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.
Objectives: 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.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.2174/0929866526666190619110430 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Green-synthesized silver nanoparticle-enhanced nanofiltration mixed matrix membranes for high-performance water purification.
Sci Rep
January 2025
College of Resource and Civil Engineering, Northeast University, Shenyang, China.
This study presents the fabrication and characterization of mixed matrix membranes (MMMs) incorporating green-synthesized silver nanoparticles (AgNPs) using Hibiscus Rosa sinensis extract within a polyethersulfone (PES) matrix for nanofiltration (NF) application. The membranes were evaluated for their pure water permeability, salt rejection, dye removal, and antifouling performance. Results showed that the membrane with 0.
View Article and Find Full Text PDFValorization of agro-industrial wastes of sugarcane bagasse and rice husk for biosorption of Yellow Tartrazine dye.
An Acad Bras Cienc
December 2024
State University of Maringá, Sustainability Graduate Program, Avenida Ângelo Moreira da Fonseca, 1800, Parque Danielle, 87506-370 Umuarama, PR, Brazil.
The use of agro-industrial wastes as biosorbents is a promising alternative for sustainable, economical and effective adsorption. However, few studies evaluate the use of Brazilian agro-industrial waste as biosorbents without physicochemical pre-treatment. This study explored the potential of sugarcane bagasse (SCB) and rice husk waste (RHW) as low-cost biosorbents for yellow tartrazine dye removal.
View Article and Find Full Text PDFInclusion of Cationic Amphiphilic Peptides in Fmoc-FF Generates Multicomponent Functional Hydrogels.
ACS Appl Bio Mater
January 2025
Department of Pharmacy and Interuniversity Research Centre on Bioactive Peptides "Carlo Pedone" (CIRPeB), University of Naples "Federico II", Via T. De Amicis 95, Naples 80145, Italy.
Article Synopsis
- Peptide building blocks can create supramolecular nanostructures that effectively deliver various drugs while their design impacts the ability of these structures to interact with specific drugs.
- The study focuses on hybrid cationic peptide hydrogels, combining a low-molecular-weight hydrogelator with different cationic amphiphilic peptides to analyze their structural properties.
- Findings indicate that the hydrogel's structure is primarily determined by the hydrogelator, while the peptides' alkyl chain lengths significantly influence the material's morphology, stiffness, and drug encapsulation capabilities.
Leveraging the Aggregated Protein Dye YAT2150 for Malaria Chemotherapy.
Pharmaceutics
September 2024
Barcelona Institute for Global Health (ISGlobal), Hospital Clínic-Universitat de Barcelona, Rosselló 149-153, 08036 Barcelona, Spain.
Article Synopsis
- YAT2150 is a new antimalarial drug that shows promise for malaria treatment and diagnosis by increasing fluorescence upon entering cells and blocking key developmental stages in malaria pathogens.
- The drug's effective uptake mechanisms and favorable pharmacokinetics make it a strong candidate for enhancing transmission-blocking strategies, especially when used in conjunction with immunoliposome encapsulation to reduce toxicity.
- YAT2150 interacts preferentially with unstructured proteins in parasites, which may lead to decreased protein aggregation, a mechanism also seen with traditional antimalarial treatments, positioning it as a potential leader in innovative malaria therapies.
Red-emissive carbon dots from Hibiscus rosa-sinensis: a detailed appraisal of tartrazine dye sensing properties.
Mikrochim Acta
October 2024
Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh, 160014, India.
An economically viable and greener approach is introduced to fabricate red emissive carbon dots (R@CQDs) via employing hydrothermal means on Hibiscus rosa-sinensis leaves as precursor source. The obtained R@CQDs displayed excitation-dependent behavior, with high aqueous stability, quantum yield of 56%, and outstanding fluorescence aptitude under the conditions of varied range of ionic strength and pH (1-12). The fluorescence emission behavior of R@CQDs displayed selective turn off fluorescence response to tartrazine over other interfering species with a limit of detection of 0.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!