Synthesis and Study of Fluorescent Probe Molecules Based on Rhodamine Class B Derivatives

In this paper, a fluorescent probe based on a rhodamine spirolactam ring was designed and synthesized. Rhodamine derivatives not only have excellent chemical and optical-physical properties, but also the "OFF-ON" characteristic of the rhodamine spiroamide ring allows specific recognition and response to metal ions. In this paper, Rh-DCP, a rhodamine B derivative with a spirolactam ring, was synthesized by the Schiff base reaction and the effects of pH, time and temperature on this probe were tested.

A novel fluorescent probe of aluminum ions based on rhodamine derivatives and its application in biological imaging

With the rapid development of fluorescence detection technology, people have put forward higher requirements for probes. Based on this, we designed and synthesized the probe RBJF, which has high selectivity...

A Fluorescent Polyurethane with Covalently Cross-Linked Rhodamine Derivatives

Rhodamine derivatives (RDs) with three reactive hydrogens were synthesized and well characterized by Fourier transform infra-red spectroscopy (FTIR), 1H nuclear magnetic resonance (1H NMR) and electrospray ionization mass spectra (ESI mass). Then, the obtained RD was covalently cross-linked into polyurethane (PU) matrix through chemical linkages to fabricate a network structure, and the fluorescent properties, mechanical properties, thermal stability, and emulsion particle size were systematically investigated. Results demonstrate that PU-RD maintains initial fluorescent properties and emits desirable yellow fluorescence under ultraviolet irradiation. Moreover, compared with linear PU without fluorescers, PU-RD shows clearly improved mechanical properties and thermal stability, on account of the formed network structures.

Comparison of Chemotherapeutic Activities of Rhodamine-Based GUMBOS and NanoGUMBOS

Rhodamine derivatives have been widely investigated for their mitochondrial targeting and chemotherapeutic properties that result from their lipophilic cationic structures. In previous research, we have found that conversion of Rhodamine 6G into nanoGUMBOS, i.e., nanomaterials derived from a group of uniform materials based on organic salts (GUMBOS), led to selective chemotherapeutic toxicity for cancer cells over normal cells. Herein, we investigate the chemotherapeutic activity of GUMBOS derived from four different rhodamine derivatives, two bearing an ester group, i.e., Rhodamine 123 (R123) and SNAFR-5, and two bearing a carboxylic acid group, i.e., rhodamine 110 (R110) and rhodamine B (RB). In this study, we evaluate (1) relative hydrophobicity via octanol–water partition coefficients, (2) cytotoxicity, and (3) cellular uptake in order to evaluate possible structure–activity relationships between these different compounds. Intriguingly, we found that while GUMBOS derived from R123 and SNAFR-5 formed nanoGUMBOS in aqueous medium, no distinct nanoparticles are observed for RB and R110 GUMBOS. Further investigation revealed that the relatively high water solubility of R110 and RB GUMBOS hinders nanoparticle formation. Subsequently, while R123 and SNAFR-5 displayed selective chemotherapeutic toxicity similar to that of previously investigated R6G nanoGUMBOS, the R110 and RB GUMBOS were lacking in this property. Additionally, the chemotherapeutic toxicities of R123 and SNAFR-5 nanoGUMBOS were also significantly greater than R110 and RB GUMBOS. Observed results were consistent with decreased cellular uptake of R110 and RB as compared to R123 and SNAFR-5 compounds. Moreover, these results are also consistent with previous observations that suggest that nanoparticle formation is critical to the observed selective chemotherapeutic properties as well as the chemotherapeutic efficacy of rhodamine nanoGUMBOS.