Oxysophocarpine | CAS# 26904-64-3 | Biochemical

MedKoo Cat#: 573972 | Name: Oxysophocarpine

Featured

Description:

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

Oxysophocarpine is an alkaloid from S. flavescens that has neuroprotective, anticancer, anti-inflammatory, and analgesic properties. It increases cell survival and decreases lactate dehydrogenase (LDH) leakage and loss of mitochondrial membrane potential in rat primary hippocampal neurons in a model of oxygen-glucose deprivation and reperfusion injury when used at concentrations of 1, 2, and 5 μM. Oxysophocarpine inhibits proliferation and reduces migration and invasion of SCC-9 and SCC-15 oral squamous cell carcinoma (OSCC) cells in vitro. It reduces tumor growth in an SCC-9 mouse xenograft model and inhibits xylene-induced ear swelling and carrageenan-induced paw edema. It also reduces carrageenan-induced decreases in the paw withdrawal threshold and prevents carrageenan-induced increases in paw tissue levels of TNF-α, IL-1β, IL-6, and prostaglandin E2 (PGE2) in mice when administered at a dose of 80 mg/kg.

Chemical Structure

Oxysophocarpine

CAS#26904-64-3

Theoretical Analysis

MedKoo Cat#: 573972

Name: Oxysophocarpine

CAS#: 26904-64-3

Chemical Formula: C15H22N2O2

Exact Mass: 262.1681

Molecular Weight: 262.35

Elemental Analysis: C, 68.67; H, 8.45; N, 10.68; O, 12.20

Price and Availability

Size	Price	Availability
10mg	USD 500.00
50mg	USD 1,050.00	2 Weeks
100mg	USD 1,600.00

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

(+)-Oxysophocarpine; Oxysophocarpine, Sophocarpine N-oxide

IUPAC/Chemical Name

(4R,7aS,13aR,13bR,13cS)-2,3,6,7,7a,8,13,13a,13b,13c-decahydro-1H,5H,10H-dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10-one, 4-oxide

InChi Key

QMGGMESMCJCABO-RDVIFRKPSA-N

InChi Code

InChI=1S/C15H22N2O2/c18-14-7-1-6-13-12-5-3-9-17(19)8-2-4-11(15(12)17)10-16(13)14/h1,7,11-13,15H,2-6,8-10H2/t11-,12+,13+,15?,17+/m0/s1

SMILES Code

O=C1C=CC[C@]2([H])[C@@]3([H])CCC[N@@+]4([O-])C3[C@](CCC4)([H])CN21

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Oxysophocarpine is an alkaloid.

In vitro activity:

The expression levels of Nrf2 in OSCC (oral squamous cell carcinoma) tissues and in cell lines were much higher than in non-cancerous tissues and normal oral keratinocytes. OSC (oxysophocarpine) reduced the expression of Nrf2 and heme oxygenase 1 (HO-1) in OSCC cells. OSC also inhibited proliferation, migration, invasion, and pro-angiogenesis of OSCC cells. Moreover, OSC induced cell cycle arrest, enhanced apoptosis of OSCC cells in vitro. Reference: Cell Physiol Biochem. 2018;49(5):1717-1733. https://pubmed.ncbi.nlm.nih.gov/30231242/

In vivo activity:

The aim of this study was to investigate the anti-nociceptive effects of OSC (oxysophocarpine) through systemic and intracerebroventricular administration in mice. The warm water tail-flick test, the hot‑plate test, acetic acid-induced abdominal constriction and formalin‑induced pain were used in mice. OSC was administered intraperitoneally (i.p.) or intracerebroventricularly (i.c.v.). Results showed that OSC (80 mg/kg, i.p.) significantly increased the tail withdrawal threshold with a peak effect of 25.46% maximal possible effect (MPE) at 60 min (P﹤0.01). Reference: Mol Med Rep. 2013 Jun;7(6):1819-25. https://pubmed.ncbi.nlm.nih.gov/23563643/

	Solvent	mg/mL	mM
Solubility
	DMSO	29.9	113.93
	Ethanol	31.0	118.16
	PBS (pH 7.2)	5.0	19.06
	Water	51.0	194.39

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 262.35 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. Li L, Shi R, Shi W, Zhang R, Wu L. Oxysophocarpine protects airway epithelial cells against inflammation and apoptosis by inhibiting miR-155 expression. Future Med Chem. 2020 Aug;12(16):1475-1487. doi: 10.4155/fmc-2020-0120. Epub 2020 Jun 30. PMID: 32603606. 2. Liu R, Peng J, Wang H, Li L, Wen X, Tan Y, Zhang L, Wan H, Chen F, Nie X. Oxysophocarpine Retards the Growth and Metastasis of Oral Squamous Cell Carcinoma by Targeting the Nrf2/HO-1 Axis. Cell Physiol Biochem. 2018;49(5):1717-1733. doi: 10.1159/000493615. Epub 2018 Sep 19. PMID: 30231242. 3. Zhi W, Jiang S, Xu Z, An Y, Chen J, Li Y, Liu Y, Zhang H. Oxysophocarpine inhibits airway inflammation and mucus hypersecretion through JNK/AP-1 pathway in vivo and in vitro. Fitoterapia. 2022 Oct;162:105278. doi: 10.1016/j.fitote.2022.105278. Epub 2022 Aug 12. PMID: 35970410. 4. Xu T, Li Y, Wang H, Xu Y, Ma L, Sun T, Ma H, Yu J. Oxysophocarpine induces anti-nociception and increases the expression of GABAAα1 receptors in mice. Mol Med Rep. 2013 Jun;7(6):1819-25. doi: 10.3892/mmr.2013.1414. Epub 2013 Apr 4. PMID: 23563643.

