scholarly journals Heteroacene-Based Amphiphile as a Molecular Scaffold for Bioimaging Probes

2021 ◽  
Vol 9 ◽  
Author(s):  
Tharindu A. Ranathunge ◽  
Mahesh Loku Yaddehige ◽  
Jordan H. Varma ◽  
Cameron Smith ◽  
Jay Nguyen ◽  
...  

The challenges faced with current fluorescence imaging agents have motivated us to study two nanostructures based on a hydrophobic dye, 6H-pyrrolo[3,2-b:4,5-b’]bis [1,4]benzothiazine (TRPZ). TRPZ is a heteroacene with a rigid, pi-conjugated structure, multiple reactive sites, and unique spectroscopic properties. Here we coupled TRPZ to a tert-butyl carbamate (BOC) protected 2,2-bis(hydroxymethyl)propanoic acid (bisMPA) dendron via azide-alkyne Huisgen cycloaddition. Deprotection of the protected amine groups on the dendron afforded a cationic terminated amphiphile, TRPZ-bisMPA. TRPZ-bisMPA was nanoprecipitated into water to obtain nanoparticles (NPs) with a hydrodynamic radius that was <150 nm. For comparison, TRPZ-PG was encapsulated in pluronic-F127 (Mw = 12 kD), a polymer surfactant to afford NPs almost twice as large as those formed by TRPZ-bisMPA. Size and stability studies confirm the suitability of the TRPZ-bisMPA NPs for biomedical applications. The photophysical properties of the TRPZ-bisMPA NPs show a quantum yield of 49%, a Stokes shift of 201 nm (0.72 eV) and a lifetime of 6.3 ns in water. Further evidence was provided by cell viability and cellular uptake studies confirming the low cytotoxicity of TRPZ-bisMPA NPs and their potential in bioimaging.

2020 ◽  
Vol 17 ◽  
Author(s):  
Ahmed Nuri Kursunlu ◽  
Elif Bastug ◽  
Ersin Guler

Background: Chemosensor compounds are useful for sensitive selective detection of cations and anions with fluorophore groups in an attempt to develop the effective selectivity of the sensors. Although familiar fluorescent sensors utilizing inter-molecular interactions with the cations and anions, an extraordinary endeavor was executed the preparation of fluorescent-based sensor compounds. 4,4-difluoro-4- bora-3a,4a-diaza-s-indacene (Bodipy) and its derivatives were firstly used as an agent in the imaging of biomolecules due to their interesting structures, complexation, and fluorogenic properties. Among the fluorescent chemosensors used for cations and anions, Bodipy-based probes stand out owing to the excellent properties such as sharp emission profile, high stability, etc. In this review, we emphasize the Bodipy-based chemosensor compounds, which have been used to image cations and anions in living cells, because of as well as the biocompatibility and spectroscopic properties. Methods: Research and online content related to chemosensor online activity is reviewed. The advances, sensing mechanisms and design strategies of the fluorophore exploiting selective detection of some cation and anions with Bodipy-based chemosensors are explained. It could be claimed that the using of Bodipy-based chemosensors is very important for cations and anions in bio-imaging applications. Results: Molecular sensors or chemosensors are molecules that show a change can be detected when affected by the analyte. They are capable of producing a measurable signal when they are selective for a particular molecule. Molecular and ion recognition that it is important in biological systems such as enzymes, genes, environment, and chemical fields. Due to the toxic properties of many heavy metal ions, it is of great importance to identify these metals due to their harmful effects on living metabolism and the pollution they create in the environment. This process can be performed with analytical methods based on atomic absorption and emission. The fluorescence methods among chemosensor systems have many advantages such as sensitivity, selectivity, low price, simplicity of using the instrument and direct determination in solutions. The fluorescence studies can be applied at nanomolar concentrations. Conclusion: During a few decades, a lot of Bodipy-based chemosensors for the detection of cations & anions have been investigated in bio-imaging applications. For the Bodipy-based fluorescent chemosensors, the Bodipy derivatives were prepared by different ligand groups for the illumination of the photophysical and photochemical properties. The synthesized Bodipy-based chemosensors have remarkable photophysical properties, such as a high quantum yield, strong molar absorption coefficient etc. Moreover, these chemosensors were successfully implemented on living organisms for the detection of analytes.


