Glaucine | CAS#475-81-0 | TNF-alpha and IL-6 production inhibitor

MedKoo Cat#: 561694 | Name: Glaucine

Featured

Description:

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

Glaucine is an inhibitor of TNF-alpha and IL-6 production induced by Toll-like receptor (TLR) ligands.

Chemical Structure

Glaucine

CAS#475-81-0

Theoretical Analysis

MedKoo Cat#: 561694

Name: Glaucine

CAS#: 475-81-0

Chemical Formula: C21H25NO4

Exact Mass: 355.1784

Molecular Weight: 355.43

Elemental Analysis: C, 70.96; H, 7.09; N, 3.94; O, 18.01

Price and Availability

Size	Price	Availability
5mg	USD 350.00	2 Weeks
10mg	USD 600.00	2 Weeks
50mg	USD 1,250.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Glaucine; Bromcholitin; d-Glaucine; Glauvent; Boldine dimethyl ether; S-(+)-Glaucine; (+)-Glaucine; NSC 34396; NSC34396; NSC-34396; 1,2,9,10-Tetramethoxyaporphine

IUPAC/Chemical Name

(6aS)-1,2,9,10-Tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline

InChi Key

RUZIUYOSRDWYQF-HNNXBMFYSA-N

InChi Code

InChI=1S/C21H25NO4/c1-22-7-6-12-9-18(25-4)21(26-5)20-14-11-17(24-3)16(23-2)10-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3/t15-/m0/s1

SMILES Code

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

Appearance

Solid powder

Purity

>95% (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

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Glaucine is a selective and orally active phosphodiesterase 4 (PDE4) inhibitor with Kis of 3.4 µM in human bronchus and polymorphonuclear leukocytes. Glaucine is also a non-selective α-adrenoceptor antagonist, a Ca2+ entry blocker, and a weak dopamine D1 and D2 receptor antagonist.

In vitro activity:

Treatment with PMA for 24 and 48 h significantly increased MCF-7 cell viability; however, treatment with >15 μM glaucine decreased cell proliferation in the presence or absence of PMA (Fig. 1b). PMA markedly enhanced the colony-forming ability of MCF-7 cells compared to untreated cells (Fig. 1c). In contrast, glaucine at 15 and 30 μM inhibited PMA-induced colony formation by 48 and 63 %, respectively (Fig. 1c). Reference: Mol Cell Biochem. 2015 May;403(1-2):85-94. https://pubmed.ncbi.nlm.nih.gov/25670016/

In vivo activity:

In electrically-stimulated rat vas deferens, (+)-glaucine (0.3-10 microM) enhanced twitch contractions and competitively antagonized the inhibitory effect of clonidine with a pA2 value of 5.91. In tissues incubated in depolarizing calcium-free high-potassium medium, (+)-glaucine (30-80 microM) inhibited Ca(2+)-induced contractions with depression of the maximal response at higher doses and with a pD'2 value of 3.65. Furthermore, (+)-glaucine (50 microM) did not modify basal 45Ca uptake but strongly inhibited the influx of 45Ca induced by K+. 7. These results suggest that (+)-glaucine has non-selective alpha 1- and alpha 2-adrenoceptor blocking properties. Reference: Br J Pharmacol. 1993 Nov;110(3):943-8. https://pubmed.ncbi.nlm.nih.gov/8298818/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	84.40
	DMSO	65.0	182.88
	Ethanol	30.0	84.40
	Ethanol:PBS (pH 7.2) (1:1)	0.5	1.41

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 355.43 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

Formulation protocol:

1. Kang H, Jang SW, Pak JH, Shim S. Glaucine inhibits breast cancer cell migration and invasion by inhibiting MMP-9 gene expression through the suppression of NF-κB activation. Mol Cell Biochem. 2015 May;403(1-2):85-94. doi: 10.1007/s11010-015-2339-9. Epub 2015 Feb 11. PMID: 25670016; PMCID: PMC4383818. 2. Cortijo J, Villagrasa V, Pons R, Berto L, Martí-Cabrera M, Martinez-Losa M, Domenech T, Beleta J, Morcillo EJ. 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. doi: 10.1038/sj.bjp.0702702. PMID: 10455321; PMCID: PMC1566148. 3. Orallo F, Fernández Alzueta A, Loza MI, Vivas N, Badía A, Campos M, Honrubia MA, Cadavid MI. Study of the mechanism of the relaxant action of (+)-glaucine in rat vas deferens. Br J Pharmacol. 1993 Nov;110(3):943-8. doi: 10.1111/j.1476-5381.1993.tb13904.x. PMID: 8298818; PMCID: PMC2175806.