In vitro protocol:

In vivo protocol:

1. Zhi W, Jiang S, Xu Z, An Y, Chen J, Li Y, Liu Y, Zhang H. Oxysophocarpine inhibits airway inflammation and mucus hypersecretion through JNK/AP-1 pathway in vivo and in vitro. Fitoterapia. 2022 Oct;162:105278. doi: 10.1016/j.fitote.2022.105278. Epub 2022 Aug 12. PMID: 35970410. 2. Xu T, Li Y, Wang H, Xu Y, Ma L, Sun T, Ma H, Yu J. Oxysophocarpine induces anti-nociception and increases the expression of GABAAα1 receptors in mice. Mol Med Rep. 2013 Jun;7(6):1819-25. doi: 10.3892/mmr.2013.1414. Epub 2013 Apr 4. PMID: 23563643.

1: Li L, Lu F, Ding S, Wang X, Wang W, Zhang W, Xu W, Zhuang C, Miao Z, Ma X. Pharmacokinetic, Tissue Distribution, Metabolite, and Toxicity Evaluation of the Matrine Derivative, (6aS, 10S, 11aR, 11bR, 11cS)-10-Methylaminododecahydro-3a, 7a-Diaza-benzo (de) Anthracene-8-thione. Molecules. 2024 Jan 6;29(2):297. doi: 10.3390/molecules29020297. PMID: 38257210; PMCID: PMC10820135. 2: Liu C, Wang R, Jiao X, Zhang J, Zhang C, Wang Z. Oxysophocarpine suppresses TRAF6 level to ameliorate oxidative stress and inflammatory factors secretion in mice with dextran sulphate sodium (DSS) induced-ulcerative colitis. Microb Pathog. 2023 Sep;182:106244. doi: 10.1016/j.micpath.2023.106244. Epub 2023 Jul 7. PMID: 37423495. 3: Thang PNT, Tran VH, Vu TA, Vinh NN, Huynh DTM, Pham DT. Determination of Antioxidant, Cytotoxicity, and Acetylcholinesterase Inhibitory Activities of Alkaloids Isolated from Sophora flavescens Ait. Grown in Dak Nong, Vietnam. Pharmaceuticals (Basel). 2022 Nov 10;15(11):1384. doi: 10.3390/ph15111384. PMID: 36355556; PMCID: PMC9696406. 4: Lin Y, Chen XJ, He L, Yan XL, Li QR, Zhang X, He MH, Chang S, Tu B, Long QD, Zeng Z. Systematic elucidation of the bioactive alkaloids and potential mechanism from Sophora flavescens for the treatment of eczema via network pharmacology. J Ethnopharmacol. 2023 Jan 30;301:115799. doi: 10.1016/j.jep.2022.115799. Epub 2022 Oct 8. PMID: 36216196. 5: Ju M, Zhang Q, Wang R, Yan S, Li Z, Li P, Gu P. Correlation in endophytic fungi community diversity and bioactive compounds of Sophora alopecuroides. Front Microbiol. 2022 Aug 31;13:955647. doi: 10.3389/fmicb.2022.955647. PMID: 36118208; PMCID: PMC9475766. 6: Zhi W, Jiang S, Xu Z, An Y, Chen J, Li Y, Liu Y, Zhang H. Oxysophocarpine inhibits airway inflammation and mucus hypersecretion through JNK/AP-1 pathway in vivo and in vitro. Fitoterapia. 2022 Oct;162:105278. doi: 10.1016/j.fitote.2022.105278. Epub 2022 Aug 12. PMID: 35970410. 7: Jiang W, Tang M, Yang L, Zhao X, Gao J, Jiao Y, Li T, Tie C, Gao T, Han Y, Jiang JD. Analgesic Alkaloids Derived From Traditional Chinese Medicine in Pain Management. Front Pharmacol. 2022 May 10;13:851508. doi: 10.3389/fphar.2022.851508. PMID: 35620295; PMCID: PMC9127080. 8: Lei L, Zhao Y, Shi K, Liu Y, Hu Y, Shao H. Phytotoxic Activity of Alkaloids in the Desert Plant Sophora alopecuroides. Toxins (Basel). 2021 Oct 6;13(10):706. doi: 10.3390/toxins13100706. PMID: 34678999; PMCID: PMC8540331. 9: Li HF, Bao JH, Tian L, Alisa, Dong ZQ, Borjigidai A. [Biopharmaceutical classification and transport mechanism of 4 alkaloids in Mongolian herbal medicine Sophorae Flavescentis Radix]. Zhongguo Zhong Yao Za Zhi. 2021 Sep;46(18):4721-4729. Chinese. doi: 10.19540/j.cnki.cjcmm.20210319.307. PMID: 34581081. 