2014 ◽  
Vol 2 (40) ◽  
pp. 7065-7072 ◽  
Author(s):  
Jia-Tao Miao ◽  
Chen Fan ◽  
Ru Sun ◽  
Yu-Jie Xu ◽  
Jian-Feng Ge

A cellular dye with properties of long-wave emission, large Stokes shift, water solubility, low cytotoxicity, and good photostability is reported.


2018 ◽  
Vol 34 (4) ◽  
pp. 2170-2179
Author(s):  
Manjula Rayanal ◽  
Prasad Pralhad Pujar ◽  
Sridhar D

The solvatochromic fluorescence behaviour of mono-carbonyl curcumin analogues has been studied in ten different solvents ranging from non-polar to polar. The solvent effect on the spectral properties of analogues has been discussed. The ground state dipole moments were estimated experimentally by Bilot-Kawski equation which is a function of Stokes shift with the solvent polarity parameters and Guggenheim method and theoretically by TD-DFT studies. The excited state dipole moment was determined using Bilot-Kawski equations. The excited state dipole moments for the two molecules were found to be higher than their corresponding ground state dipole moments. Theoretically Frontier molecular orbital (HOMO/ LUMO) energies were determined by Gaussian 09 W software using TD-DFT.


2020 ◽  
Vol 18 (27) ◽  
pp. 5238-5244 ◽  
Author(s):  
Jin Gong ◽  
Chang Liu ◽  
Xiaojie Jiao ◽  
Song He ◽  
Liancheng Zhao ◽  
...  

A novel mitochondrial targeting Hg2+ probe JRQNS with NIR emission (691 nm) and a large Stokes shift (78 nm) was developed by enhancing the electron donating ability of amine groups.


ChemPhysChem ◽  
2012 ◽  
Vol 13 (16) ◽  
pp. 3714-3722 ◽  
Author(s):  
Jun-Ling Jin ◽  
Hai-Bin Li ◽  
Yun Geng ◽  
Yong Wu ◽  
Yu-Ai Duan ◽  
...  

2015 ◽  
Vol 14 (12) ◽  
pp. 2251-2260 ◽  
Author(s):  
Małgorzata Wierzbicka ◽  
Irena Bylińska ◽  
Artur Sikorski ◽  
Cezary Czaplewski ◽  
Wiesław Wiczk

A series of symmetrically substituted diphenylbuta-1,3-diyne (DPB) derivatives possessing electron-donating or electron-accepting groups have been prepared and studied with emphasis on their spectral and photophysical properties.


2002 ◽  
Vol 09 (01) ◽  
pp. 621-626 ◽  
Author(s):  
V. N. MAKHOV ◽  
N. YU. KIRIKOVA ◽  
N. M. KHAIDUKOV ◽  
M. KIRM ◽  
E. NEGODIN ◽  
...  

The spectroscopic properties of several fluoride crystals ( LiYF 4, KYF 4, K 2 YF 5, KLiYF 5, CsY 2 F 7, SrF 2) doped with Nd 3+, Er 3+ or Tm 3+ are analyzed from the viewpoint of their possible applications as active media for VUV solid state lasers. It has been found that in many crystals there exists very efficient nonradiative relaxation from higher-lying 5d states to the lowest 5d level responsible for the spin-forbidden luminescence. In fact, the energy level diagram of 5d–4f transitions for these two ions represents a typical four-level laser scheme with a considerably larger Stokes shift of 5d–4f luminescence from the edge of the strong spin-allowed 4f–5d absorption than for Nd 3+, which causes smaller reabsorption of emitted VUV radiation in the crystals doped with Er 3+ or Tm 3+. Two crystals LiYF 4: Nd 3+ and SrF 2: Er 3+ were tested for laser action under pumping by a pulsed F 2 laser operating at 157 nm. However, no indications of the appearance of stimulated emission have been detected for both crystals. The possible reasons for the absence of lasing are discussed.


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