A fluorescent probe of N′-formyl-rhodamine B hydrazide: structure and spectral properties of protonation behaviour

2012 ◽  
Vol 10 (38) ◽  
pp. 7677 ◽  
Author(s):  
Jingze Wang ◽  
Qiwu Yang ◽  
Haibin Song ◽  
Wenqin Zhang
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.


2013 ◽  
Vol 295-298 ◽  
pp. 475-478 ◽  
Author(s):  
Zhi Xiang Han ◽  
Ming Hui Du ◽  
Guo Xi Liang ◽  
Xiang Yang Wu

Rhodamine B thiohydrazide (RBS) was firstly employed as turn-on fluorescent probe for hypochlorite in aqueous solution and living cells. It exhibits a stable response to hypochlorite from 1.0×10-6to 1.0×10-5M with a detection limit of 3.3×10-7M. The response of this probe to hypochlorite is fast and highly selective compared with other reactive oxygen species (such as.OH,1O2, H2O2) and other common anions (such as X-, ClO2-, ClO4-, NO3-, NO2-, OH-, Ac-, CO32-, SO42-).


2018 ◽  
Vol 59 (42) ◽  
pp. 3756-3762 ◽  
Author(s):  
Yu Wang ◽  
Fan Song ◽  
Jing Zhu ◽  
Yuqi Zhang ◽  
Lei Du ◽  
...  

2013 ◽  
Vol 96 (1) ◽  
pp. 38-44 ◽  
Author(s):  
Chunwei Yu ◽  
Ting Wang ◽  
Ke Xu ◽  
Jing Zhao ◽  
Maohua Li ◽  
...  

2017 ◽  
Vol 9 (3) ◽  
pp. 533-540 ◽  
Author(s):  
Sheng Wang ◽  
Chengpeng Li ◽  
Li Xu ◽  
Tang Xu ◽  
Yingnian Lv ◽  
...  

2016 ◽  
Vol 390 ◽  
pp. 422-429 ◽  
Author(s):  
Donglai Peng ◽  
Bin Hu ◽  
Mengmeng Kang ◽  
Minghua Wang ◽  
Linghao He ◽  
...  

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