A novel polythioether-based rhodamine B fluorescent probe via successive click reaction and its application in iron ion detection and cell imaging

Author(s):  
Xiaomei Zhang ◽  
Zhiming Gou ◽  
Yujing Zuo ◽  
Weiying Lin
Polymers ◽  
2019 ◽  
Vol 11 (8) ◽  
pp. 1235 ◽  
Author(s):  
Zhiming Gou ◽  
Xiaomei Zhang ◽  
Yujing Zuo ◽  
Weiying Lin

A series of poly(thioether)s containing silicon atom with unconventional fluorescence were synthesized via successive thiol click reaction at room temperature. Although rigid π-conjugated structure did not exist in the polymer chain, the poly(thioether)s exhibited excellent fluorescent properties in solutions and showed visible blue fluorescence in living cells. The strong blue fluorescence can be attributed to the aggregation of lone pair electron of heteroatom and coordination between heteroatom and Si atom. In addition, the responsiveness of poly(thioether) to metal ions suggested that the selectivity of poly(thioether) to Fe3+ ion could be enhanced by end-modifying with different sulfhydryl compounds. This study further explored their application in cell imaging and studied their responsiveness to Fe3+ in living cells. It is expected that the described synthetic route could be extended to synthesize novel poly(thioether)s with superior optical properties. Their application in cell imaging and ion detection will broaden the range of application of poly(thioether)s.


2016 ◽  
Vol 8 (5) ◽  
pp. 1044-1051 ◽  
Author(s):  
Xianfu Meng ◽  
Yanxia Xu ◽  
Jinliang Liu ◽  
Lining Sun ◽  
Liyi Shi

A novel fluorescent chemosensor containing two rhodamine B moieties per molecule was synthesized and characterized as an “off–on” fluorescent probe for copper ions. Live cell imaging experiments demonstrate its nontoxic nature in bioimaging intracellular Cu2+.


2019 ◽  
Vol 26 (10) ◽  
pp. 758-767
Author(s):  
Vicente Rubio ◽  
Vijaya Iragavarapu ◽  
Maciej J. Stawikowski

Background: Herein we report the multigram-scale synthesis, characterization and application of a rhodamine B-based fluorophore (ROSA) suitable for fluorescent studies in biological applications. This fluorophore is devoid of rhodamine spirolactone formation and furthermore characterized by a high molar extinction coefficient (ϵ=87250 ± 1630 M-1cm-1) and quantum yield (φ) of 0.589 ± 0.070 in water. Reported here is also the application of ROSA towards synthesis of a ROSA-PEG-GRGDS-NH2 fluorescent probe suitable for live cell imaging of αvβ3 integrins for in vitro assays. Objective: The main objective of this study is to efficiently prepare rhodamine B derivative, devoid of spirolactone formation that would be suitable for bioconjugation and subsequent bioimaging. Methods: Rhodamine B was transformed into rhodamine B succinimide ester (RhoB-OSu) using N-hydroxysuccinimide. RhoB-OSu was further coupled to sarcosine to obtain rhodamine Bsarcosine dye (ROSA) in good yield. The ROSA dye was then coupled to a αvβ3 integrin binding sequence using standard solid-phase conditions. Resulting ROSA-PEG-GRGDS-NH2 probe was used to image integrins on cancer cells. Results: The rhodamine B-sarcosine dye (ROSA) was obtained in multigram scale in good total yield of 47%. Unlike rhodamine B, the ROSA dye does not undergo pH-dependent spirolactone/spirolactam formation as compared with rhodamine B-glycine. It is also characterized by excellent quantum yield (φ) of 0.589 ± 0.070 in water and high molar extinction coefficient of 87250 ± 1630 M-1cm-1. ROSA coupling to the RGD-like peptide was proved to be efficient and straightforward. Imaging using standard filters on multimode plate reader and confocal microscope was performed. The αvβ3 integrins present on the surface of live WM-266-4 (melanoma) and MCF- 7 (breast cancer) cells were successfully imaged. Conclusion: We successfully derivatized rhodamine B to create an inexpensive, stable and convenient to use fluorescent probe. The obtained derivative has excellent photochemical properties and it is suitable for bioconjugation and many imaging applications.


2018 ◽  
Vol 15 (1) ◽  
pp. 47-55
Author(s):  
Xuebing Li ◽  
Haifen Yang ◽  
Ning Wang ◽  
Tijian Sun ◽  
Wei Bian ◽  
...  

Background: Morin has many pharmacological functions including antioxidant, anticancer, anti-inflammatory, and antibacterial effects. It is commonly used in the treatment of antiviral infection, gastropathy, coronary heart disease and hepatitis B in clinic. However, researches have shown that morin is likely to show prooxidative effects on the cells when the amount of treatment is at high dose, leading to the decrease of intracellular ATP levels and the increase of necrosis process. Therefore, it is necessary to determine the concentration of morin in biologic samples. Method: Novel water-soluble and green nitrogen and sulfur co-doped carbon dots (NSCDs) were prepared by a microwave heating process with citric acid and L-cysteine. The fluorescence spectra were collected at an excitation wavelength of 350 nm when solutions of NSCDs were mixed with various concentrations of morin. Results: The as-prepared NSCDs were characterized by transmission electron microscopy, X-ray diffraction and X-ray photoelectron spectroscopy. The fluorescence intensity of NSCDs decreased significantly with the increase of morin concentration. The fluorescence intensity of NSCDs displayed a linear response to morin in the concentration 0.10-30 μM with a low detection limit of 56 nM. The proposed fluorescent probe was applied to analysis of morin in human body fluids with recoveries of 98.0-102%. Conclusion: NSCDs were prepared by a microwave heating process. The present analytical method is sensitive to morin. The quenching process between NSCDs and morin is attributed to the static quenching. In addition, the cellular toxicity on HeLa cells indicated that the as-prepared NSCDs fluorescent probe does not show obvious cytotoxicity in cell imaging. Our proposed method possibly opens up a rapid and nontoxic way for preparing heteroatom doped carbon dots with a broad application prospect.


Author(s):  
Mahesh Gosi ◽  
Nagaraju Marepu ◽  
Yeturu Sunandamma

RSC Advances ◽  
2020 ◽  
Vol 10 (36) ◽  
pp. 21399-21405
Author(s):  
Chunwei Yu ◽  
Shuhua Cui ◽  
Yuxiang Ji ◽  
Shaobai Wen ◽  
Li Jian ◽  
...  

In this study, a naphthalene Schiff-base P which serves as a dual-analyte probe for the quantitative detection of Al3+ and Mg2+ has been designed.


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