100189-84-2Relevant academic research and scientific papers
Rational Design of a Near-infrared Fluorescence Probe for Ca2+ Based on Phosphorus-substituted Rhodamines Utilizing Photoinduced Electron Transfer
Takahashi, Shodai,Hanaoka, Kenjiro,Okubo, Yohei,Echizen, Honami,Ikeno, Takayuki,Komatsu, Toru,Ueno, Tasuku,Hirose, Kenzo,Iino, Masamitsu,Nagano, Tetsuo,Urano, Yasuteru
, p. 524 - 530 (2020)
Fluorescence imaging in the near-infrared (NIR) region (650–900 nm) is useful for bioimaging because background autofluorescence is low and tissue penetration is high in this range. In addition, NIR fluorescence is useful as a complementary color window t
Tetracationic Bis-Triarylborane 1,3-Butadiyne as a Combined Fluorimetric and Raman Probe for Simultaneous and Selective Sensing of Various DNA, RNA, and Proteins
Amini, Hashem,Ban, ?eljka,Crnolatac, Ivo,Ferger, Matthias,Friedrich, Alexandra,Ken?el, Adriana,Lorenzen, Sabine,Marder, Todd B.,Miljani?, Sne?ana,Piantanida, Ivo,Rauch, Florian
, (2020)
A bis-triarylborane tetracation (4-Ar2B-3,5-Me2C6H2)-C≡C?C≡C-(3,5-Me2C6H2-4-BAr2 [Ar=(2,6-Me2-4-NMe3-C6H2)+] (24+) shows distinctly different behaviour in its fluorimetric response than that of our recently published bis-triarylborane 5-(4-Ar2B-3,5-Me2C6H2)-2,2′-(C4H2S)2–5′-(3,5-Me2C6H2-4-BAr2) (34+). Single-crystal X-ray diffraction data on the neutral bis-triarylborane precursor 2 N confirm its rod-like dumbbell structure, which is shown to be important for DNA/RNA targeting and also for BSA protein binding. Fluorimetric titrations with DNA/RNA/BSA revealed the very strong affinity of 24+ and indicated the importance of the properties of the linker connecting the two triarylboranes. Using the butadiyne rather than a bithiophene linker resulted in an opposite emission effect (quenching vs. enhancement), and 24+ bound to BSA 100 times stronger than 34+. Moreover, 24+ interacted strongly with ss-RNA, and circular dichroism (CD) results suggest ss-RNA chain-wrapping around the rod-like bis-triarylborane dumbbell structure like a thread around a spindle, a very unusual mode of binding of ss-RNA with small molecules. Furthermore, 24+ yielded strong Raman/SERS signals, allowing DNA or protein detection at ca. 10 nm concentrations. The above observations, combined with low cytotoxicity, efficient human cell uptake and organelle-selective accumulation make such compounds intriguing novel lead structures for bio-oriented, dual fluorescence/Raman-based applications.
Development of a Series of Practical Fluorescent Chemical Tools to Measure pH Values in Living Samples
Takahashi, Shodai,Kagami, Yu,Hanaoka, Kenjiro,Terai, Takuya,Komatsu, Toru,Ueno, Tasuku,Uchiyama, Masanobu,Koyama-Honda, Ikuko,Mizushima, Noboru,Taguchi, Tomohiko,Arai, Hiroyuki,Nagano, Tetsuo,Urano, Yasuteru
, p. 5925 - 5933 (2018)
In biological systems, the pH in intracellular organelles or tissues is strictly regulated, and differences of pH are deeply related to key biological events such as protein degradation, intracellular trafficking, renal failure, and cancer. Ratiometric fluorescence imaging is useful for determination of precise pH values, but existing fluorescence probes have substantial limitations, such as inappropriate pKa for imaging in the physiological pH range, inadequate photobleaching resistance, and insufficiently long excitation and emission wavelengths. Here we report a versatile scaffold for ratiometric fluorescence pH probes, based on asymmetric rhodamine. To demonstrate its usefulness for biological applications, we employed it to develop two probes. (1) SiRpH5 has suitable pKa and water solubility for imaging in acidic intracellular compartments; by using transferrin tagged with SiRpH5, we achieved time-lapse imaging of pH in endocytic compartments during protein trafficking for the first time. (2) Me-pEPPR is a near-infrared (NIR) probe; by using dextrin tagged with Me-pEPPR, we were able to image extracellular pH of renal tubules and tumors in situ. These chemical tools should be useful for studying the influence of intra- and extracellular pH on biological processes, as well as for in vivo imaging.
NEAR-INFRARED FLUORESCENT CALCIUM PROBE
-
Paragraph 0072; 0073; 0082; 0083, (2018/07/28)
PROBLEM TO BE SOLVED: To provide a novel near-infrared fluorescent Ca2+ probe showing a fluorescence rise higher than that of conventional one. SOLUTION: The present invention provides a P rhodamine compound having a calcium ion scavenging grou
NEAR-INFRARED FLUORESCENT RATIO TYPE PROBE
-
Paragraph 0098; 0099; 0100; 0101, (2018/07/31)
PROBLEM TO BE SOLVED: To provide a novel near-infrared fluorescent pH probe. SOLUTION: The invention provides a compound represented by general formula (I), or a salt thereof. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
Apical functionalization of chiral heterohelicenes
Surampudi, Sravan K.,Nagarjuna,Okamoto, Daiki,Chaudhuri, Piyali D.,Venkataraman
scheme or table, p. 2074 - 2079 (2012/03/27)
We describe a synthetic protocol to selectively functionalize chiral bridged triarylamines at the apical position using regioselective copper-catalyzed amination reaction. This protocol allows the coupling of diphenylamines with a sterically hindered but
Synthesis and characterization of new tetra-substituted porphyrins with exo-donor carboxylic groups as building blocks for supramolecular architectures. Catalytic and structural studies of their metalated derivatives
Carlucci, Lucia,Ciani, Gianfranco,Maggini, Simona,Proserpio, Davide M.,Ragaini, Fabio,Gallo, Emma,Ranocchiari, Marco,Caselli, Alessandro
experimental part, p. 804 - 814 (2011/09/15)
We report herein the synthesis of the porphyrins 5,10,15,20-tetrakis(4- carboxybiphenyl)-porphyrin (H2TCBP) and 5,10,15,20-tetrakis(4- carboxy-2,6-dimethylbiphenyl)porphyrin (H2TCDMBP) bearing diphenyl units on meso-positions, and of
Preparation and properties of phosphaethynes bearing bulky aryl groups with electron-donating substituents at the para position
Toyota, Kozo,Kawasaki, Subaru,Yoshifuji, Masaaki
, p. 5065 - 5070 (2007/10/03)
Phosphaethynes bearing a 2,6-di-tert-butyl-4-(dimethylamino)phenyl, 2,6-di-tert-butyl-4-methoxyphenyl, or 2,6-di-tert-butylphenyl group were prepared. A 31P NMR spectroscopic investigation of the chemical shifts indicated that electron-donating
