Fangchinoline | CAS#33889-68-8 | adenocarcinoma inhibitor

MedKoo Cat#: 598885 | Name: Fangchinoline

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Description:

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

Fangchinoline is an isolate from Stephania Tetrandra that shows anti-cancer activity. It inhibits breast adenocarcinoma proliferation through apoptosis induction. In addition, it has been shown to inhibit HIV-Type 1 replication.

Chemical Structure

Fangchinoline

CAS#33889-68-8

Theoretical Analysis

MedKoo Cat#: 598885

Name: Fangchinoline

CAS#: 33889-68-8

Chemical Formula: C37H40N2O6

Exact Mass: 608.2886

Molecular Weight: 608.73

Elemental Analysis: C, 73.01; H, 6.62; N, 4.60; O, 15.77

Price and Availability

Size	Price	Availability
25mg	USD 350.00	2 Weeks
50mg	USD 550.00	2 Weeks
100mg	USD 950.00	2 Weeks

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Related CAS #

436-77-1 33889-68-8

Synonym

Fangchinoline; Isofangchinoline; Thaligine; Thalrugosine; (+)-Limacine, 7-O-Demethyltetrandine; Demethyl tetrandrine; NSC 277171; NSC-277171; NSC277171;

IUPAC/Chemical Name

(11S,31R)-16,36,54-trimethoxy-12,32-dimethyl-11,12,13,14,31,32,33,34-octahydro-2,6-dioxa-1(7,1),3(8,1)-diisoquinolina-5(1,3),7(1,4)-dibenzenacyclooctaphan-37-ol

InChi Key

IIQSJHUEZBTSAT-URLMMPGGSA-N

InChi Code

InChI=1S/C37H40N2O6/c1-38-14-12-24-19-31(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-32-18-23(8-11-30(32)41-3)17-29-35-25(13-15-39(29)2)20-34(43-5)36(40)37(35)45-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3/t28-,29+/m0/s1

SMILES Code

CN1CCC2=CC(OC)=C3C=C2[C@@H]1CC4=CC=C(OC5=C(OC)C=CC(C[C@@H]6C7=C(C(O)=C(OC)C=C7CCN6C)O3)=C5)C=C4

Appearance

Solid powder

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

Soluble in DMSO

Shelf Life

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

(R)-Fangchinoline (Thalrugosine), a alkaloids from genus Stephania，exhibits antimicrobial and hypotensive activity.

In vitro activity:

PI and Annexin-V-FITC staining analysis confirmed that the number of Annexin V-positive cells (apoptosis marker) increased significantly after FCL (fangchinoline) treatment (Figures 3A, B ). Furthermore, FCL-treated ESCC cells had increased levels of cleaved PARP, a classical marker of apoptosis (Figure 3C). Therefore, these findings demonstrated that FCL triggered apoptosis in ESCC cells. Reference: Front Oncol. 2021; 11: 666549. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8236818/

In vivo activity:

As shown in Fig. 1C, the CM-AS16 tumour growth was significantly inhibited after intraperitoneal (i.p.) treatment of the NCG male mice with fangchinoline at a dosage of 50 mg/kg/day compared to the control group (p < 0.01). Reference: Cell Death Dis. 2021 Apr; 12(4): 380. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8027391/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	164.28
	Ethanol	5.0	8.21

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 608.73 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. Zhang Y, Wang S, Chen Y, Zhang J, Yang J, Xian J, Li L, Zhao H, Hoffman RM, Zhang Y, Jia L. Fangchinoline Inhibits Human Esophageal Cancer by Transactivating ATF4 to Trigger Both Noxa-Dependent Intrinsic and DR5-Dependent Extrinsic Apoptosis. Front Oncol. 2021 Jun 14;11:666549. doi: 10.3389/fonc.2021.666549. PMID: 34195076; PMCID: PMC8236818. 2. Jiang F, Ren S, Chen Y, Zhang A, Zhu Y, Zhang Z, Li Z, Piao D. Fangchinoline exerts antitumour activity by suppressing the EGFR‑PI3K/AKT signalling pathway in colon adenocarcinoma. Oncol Rep. 2021 Jan;45(1):139-150. doi: 10.3892/or.2020.7857. Epub 2020 Nov 18. PMID: 33416119; PMCID: PMC7709815. 3. Bao K, Li Y, Wei J, Li R, Yang J, Shi J, Li B, Zhu J, Mao F, Jia R, Li J. Fangchinoline suppresses conjunctival melanoma by directly binding FUBP2 and inhibiting the homologous recombination pathway. Cell Death Dis. 2021 Apr 7;12(4):380. doi: 10.1038/s41419-021-03653-4. PMID: 33828201; PMCID: PMC8027391. 4. Xiang X, Tian Y, Hu J, Xiong R, Bautista M, Deng L, Yue Q, Li Y, Kuang W, Li J, Liu K, Yu C, Feng G. Fangchinoline exerts anticancer effects on colorectal cancer by inducing autophagy via regulation AMPK/mTOR/ULK1 pathway. Biochem Pharmacol. 2021 Apr;186:114475. doi: 10.1016/j.bcp.2021.114475. Epub 2021 Feb 18. PMID: 33609560.

