20064-98-6Relevant articles and documents
Cyanine dye conjugates as probes for live cell imaging
Carreon, Jay R.,Stewart, Kelly M.,Mahon Jr., Kerry P.,Shin, Stephanie,Kelley, Shana O.
, p. 5182 - 5185 (2007)
A series of fluorescent compounds suitable for live cell imaging is described. Functionalized forms of four different asymmetric cyanine dyes are reported that are amenable to peptide conjugation. The photophysical properties of the modified dyes and conj
New cyanine-oligonucleotide conjugates: Relationships between chemical structures and properties
Lartia, Remy,Asseline, Ulysse
, p. 2270 - 2281 (2006)
Because the influence of the chemical structure of monomethine cyanine-oligo-2′-deoxyribonudeotide (ODN) conjugates on their binding and fluorescence properties has remained largely undetermined, we synthesized and studied a wide range of conjugates with various structural patterns. Different cyanine dyes such as thiocyanine, quinocyanine, and thiazole orange isomers were obtained. In the case of unsymmetrical cyanines. the linker was attached to either the quinoline or the benzothiazole nucleus. The influence of the ODN counterpart was evaluated by linking the cyanines to the 5'-end or to an internucleotidic phosphate. In the first case, the influence of neighboring nucleic bases was studied, whereas in the second, the stereochemical configuration at the phosphorus atom bearing the cyanine was investigated. We report here on relationships between the structures of the dyes and conjugates and some of their properties, such as the stability and fluorescence changes observed on their hybridization with the target sequence. This study provides useful information towards the design of ODN-cyanine conjugates.
Synthesis, spectral properties of rhodanine complex merocyanine dyes as well as their effect on K562 leukemia cells
Xiang, Jun-Feng,Liu, Yan-Xia,Sun, Dan,Zhang, Su-Juan,Fu, Yi-Le,Zhang, Xiang-Han,Wang, Lan-Ying
, p. 1481 - 1487 (2012)
Two rhodanine complex merocyanine dyes 9a and 9b were synthesized and their structures were confirmed by 1H NMR, IR, MS, HRMS and UV-Vis spectra. From the spectral properties of the two dyes, it could be found that the λmax of the dyes showed hypsochromic shifts with the increase of permittivity in protonic solvents, and bathochromic shifts with the increase of refractive index in non protonic solvents. The interactions of two dyes with DNA or BSA were also studied under physiological conditions. The results showed that the quantum yield of DNA-dye 9a was up to 29.5 times compared with free dye 9a. Dyes 9a and 9b were researched in Photodynamic Therapy (PDT) as well. It was demonstrated that supplementation of dye 9a or 9b as photosensitizers for PDT in K562 cells decreases the survival rate.
Twisted cyanines: A non-planar fluorogenic dye with superior photostability and its use in a protein-based fluoromodule
Shank, Nathaniel I.,Pham, Ha H.,Waggoner, Alan S.,Armitage, Bruce A.
, p. 242 - 251 (2013)
The cyanine dye thiazole orange (TO) is a well-known fluorogenic stain for DNA and RNA, but this property precludes its use as an intracellular fluorescent probe for non-nucleic acid biomolecules. Further, as is the case with many cyanines, the dye suffer
Tunable Amine-Reactive Electrophiles for Selective Profiling of Lysine
Backus, Keriann M.,Boatner, Lisa M.,Cao, Jian,Farhi, Jonathan,Houk, Kendall N.,Li, Linwei,Raj, Monika,Spangle, Jennifer,Tang, Kuei-Chien
supporting information, (2021/12/22)
Proteome profiling by activated esters identified >9000 ligandable lysines but they are limited as covalent inhibitors due to poor hydrolytic stability. Here we report our efforts to design and discover a new series of tunable amine-reactive electrophiles (TAREs) for selective and robust labeling of lysine. The major challenges in developing selective probes for lysine are the high nucleophilicity of cysteines and poor hydrolytic stability. Our work circumvents these challenges by a unique design of the TAREs that form stable adducts with lysine and on reaction with cysteine generate another reactive electrophiles for lysine. We highlight that TAREs exhibit substantially high hydrolytic stability as compared to the activated esters and are non-cytotoxic thus have the potential to act as covalent ligands. We applied these alternative TAREs for the intracellular labeling of proteins in different cell lines, and for the selective identification of lysines in the human proteome on a global scale.
Synthesis and antileishmanial evaluation of thiazole orange analogs
Abdelhameed, Ahmed,Liao, Xiaoping,McElroy, Craig A.,Joice, April C.,Rakotondraibe, Liva,Li, Junan,Slebodnick, Carla,Guo, Pu,Wilson, W. David,Werbovetz, Karl A.
supporting information, (2019/11/28)
Cyanine compounds have previously shown excellent in vitro and promising in vivo antileishmanial efficacy, but the potential toxicity of these agents is a concern. A series of 22 analogs of thiazole orange ((Z)-1-methyl-4-((3-methylbenzo[d]thiazol-2(3H)-ylidene)methyl)quinolin-1-ium salt), a commercial cyanine dye with antileishmanial activity, were synthesized in an effort to increase the selectivity of such compounds while maintaining efficacy. Cyanines possessing substitutions on the quinolinium ring system displayed potency against Leishmania donovani axenic amastigotes that differed little from the parent compound (IC50 12–42 nM), while ring disjunction analogs were both less potent and less toxic. Changes in DNA melting temperature were modest when synthetic oligonucleotides were incubated with selected analogs (ΔTm ≤ 5 °C), with ring disjunction analogs showing the least effect on this parameter. Despite the high antileishmanial potency of the target compounds, their toxicity and relatively flat SAR suggests that further information regarding the target(s) of these molecules is needed to aid their development as antileishmanials.
