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MedKoo Cat#: 597936 | Name: Sophoridine
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Description:

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

Sophoridine is an anticancer agent, with a promising anti-rumor effect and lower toxicity. Anti-inflammatory.

Chemical Structure

Sophoridine
Sophoridine
CAS#6882-68-4

Theoretical Analysis

MedKoo Cat#: 597936

Name: Sophoridine

CAS#: 6882-68-4

Chemical Formula: C15H24N2O

Exact Mass: 248.1889

Molecular Weight: 248.37

Elemental Analysis: C, 72.54; H, 9.74; N, 11.28; O, 6.44

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 weeks
250mg USD 700.00 2 weeks
500mg USD 1,000.00 2 Weeks
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Related CAS #
145572-44-7 (hydrate)
Synonym
Sophoridin; l-Sophoridine; (−)-Sophoridine; (−) Sophoridine
IUPAC/Chemical Name
(41S,7aR,13aR,13bR)-dodecahydro-1H,5H,10H-dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10-one
InChi Key
ZSBXGIUJOOQZMP-BHPKHCPMSA-N
InChi Code
InChI=1S/C15H24N2O/c18-14-7-1-6-13-12-5-3-9-16-8-2-4-11(15(12)16)10-17(13)14/h11-13,15H,1-10H2/t11-,12-,13-,15+/m1/s1
SMILES Code
O=C1CCC[C@H]2N1C[C@H]3CCCN4[C@@H]3[C@@H]2CCC4
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, DMF, and ethanol
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
Biological target:
Sophoradine has diverse biological activities. It reduces viral titers in neonatal rat cardiomyocytes infected with coxsackievirus B3 at concentrations of 1 and 5 µg/ml. Sophoradine inhibits growth and induces apoptosis in SW480 colorectal cancer cells, and decreases tumor growth in a mouse xenograft model. Sophoradine reduces levels of inflammatory markers TNF-α, IL-8, and prostaglandin E2 in a mouse model of carrageenan-induced paw edema when administered at doses of 12.15 and 48.6 mg/kg.
In vitro activity:
Sophoridine has potential for pancreatic cancer treatment. Sophoridine killed cancer cells but had low cytotoxicity to normal cells. Pancreatic cancer cells were particularly sensitive. Sophoridine inhibited the proliferation of pancreatic cancer cells and induced cell cycle arrest at S phase and mitochondrial-related apoptosis. Sophoridine induced a sustained activation of the phosphorylation of ERK and JNK and provoked the generation of ROS in pancreatic cancer cells. Reference: J Exp Clin Cancer Res. 2020 Nov 26;39(1):263. https://pubmed.ncbi.nlm.nih.gov/28893319/
In vivo activity:
Sophoridine may represent a potential therapeutic agent for viral myocarditis. Sophoridine exhibited obvious antiviral effects both in vitro and in vivo, and serum samples obtained from rats with oral administration of sophoridine reduced the virus titers in infected myocardial cells. The serum concentration profile correlated closely with antiviral activity profile. Sophoridine significantly enhanced mRNA expression of IL-10 and IFN-gamma, but decreased TNF-alpha mRNA expression. Reference: Life Sci. 2006 Mar 20;78(17):1998-2005. https://pubmed.ncbi.nlm.nih.gov/16309710/
Solvent mg/mL mM comments
Solubility
DMF 30.0 120.79
DMSO 10.0 40.26
Ethanol 30.0 120.79
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 248.37 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.

