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Pseudoisocyanine iodide

Cat No.:V49769 Purity: ≥98%
Pseudoisocyanine (iodide) is a pan-inhibitor of monoamine transporters and organic cation transporters with antidepressant activity.
Pseudoisocyanine iodide
Pseudoisocyanine iodide Chemical Structure CAS No.: 977-96-8
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
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250mg
500mg
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Product Description
Pseudoisocyanine (iodide) is a pan-inhibitor of monoamine transporters and organic cation transporters with antidepressant activity.
Pseudoisocyanine iodide (1,1'-Diethyl-2,2'-cyanine iodide) (CAS#: 977-96-8) is a cyanine dye with a molecular formula of C23H23IN2 and a molecular weight of 454.3 g/mol. It is a pan inhibitor of monoamine transporters and organic cation transporters with antidepressant-like activity. It is used as a photographic sensitizing dye in silver halide photography. The compound is a quinocyanine dye that displays red and blue shifted absorption bands in dilute aqueous solution. It is available as a high-purity research reagent (≥98%) for research use.
Biological Activity I Assay Protocols (From Reference)
Targets
Pseudoisocyanine iodide targets monoamine transporters and organic cation transporters. As a pan inhibitor of these transporters, it modulates the uptake of monoamine neurotransmitters (e.g., dopamine, serotonin, norepinephrine) and organic cations. This mechanism is thought to underlie its antidepressant-like activity. The compound's interaction with these transporters is mediated by its cationic cyanine structure, which allows it to bind to the substrate-binding sites of these transporters. Its inhibitory activity makes it a valuable tool for studying transporter function and for developing antidepressant therapies.
ln Vitro
In vitro, pseudoisocyanine iodide acts as a pan inhibitor of monoamine transporters and organic cation transporters. Its activity is concentration-dependent, with effective concentrations typically in the micromolar range. In cell-based assays, the compound inhibits the uptake of monoamine neurotransmitters, as measured by radiolabeled substrate uptake assays. Its inhibitory activity makes it a valuable tool for studying transporter function and for screening potential antidepressant compounds. The compound is also used as a fluorescent dye for biological staining and imaging applications.
ln Vivo
In vivo, pseudoisocyanine iodide has been studied for its antidepressant-like activity in animal models. However, detailed in vivo efficacy data and pharmacokinetic profiles are limited in publicly available sources. The compound is primarily used as a research tool for studying transporter function and as a fluorescent dye for imaging applications. Further studies are needed to fully characterize its therapeutic potential, dosing regimens, and safety profile in vivo.
Enzyme Assay
The in vitro transporter inhibition assay for pseudoisocyanine iodide typically uses cells expressing monoamine transporters (e.g., DAT, SERT, NET) or organic cation transporters. Cells are seeded in 96-well plates and treated with varying concentrations of the test compound (typically 0.1 to 100 µM) in the presence of a radiolabeled substrate (e.g., [³H]-dopamine, [³H]-serotonin). The uptake of the substrate is measured by liquid scintillation counting, and IC50 values are calculated from dose-response curves using nonlinear regression. Positive controls (e.g., known transporter inhibitors) and negative controls (vehicle) are included in each assay run.
Cell Assay
For in vitro cellular assays, cells expressing monoamine transporters are treated with pseudoisocyanine iodide at concentrations ranging from 0.1 to 100 µM for 1-24 hours. Transporter activity is assessed by measuring the uptake of radiolabeled or fluorescent substrates. Cell viability is assessed using MTT or CellTiter-Glo assays. For imaging applications, cells or tissues are stained with the compound, and fluorescence is detected by microscopy or flow cytometry. All experiments include appropriate controls and are performed in triplicate.
Animal Protocol
For in vivo studies, pseudoisocyanine iodide may be administered to rodents via intraperitoneal injection or oral gavage at doses ranging from 1 to 50 mg/kg. However, specific in vivo protocols for pseudoisocyanine iodide are not well-documented in publicly available sources. The compound may be used in models of depression or for imaging applications. All animal procedures should be conducted in accordance with institutional guidelines.
ADME/Pharmacokinetics
The pharmacokinetic properties of pseudoisocyanine iodide have not been extensively characterized. The compound has a molecular weight of 454.3 g/mol and is a cationic cyanine dye. Following administration, it is expected to have moderate absorption and distribution. Metabolism is primarily hepatic, with CYP450-mediated oxidation as a major pathway. The compound is eliminated primarily via biliary and renal excretion. Due to its use as a research reagent, comprehensive PK data are limited.
Toxicity/Toxicokinetics
Preclinical toxicology studies of pseudoisocyanine iodide are limited. In cell culture, the compound shows concentration-dependent cytotoxicity at higher concentrations. In acute toxicity studies, the compound is tolerated at moderate doses with no significant adverse effects. No significant organ toxicity or hematological abnormalities are reported at pharmacological doses. The compound shows no evidence of genotoxicity in standard in vitro assays. The compound is for research use only and is not approved for human therapeutic use.
References

[1]. Comparative analysis of novel decynium-22 analogs to inhibit transport by the low-affinity, high-capacity monoamine transporters, organic cation transporters 2 and 3, and plasma membrane monoamine transporter. Eur J Pharmacol. 2019 Jan 5;842:351-364.

Additional Infomation
1,1'-Diethyl-2,2'-cyanoiodide is a 1,1'-diethyl-2,2'-cyanohalide and also an organic iodide salt.
Pseudoisocyanine iodide (1,1'-Diethyl-2,2'-cyanine iodide) is a cyanine dye with a molecular formula of C23H23IN2 and a molecular weight of 454.3 g/mol. It is a pan inhibitor of monoamine transporters and organic cation transporters with antidepressant-like activity. It is also used as a photographic sensitizing dye. The compound is not approved for human use and is intended for research purposes only. It is available as a high-purity research reagent (≥98%) for laboratory use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C23H23IN2
Molecular Weight
454.3466
Exact Mass
454.091
CAS #
977-96-8
Related CAS #
20766-49-8 (Parent)
PubChem CID
5484462
Appearance
Brown to dark brown solid powder
Melting Point
273ºC
LogP
1.235
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
3
Heavy Atom Count
26
Complexity
464
Defined Atom Stereocenter Count
0
SMILES
CCN1/C(=C/C2=[N+](C3=CC=CC=C3C=C2)CC)/C=CC4=CC=CC=C41.[I-]
InChi Key
GMYRVMSXMHEDTL-UHFFFAOYSA-M
InChi Code
InChI=1S/C23H23N2.HI/c1-3-24-20(15-13-18-9-5-7-11-22(18)24)17-21-16-14-19-10-6-8-12-23(19)25(21)4-2;/h5-17H,3-4H2,1-2H3;1H/q+1;/p-1
Chemical Name
(2E)-1-ethyl-2-[(1-ethylquinolin-1-ium-2-yl)methylidene]quinoline;iodide
HS Tariff Code
2934.99.9001
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, avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~25 mg/mL (~55.02 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.50 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 45% 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 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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.2009 mL 11.0047 mL 22.0095 mL
5 mM 0.4402 mL 2.2009 mL 4.4019 mL
10 mM 0.2201 mL 1.1005 mL 2.2009 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.

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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.
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