In vitro protocol:

In vivo protocol:

1. Bao K, Li Y, Wei J, Li R, Yang J, Shi J, Li B, Zhu J, Mao F, Jia R, Li J. Fangchinoline suppresses conjunctival melanoma by directly binding FUBP2 and inhibiting the homologous recombination pathway. Cell Death Dis. 2021 Apr 7;12(4):380. doi: 10.1038/s41419-021-03653-4. PMID: 33828201; PMCID: PMC8027391. 2. Xiang X, Tian Y, Hu J, Xiong R, Bautista M, Deng L, Yue Q, Li Y, Kuang W, Li J, Liu K, Yu C, Feng G. Fangchinoline exerts anticancer effects on colorectal cancer by inducing autophagy via regulation AMPK/mTOR/ULK1 pathway. Biochem Pharmacol. 2021 Apr;186:114475. doi: 10.1016/j.bcp.2021.114475. Epub 2021 Feb 18. PMID: 33609560.

1: Guo B, Su J, Zhang T, Wang K, Li X. Fangchinoline as a kinase inhibitor targets FAK and suppresses FAK-mediated signaling pathway in A549. J Drug Target. 2015 Apr;23(3):266-74. doi: 10.3109/1061186X.2014.992898. Epub 2014 Dec 24. PubMed PMID: 25539072. 2: Li D, Lu Y, Sun P, Feng LX, Liu M, Hu LH, Wu WY, Jiang BH, Yang M, Qu XB, Guo DA, Liu X. Inhibition on Proteasome β1 Subunit Might Contribute to the Anti-Cancer Effects of Fangchinoline in Human Prostate Cancer Cells. PLoS One. 2015 Oct 29;10(10):e0141681. doi: 10.1371/journal.pone.0141681. eCollection 2015. PubMed PMID: 26512898; PubMed Central PMCID: PMC4626104. 3: Tian F, Ding D, Li D. Fangchinoline targets PI3K and suppresses PI3K/AKT signaling pathway in SGC7901 cells. Int J Oncol. 2015;46(6):2355-63. doi: 10.3892/ijo.2015.2959. Epub 2015 Apr 9. PubMed PMID: 25872479; PubMed Central PMCID: PMC4441295. 4: Xing Z, Zhang Y, Zhang X, Yang Y, Ma Y, Pang D. Fangchinoline induces G1 arrest in breast cancer cells through cell-cycle regulation. Phytother Res. 2013 Dec;27(12):1790-4. doi: 10.1002/ptr.4936. Epub 2013 Feb 11. PubMed PMID: 23401195. 5: Lu X, Zhang R, Fu F, Shen J, Nian H, Wu T. Simultaneous Determination of Fangchinoline and Tetrandrine in Qi-Fang-Xi-Bi-Granules by RP-HPLC. J Chromatogr Sci. 2015 Sep;53(8):1328-32. doi: 10.1093/chromsci/bmv016. Epub 2015 Mar 8. PubMed PMID: 25754692. 6: Sun YF, Wink M. Tetrandrine and fangchinoline, bisbenzylisoquinoline alkaloids from Stephania tetrandra can reverse multidrug resistance by inhibiting P-glycoprotein activity in multidrug resistant human cancer cells. Phytomedicine. 2014 Jul-Aug;21(8-9):1110-9. doi: 10.1016/j.phymed.2014.04.029. Epub 2014 May 22. PubMed PMID: 24856768. 7: Wang X, Liu X, Cai H, Pei K, Cao G, Xu X, Shi F, Cai B. Ultra high performance liquid chromatography with tandem mass spectrometry method for the determination of tetrandrine and fangchinoline in rat plasma after oral administration of Fangji Huangqi Tang and Stephania tetrandra S. Moore extracts. J Sep Sci. 2015 May;38(8):1286-93. doi: 10.1002/jssc.201401384. Epub 2015 Mar 10. PubMed PMID: 25645647. 8: Guo B, Xie P, Su J, Zhang T, Li X, Liang G. Fangchinoline suppresses the growth and invasion of human glioblastoma cells by inhibiting the kinase activity of Akt and Akt-mediated signaling cascades. Tumour Biol. 2016 Feb;37(2):2709-19. doi: 10.1007/s13277-015-3990-1. Epub 2015 Sep 25. PubMed PMID: 26408176. 