Recalculate based on batch purity %
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. Xu Z, Zhang F, Bai C, Yao C, Zhong H, Zou C, Chen X. Sophoridine induces apoptosis and S phase arrest via ROS-dependent JNK and ERK activation in human pancreatic cancer cells. J Exp Clin Cancer Res. 2017 Sep 11;36(1):124. doi: 10.1186/s13046-017-0590-5. Erratum in: J Exp Clin Cancer Res. 2020 Nov 26;39(1):263. PMID: 28893319; PMCID: PMC5594456. 2. Zhao Z, Zhang D, Wu F, Tu J, Song J, Xu M, Ji J. Sophoridine suppresses lenvatinib-resistant hepatocellular carcinoma growth by inhibiting RAS/MEK/ERK axis via decreasing VEGFR2 expression. J Cell Mol Med. 2021 Jan;25(1):549-560. doi: 10.1111/jcmm.16108. Epub 2020 Nov 18. PMID: 33210432; PMCID: PMC7810959. 3. Sun J, Wang X, He Y, Tian X, Yuan T, Yang G, Yu T. Sophoridine Counteracts Obesity via Src-Mediated Inhibition of VEGFR Expression and PI3K/AKT Phosphorylation. Int J Mol Sci. 2024 Jan 19;25(2):1206. doi: 10.3390/ijms25021206. PMID: 38279206; PMCID: PMC10816114. 4. Zhang Y, Zhu H, Ye G, Huang C, Yang Y, Chen R, Yu Y, Cui X. Antiviral effects of sophoridine against coxsackievirus B3 and its pharmacokinetics in rats. Life Sci. 2006 Mar 20;78(17):1998-2005. doi: 10.1016/j.lfs.2005.09.034. Epub 2005 Nov 23. PMID: 16309710.
In vitro protocol:
1. Xu Z, Zhang F, Bai C, Yao C, Zhong H, Zou C, Chen X. Sophoridine induces apoptosis and S phase arrest via ROS-dependent JNK and ERK activation in human pancreatic cancer cells. J Exp Clin Cancer Res. 2017 Sep 11;36(1):124. doi: 10.1186/s13046-017-0590-5. Erratum in: J Exp Clin Cancer Res. 2020 Nov 26;39(1):263. PMID: 28893319; PMCID: PMC5594456. 2. Zhao Z, Zhang D, Wu F, Tu J, Song J, Xu M, Ji J. Sophoridine suppresses lenvatinib-resistant hepatocellular carcinoma growth by inhibiting RAS/MEK/ERK axis via decreasing VEGFR2 expression. J Cell Mol Med. 2021 Jan;25(1):549-560. doi: 10.1111/jcmm.16108. Epub 2020 Nov 18. PMID: 33210432; PMCID: PMC7810959.
In vivo protocol:
1. Sun J, Wang X, He Y, Tian X, Yuan T, Yang G, Yu T. Sophoridine Counteracts Obesity via Src-Mediated Inhibition of VEGFR Expression and PI3K/AKT Phosphorylation. Int J Mol Sci. 2024 Jan 19;25(2):1206. doi: 10.3390/ijms25021206. PMID: 38279206; PMCID: PMC10816114. 2. Zhang Y, Zhu H, Ye G, Huang C, Yang Y, Chen R, Yu Y, Cui X. Antiviral effects of sophoridine against coxsackievirus B3 and its pharmacokinetics in rats. Life Sci. 2006 Mar 20;78(17):1998-2005. doi: 10.1016/j.lfs.2005.09.034. Epub 2005 Nov 23. PMID: 16309710.
1: Li XM, Wu YG, Chen SL, Pan DX, Wu JN, Yu YH. [Antitumor action of sophoridine]. Zhongguo Yao Li Xue Bao. 1987 Mar;8(2):153-8. Chinese. PMID: 2959003. 2: Huang SK, Chen JF, Xie YX, Yuan HN. [Method of GC determination and pharmacokinetics of sophoridine in rabbits]. Yao Xue Xue Bao. 1988;23(8):561-5. Chinese. PMID: 3254035. 3: Zhang YL, Yao LY, Long YD, Luo W, Ding XL, Xiao LM. [Protective action of sophoridine on acute myocardial infarction in anesthetized dogs]. Zhongguo Yao Li Xue Bao. 1991 May;12(3):263-6. Chinese. PMID: 1781291. 4: Jin LX, Cui YY, Zhang GD. [HPLC analysis of alkaloids in Sophora flavescens Ait]. Yao Xue Xue Bao. 1993;28(2):136-9. Chinese. PMID: 8328283. 5: Wang X, Li J, Wei L, Omiya S. [Alkaloid constituents in the seeds of Sophora viciifolia Hance]. Zhongguo Zhong Yao Za Zhi. 1995 Mar;20(3):168-9, 192. Chinese. PMID: 7646780. 