633-65-8 Usage
Description
Berberine hydrochloride is an isoquinoline alkaloid derived from various plant sources, such as barberry, goldenseal, and Oregon grape. It exhibits a wide range of pharmacological properties, including antiarrhythmic, alpha2 agonist, anticonvulsant, anti-inflammatory, antibacterial, antifungal, antitrypanosomal, antineoplastic, and immunostimulant activities. Berberine hydrochloride has gained attention for its potential chemopreventive properties and its ability to inhibit the enzyme cyclooxygenase-2 (COX-2) and Activator Protein 1 (AP-1), which play critical roles in inflammation and carcinogenesis.
Uses
Used in Pharmaceutical Industry:
Berberine hydrochloride is used as an active pharmaceutical ingredient for its various therapeutic properties, such as antiarrhythmic, alpha2 agonist, anticonvulsant, anti-inflammatory, antibacterial, antifungal, antitrypanosomal, antineoplastic, and immunostimulant activities. Its broad-spectrum action makes it a valuable compound in the development of drugs for treating a wide range of diseases and conditions.
Used in Ophthalmic Industry:
Berberine hydrochloride is used as an ingredient in some commercial eyewash products, where it can provide antibacterial and anti-inflammatory properties to help maintain eye health and hygiene.
Used in Cancer Prevention:
Berberine hydrochloride is used as a chemopreventive agent against colon tumor formation by inhibiting the enzyme cyclooxygenase-2 (COX-2), which is abundantly expressed in colon cancer cells. It also inhibits Activator Protein 1 (AP-1), a transcription factor that plays a critical role in inflammation and carcinogenesis. Treatment with berberine hydrochloride may potentially result in the reduced accumulation of chemotherapeutic drugs, thus offering a promising approach for cancer prevention and treatment.
Biochem/physiol Actions
An alkaloid with weak antibiotic properties. Substrate for MDR efflux pumps. Antimicrobial activities of berberine is potentiated by the MDR inhibitor 5′-methoxyhydnocarpin (5′-MHC). Berberine upregulates the expression of Pgp in hepatoma cells. Treatment with berberine potentially results in the reduced accumulation of chemotherapeutic drugs.
Safety Profile
Poison by intraperitoneal route.Slightly toxic by ingestion. Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx andCl-.
Check Digit Verification of cas no
The CAS Registry Mumber 633-65-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,3 and 3 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 633-65:
(5*6)+(4*3)+(3*3)+(2*6)+(1*5)=68
68 % 10 = 8
So 633-65-8 is a valid CAS Registry Number.
InChI:InChI=1/C20H18NO4.ClH/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2;/h3-4,7-10H,5-6,11H2,1-2H3;1H/q+1;
633-65-8Relevant articles and documents
Thermodynamic study on the effects of β-cyclodextrin inclusion with berberine
Yu,Wei,Gao,Zhao
, p. 249 - 256 (2002)
The fluorescence enhancement of berberine (Berb) as a result of complex with β-cyclodextrin (β-CD) is investigated. The association constants of α-CD and β-CD with Berb are 60 and 137 M-1 at 20°C in pH 7.20 aqueous solution. Effects of temperature on the forming inclusion complexes of β-CD with Berb have been examined through using fluorescence titration. Enthalpy and entropy values calculated from fluorescence data are -33.7 kJ·mol-1 and 74.3 J·mol-1·K-1, respectively. It was found that the dielectric constant of β-CD cavity is about 24 in a rough analogy with absolute alcohol. These results suggest that the extrusion of 'high energy water' molecules from the cavity of β-CD and hydrophobic interaction upon the inclusion complex formation are the main forces of the inclusion reaction. Effect of pH on the association of β-CD with Berb was also studied. Mechanism of the inclusion of β-CD with Berb is further studied by absorption and NMR measurements. Results show that β-CD forms a 1:1 inclusion complex with Berb.
Modular and Divergent Syntheses of Protoberberine and Protonitidine Alkaloids
Liu, Kai,Jiang, Xuefeng
, p. 1327 - 1332 (2021/03/03)
A modularly convergent and divergent strategy was established for the family synthesis of both protoberberine and protonitidine alkaloids. The robust, scalable, and flexible synthetic route featured a collective preparation of protoberberine and protonitidine alkaloids from a common isoquinoline assembled from pyridyne as the key synthon, which was based on the selective N-C or C-C cyclization via distinct processes. Through the strategy, 20 protoberberine alkaloids, 5 protonitidine alkaloids, and 11 analogues with diverse substituents were comprehensively aquired.
The ring formation mechanism in cyclization of berberine
Han, Siyu,Wang, Guosheng,Wang, Yuelan,Xu, Ronghui
, p. 308 - 313 (2021/07/19)
Berberine hydrochloride is a natural alkaloid with significant antitumor activities against many types of cancer cells, can be synthesized by cyclic reaction with hydrochloride condensate and glyoxal as raw materials and copper chloride as catalyst. In this study, the transition and energy change for the each reaction step was calculated by the density functional theory program Dmol3 in Materials Studio 2017. and the results testified that there are two ring formation in the cycliztion process, and according to the result we proposed the mechanism of this cyclization reaction. We also use infrared and ultraviolet spectroscopy to monitor the reaction process in real time and prove the ring formation process. The reaction mechanism was firstly proposed at the basic results of above.