In vitro protocol:

In vivo protocol:

1. Orallo F, Fernández Alzueta A, Loza MI, Vivas N, Badía A, Campos M, Honrubia MA, Cadavid MI. Study of the mechanism of the relaxant action of (+)-glaucine in rat vas deferens. Br J Pharmacol. 1993 Nov;110(3):943-8. doi: 10.1111/j.1476-5381.1993.tb13904.x. PMID: 8298818; PMCID: PMC2175806.

1: He SM, Song WL, Cong K, Wang X, Dong Y, Cai J, Zhang JJ, Zhang GH, Yang JL, Yang SC, Fan W. Identification of candidate genes involved in isoquinoline alkaloids biosynthesis in Dactylicapnos scandens by transcriptome analysis. Sci Rep. 2017 Aug 22;7(1):9119. doi: 10.1038/s41598-017-08672-w. PubMed PMID: 28831066; PubMed Central PMCID: PMC5567367. 2: Zhang Q, Chen C, Wang FQ, Li CH, Zhang QH, Hu YJ, Xia ZN, Yang FQ. Simultaneous screening and analysis of antiplatelet aggregation active alkaloids from Rhizoma Corydalis. Pharm Biol. 2016 Dec;54(12):3113-3120. Epub 2016 Aug 25. PubMed PMID: 27558975. 3: Menezes LR, Costa CO, Rodrigues AC, Santo FR, Nepel A, Dutra LM, Silva FM, Soares MB, Barison A, Costa EV, Bezerra DP. Cytotoxic Alkaloids from the Stem of Xylopia laevigata. Molecules. 2016 Jul 8;21(7). pii: E890. doi: 10.3390/molecules21070890. PubMed PMID: 27399666. 4: Chan JD, Acharya S, Day TA, Marchant JS. Pharmacological profiling an abundantly expressed schistosome serotonergic GPCR identifies nuciferine as a potent antagonist. Int J Parasitol Drugs Drug Resist. 2016 Dec;6(3):364-370. doi: 10.1016/j.ijpddr.2016.06.001. Epub 2016 Jun 23. PubMed PMID: 27397763; PubMed Central PMCID: PMC5196489. 5: Yang XH, Cheng XL, Qin B, Cai ZY, Cai X, Liu S, Wang Q, Qin Y. Ultra-high performance liquid chromatography coupled with quadrupole/time of flight mass spectrometry based chemical profiling approach for the holistic quality control of complex Kang-Jing formula preparations. J Pharm Biomed Anal. 2016 May 30;124:319-36. doi: 10.1016/j.jpba.2016.03.012. Epub 2016 Mar 6. PubMed PMID: 26977585. 6: Yang LX, Zhang YX, Feng WH, Li C. [Establishment of simultaneous quantitative model of five alkaloids from Corydalis Rhizoma by near-infrared spectrometry]. Zhongguo Zhong Yao Za Zhi. 2015 Oct;40(19):3830-7. Chinese. PubMed PMID: 26975110. 7: Chang L, Hagel JM, Facchini PJ. Isolation and Characterization of O-methyltransferases Involved in the Biosynthesis of Glaucine in Glaucium flavum. Plant Physiol. 2015 Oct;169(2):1127-40. doi: 10.1104/pp.15.01240. Epub 2015 Aug 21. PubMed PMID: 26297140; PubMed Central PMCID: PMC4587479. 8: Zhang X, Zhang S, Yang Q, Cao W, Xie Y, Qiu P, Wang S. Simultaneous Quantitative Determination of 12 Active Components in Yuanhu Zhitong Prescription by RP-HPLC Coupled with Photodiode Array Detection. Pharmacogn Mag. 2015 Jan-Mar;11(41):61-8. doi: 10.4103/0973-1296.149705. PubMed PMID: 25709212; PubMed Central PMCID: PMC4329634. 9: Kang H, Jang SW, Pak JH, Shim S. Glaucine inhibits breast cancer cell migration and invasion by inhibiting MMP-9 gene expression through the suppression of NF-κB activation. Mol Cell Biochem. 2015 May;403(1-2):85-94. doi: 10.1007/s11010-015-2339-9. Epub 2015 Feb 11. PubMed PMID: 25670016; PubMed Central PMCID: PMC4383818. 