5-Bromoquinolin-8-ol
5-Bromoquinolin-8-ol
- CAT Number : Gly-GMSM-116
- CAS Number : 1198-14-7
- Molecular Weight : 224.05
- Molecular Formula : C9H6BrNO
- Pack size: 2 g
5-Bromoquinolin-8-ol is an organic compound with the molecular formula C9H6BrNO. It is a derivative of quinoline with bromine and hydroxyl substituents.
Properties
- Molecular weight: 224.05 g/mol
- Chemical formula: C9H6BrNO
- CAS Number: 1198-14-7
- Application and usage
- Used as an intermediate in organic synthesis
- Potential applications in pharmaceutical research and development
Safety and handling
- Store at room temperature
- Handle with care in a well-ventilated area
- Wear appropriate personal protective equipment (PPE) such as gloves, safety glasses, and lab coat
- Avoid skin contact, inhalation, or ingestion
Involved human diseases
Anticancer Activity
5-Bromoquinolin-8-ol and its derivatives have shown promising anticancer properties. Compounds containing the 8-hydroxyquinoline nucleus, such as 5-bromoquinolin-8-ol, have been reported to exhibit antiproliferative activities against various cancer cell lines. These compounds can act as inhibitors of matrix metalloproteinases (MMPs), which are enzymes involved in the breakdown of extracellular matrix and are often associated with cancer progression13. The inhibition of MMPs suggests that these compounds could potentially be developed into anticancer therapies.
Antimicrobial and Antifungal Activities
Derivatives of 8-hydroxyquinoline, including those with bromine substitutions like 5-bromoquinolin-8-ol, have demonstrated antimicrobial and antifungal properties. These compounds can inhibit the growth of various bacterial and fungal strains, making them candidates for developing new antibiotics35.
Neurological Effects
Compounds related to 8-hydroxyquinoline have been identified as potent inhibitors of catechol O-methyltransferase (COMT), an enzyme that plays a role in the metabolism of dopamine. By inhibiting COMT, these compounds could potentially be used to treat neurological and psychiatric conditions associated with impaired dopamine signaling2.
Potential in Drug Resistance Reversal
Some derivatives of 8-hydroxyquinoline have been explored for their ability to reverse multidrug resistance (MDR) in cancer cells. This property is particularly valuable in enhancing the efficacy of existing anticancer drugs by overcoming resistance mechanisms6.
Overall, 5-bromoquinolin-8-ol exhibits a range of pharmacological activities that could be harnessed for therapeutic purposes in treating cancer, infections, and neurological disorders. However, further research is needed to fully understand its efficacy and safety in clinical settings.
Cellular Signaling Pathways Affected
Apoptosis Pathway: 5-Bromoquinolin-8-ol has been shown to activate the p53 pathway, which leads to the increased expression of pro-apoptotic genes. This activation suggests that the compound can induce programmed cell death, a critical process for eliminating damaged or cancerous cells2.
Cell Proliferation Pathway: The compound influences cell proliferation by modulating the activity of various enzymes and proteins involved in cell cycle regulation. This modulation can lead to altered rates of cell division and growth, impacting cancer progression and other proliferative disorders2.
Metabolic Pathways: It affects cellular metabolism by inhibiting key metabolic enzymes, thereby altering the metabolic flux within the cell. This can have downstream effects on energy production and biosynthetic processes2.
Stress Response Pathways: Although not directly mentioned for 5-bromoquinolin-8-ol, compounds like QN523 that share similar mechanisms are known to activate stress response pathways, such as the unfolded protein response and endoplasmic reticulum stress pathways. These pathways can lead to autophagy and apoptosis under conditions of cellular stress4.
