| Size | Price | Stock | Qty |
|---|---|---|---|
| 50mg |
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| 100mg | |||
| Other Sizes |
| Targets |
3,3'-Dihexyloxacarbocyanine iodide (DiOC6(3)) targets cellular membranes, specifically the endoplasmic reticulum (ER) and mitochondria, depending on the concentration used. At high concentrations, the dye accumulates in the ER and has been used to visualize ER in moss, yeast, and muscle cells. At low concentrations, it accumulates in mitochondria and has been used to assess mitochondrial dislocations, fusion, and fission in living cells. The dye's lipophilic cationic nature allows it to partition into membrane bilayers and respond to membrane potential changes.
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| ln Vitro |
When cells are added to cuvettes containing 0.25 μM 3,3'-dihexyloxycarbocyanine iodide (DiOCg(3)), the fluorescence increases and equilibration happens quickly—it takes 4 minutes to finish. There is a 5-second lag phase when f-met-leu-phe (10-7 M) is added to neutrophils that have been pre-equilibrated with 3,3'-Dihexyloxacarbocyanine iodide. Fluorescence quickly vanishes following the lag phase. Fluorescence microscopy analysis of 3,3'-dihexyloxycarbocyanine iodide-loaded neutrophils revealed that the strongest fluorescence in resting neutrophils is linked to elongated organelles, which are equivalent to mitochondria. distribution [1].
In vitro, 3,3'-Dihexyloxacarbocyanine iodide (DiOC6(3)) is used to monitor changes in mitochondrial membrane potential. When cells are added to a cuvette containing 0.25 microM DiOC6(3), there is a rapid increase in fluorescence that equilibrates and is complete within 4 minutes. The dye's fluorescence intensity correlates with mitochondrial membrane potential, with higher fluorescence indicating more negative membrane potential. The compound has been used to visualize ER in moss, yeast, and muscle cells at high concentrations. It is also used to assess mitochondrial dynamics including dislocations, fusion, and fission in living cells. |
| ln Vivo |
In vivo applications of 3,3'-Dihexyloxacarbocyanine iodide are primarily related to its use as a fluorescent tracer and vital dye. The compound has been used to visualize ER in various organisms including moss and yeast. While the dye is primarily used in in vitro and ex vivo applications, it may be used in whole-organism imaging studies where its fluorescence properties allow visualization of cellular structures. The compound's use as a vital dye makes it valuable for studying cellular dynamics in living systems, though its application is typically limited to short-term imaging studies due to potential phototoxicity and dye efflux.
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| Enzyme Assay |
The in vitro fluorescence assay for 3,3'-Dihexyloxacarbocyanine iodide does not involve enzyme/receptor binding in the traditional sense, as the compound is a fluorescent dye rather than a drug targeting a specific protein. The assay involves incubating cells or isolated organelles with DiOC6(3) and measuring fluorescence intensity. Typically, cells are incubated with 0.25 microM DiOC6(3) in buffer or culture medium at 37degC for 4-30 minutes, after which fluorescence is measured using a fluorometer or flow cytometer with excitation at 484 nm and emission at 501 nm. For mitochondrial membrane potential measurements, cells are treated with DiOC6(3) and fluorescence is monitored over time.
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| Cell Assay |
In vitro cellular assays for 3,3'-Dihexyloxacarbocyanine iodide typically involve staining cells in suspension or adherent cultures. Cells are harvested and resuspended in buffer or culture medium at a concentration of 1-5 × 10⁶ cells/mL. DiOC6(3) is added at a final concentration of 0.1-1.0 microM, and cells are incubated at 37degC for 4-30 minutes in the dark. After incubation, cells are washed to remove excess dye and fluorescence is measured by flow cytometry (FL1 channel) or fluorescence microscopy. For mitochondrial membrane potential studies, cells may be treated with ionophores such as carbonyl cyanide m-chlorophenyl hydrazone (CCCP) as a positive control for membrane potential dissipation. Fluorescence intensity is proportional to membrane potential.
