Daurisoline | CAS#70553-76-3 | Alkaloid

MedKoo Cat#: 558994 | Name: Daurisoline

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Description:

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

An alkaloid with diverse biological activities

Chemical Structure

Daurisoline

CAS#70553-76-3

Theoretical Analysis

MedKoo Cat#: 558994

Name: Daurisoline

CAS#: 70553-76-3

Chemical Formula: C37H42N2O6

Exact Mass: 610.3043

Molecular Weight: 610.75

Elemental Analysis: C, 72.76; H, 6.93; N, 4.59; O, 15.72

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 350.00	2 Weeks
25mg	USD 750.00	2 Weeks

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Related CAS #

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Synonym

(–)-Daurisoline; (R,R)-Daurisoline; O7-Demethyldauricine; Daruisoline

IUPAC/Chemical Name

(1R)-1,2,3,4-tetrahydro-1-[[4-hydroxy-3-[4-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl]methyl]phenoxy]phenyl]methyl]-6-methoxy-2-methyl-7-isoquinolinol

InChi Key

BURJAQFYNVMZDV-FIRIVFDPSA-N

InChi Code

InChI=1S/C37H42N2O6/c1-38-15-13-26-20-36(43-4)37(44-5)22-29(26)30(38)16-23-6-9-27(10-7-23)45-35-18-24(8-11-32(35)40)17-31-28-21-33(41)34(42-3)19-25(28)12-14-39(31)2/h6-11,18-22,30-31,40-41H,12-17H2,1-5H3/t30-,31-/m1/s1

