| Field | Specification |
|---|---|
| Alternative names | DiOC2(3) |
| CAS no. | |
| Applications | |
| Molecular weight | |
| Molecular formula | C21H21IN2O2 |
| Purity | |
| SMILES | |
| Form | Solid |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
3,3'-Diethyloxacarbocyanine iodide (DiOC2(3)) is a fluorescent probe used for microviscosity detection, micelle and microemulsion probing, critical micelle concentration determination, photophysical property research, and assessment of bacterial membrane potential. Its excitation wavelength is 355 nm[1][2][3]. It is supplied as a purplish red to red solid (C21H21IN2O2, MW 460.31) at 99.42% purity.
Physical & Chemical Properties
| CAS Number | 905-96-4 |
|---|---|
| Molecular Formula | C21H21IN2O2 |
| Molecular Weight | 460.31 g/mol |
| Purity | 99.42% |
| Appearance | Solid |
| Color | Purplish red to red |
| SMILES | CCN1C2=C(C=CC=C2)O/C1=C/C=C/C(OC3=C4C=CC=C3)=[N+]4CC.[I-] |
| Solubility | In Vitro: DMSO: 16.67 mg/mL (36.21 mM; Requires sonication; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO) |
| Storage | Powder: -20°C, 3 years; 4°C, 2 years. In solvent: -80°C, 6 months; -20°C, 1 month. |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
[1]. Basu S, Mondal S, Mandal D. 3, 3′-Diethyloxacarbocyanine iodide: a new microviscosity probe for micelles and microemulsions[J]. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2010, 363(1-3): 41-48.
[2]. Oliveira A S, et al. Photophysics of oxacyanine dyes on surfaces. Re-examination of the origins of the ‘new emission’observed with laser excitation and high concentrations of adsorbed dyes[J]. Journal of the Chemical Society, Faraday Transactions, 1996, 92(23): 4809-4814.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with the Safety Data Sheet and your institution's chemical hygiene plan.
In Vitro
| Solvent | Solubility | Notes |
|---|---|---|
| DMSO | 16.67 mg/mL (36.21 mM) | requires sonication; use freshly opened DMSO (absorbed moisture lowers solubility) |
Aliquot the stock solution and store it at -80°C (up to 6 months) or -20°C (up to 1 month); avoid repeated freeze-thaw cycles.
In Vivo
Choose the formulation that suits the animal model and route of administration; percentages are volume ratios of the final working solution. Start from a clear DMSO stock (see In Vitro above), add the co-solvents one at a time in the order listed, mixing after each addition, and prepare the working solution fresh on the day of dosing. If precipitation or phase separation occurs, gentle warming or sonication can help.
Protocol 1
| Composition | 10% DMSO + 90% (20% SBE-β-CD in saline) |
|---|---|
| Result | ≥ 2.08 mg/mL (4.52 mM); clear solution |
| How to prepare | Gives a clear solution at ≥ 2.08 mg/mL (saturation not determined). For 1 mL of working solution: add 100 μL DMSO stock (20.8 mg/mL) to 900 μL 20% SBE-β-CD in saline. 20% SBE-β-CD in saline: dissolve 2 g SBE-β-CD powder in 10 mL saline until clear (4°C, store up to one week). |
Data provided by the manufacturer.
In Vitro
Guide (This recommended protocol is for guidance only; modify it according to specific needs). 1. Stock Solution Preparation 1.1 Solvent: spectroscopic-grade monohydroxy alcohols, triply distilled water, n-heptane, a 9:1 (v/v) mixture of iso-octane/1-hexanol, or PBS. 1.2 Recommended concentration: from 0.005 μM g-1 up to 25.0 μM g-1, or alternatively 30 mM. 2. Working Solution Preparation 2.1 Diluent: spectroscopic-grade monohydroxy alcohols, triply distilled water, AOT at 0.09 M in n-heptane, CTAB at 0.05 M in a 9:1 (v/v) mixture of iso-octane/1-hexanol, or PBS. 2.2 Working concentration is 30 μM. 2.3 Note: adjust the working concentration as needed and prepare fresh before use. 3. Staining Procedure 3.1 Sample types 3.1.1 Supramolecular assemblies (micelles and microemulsions)[1]: 3.1.1.1 Aqueous micelles: use CTAB, SDS, TX-100, or Pluronic F-68 at the specified concentrations. 3.1.1.2 Reverse microemulsions: prepare with AOT at 0.09 M in n-heptane (w = [H2O]/[AOT] from 0 to 10) or CTAB at 0.05 M in a 9:1 (v/v) mixture of iso-octane/1-hexanol (w = [H2O]/[CTAB] from 5 to 40). 3.1.2 Microcrystalline cellulose powder[2]: 3.1.3 Bacterial cell suspension (E. coli MDR ESBL)[3]: 3.1.3.1 Use a bacterial suspension at 2.5 × 106 CFU mL-1; no centrifugation step is specified. 3.2 Incubation conditions 3.2.1 Supramolecular assemblies (micelles and microemulsions)[1]: incubate at 22°C. 3.2.2 Microcrystalline cellulose powder[2]: air-equilibrate the samples unless otherwise specified. 3.2.3 Bacterial cell suspension (E. coli MDR ESBL)[3]: incubate in 30 μM DiOC2(3) for 1 h at 37°C. 3.3 Washing steps 3.3.1 Microcrystalline cellulose powder[2]: not applicable. 3.3.2 Bacterial cell suspension (E. coli MDR ESBL)[3]: no washing steps specified. 4. Controls 4.1 Use untreated (polarized) bacterial cells as the negative control. 4.2 Use bacterial cells treated with 5 mM carbonyl cyanide CCCP as the positive control (fully depolarized state). 5. Detection & Analysis 5.1 Instruments: fluorimeter, TCSPC (time-correlated single photon counting) setup, spectrophotometer, steady-state fluorescence spectrometer, laser-excited fluorescence spectrometer, a diffuse reflectance laser flash photolysis system, or a flow cytometer. 5.2 Ex/Em wavelengths 5.3 Result analysis 5.3.1 Supramolecular assemblies (micelles and microemulsions)[1]: fluorescence intensity and lifetime rise as solvent/microenvironment viscosity increases. 5.3.2 Microcrystalline cellulose powder[2]: 5.3.2.1 Fluorescence intensity falls as dye loading concentration rises; laser-excited fluorescence intensity rises as laser fluence increases. 5.3.2.2 The dye adsorbs on the surface of microcrystalline cellulose. 5.3.2.3 DOCI forms H (hypsochromically shifted absorption) and J (bathochromically shifted absorption) aggregates at concentrations >10 μM g-1; samples at high concentration show fluorescence distortion from aggregate reabsorption. 5.3.3 Bacterial cell suspension (E. coli MDR ESBL)[3]: 5.3.3.1 Evaluate membrane potential from the ratio of red/green fluorescence signals. 5.3.3.2 A reduced red/green fluorescence ratio indicates bacterial membrane depolarization. 5.3.3.3 The positive control (CCCP-treated cells) shows a fully depolarized state with an altered red/green fluorescence ratio. 5.3.3.4 Treated cells with dissipated membrane potential show a changed red/green fluorescence ratio similar to the positive control.
Data provided by the manufacturer.
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