A Modular Approach for the Synthesis of Diverse Heterobifunctional Cyanine Dyes

被引:2
|
作者
Maller, Corina [1 ,2 ,3 ]
Schedel, Franziska [3 ,4 ,5 ]
Koehn, Maja [1 ,3 ]
机构
[1] Univ Freiburg, Signalling Res Ctr BIOSS & CIBSS, D-79104 Freiburg, Germany
[2] Univ Freiburg, Fac Chem & Pharm, D-79104 Freiburg, Germany
[3] Univ Freiburg, Fac Biol, Freiburg 79104, Germany
[4] Univ Freiburg, Fac Chem & Pharm, Signalling Res Ctr BIOSS & CIBSS, D-79104 Freiburg, Germany
[5] Univ Freiburg, Spemann Grad Sch Biol & Med SGBM, D-79104 Freiburg, Germany
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 06期
基金
欧洲研究理事会;
关键词
ENHANCED PHOTOSTABILITY; CY5; DERIVATIVES; FLUORESCENCE; CHEMISTRY; PROTEIN; PROBES;
D O I
10.1021/acs.joc.3c02673
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we present a straightforward synthetic route for the design and synthesis of diverse heterobifunctional cyanine 5 dyes. We optimized the workup by harnessing the pH- and functional group-dependent solubility of the asymmetric cyanine 5 dyes. Therefore, purification through chromatography is deferred until the last synthesis step. Demonstrating successful large-scale synthesis, our modular approach prevents functional group degradation by introducing them in the last synthesis step. These modifiable heterobifunctional dyes offer significant utility in advancing biological studies.
引用
收藏
页码:3844 / 3856
页数:13
相关论文
共 50 条
  • [41] Synthesis and absorption spectra of new polymethine cyanine dyes
    El-Aal, RMA
    DYES AND PIGMENTS, 2002, 52 (02) : 129 - 136
  • [42] Synthesis and physical performance of indole and benzimidazole cyanine dyes
    Peng, ZH
    Qun, L
    Zhou, XF
    Carroll, S
    Geise, HJ
    Peng, BX
    Dommisse, R
    Carleer, R
    JOURNAL OF MATERIALS CHEMISTRY, 1996, 6 (04) : 559 - 565
  • [43] Synthesis of some bridgehead heterocyclic monomethine cyanine dyes
    Aswan Faculty of Science, Aswan, Egypt
    Dyes Pigm, 4 (267-280):
  • [44] Synthesis and spectral properties of dihydroxy heptamethine cyanine dyes
    Liu, Zhanhui
    Bao, Lihong
    Jingxi Huagong/Fine Chemicals, 2020, 37 (03): : 609 - 614
  • [45] BEHAVIOR AND REACTIVITY OF HETEROCYCLOAMMONIUM COMPOUNDS IN SYNTHESIS OF CYANINE AND CARBOCYANINE DYES .11. DEGRADTAION OF MONO AND POLYMETHINIC CYANINE DYES
    METZGER, J
    LARIVE, H
    DENNILAU.R
    BARALLE, R
    GAURAT, C
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1969, (04): : 1284 - &
  • [46] Synthesis and characterization of new photosensitizer bridgehead cyanine dyes
    Reda Mahmoud Abd El-Aal
    Proceedings / Indian Academy of Sciences, 1999, 111 (2): : 343 - 352
  • [47] SYNTHESIS AND SPECTRA OF SOME ASYMMETRIC TRIMETHINE CYANINE DYES
    KORAIEM, AIM
    KHALIL, ZH
    ELHAMD, RMA
    DYES AND PIGMENTS, 1990, 13 (04) : 289 - 299
  • [48] Solid-phase methods for the synthesis of cyanine dyes
    Mason, SJ
    Hake, JL
    Nairne, J
    Cummins, WJ
    Balasubramanian, S
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08): : 2939 - 2949
  • [49] Solid-phase synthesis of asymmetric cyanine dyes
    Isacsson, J
    Westman, G
    TETRAHEDRON LETTERS, 2001, 42 (18) : 3207 - 3210
  • [50] The use of metal chelators in the synthesis of monomethine cyanine dyes
    El-Aala, RMA
    Belal, AAM
    DYES AND PIGMENTS, 2005, 65 (02) : 129 - 136