Illuminating the Chemistry of Life: Design, Synthesis, and Applications of "Caged" and Related Photoresponsive Compounds

被引:341
作者
Lee, Hsien-Ming [1 ,2 ,3 ]
Larson, Daniel R. [4 ]
Lawrence, David S. [1 ,2 ,3 ]
机构
[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA
[2] Univ N Carolina, Dept Med Chem & Nat Prod, Chapel Hill, NC 27599 USA
[3] Univ N Carolina, Dept Pharmacol, Chapel Hill, NC 27599 USA
[4] Yeshiva Univ, Albert Einstein Coll Med, Dept Anat & Struct Biol, Bronx, NY 10461 USA
基金
美国国家卫生研究院;
关键词
Phototysis; Photoisomerization; Caged compound; Quantum yield (Theta) of uncaging; PHOTOREMOVABLE PROTECTING GROUPS; PROTEIN-KINASE-C; ONE-PHOTON; CYCLIC-NUCLEOTIDES; CELL-ADHESION; ION CHANNELS; AMINO-ACID; PHOTOCHEMICAL ACTIVATION; PHOTOLABILE PRECURSORS; CATALYTIC SUBUNIT;
D O I
10.1021/cb900036s
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Biological systems are characterized by a level of spatial and temporal organization that often ties beyond the grasp of present day methods. Light-modulated bioreagents, including analogs of low molecular weight compounds, peptides, proteins, and nucleic acids, represent a compelling strategy to probe, perturb, or sample biological phenomena with the requisite control to address many of these organizational complexities. Although this technology has created considerable excitement in the chemical community, its application to biological questions has been relatively limited. We describe the challenges associated with the design, synthesis, and use of light-responsive bioreagents; the scope and limitations associated with the instrumentation required for their application; and recent chemical and biological advances in this field.
引用
收藏
页码:409 / 427
页数:19
相关论文
共 151 条
[1]   Caged O-phosphorothioyl amino acids as building blocks for Fmoc-based solid phase peptide synthesis [J].
Aemissegger, Andreas ;
Carrigan, Christina N. ;
Imperiali, Barbara .
TETRAHEDRON, 2007, 63 (27) :6185-6190
[2]   Photo-mediated gene activation using caged RNA/DNA in zebrafish embryos [J].
Ando, H ;
Furuta, T ;
Tsien, RY ;
Okamoto, H .
NATURE GENETICS, 2001, 28 (04) :317-325
[3]  
Arroyo JG, 1997, THROMB HAEMOSTASIS, V78, P791
[4]   Photoswitched cell adhesion on surfaces with RGD peptides [J].
Auernheimer, J ;
Dahmen, C ;
Hersel, U ;
Bausch, A ;
Kessler, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) :16107-16110
[5]   o-Nitrobenzyl photolabile protecting groups with red-shifted absorption:: Syntheses and uncaging cross-sections for one- and two-photon excitation [J].
Aujard, Isabelle ;
Benbrahim, Chouaha ;
Gouget, Marine ;
Ruel, Odile ;
Baudin, Jean-Bernard ;
Neveu, Pierre ;
Jullien, Ludovic .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (26) :6865-6879
[6]   Light-activated ion channels for remote control of neuronal firing [J].
Banghart, M ;
Borges, K ;
Isacoff, E ;
Trauner, D ;
Kramer, RH .
NATURE NEUROSCIENCE, 2004, 7 (12) :1381-1386
[7]   Engineering light-gated ion channels [J].
Banghart, Matthew R. ;
Volgraf, Matthew ;
Trauner, Dirk .
BIOCHEMISTRY, 2006, 45 (51) :15129-15141
[8]   Wavelength-controlled orthogonal photolysis of protecting groups [J].
Blanc, A ;
Bochet, CG .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5567-5577
[9]   The incorporation of a photoisomerizable amino acid into proteins in E-coli [J].
Bose, M ;
Groff, D ;
Xie, JM ;
Brustad, E ;
Schultz, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) :388-389
[10]   Development of photolabile caged analogs of endothelin-1 [J].
Bourgault, S. ;
Letourneau, M. ;
Fournier, A. .
PEPTIDES, 2007, 28 (05) :1074-1082