Glaucine

Glaucine (O, O-Dimethylisoboldine) is an alkaloid extracted from Glaucium flavum that possesses various activities, including cough relief, bronchodilation, anti-inflammatory effects, analgesia, antipyretic properties, and anticancer effects. Glaucine acts as a selective and orally active inhibitor of phosphodiesterase 4 (PDE4), with a Ki of 3.4 µM in human bronchial tissues and polymorphonuclear leukocytes. Glaucine induces relaxation of human isolated bronchi by antagonizing calcium channels. Additionally, Glaucine inhibits the activation of NF-κB, leading to a reduction in the expression of the MMP-9 gene, thereby suppressing the migration and invasion of breast cancer cells. Therefore, Glaucine holds potential for research in asthma and breast cancer[1][2][3][4][5][6].

Product Specifications

CAS Number

[475-81-0]

Product Name Alternative

O, O-Dimethylisoboldine; S- (+) -Glaucine; NSC 34396

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Calcium Channel; MMP; NF-κB; Phosphodiesterase (PDE)

Type

Natural Products

Related Pathways

Membrane Transporter/Ion Channel; Metabolic Enzyme/Protease; Neuronal Signaling; NF-κB

Applications

COVID-19-anti-virus

Field of Research

Cancer; Inflammation/Immunology

Assay Protocol

https://www.medchemexpress.com/glaucine.html

Purity

99.57

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

CN1CCC2=CC(OC)=C(OC)C3=C2[C@]1([H])CC4=CC(OC)=C(OC)C=C34

Molecular Formula

C21H25NO4

Molecular Weight

355.43

Precautions

H302, H315, H319, H335

References & Citations

[1]J Cortijo, et al. Bronchodilator and Anti-Inflammatory Activities of Glaucine: In Vitro Studies in Human Airway Smooth Muscle and Polymorphonuclear Leukocytes. Br J Pharmacol. 1999 Aug;127 (7) :1641-51.|[2]Golo M J Meyer, et al. Studies on the in Vivo Contribution of Human Cytochrome P450s to the Hepatic Metabolism of Glaucine, a New Drug of Abuse. Biochem Pharmacol. 2013 Nov 15;86 (10) :1497-506.|[3]Maya Spasova, et al. Cinnamoyl- And Hydroxycinnamoyl Amides of Glaucine and Their Antioxidative and Antiviral Activities. Bioorg Med Chem. 2008 Aug 1;16 (15) :7457-61.|[4]Hyereen Kang, et al. "Glaucine inhibits breast cancer cell migration and invasion by inhibiting MMP-9 gene expression through the suppression of NF-κB activation." Molecular and cellular biochemistry 403 (2015) : 85-94.|[5]Pons, et al. "Effects of inhaled glaucine on pulmonary responses to antigen in sensitized guinea pigs." European journal of pharmacology 397.1 (2000) : 187-195.|[6]PINTO, et al. "Anti‐inflammatory, analgesic and antipyretic effects of glaucine in rats and mice." Pharmacy and Pharmacology Communications 4.10 (1998) : 502-505.