhu, Nianyong ;
Li, Guang-Yu ;
Che, Chi-Ming .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (41) :10707-10712
[10]   Synthesis of green light emitting fused pyrazolinopiperidines - photophysical and electrochemical studies [J].
Easwaramoorthi, Shanmugam ;
Umamahesh, Balijapalli ;
Cheranmadevi, Pugalendhi ;
Rathore, Ravindranath S. ;
Sathiyanarayanan, Kulathu Iyer .
RSC ADVANCES, 2013, 3 (04) :1243-1254