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| Animal Protocol |
In vivo animal studies for 3,3'-Dihexyloxacarbocyanine iodide are limited as the compound is primarily a research dye used for in vitro and ex vivo applications. When used in animal models, the dye may be administered by intravenous injection or local application to visualize specific tissues or cellular structures. The compound has been used to visualize ER in moss, yeast, and muscle cells. Its use in whole-animal imaging is limited by its lipophilic nature, rapid clearance, and potential phototoxicity. Standard protocols involve administration of the dye at concentrations of 0.1-1.0 mg/kg followed by imaging at various time points. The dye's fluorescence properties (Ex/Em = 484/501 nm) allow detection using standard fluorescence imaging systems.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 3,3'-Dihexyloxacarbocyanine iodide (DiOC6(3)) are characteristic of a lipophilic cationic dye. The compound has a molecular weight of 572.52 and a molecular formula of C29H37IN2O2. It is soluble in DMF, DMSO, and ethanol at 30 mg/mL. The compound is a crystalline solid with a purity of ≥98%. It should be stored at -20degC and shipped at room temperature. The dye's lipophilic nature allows it to partition into membrane bilayers, and its fluorescence is sensitive to membrane potential. Detailed ADME parameters are not documented as the compound is primarily used as a research dye rather than a therapeutic agent.
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| Toxicity/Toxicokinetics |
The toxicological profile of 3,3'-Dihexyloxacarbocyanine iodide (DiOC6(3)) is characteristic of fluorescent dyes used in biological research. As a lipophilic cationic dye, it can accumulate in mitochondria and affect mitochondrial function at high concentrations. The compound is for research use only and is not intended for human therapeutic or diagnostic use. Standard safety precautions should be followed when handling the dye, including the use of appropriate personal protective equipment. Potential toxicity includes phototoxicity due to the generation of reactive oxygen species upon light exposure, and mitochondrial dysfunction at high concentrations. No specific LD50 values have been reported in the available literature.
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| References | |
| Additional Infomation |
See also: 3,3'-dihexyl-2,2'-oxacarbazine (note moved to).
3,3'-Dihexyloxacarbocyanine iodide (CAS 53213-82-4) is also known as DiOC6(3) and NK 2280. It is a carbocyanine dye with excitation and emission spectra of 484/501 nm. At high concentrations, DiOC6(3) accumulates in the endoplasmic reticulum and has been used to visualize ER in moss, yeast, and muscle cells. At low concentrations, it accumulates in mitochondria and has been used to assess mitochondrial dynamics including dislocations, fusion, and fission in living cells. The compound is a lipophilic fluorescent dye that can be used to monitor changes in mitochondrial membrane potential. It is available for research purposes only. |
| Molecular Formula |
C29H37N2O2+.I-
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|---|---|
| Molecular Weight |
572.52028
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| Exact Mass |
572.19
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| CAS # |
53213-82-4
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| PubChem CID |
5702702
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| Appearance |
Orange to red solid powder
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| Melting Point |
219-221 °C(lit.)
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| LogP |
4.207
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
12
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| Heavy Atom Count |
34
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| Complexity |
581
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCCCCCN\1C2=CC=CC=C2O/C1=C\C=C\C3=[N+](C4=CC=CC=C4O3)CCCCCC.[I-]
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| InChi Key |
XVLXYDXJEKLXHN-UHFFFAOYSA-M
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| InChi Code |
InChI=1S/C29H37N2O2.HI/c1-3-5-7-13-22-30-24-16-9-11-18-26(24)32-28(30)20-15-21-29-31(23-14-8-6-4-2)25-17-10-12-19-27(25)33-29;/h9-12,15-21H,3-8,13-14,22-23H2,1-2H3;1H/q+1;/p-1
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| Chemical Name |
(2Z)-3-hexyl-2-[(E)-3-(3-hexyl-1,3-benzoxazol-3-ium-2-yl)prop-2-enylidene]-1,3-benzoxazole;iodide
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~33.33 mg/mL (~58.22 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (4.37 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (4.37 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.7467 mL | 8.7333 mL | 17.4666 mL | |
| 5 mM | 0.3493 mL | 1.7467 mL | 3.4933 mL | |
| 10 mM | 0.1747 mL | 0.8733 mL | 1.7467 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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