10: Meyer MR, Wagmann L, Schneider-Daum N, Loretz B, de Souza Carvalho C, Lehr CM, Maurer HH. P-glycoprotein interactions of novel psychoactive substances - stimulation of ATP consumption and transport across Caco-2 monolayers. Biochem Pharmacol. 2015 Apr 1;94(3):220-6. doi: 10.1016/j.bcp.2015.01.008. Epub 2015 Jan 28. PubMed PMID: 25637762. 11: Gyurkovska V, Philipov S, Kostova N, Ivanovska N. Acetylated derivative of glaucine inhibits joint inflammation in collagenase-induced arthritis. Immunopharmacol Immunotoxicol. 2015 Feb;37(1):56-62. doi: 10.3109/08923973.2014.972414. Epub 2014 Oct 20. PubMed PMID: 25328086. 12: Kim JH, Ryu YB, Lee WS, Kim YH. Neuraminidase inhibitory activities of quaternary isoquinoline alkaloids from Corydalis turtschaninovii rhizome. Bioorg Med Chem. 2014 Nov 1;22(21):6047-52. doi: 10.1016/j.bmc.2014.09.004. Epub 2014 Sep 15. PubMed PMID: 25277281. 13: Mohamed ME, Arafa AM, Soliman SS, Eldahmy SI. Plant germination and production of callus from the yellow hornpoppy (Glaucium flavum): the first stage of micropropagation. Pharmazie. 2014 Sep;69(9):715-20. PubMed PMID: 25272947. 14: Peng CY, Liu JQ, Zhang R, Shu JC. A new alkaloid from the fruit of Nandina domestica Thunb. Nat Prod Res. 2014;28(15):1159-64. doi: 10.1080/14786419.2014.921166. Epub 2014 Jun 4. PubMed PMID: 24897106. 15: Ujváry I. Psychoactive natural products: overview of recent developments. Ann Ist Super Sanita. 2014;50(1):12-27. doi: DOI: 10.4415/ANN_14_01_04. Review. PubMed PMID: 24695249. 16: Bournine L, Bensalem S, Wauters JN, Iguer-Ouada M, Maiza-Benabdesselam F, Bedjou F, Castronovo V, Bellahcène A, Tits M, Frédérich M. Identification and quantification of the main active anticancer alkaloids from the root of Glaucium flavum. Int J Mol Sci. 2013 Dec 2;14(12):23533-44. doi: 10.3390/ijms141223533. PubMed PMID: 24317429; PubMed Central PMCID: PMC3876061. 17: Eid SY, El-Readi MZ, Eldin EE, Fatani SH, Wink M. Influence of combinations of digitonin with selected phenolics, terpenoids, and alkaloids on the expression and activity of P-glycoprotein in leukaemia and colon cancer cells. Phytomedicine. 2013 Dec 15;21(1):47-61. doi: 10.1016/j.phymed.2013.07.019. Epub 2013 Aug 30. PubMed PMID: 23999162. 18: Meyer GM, Meyer MR, Wink CS, Zapp J, Maurer HH. 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. doi: 10.1016/j.bcp.2013.08.025. Epub 2013 Aug 26. PubMed PMID: 23988488. 19: da Silva FM, de Souza AD, Koolen HH, Barison A, Vendramin ME, Costa EV, Ferreira AG, Pinheiro ML. Phytochemical study of the alkaloidal fractions of Unonopsis duckei R. E. Fr. guided by electrospray ionisation ion-trap tandem mass spectrometry. Phytochem Anal. 2014 Jan-Feb;25(1):45-9. doi: 10.1002/pca.2458. Epub 2013 Aug 6. PubMed PMID: 23922254. 20: Meyer GM, Meyer MR, Wissenbach DK, Maurer HH. Studies on the metabolism and toxicological detection of glaucine, an isoquinoline alkaloid from Glaucium flavum (Papaveraceae), in rat urine using GC-MS, LC-MS(n) and LC-high-resolution MS(n). J Mass Spectrom. 2013 Jan;48(1):24-41. doi: 10.1002/jms.3112. PubMed PMID: 23303745.