- “Turn on” fluorescence response of monomethine cyanines caused by noncovalent binding to ct-DNA
-
Monomethine cyanines have been extensively studied for their use as probes for nucleic acids among other biological systems. Four monomethine cyanine dyes were synthesized with various heterocyclic moieties including quinoline, benzoxazole, benzothiazole, and 3,3-dimethylindolenine adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. The dyes were characterized by 1H and 13C NMR and HRMS. In this study the twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the benzoxazole containing sensor displayed up to 700-fold increase in fluorescence when bound to the DNA compared to the unbound form.
- Levitz, Andrew,Holder, Cory,Soriano, Eduardo,Henary, Maged
-
p. 202 - 207
(2017/06/14)
-
- C8-H bond activation vs. C2-H bond activation: From naphthyl amines to lactams
-
Pd-catalyzed selective amine-oriented C8-H bond functionalization/N-dealkylative carbonylation of naphthyl amines has been achieved. The amine group from dealkylation is proposed to be the directing group for promoting this process. It represents a straightforward and easy method to access various biologically important benzo[cd]indol-2(1H)-one derivatives.
- Shi, Renyi,Lu, Lijun,Xie, Hangyu,Yan, Jingwen,Xu, Ting,Zhang, Hua,Qi, Xiaotian,Lan, Yu,Lei, Aiwen
-
p. 13307 - 13310
(2016/11/17)
-
- Benz[c,d]indolium-containing monomethine cyanine dyes: Synthesis and photophysical properties
-
Asymmetric monomethine cyanines have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazole, dimethyl indole, and benz[e]indole adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. In this study the optical properties vs. structural changes were investigated using nuclear magnetic resonance and computational approaches. The twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the newly designed sensor displayed an increase in fluorescence when bound in the DNA grooves compared to the unbound form.
- Soriano, Eduardo,Holder, Cory,Levitz, Andrew,Henary, Maged
-
-
- Synthesis of asymmetric monomethine cyanine dyes with red-shifted optical properties
-
Six novel asymmetrical monomethine cyanine dyes were synthesized via the condensation reaction of 1-butyl-2-(methylthio)benzo[c,d]indol-1-ium iodide and various 1,5-substituted indolenine salts under basic conditions. The dyes were characterized using UV-vis spectroscopy, fluorescence, 1H NMR, 13C NMR, and mass spectrometry; furthermore, the purity of these compounds was observed using LC/ELSD/MS.
- Soriano, Eduardo,Outler, Loretta,Owens, Eric A.,Henary, Maged
-
p. 180 - 184
(2015/01/30)
-
- Synthesis and biological evaluation of a benz[cd]indol-2(1H)-one derivatives
-
Virtual screening of a library of 6.4 million compounds versus the structure of Xenopus Laevis' Aurora B kinase identified 1-(n-propyl)-6-[2-(carboxyl)tetrahydropyrrol-1-yl]sulfonyl-benzo[cd]indol-2(1H)-one 1 as a possible lead compound. Then, a novel series of benz[cd]indol-2(1H)-one derivatives were synthesized and evaluated as Aurora B kinase inhibitors. The structures of the synthetic compounds were confirmed by 1H NMR, IR, mass spectrometry and elemental analysis. These compounds were evaluated by in vitro enzyme assay using spectrophotometry. Among them, compound 7e displayed potent antitumor activity against Aurora B kinase.
- Nie, Jing,Dong, Dan-Dan,Zhang, Yan,Wang, Tai-Yi,Liu, Wei,Yi, Shou-Zhi
-
p. 7329 - 7336
(2015/04/22)
-
- Alkylation of 1H-benz[de]isoquinoline-1,3(2H)dione and benz[cd]indol-2(1H)one under conditions of phase-transfer catalysis
-
The possibility of phase-transfer N-alkylation of 1H-benz[de]isoquinoline-1,3(2H)-dione (naphthalimide) and benz[cd]indol-2(1H)-one (naphthostyril), catalyzed with tetraalkylammonium nitrates, was studied.
- Anikin,Krasnova,Kupriyan
-
p. 486 - 489
(2007/10/03)
-