9: Wang CD, Yuan CF, Bu YQ, Wu XM, Wan JY, Zhang L, Hu N, Liu XJ, Zu Y, Liu GL, Song FZ. Fangchinoline inhibits cell proliferation via Akt/GSK-3beta/ cyclin D1 signaling and induces apoptosis in MDA-MB-231 breast cancer cells. Asian Pac J Cancer Prev. 2014;15(2):769-73. PubMed PMID: 24568493. 10: Wan Z, Lu Y, Liao Q, Wu Y, Chen X. Fangchinoline inhibits human immunodeficiency virus type 1 replication by interfering with gp160 proteolytic processing. PLoS One. 2012;7(6):e39225. doi: 10.1371/journal.pone.0039225. Epub 2012 Jun 13. PubMed PMID: 22720080; PubMed Central PMCID: PMC3374765. 11: Xing ZB, Yao L, Zhang GQ, Zhang XY, Zhang YX, Pang D. Fangchinoline inhibits breast adenocarcinoma proliferation by inducing apoptosis. Chem Pharm Bull (Tokyo). 2011;59(12):1476-80. PubMed PMID: 22130369. 12: Wang Y, Chen J, Wang L, Huang Y, Leng Y, Wang G. Fangchinoline induces G0/G1 arrest by modulating the expression of CDKN1A and CCND2 in K562 human chronic myelogenous leukemia cells. Exp Ther Med. 2013 Apr;5(4):1105-1112. Epub 2013 Jan 24. PubMed PMID: 23596478; PubMed Central PMCID: PMC3627453. 13: Wang N, Pan W, Zhu M, Zhang M, Hao X, Liang G, Feng Y. Fangchinoline induces autophagic cell death via p53/sestrin2/AMPK signalling in human hepatocellular carcinoma cells. Br J Pharmacol. 2011 Sep;164(2b):731-42. doi: 10.1111/j.1476-5381.2011.01349.x. PubMed PMID: 21418191; PubMed Central PMCID: PMC3188903. 14: Tang Y, Sun A, Liu R, Zhang Y. Simultaneous determination of fangchinoline and tetrandrine in Stephania tetrandra S. Moore by using 1-alkyl-3-methylimidazolium-based ionic liquids as the RP-HPLC mobile phase additives. Anal Chim Acta. 2013 Mar 12;767:148-54. doi: 10.1016/j.aca.2013.01.001. Epub 2013 Jan 9. PubMed PMID: 23452799. 15: Bao X, Hu M, Zhang Y, Machibya F, Zhang Y, Jiang H, Yu D. Effect of fangchinoline on root resorption during rat orthodontic tooth movement. Korean J Orthod. 2012 Jun;42(3):138-43. doi: 10.4041/kjod.2012.42.3.138. Epub 2012 Jun 28. PubMed PMID: 23112944; PubMed Central PMCID: PMC3481979. 16: Luo X, Peng JM, Su LD, Wang DY, Yu YJ. Fangchinoline inhibits the proliferation of SPC-A-1 lung cancer cells by blocking cell cycle progression. Exp Ther Med. 2016 Feb;11(2):613-618. Epub 2015 Dec 4. PubMed PMID: 26893655; PubMed Central PMCID: PMC4734059. 17: He L, Yang J, Hu L. [Transmembrane transport activity of paclitaxel regulated by fangchinoline in MDR1-mDCK II cells]. Zhongguo Zhong Yao Za Zhi. 2010 Jun;35(11):1478-81. Chinese. PubMed PMID: 20822025. 18: Lin TY, Lu CW, Tien LT, Chuang SH, Wang YR, Chang WH, Wang SJ. Fangchinoline inhibits glutamate release from rat cerebral cortex nerve terminals (synaptosomes). Neurochem Int. 2009 Jul;54(8):506-12. doi: 10.1016/j.neuint.2009.02.001. Epub 2009 Feb 21. PubMed PMID: 19428795. 19: Tsutsumi T, Kobayashi S, Liu YY, Kontani H. Anti-hyperglycemic effect of fangchinoline isolated from Stephania tetrandra Radix in streptozotocin-diabetic mice. Biol Pharm Bull. 2003 Mar;26(3):313-7. PubMed PMID: 12612439. 20: Choi HS, Kim HS, Min KR, Kim Y, Lim HK, Chang YK, Chung MW. Anti-inflammatory effects of fangchinoline and tetrandrine. J Ethnopharmacol. 2000 Feb;69(2):173-9. PubMed PMID: 10687873.