SMILES Code

OC(C(OC)=C1)=CC2=C1CCN(C)[C@@H]2CC3=CC=C(OC4=C(O)C=CC(C[C@H]5N(C)CCC6=C5C=C(O)C(OC)=C6)=C4)C=C3

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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 610.75 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: Huang K, Chen Q, Deng L, Zou Q, Min S. Daurisoline Inhibiting Tumor Angiogenesis and Epithelial-Mesenchymal Transition in Bladder Cancer by Mediating HAKAI Protein Stability. Iran J Pharm Res. 2022 Dec 3;21(1):e129798. doi: 10.5812/ijpr-129798. PMID: 36937208; PMCID: PMC10016139. 2: Wang D, Zhang W, Zhang X, Li M, Wu Q, Li X, Zhao L, Yuan Q, Yu Y, Lu J, Zhao J, Dong Z, Liu K, Jiang Y. Daurisoline suppresses esophageal squamous cell carcinoma growth in vitro and in vivo by targeting MEK1/2 kinase. Mol Carcinog. 2023 Apr;62(4):517-531. doi: 10.1002/mc.23503. Epub 2023 Jan 16. PMID: 36645220. 3: Xue L, Liu P. Daurisoline inhibits hepatocellular carcinoma progression by restraining autophagy and promoting cispaltin-induced cell death. Biochem Biophys Res Commun. 2021 Jan 1;534:1083-1090. doi: 10.1016/j.bbrc.2020.09.068. Epub 2020 Nov 17. PMID: 33213840. 4: Zhang Y, Liu W, Liu Z, Liu Y. Daurisoline attenuates H2O2-induced chondrocyte autophagy by activating the PI3K/Akt/mTOR signaling pathway. J Orthop Surg Res. 2023 Mar 27;18(1):248. doi: 10.1186/s13018-023-03717-5. PMID: 36973772; PMCID: PMC10041752. 5: Huang XH, Yan X, Zhang QH, Hong P, Zhang WX, Liu YP, Xu WW, Li B, He QY. Direct targeting of HSP90 with daurisoline destabilizes β-catenin to suppress lung cancer tumorigenesis. Cancer Lett. 2020 Oct 1;489:66-78. doi: 10.1016/j.canlet.2020.05.024. Epub 2020 Jun 13. PMID: 32544514. 6: Zhou J, Wu H, Hou J, Wang J, Wang J, Li M, Yao X, Gao J, Zhang Q. Daurisoline alleviated experimental colitis in vivo and in vitro: Involvement of NF-κB and Wnt/β-Catenin pathway. Int Immunopharmacol. 2022 Jul;108:108714. doi: 10.1016/j.intimp.2022.108714. Epub 2022 Mar 30. PMID: 35366641. 7: Yuan S, Pan Y, Xu T, Zhang L, Chen X, Wang F, Liu Q, Jia L. Daurisoline Inhibits ESCC by Inducing G1 Cell Cycle Arrest and Activating ER Stress to Trigger Noxa-Dependent Intrinsic and CHOP-DR5-Dependent Extrinsic Apoptosis via p-eIF2α-ATF4 Axis. Oxid Med Cell Longev. 2022 Aug 4;2022:5382263. doi: 10.1155/2022/5382263. PMID: 35965681; PMCID: PMC9371853. 8: Wang K, Zhang Z, Hang J, Liu J, Guo F, Ding Y, Li M, Nie Q, Lin J, Zhuo Y, Sun L, Luo X, Zhong Q, Ye C, Yun C, Zhang Y, Wang J, Bao R, Pang Y, Wang G, Gonzalez FJ, Lei X, Qiao J, Jiang C. Microbial-host-isozyme analyses reveal microbial DPP4 as a potential antidiabetic target. Science. 2023 Aug 4;381(6657):eadd5787. doi: 10.1126/science.add5787. Epub 2023 Aug 4. PMID: 37535747. 9: Liu QN, Zhang L, Gong PL, Yang XY, Zeng FD. Daurisoline suppressed early afterdepolarizations and inhibited L-type calcium current. Am J Chin Med. 2010;38(1):37-49. doi: 10.1142/S0192415X1000766X. PMID: 20128043. 10: Lu YM, Liu GQ. The effects of (-)-daurisoline on Ca2+ influx in presynaptic nerve terminals. Br J Pharmacol. 1990 Sep;101(1):45-8. doi: 10.1111/j.1476-5381.1990.tb12086.x. PMID: 2282465; PMCID: PMC1917626. 11: Zhang X, Zhang JG, Mu W, Zhou HM, Liu GL, Li Q. The role of daurisoline treatment in hepatocellular carcinoma: Inhibiting vasculogenic mimicry formation and enhancing sensitivity to sorafenib. Phytomedicine. 2021 Nov;92:153740. doi: 10.1016/j.phymed.2021.153740. Epub 2021 Sep 8. PMID: 34600176. 12: Liu Q, Mao X, Zeng F, Jin S, Yang X. Effect of daurisoline on HERG channel electrophysiological function and protein expression. J Nat Prod. 2012 Sep 28;75(9):1539-45. doi: 10.1021/np300232b. Epub 2012 Sep 13. PMID: 22974355. 13: Osmakov DI, Koshelev SG, Lyukmanova EN, Shulepko MA, Andreev YA, Illes P, Kozlov SA. Multiple Modulation of Acid-Sensing Ion Channel 1a by the Alkaloid Daurisoline. Biomolecules. 2019 Aug 2;9(8):336. doi: 10.3390/biom9080336. PMID: 31382492; PMCID: PMC6722837. 14: Shi SJ, Chen H, Gu SF, Zeng FD. Pharmacokinetic-pharmacodynamic modeling of daurisoline and dauricine in beagle dogs. Acta Pharmacol Sin. 2003 Oct;24(10):1011-5. PMID: 14531944. 15: Hu ZY, Xu LM, Sun Y, Chen SL, Cai HM. Daurisoline derivatives inhibit the ability of calmodulin to stimulate cyclic nucleotide phosphodiesterase activity. Cell Signal. 1990;2(4):353-7. doi: 10.1016/0898-6568(90)90065-i. PMID: 2252839. 16: Wang ZX, Zhu JQ, Zeng FD, Hu CJ, Ma YL, Zhong SM. Effects of daurisoline on intracellular Ca2+ activity in myocardium. Zhongguo Yao Li Xue Bao. 1996 May;17(3):248-51. PMID: 9812749. 17: Liu J, Li R, Liu G, Wang J. [Protective effects of (-)-S.R-daurisoline on neuronal injury in rat primary cortical cultures]. Yao Xue Xue Bao. 1998;33(3):171-4. Chinese. PMID: 11938960. 18: Wu MY, Wang SF, Cai CZ, Tan JQ, Li M, Lu JJ, Chen XP, Wang YT, Zheng W, Lu JH. Natural autophagy blockers, dauricine (DAC) and daurisoline (DAS), sensitize cancer cells to camptothecin-induced toxicity. Oncotarget. 2017 Sep 8;8(44):77673-77684. doi: 10.18632/oncotarget.20767. PMID: 29100416; PMCID: PMC5652807. 19: Waldmeier PC, Wicki P, Fröstl W, Bittiger H, Feldtrauer JJ, Baumann PA. Effects of the putative P-type calcium channel blocker, R,R-(-)-daurisoline on neurotransmitter release. Naunyn Schmiedebergs Arch Pharmacol. 1995 Dec;352(6):670-8. doi: 10.1007/BF00171327. PMID: 9053740. 20: Liu JG, Li R, Liu GQ. l-S.R-daurisoline protects cultured hippocampal neurons against glutamate neurotoxicity by reducing nitric oxide production. Zhongguo Yao Li Xue Bao. 1999 Jan;20(1):21-6. PMID: 10437119.