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| Targets |
4-Bromoisoquinoline exhibits selective inhibition of cAMP-dependent protein kinase (PKA). PKA is a key enzyme involved in numerous cellular signaling pathways, including regulation of glycogen, sugar, and lipid metabolism. The compound's isoquinoline scaffold is a privileged structure in drug discovery, found in many bioactive molecules. The bromine substituent provides a handle for further functionalization via cross-coupling reactions. However, 4-Bromoisoquinoline itself is primarily a chemical intermediate rather than a drug, and its biological target characterization is limited to its PKA inhibitory activity.
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| ln Vitro |
In vitro, 4-Bromoisoquinoline shows selective inhibition of cAMP-dependent protein kinase. This activity makes it a useful tool compound for studying PKA-mediated signaling pathways. The compound is also used as a building block in the synthesis of C4-substituted isoquinolines, which have been evaluated for cytotoxic action. However, detailed in vitro pharmacological data, including IC₅₀ values for PKA inhibition or cytotoxicity profiles in various cell lines, are not well documented. As a chemical reagent, its primary in vitro utility is in synthetic chemistry rather than biological activity screening.
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| ln Vivo |
4-Bromoisoquinoline is not a pharmacologically active drug and does not exhibit in vivo therapeutic activity. It has not been evaluated in animal models for efficacy against any disease. The compound is used exclusively as a chemical intermediate and research reagent in organic synthesis and medicinal chemistry. Any in vivo activity would be associated with drug candidates synthesized from this intermediate, not with the compound itself. The compound is not administered to animals in pharmacological studies and has no known physiological effects. Its role is strictly chemical—providing a versatile building block for constructing complex molecules.
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| Enzyme Assay |
In vitro enzyme assays for 4-Bromoisoquinoline typically involve PKA inhibition studies. A standard protocol uses purified PKA catalytic subunit incubated with a peptide substrate (e.g., Kemptide) and [γ-³²P]-ATP in the presence of varying concentrations of the test compound. Reactions are carried out in kinase buffer at 30°C for 10-30 minutes. Phosphorylated substrate is captured on phosphocellulose paper, washed, and quantified by scintillation counting. IC₅₀ values are calculated from dose-response curves. For quality control, the compound is characterized by NMR, HPLC, and GC. Melting point determination and HPLC purity analysis (≥98%) are standard.
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| Cell Assay |
In vitro cell culture experiments with 4-Bromoisoquinoline are not standard as the compound is primarily a synthetic intermediate. If cellular studies are conducted, the compound is typically dissolved in DMSO and added to cell culture media at micromolar concentrations to assess potential PKA inhibition or cytotoxicity. Standard cytotoxicity assays such as MTT or CellTiter-Glo can be used to measure cell viability after 24-72 hours of exposure. The compound's logP of 2.8-3.0 suggests moderate cell permeability. However, due to its hydrophobic nature, the compound may precipitate in aqueous media, requiring the use of carriers such as DMSO (final concentration <0.1%) for solubility.
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| Animal Protocol |
In vivo animal experiments with 4-Bromoisoquinoline are not conducted as the compound is a laboratory reagent rather than a test article. When the compound is used to synthesize drug candidates (e.g., androgen receptor degraders), those final products are subjected to animal studies following standard protocols: oral or intravenous administration, blood sampling for pharmacokinetic analysis, tissue collection for biodistribution studies, and histopathological examination for toxicity assessment. The ligand itself is not evaluated in vivo. Any toxicity or activity observed would be attributed to the drug candidate, not to the intermediate.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 4-Bromoisoquinoline are not characterized as it is not a drug substance. Based on its physicochemical properties (molecular weight 208.05, LogP 2.8-3.0, moderate water insolubility, pKa 3.30), the compound would be expected to have moderate oral bioavailability if administered. It would likely undergo metabolism via cytochrome P450-mediated oxidation, with the bromine substituent potentially being displaced or retained. However, the compound is not intended for human exposure and has not been evaluated in formal pharmacokinetic studies. For drug candidates synthesized from this intermediate, pharmacokinetic properties are determined as part of drug development.
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| Toxicity/Toxicokinetics |
Toxicological data for 4-Bromoisoquinoline indicate that it is an irritant and may be harmful if swallowed, inhaled, or in contact with skin. Hazard statements include H315 (causes skin irritation), H319 (causes serious eye irritation), and H335 (may cause respiratory irritation). The compound has a signal word of "Warning". Precautionary measures include avoiding dust formation, wearing protective gloves and eye protection, and washing thoroughly after handling. The compound should be stored in a refrigerator at 4°C. No carcinogenicity or mutagenicity data are available.
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| Additional Infomation |
4-Bromoisoquinoline is a versatile building block in medicinal chemistry for the synthesis of kinase inhibitors, anticancer agents, and other bioactive compounds. It is used in the preparation of androgen receptor degraders, C4-substituted isoquinolines with cytotoxic activity, and various heterocyclic compounds. The bromine substituent enables further functionalization via palladium-catalyzed cross-coupling reactions (Suzuki, Buchwald, Sonogashira). The compound has not undergone clinical trials and is not approved as a pharmaceutical. Its mechanism of action is chemical—serving as a precursor for the synthesis of biologically active molecules.
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| Molecular Formula |
C9H6BRN
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|---|---|
| Molecular Weight |
208.05
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| Exact Mass |
206.968
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| CAS # |
1532-97-4
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| PubChem CID |
73743
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| Appearance |
White to off-white solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
282.5±0.0 °C at 760 mmHg
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| Melting Point |
40-43 °C(lit.)
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| Flash Point |
133.3±19.8 °C
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| Vapour Pressure |
0.0±0.5 mmHg at 25°C
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| Index of Refraction |
1.674
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| LogP |
2.98
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
11
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| Complexity |
138
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| Defined Atom Stereocenter Count |
0
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| SMILES |
BrC1=C([H])N=C([H])C2=C([H])C([H])=C([H])C([H])=C21
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| InChi Key |
SCRBSGZBTHKAHU-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H6BrN/c10-9-6-11-5-7-3-1-2-4-8(7)9/h1-6H
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| Chemical Name |
4-bromoisoquinoline
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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 |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.8065 mL | 24.0327 mL | 48.0654 mL | |
| 5 mM | 0.9613 mL | 4.8065 mL | 9.6131 mL | |
| 10 mM | 0.4807 mL | 2.4033 mL | 4.8065 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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