Oxoglaucine | CAS#5574-24-3 | cation inhibitor

MedKoo Cat#: 145039 | Name: Oxoglaucine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Oxoglaucine is a novel inhibitor of TRPV5 cation channels. Oxoglaucine suppresses expression of proinflammatory and apoptosis-related proteins, including TNF-α, IL-6, IL-1β, MMP-13, CASP-3, and BAX, and prevents matrix degradation in OA chondrocytes. It also blocks Ca2+ influx, preventing the apoptosis and matrix degradation of articular cartilage in a rat model of OA. Oxoglaucine protects against cartilage damage by blocking the TRPV5/CAMK-II/calmodulin pathway to inhibit Ca2+ influx and activate autophagy.

Chemical Structure

Oxoglaucine

CAS#5574-24-3

Theoretical Analysis

MedKoo Cat#: 145039

Name: Oxoglaucine

CAS#: 5574-24-3

Chemical Formula: C20H17NO5

Exact Mass: 351.1107

Molecular Weight: 351.36

Elemental Analysis: C, 68.37; H, 4.88; N, 3.99; O, 22.77

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Oxoglaucine; NSC-141543;

IUPAC/Chemical Name

1,2,9,10-tetramethoxy-7H-dibenzo[de,g]quinolin-7-one

InChi Key

ZYKCETVKVRJFGD-UHFFFAOYSA-N

InChi Code

1S/C20H17NO5/c1-23-13-8-11-12(9-14(13)24-2)19(22)18-16-10(5-6-21-18)7-15(25-3)20(26-4)17(11)16/h5-9H,1-4H3

