132752-00-2Relevant articles and documents
External Iodine Atoms Influence over the Intersystem Crossing Rate of a Cyanine Iodide Ion Pair in Benzene Solution
Sauerwein, Bjoern,Schuster, Gary B.
, p. 1903 - 1906 (1991)
The photochemical and photophysical properties of N,N'-dibutyltetramethylindocarbocyanine iodide (Bu+I-) in benzene solution were examined by absorption spectroscopy and flash photolysis on a picosecond time scale.In benzene solution the dye iodide exists nearly exclusively as an ion pair.Under these conditions the absorption spectrum of the cyanine dye is perturbed by the iodide ion by a dispersion interaction.Irradiation of the cyanine iodide ion pair generates the triplet state cyanine.
Selective G-quadruplex DNA recognition by a new class of designed cyanines
Nanjunda, Rupesh,Owens, Eric A.,Mickelson, Leah,Dost, Tyler L.,Stroeva, Ekaterina M.,Huynh, Hang T.,Germann, Markus W.,Henary, Maged M.,Wilson, W. David
, p. 13588 - 13607 (2014/01/06)
A variety of cyanines provide versatile and sensitive agents acting as DNA stains and sensors and have been structurally modified to bind in the DNA minor groove in a sequence dependent manner. Similarly, we are developing a new set of cyanines that have been designed to achieve highly selective binding to DNA G-quadruplexes with much weaker binding to DNA duplexes. A systematic set of structurally analogous trimethine cyanines has been synthesized and evaluated for quadruplex targeting. The results reveal that elevated quadruplex binding and specificity are highly sensitive to the polymethine chain length, heterocyclic structure and intrinsic charge of the compound. Biophysical experiments show that the compounds display significant selectivity for quadruplex binding with a higher preference for parallel stranded quadruplexes, such as cMYC. NMR studies revealed the primary binding through an end-stacking mode and SPR studies showed the strongest compounds have primary KD values below 100 nM that are nearly 100-fold weaker for duplexes. The high selectivity of these newly designed trimethine cyanines for quadruplexes as well as their ability to discriminate between different quadruplexes are extremely promising features to develop them as novel probes for targeting quadruplexes in vivo.
Synthesis and evaluation of carbocyanine dyes as PRMT inhibitors and imaging agents
Sinha, Sarmistha Halder,Owens, Eric A.,Feng, You,Yang, Yutao,Xie, Yan,Tu, Yaping,Henary, Maged,Zheng, Yujun George
experimental part, p. 647 - 659 (2012/09/08)
Protein arginine methylation regulates multiple biological processes. Deregulation of protein arginine methyltransferase (PRMT) activities has been observed in many disease phenotypes. Small molecule probes that target PRMTs with strong affinity and selectivity can be used as valuable tools to dissect biological mechanisms of arginine methylation and establish the role of PRMT proteins in a disease process. In this work, we report synthesis and evaluation of a class of carbocyanine compounds containing indolium, benz[e]indolium or benz[c,d]indolium heterocyclic moieties that bind to the predominant arginine methyltransferase PRMT1 and inhibit its methyltransferase activity at low micromolar potencies. In particular, the developed molecules have long wavelength colorimetric and fluorometric photoactivities, which can be used for optical and near-infrared fluorescence imaging in cells or biological tissues. Together, these new chemical probes have potential application in PRMT studies both as enzyme inhibitors and as fluorescent dyes for microscope imaging.