10: Zhao JY, Wang ZM, Yi H, Chen LM, Si Q, Yan Y, Gao HM, Li C, Liu XQ, Yang H. [Discussion on rationality of Yinpian commodity grades--Sophora flavescentis as an example]. Zhongguo Zhong Yao Za Zhi. 2021 Aug;46(16):4040-4050. Chinese. doi: 10.19540/j.cnki.cjcmm.20210507.302. PMID: 34467713. 11: Yang Y, Sun M, Li W, Liu C, Jiang Z, Gu P, Li J, Wang W, You R, Ba Q, Li X, Wang H. Rebalancing TGF-β/Smad7 signaling via Compound kushen injection in hepatic stellate cells protects against liver fibrosis and hepatocarcinogenesis. Clin Transl Med. 2021 Jul;11(7):e410. doi: 10.1002/ctm2.410. PMID: 34323416; PMCID: PMC8255064. 12: Zhao Z, Song J, Zhang D, Wu F, Tu J, Ji J. Oxysophocarpine suppresses FGFR1-overexpressed hepatocellular carcinoma growth and sensitizes the therapeutic effect of lenvatinib. Life Sci. 2021 Jan 1;264:118642. doi: 10.1016/j.lfs.2020.118642. Epub 2020 Oct 24. PMID: 33148422. 13: Wang J, Wei W, Tang Q, Lu L, Luo Z, Li W, Lu Y, Pu J. Oxysophocarpine suppresses hepatocellular carcinoma growth and sensitizes the therapeutic blockade of anti-Lag-3 via reducing FGL1 expression. Cancer Med. 2020 Oct;9(19):7125-7136. doi: 10.1002/cam4.3151. Epub 2020 Aug 18. PMID: 32810392; PMCID: PMC7541159. 14: Yang D, Chen F, Gu Z, Lü L, Ding G, Peng Z, Shang J, Zhang T. Oxysophocarpine reduces oxidative stress and inflammation in tuberculosis- infected neutrophils and mouse lungs. Int J Clin Exp Pathol. 2020 Jul 1;13(7):1506-1517. PMID: 32782669; PMCID: PMC7414503. 15: Li L, Shi R, Shi W, Zhang R, Wu L. Oxysophocarpine protects airway epithelial cells against inflammation and apoptosis by inhibiting miR-155 expression. Future Med Chem. 2020 Aug;12(16):1475-1487. doi: 10.4155/fmc-2020-0120. Epub 2020 Jun 30. PMID: 32603606. 16: Fang YG, Zhu HD, Liu XQ, Chen LM, Meng CX, Zhang D, Gao HM, Wang ZM. [Study on revision of quality standard of Sophorae Flavescentis Radix and its processed slices]. Zhongguo Zhong Yao Za Zhi. 2020 Apr;45(8):1756-1763. Chinese. doi: 10.19540/j.cnki.cjcmm.20200314.201. PMID: 32489058. 17: Aung TN, Nourmohammadi S, Qu Z, Harata-Lee Y, Cui J, Shen HY, Yool AJ, Pukala T, Du H, Kortschak RD, Wei W, Adelson DL. Fractional Deletion of Compound Kushen Injection Indicates Cytokine Signaling Pathways are Critical for its Perturbation of the Cell Cycle. Sci Rep. 2019 Oct 2;9(1):14200. doi: 10.1038/s41598-019-50271-4. PMID: 31578346; PMCID: PMC6775143. 18: Dong X, Li X, Li N, Zhao H, GuLa A, Zhang X, Zhang P, Bao B. A target-group- change couple with mass defect filtering strategy to identify the metabolites of "Dogel ebs" in rats plasma, urine and bile. J Sep Sci. 2019 Nov;42(21):3382-3389. doi: 10.1002/jssc.201900466. Epub 2019 Oct 3. PMID: 31503388. 19: Wang R, Deng X, Gao Q, Wu X, Han L, Gao X, Zhao S, Chen W, Zhou R, Li Z, Bai C. Sophora alopecuroides L.: An ethnopharmacological, phytochemical, and pharmacological review. J Ethnopharmacol. 2020 Feb 10;248:112172. doi: 10.1016/j.jep.2019.112172. Epub 2019 Aug 20. PMID: 31442619. 20: Cang S, Liu R, Wang T, Jiang X, Zhang W, Bi K, Li Q. Simultaneous determination of five active alkaloids from Compound Kushen Injection in rat plasma by LC-MS/MS and its application to a comparative pharmacokinetic study in normal and NSCLC nude rats. J Chromatogr B Analyt Technol Biomed Life Sci. 2019 Sep 15;1126-1127:121734. doi: 10.1016/j.jchromb.2019.121734. Epub 2019 Jul 24. PMID: 31401450.