6: Yan Y, Wang X, Li J, Lao Q, Ji X. [Alkaloids in the flowers of Sophora viciifolia Hance]. Zhongguo Zhong Yao Za Zhi. 1996 Apr;21(4):232-3, 256. Chinese. PMID: 9208555. 7: Xiao P, Kubo H, Ohsawa M, Higashiyama K, Nagase H, Yan YN, Li JS, Kamei J, Ohmiya S. kappa-Opioid receptor-mediated antinociceptive effects of stereoisomers and derivatives of (+)-matrine in mice. Planta Med. 1999 Apr;65(3):230-3. doi: 10.1055/s-1999-14080. PMID: 10232067. 8: Song JZ, Xu HX, Tian SJ, But PP. Determination of quinolizidine alkaloids in traditional Chinese herbal drugs by nonaqueous capillary electrophoresis. J Chromatogr A. 1999 Oct 1;857(1-2):303-11. doi: 10.1016/s0021-9673(99)00758-x. PMID: 10536849. 9: Atta-Ur-Rahman, Choudhary MI, Parvez K, Ahmed A, Akhtar F, Nur-E-Alam M, Hassan NM. Quinolizidine Alkaloids from Sophora alopecuroides. J Nat Prod. 2000 Feb;63(2):190-192. PMID: 28054778. 10: Atta-Ur-Rahman Au, Choudhary MI, Parvez K, Ahmed A, Akhtar F, Nur-E-Alam M, Hassan NM. Quinolizidine alkaloids from Sophora alopecuroides. J Nat Prod. 2000 Feb;63(2):190-2. PMID: 10691706. 11: Zhang HM, Li HQ. Anti-arrhythmic effects of sophoridine and oxysophoridine. Zhongguo Yao Li Xue Bao. 1999 Jun;20(6):517-20. PMID: 10678144. 12: Zhang L, Li G, Houghton PJ, Jackson S, Twentyman PR. [Alkaloids in Sophora alopecuroides seed and relevant tests for activity]. Zhongguo Zhong Yao Za Zhi. 1997 Dec;22(12):740-3, 764. Chinese. PMID: 11243172. 13: Li K, Wang H. Simultaneous determination of matrine, sophoridine and oxymatrine in Sophora flavescens Ait. by high performance liquid chromatography. Biomed Chromatogr. 2004 Apr;18(3):178-82. doi: 10.1002/bmc.308. PMID: 15103704. 14: Li Y, Min G, Xue Q, Chen L, Liu W, Chen H. High-performance liquid chromatographic method for simultaneous determination of sophoridine and matrine in rat plasma. Biomed Chromatogr. 2004 Nov;18(9):619-24. doi: 10.1002/bmc.348. PMID: 15484226. 15: Chen X, Yi C, Yang X, Wang X. Liquid chromatography of active principles in Sophora flavescens root. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Dec 5;812(1-2):149-63. doi: 10.1016/j.jchromb.2004.08.032. PMID: 15556494. 16: Li XM, Zhuang WH, Jiang ZZ, Pan DX, Yu YH, Gong ZL. [Observation of pathological morphology on nervous system of rat with maximum dose sophoridine in chronic toxic test]. Ai Zheng. 2004 Nov;23(11 Suppl):1376-8. Chinese. PMID: 15566640. 17: Wu YJ, Chen JJ, Cheng YY. A sensitive and specific HPLC-MS method for the determination of sophoridine, sophocarpine and matrine in rabbit plasma. Anal Bioanal Chem. 2005 Aug;382(7):1595-600. doi: 10.1007/s00216-005-3316-z. Epub 2005 Jul 5. PMID: 15997382. 18: Yao HQ, Gao ZN, Han XX, Yu JQ, Du YP. [Study on direct electrochemical behaviors and the electroanalytical method of matrine type alkaloids at glassy carbon electrode]. Zhongguo Zhong Yao Za Zhi. 2005 May;30(10):765-8, 788. Chinese. PMID: 16075717. 19: Wu Y, Shao Q, Zhen Z, Cheng Y. Determination of quinolizidine alkaloids in Sophora flavescens and its preparation using capillary electrophoresis. Biomed Chromatogr. 2006 May;20(5):446-50. doi: 10.1002/bmc.581. PMID: 16167304. 20: Zhang Y, Zhu H, Ye G, Huang C, Yang Y, Chen R, Yu Y, Cui X. Antiviral effects of sophoridine against coxsackievirus B3 and its pharmacokinetics in rats. Life Sci. 2006 Mar 20;78(17):1998-2005. doi: 10.1016/j.lfs.2005.09.034. Epub 2005 Nov 23. PMID: 16309710.