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A 2023 study introduced 3-phosphonorhodamines, a new subset of rhodamine dyes, and found that its test compound phosTMR dissolved in phosphate-buffered saline (PBS) at 12 ± 0.6 mM. Under the study’s measurement conditions, that was about 12 times the solubility of carboxyTMR and 500 times that of sulfoTMR. The researchers also reported cellular-imaging applications and a phosphonate-containing voltage reporter, while the chemical reason for the solubility increase remains uncertain.
What are 3-phosphonorhodamines?
Rhodamines are fluorescent dyes used in chemical and biological imaging. Joshua L. Turnbull, Ryan P. Golden, Brittany R. Benlian, Katharine M. Henn, Soren M. Lipman and Evan W. Miller reported 3-phosphonorhodamines as a previously unreported rhodamine subset in a 2023 paper in Chemical Science, volume 14, pages 11365–11373. The study focused on adding a phosphonate group, then measuring how that change affected synthesis, solubility and imaging behavior. Read the paper in Chemical Science.
How did the researchers make them?
The synthesis condenses aminophenols with 2-phosphonobenzaldehyde. The phosphonic acid group activates the aldehyde within the reacting molecule, so the route does not require an added acid catalyst. The authors report making tetramethyl-3-phosphonorhodamine derivatives on a 1.5 mmol scale in up to 98% yield over two steps; many products were obtained without chromatography.
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How much more soluble is phosTMR?
In the paper’s PBS measurements, phosTMR reached 12 ± 0.6 mM. The corresponding values were 0.9 ± 0.02 mM for carboxyTMR and 0.02 ± 0.002 mM for sulfoTMR. The authors summarize these results as roughly 12-fold higher solubility than carboxyTMR and 500-fold higher than sulfoTMR.
| Dye | Solubility in PBS, as reported by Turnbull et al. (2023) | Context |
|---|---|---|
| phosTMR | 12 ± 0.6 mM | Phosphonate-substituted test dye |
| carboxyTMR | 0.9 ± 0.02 mM | Carboxy analogue comparator |
| sulfoTMR | 0.02 ± 0.002 mM | Sulfo analogue comparator |
These are comparisons for the named compounds under the paper’s PBS measurement conditions, not a universal ranking in every solvent, buffer or formulation. The authors’ report does not establish a proven molecular mechanism for the difference. Chemistry World relays the researchers’ suggestion that phosphonic acid’s two ionisable sites, compared with one for carboxylic and sulfonic acids, could help account for the greater solubility; that remains a possible explanation rather than a demonstrated cause. Chemistry World’s report also quotes organic chemist Colleen Scott saying, “There is a deficiency in water soluble emissive dyes for cellular imaging and the incorporation of the phosphate group, to increase the water solubility in the dyes, is beneficial to the field.”
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Did phosphonate substitution change fluorescence?
The authors report that phosphonate substitution had little effect on photophysical properties. For phosTMR in PBS, they measured absorption and emission maxima of 546 nm and 564 nm, respectively, and a quantum yield of 0.52.
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1Repair Windows errors before they cause bigger problems2Fix the driver behind crashes, sound loss and screen glitches3Clear out junk files and repair common Windows errors| phosTMR measurement in PBS | Reported value |
|---|---|
| Absorption maximum | 546 nm |
| Emission maximum | 564 nm |
| Quantum yield | 0.52 |
These figures describe phosTMR in the stated buffer; they should not be taken as measurements for every dye in the family or every imaging environment.
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- This item will be vacuum packed in a bag when posting in order to maintain original appearance;
- This material is widely used in laboratory research experiments feld as fluorescent dye, staining and as dyeing material in textile industry areas etc.
What did the study show in cellular imaging?
The researchers tested esterified phosTMR derivatives for cellular imaging. Esterification facilitated intracellular delivery, and the resulting dyes showed localization profiles that differed from carboxyrhodamines. In the experiments reported, phosphonorhodamine AM esters also produced increased cellular brightness and improved retention compared with traditional carboxy analogues.
Higher water solubility can be useful in imaging because excess unreacted dye may be easier to wash away, potentially reducing fluorescent background. It is not, by itself, proof that a dye will perform better in every cell type or protocol. The study reports experimental cellular imaging results, not clinical use or independent replication. Miller described the rationale to Chemistry World this way: “Our hope is that by washing away the unreacted dye, the experiment becomes more like turning on a flashlight at night-time – the protein of interest is very noticeable. If you can’t wash away excess dye, the experiment is more like turning on a flashlight during the day – hard to pick out from the background.”
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What is phosphonoRhoVR 1 used for?
PhosphonoRhoVR 1 is a phosphonate-containing molecular-wire voltage reporter designed for imaging changes in cellular membrane voltage. The authors made it in six steps at 37% overall yield, producing more than 400 mg. They compare that route with the earlier RhoVR 1 synthesis, which also took six steps but gave approximately 2% overall yield.
| Voltage reporter | Synthesis reported | Imaging result reported |
|---|---|---|
| PhosphonoRhoVR 1 | Six steps; 37% overall yield; more than 400 mg produced | 37% ΔF/F voltage sensitivity; twice the cellular brightness of RhoVR 1 |
| RhoVR 1 comparator | Six steps; approximately 2% overall yield in the earlier synthesis cited by the authors | Baseline for the reported brightness comparison; a comparable voltage-sensitivity value is not stated in the study summary |
The 37% ΔF/F sensitivity and twofold brightness difference are results reported for this study’s reporter and comparator, not general performance guarantees for other probes or experiments.
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- We are providing 25 grams Rhodamine B powder. Approx. 0.88 oz;
- Purity: 99%; Molecular: 479.01 g/mol; CAS: 81-88-9; Molecular Formula: C28H31ClN2O3;
- Solubility: Soluble in water; Appearance: Reddish brown or dark green crystalline Powder;
- This item will be vacuum packed in a bag when posting in order to maintain original appearance;
- This material is widely used in laboratory research experiments feld as fluorescent dye, staining and as dyeing material in textile industry areas etc.
What the findings establish—and what they do not
- The study introduced 3-phosphonorhodamines and reported a synthesis using intramolecular aldehyde activation.
- In PBS, the measured solubility of phosTMR substantially exceeded that of the specific carboxyTMR and sulfoTMR comparators.
- The reported phosTMR photophysical measurements show that high solubility was achieved alongside fluorescence properties the authors describe as little changed by phosphonate substitution.
- Cellular delivery, localization, brightness and retention were tested using esterified dyes; the voltage-reporter findings concern phosphonoRhoVR 1 in the reported experiments.
- The study is laboratory chemistry and imaging research. It does not establish clinical readiness, regulatory approval, consumer availability or independent replication.
Miller told Chemistry World, “No one had made these compounds before. And we were surprised because it seems like an obvious modification to try. One of the joys of science is making – or describing or uncovering – something that no one else has done before.”
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