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A 2023 study introduced 3-phosphonorhodamines, a previously unreported subset of rhodamine dyes, and found that its test compound phosTMR dissolved at 12 ± 0.6 mM in phosphate-buffered saline (PBS)—about 12 times the measured solubility of carboxyTMR and 500 times that of sulfoTMR under the same study conditions. The work also reports broadly similar photophysical properties to related rhodamines and tests phosphonorhodamine derivatives in cellular imaging, including a voltage reporter.
What the researchers made
Joshua L. Turnbull, Ryan P. Golden, Brittany R. Benlian, Katharine M. Henn, Soren M. Lipman, and Evan W. Miller reported 3-phosphonorhodamines in Chemical Science in 2023. The compounds add a phosphonate group to the rhodamine scaffold. Their paper describes the molecules as previously unreported and presents a mild, scalable way to synthesize them. Read the paper in Chemical Science.
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How the synthesis works
The route condenses aminophenols with 2-phosphonobenzaldehyde. The aldehyde’s phosphonic acid group activates it intramolecularly, so the reaction 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, often without chromatography.
For one application, the team incorporated a phosphonate into a molecular-wire voltage reporter. PhosphonoRhoVR 1 was prepared in six steps at 37% overall yield, producing more than 400 mg. The paper compares this with the previously reported synthesis of RhoVR 1, which also took six steps but gave approximately 2% overall yield.
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How much more soluble is phosTMR?
In the study’s PBS solubility measurements, phosTMR reached 12 ± 0.6 mM. The authors reported 0.9 ± 0.02 mM for carboxyTMR and 0.02 ± 0.002 mM for sulfoTMR. On those measurements, phosTMR was about 12 times as soluble as carboxyTMR and 500 times as soluble as sulfoTMR.
| Compound | Solubility in PBS reported by Turnbull et al. (2023) | Role in the study |
|---|---|---|
| phosTMR | 12 ± 0.6 mM | Phosphonorhodamine test compound |
| carboxyTMR | 0.9 ± 0.02 mM | Carboxyrhodamine comparator |
| sulfoTMR | 0.02 ± 0.002 mM | Sulforhodamine comparator |
These are comparisons in the paper’s PBS measurement conditions, not a universal ranking for every buffer, formulation, or experimental setup. The study does not establish a definitive mechanism for the solubility difference. Chemistry World relays the researchers’ suggestion that phosphonic acid’s two ionisable sites, compared with one in carboxylic and sulfonic acids, could help explain it; that remains a proposed explanation rather than a demonstrated cause. Chemistry World’s 2023 report includes the researchers’ comments.
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Does the added group change fluorescence?
The authors report that phosphonate substitution has 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. These values accompany the solubility results; the paper does not suggest that the numerical solubility advantage alone predicts brightness in every imaging context.
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The researchers esterified phosTMR to facilitate intracellular delivery. In their cellular imaging experiments, phosphonorhodamine AM esters produced localization profiles different from carboxyrhodamines, along with increased cellular brightness and improved retention compared with traditional carboxy analogues. These are reported results for the tested compounds and conditions, not a general performance guarantee for all cells or imaging protocols.
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The rationale is practical: a dye that can be prepared and handled in aqueous conditions may be useful in imaging workflows, while intracellular delivery and retention affect where signal appears and how long it remains. The study tests these properties in cellular imaging; it does not establish clinical use or regulatory approval, and it does not establish consumer availability of phosTMR.
What phosphonoRhoVR 1 adds
PhosphonoRhoVR 1 is the paper’s phosphonate-containing molecular-wire voltage reporter. Turnbull and colleagues report 37% ΔF/F voltage sensitivity and twice the cellular brightness of RhoVR 1 in their comparison. Those findings are study-specific results, not a guarantee of performance across other cells, instruments, or experimental conditions.
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| Measure | PhosphonoRhoVR 1 | RhoVR 1 comparator |
|---|---|---|
| Synthesis reported | Six steps; 37% overall yield; more than 400 mg produced | Six steps; approximately 2% overall yield, as previously reported |
| Voltage sensitivity | 37% ΔF/F reported in the study | Not stated in the supplied paper summary |
| Cellular brightness | Twice that of RhoVR 1 in the study’s comparison | Comparator baseline |
What the results do—and do not—show
The paper combines a synthetic route, aqueous solubility measurements, photophysical characterization, and cellular imaging applications. It shows that this phosphonate substitution can produce highly soluble rhodamines while retaining useful fluorescence properties in the reported measurements. The cellular experiments and voltage-reporter comparison demonstrate potential research uses, but they do not establish clinical readiness or independent replication.
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