SMILES Code

COC1=CC2=C(C=C1OC)C3=C(OC)C(OC)=CC4=CC=NC(C2=O)=C34

Appearance

To be determined

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 351.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Zhong G, Long H, Chen F, Yu Y. Oxoglaucine mediates Ca2+ influx and activates autophagy to alleviate osteoarthritis through the TRPV5/calmodulin/CAMK-II pathway. Br J Pharmacol. 2021 Aug;178(15):2931-2947. doi: 10.1111/bph.15466. Epub 2021 May 5. PMID: 33786819. 2: Azamov B, Lee KM, Hur J, Muradillaeva S, Shim WS, Lee C, Song P. Oxoglaucine Suppresses Hepatic Fibrosis by Inhibiting TGFβ-Induced Smad2 Phosphorylation and ROS Generation. Molecules. 2023 Jun 24;28(13):4971. doi: 10.3390/molecules28134971. PMID: 37446633; PMCID: PMC10343928. 3: Eid N, Ito Y. Oxoglaucine alleviates osteoarthritis by activation of autophagy via blockade of Ca2+ influx and TRPV5/calmodulin/CAMK-II pathway. Br J Pharmacol. 2022 Mar;179(6):1282-1283. doi: 10.1111/bph.15706. Epub 2021 Nov 3. PMID: 34734425. 4: Liu YC, Chen ZF, Shi YF, Huang KB, Geng B, Liang H. Oxoglaucine-lanthanide complexes: synthesis, crystal structure and cytotoxicity. Anticancer Res. 2014 Jan;34(1):531-6. PMID: 24403512. 5: Chen ZF, Shi YF, Liu YC, Hong X, Geng B, Peng Y, Liang H. TCM active ingredient oxoglaucine metal complexes: crystal structure, cytotoxicity, and interaction with DNA. Inorg Chem. 2012 Feb 20;51(4):1998-2009. doi: 10.1021/ic200443p. Epub 2012 Feb 6. PMID: 22309171. 6: Ivanovska N, Philipov S, Georgieva P. Immunopharmacological activity of aporphinoid alkaloid oxoglaucine. Pharmacol Res. 1997 Apr;35(4):267-72. doi: 10.1006/phrs.1996.9994. PMID: 9264041. 7: Wei JH, Chen ZF, Qin JL, Liu YC, Li ZQ, Khan TM, Wang M, Jiang YH, Shen WY, Liang H. Water-soluble oxoglaucine-Y(III), Dy(III) complexes: in vitro and in vivo anticancer activities by triggering DNA damage, leading to S phase arrest and apoptosis. Dalton Trans. 2015 Jul 7;44(25):11408-19. doi: 10.1039/c5dt00926j. PMID: 26017376. 8: Remichkova M, Dimitrova P, Philipov S, Ivanovska N. Toll-like receptor- mediated anti-inflammatory action of glaucine and oxoglaucine. Fitoterapia. 2009 Oct;80(7):411-4. doi: 10.1016/j.fitote.2009.05.016. Epub 2009 May 27. PMID: 19481591. 9: Ivanovska N, Hristova M, Philipov S. Immunosuppression and recovery of drug- impaired host resistance against Candida albicans infection by oxoglaucine. Pharmacol Res. 2000 Jan;41(1):101-7. doi: 10.1006/phrs.1999.0567. PMID: 10600277. 10: Arita M, Philipov S, Galabov AS. Phosphatidylinositol 4-kinase III beta is the target of oxoglaucine and pachypodol (Ro 09-0179) for their anti-poliovirus activities, and is located at upstream of the target step of brefeldin A. Microbiol Immunol. 2015 Jun;59(6):338-47. doi: 10.1111/1348-0421.12261. PMID: 25891300. 11: Flors C, Prat C, Suau R, Nájera F, Nonell S. Photochemistry of phytoalexins containing phenalenone-like chromophores: photophysics and singlet oxygen photosensitizing properties of the plant oxoaporphine alkaloid oxoglaucine. Photochem Photobiol. 2005 Jan-Feb;81(1):120-4. doi: 10.1562/2004-07-23-RA-243. PMID: 15493958. 12: Stoyanova A, Nikolova I, Pürstinger G, Dobrikov G, Dimitrov V, Philipov S, Galabov AS. Anti-enteroviral triple combination of viral replication inhibitors: activity against coxsackievirus B1 neuroinfection in mice. Antivir Chem Chemother. 2015 Dec;24(5-6):136-147. doi: 10.1177/2040206616671571. Epub 2016 Nov 4. PMID: 27815331; PMCID: PMC5890508. 13: Galabov AS, Nikolova I, Vassileva-Pencheva R, Stoyanova A. Antiviral Combination Approach as a Perspective to Combat Enterovirus Infections. Pril (Makedon Akad Nauk Umet Odd Med Nauki). 2015;36(2):91-9. doi: 10.1515/prilozi-2015-0057. PMID: 27442375. 14: Ivanovska N, Hristova M, Philipov S. IMMUNOSUPPRESSION AND RECOVERY OF DRUG- IMPAIRED HOST RESISTANCE AGAINST CANDIDA ALBICANS INFECTION BY OXOGLAUCINE. Pharmacol Res. 2000 Jan;41(1):99-105. doi: 10.1006/phrs.1999.0567. PMID: 10712834. 15: Ivanovska N, Hristova M. Treatment with oxoglaucine can enhance host resistance to Candida albicans infection of mice with adjuvant arthritis. Diagn Microbiol Infect Dis. 2000 Sep;38(1):17-20. doi: 10.1016/s0732-8893(00)00167-x. PMID: 11025179. 16: Ivanovska N, Philipov S. A low dose immunorestorative effect of aporphinoid alkaloid oxoglaucine on experimentally immunosuppressed and infected mice. Methods Find Exp Clin Pharmacol. 1997 Nov;19(9):579-83. PMID: 9500120. 17: Stoyanova A, Nikolova I, Galabov AS. Effect of consecutive alternating administration (CAA) of a triple anti-enteroviral combination on Coxsackievirus B1 neuroinfection in mice. Antiviral Res. 2015 Sep;121:138-44. doi: 10.1016/j.antiviral.2015.07.004. Epub 2015 Jul 18. PMID: 26196747. 18: Stoyanova A, Galabov AS. Effects of double combinations of enterovirus replication inhibitors against Coxsackie B viruses. Acta Virol. 2021;65(4):411-419. doi: 10.4149/av_2021_410. PMID: 34978843. 19: Chang FR, Wei JL, Teng CM, Wu YC. Antiplatelet aggregation constituents from Annona purpurea. J Nat Prod. 1998 Dec;61(12):1457-61. doi: 10.1021/np9800046. PMID: 9868142. 20: Stoyanova A, Galabov AS. Consecutive alternating administration as an effective anti-coxsackievirus B3 in vivo treatment scheme. Arch Virol. 2021 Jul;166(7):1869-1875. doi: 10.1007/s00705-021-05057-3. Epub 2021 Apr 20. PMID: 33877422.