Synthesis of new cholesterol- and sugar-anchored squaraine dyes: Further evidence of how electronic factors influence dye formation

被引：44
作者：
Jyothish, K [1 ]
Avirah, RR [1 ]
Ramaiah, D [1 ]
机构：
[1] CSIR, Reg Res Lab, Photosci & Photo Div, Trivandrum 695019, Kerala, India
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 01期
关键词：
D O I：
10.1021/ol052639j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Synthesis of new quinaldine-based squaraine dyes linked to cellular recognition elements that exhibit near-infrared absorption (> 740 nm) are described. Both product analysis and theoretical calculations substantiate the interesting electronic effects of various substituents in the dye formation reaction. These results are useful in the synthesis of symmetrical and unsymmetrical squaraine dyes that can have potential biological and photodynamic therapeutical applications.
引用
收藏
页码：111 / 114
页数：4
相关论文
共 36 条
  • [1] Near-infrared fluorescent probes: Synthesis and spectroscopic investigations of a few amphiphilic squaraine dyes
    Arun, KT
    Ramaiah, D
    [J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2005, 109 (25) : 5571 - 5578
  • [2] Aggregation Behavior of halogenated squaraine dyes in buffer, electrolytes, organized media, and DNA
    Arun, KT
    Epe, B
    Ramaiah, D
    [J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2002, 106 (44) : 11622 - 11627
  • [3] Squaraine-derived rotaxanes: Sterically protected fluorescent near-IR dyes
    Arunkumar, E
    Forbes, CC
    Noll, BC
    Smith, BD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) : 3288 - 3289
  • [4] Selective calcium ion sensing with a bichromophoric squaraine foldamer
    Arunkumar, E
    Ajayaghosh, A
    Daub, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (09) : 3156 - 3164
  • [5] BELL GI, 1993, J BIOL CHEM, V268, P19161
  • [6] New π-extended water-soluble squaraines as singlet oxygen generators
    Beverina, L
    Abbotto, A
    Landenna, M
    Cerminara, M
    Tubino, R
    Meinardi, F
    Bradamante, S
    Pagani, GA
    [J]. ORGANIC LETTERS, 2005, 7 (19) : 4257 - 4260
  • [7] Avenues into the synthesis of illusive poly(m-phenylene-alt-squaraine)s:: Polycondensation of m-phenylenediamines with squaric acid intercepted by intermediate semisquaraines of exceptionally low reactivity
    Block, MAB
    Khan, A
    Hecht, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (01) : 184 - 187
  • [8] Synthesis, characterization, and cellular uptake of DNA-binding rose bengal peptidoconjugates
    Carreon, JR
    Roberts, MA
    Wittenhagen, LM
    Kelley, SO
    [J]. ORGANIC LETTERS, 2005, 7 (01) : 99 - 102
  • [9] Aggregation of surfactant squaraine dyes in aqueous solution and microheterogeneous media: Correlation of aggregation behavior with molecular structure
    Chen, HJ
    Farahat, MS
    Law, KY
    Whitten, DG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (11) : 2584 - 2594
  • [10] Efficient synthesis and photodynamic activity of porphyrin-saccharide conjugates: Targeting and incapacitating cancer cells
    Chen, X
    Hui, L
    Foster, DA
    Drain, CM
    [J]. BIOCHEMISTRY, 2004, 43 (34) : 10918 - 10929
1234