Salvicine | CAS#240423-23-8 | diterpenoid quinone

MedKoo Cat#: 145231 | Name: Salvicine

Description:

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

Salvicine is a novel diterpenoid quinone compound. Salvicine is obtained by structural modification of a natural product lead isolated from a Chinese herb. Salvicine is shown to inactivate the β1 integrin and inhibit integrin-mediated cell adhesion to fibronectin. Salvicine has potent anti-angiogenic activity through the inhibition on the sequential angiogenic cascades.

Chemical Structure

Salvicine

CAS#240423-23-8

Theoretical Analysis

MedKoo Cat#: 145231

Name: Salvicine

CAS#: 240423-23-8

Chemical Formula: C20H26O4

Exact Mass: 330.1831

Molecular Weight: 330.42

Elemental Analysis: C, 72.70; H, 7.93; O, 19.37

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Salvicine; Sarubicin;

IUPAC/Chemical Name

8-(3,4-dihydroxy-4-methylpentyl)-3-isopropyl-7-methylnaphthalene-1,2-dione

InChi Key

NZIUPDOWWMGNCV-UHFFFAOYSA-N

InChi Code

1S/C20H26O4/c1-11(2)15-10-13-7-6-12(3)14(17(13)19(23)18(15)22)8-9-16(21)20(4,5)24/h6-7,10-11,16,21,24H,8-9H2,1-5H3

SMILES Code

CC(C)C1=CC2=C(C(=O)C1=O)C(CCC(O)C(C)(C)O)=C(C)C=C2

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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 330.42 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: Dey D, Hasan MM, Biswas P, Papadakos SP, Rayan RA, Tasnim S, Bilal M, Islam MJ, Arshe FA, Arshad EM, Farzana M, Rahaman TI, Baral SK, Paul P, Bibi S, Rahman MA, Kim B. Investigating the Anticancer Potential of Salvicine as a Modulator of Topoisomerase II and ROS Signaling Cascade. Front Oncol. 2022 Jun 1;12:899009. doi: 10.3389/fonc.2022.899009. PMID: 35719997; PMCID: PMC9198638. 2: Meng LH, Ding J. Salvicine, a novel topoisomerase II inhibitor, exerts its potent anticancer activity by ROS generation. Acta Pharmacol Sin. 2007 Sep;28(9):1460-5. doi: 10.1111/j.1745-7254.2007.00698.x. PMID: 17723179. 3: Zhang Y, Wang L, Chen Y, Qing C. Anti-angiogenic activity of salvicine. Pharm Biol. 2013 Aug;51(8):1061-5. doi: 10.3109/13880209.2013.776612. Epub 2013 Jun 10. PMID: 23750780. 4: Hu CX, Zuo ZL, Xiong B, Ma JG, Geng MY, Lin LP, Jiang HL, Ding J. Salvicine functions as novel topoisomerase II poison by binding to ATP pocket. Mol Pharmacol. 2006 Nov;70(5):1593-601. doi: 10.1124/mol.106.027714. Epub 2006 Aug 16. PMID: 16914642. 5: Meng LH, Zhang JS, Ding J. Salvicine, a novel DNA topoisomerase II inhibitor, exerting its effects by trapping enzyme-DNA cleavage complexes. Biochem Pharmacol. 2001 Sep 15;62(6):733-41. doi: 10.1016/s0006-2952(01)00732-8. PMID: 11551518. 6: Zhou J, Chen Y, Lang JY, Lu JJ, Ding J. Salvicine inactivates beta 1 integrin and inhibits adhesion of MDA-MB-435 cells to fibronectin via reactive oxygen species signaling. Mol Cancer Res. 2008 Feb;6(2):194-204. doi: 10.1158/1541-7786.MCR-07-0197. PMID: 18314480. 7: Miao ZH, Tong LJ, Zhang JS, Han JX, Ding J. Characterization of salvicine- resistant lung adenocarcinoma A549/SAL cell line. Int J Cancer. 2004 Jul 10;110(5):627-32. doi: 10.1002/ijc.20026. PMID: 15146550. 8: Cai YJ, Lu JJ, Zhu H, Xie H, Huang M, Lin LP, Zhang XW, Ding J. Salvicine triggers DNA double-strand breaks and apoptosis by GSH-depletion-driven H2O2 generation and topoisomerase II inhibition. Free Radic Biol Med. 2008 Sep 1;45(5):627-35. doi: 10.1016/j.freeradbiomed.2008.05.017. Epub 2008 May 28. PMID: 18582559. 9: Lang JY, Chen H, Zhou J, Zhang YX, Zhang XW, Li MH, Lin LP, Zhang JS, Waalkes MP, Ding J. Antimetastatic effect of salvicine on human breast cancer MDA-MB-435 orthotopic xenograft is closely related to Rho-dependent pathway. Clin Cancer Res. 2005 May 1;11(9):3455-64. doi: 10.1158/1078-0432.CCR-04-2026. PMID: 15867248. 10: Qing C, Zhang JS, Ding J. In vitro cytotoxicity of salvicine, a novel diterpenoid quinone. Zhongguo Yao Li Xue Bao. 1999 Apr;20(4):297-302. PMID: 10452112. 11: Qing C, Miao ZH, Tong LJ, Zhang JS, Ding J. Actinomycin D inhibiting K562 cell apoptosis elicited by salvicine but not decreasing its cytotoxicity. Acta Pharmacol Sin. 2003 May;24(5):415-21. PMID: 12740176. 12: Li YP, Zhou ZH, Pei YY, Zhang XY, Gu ZH, Yuan WF. PEGylated polycyanoacrylate nanoparticles as salvicine carriers: synthesis, preparation, and in vitro characterization. Acta Pharmacol Sin. 2001 Jul;22(7):645-50. PMID: 11749831. 13: Liu WJ, Zhang YW, Shen Y, Jiang JF, Miao ZH, Ding J. Telomerase inhibition is a specific early event in salvicine-treated human lung adenocarcinoma A549 cells. Biochem Biophys Res Commun. 2004 Oct 15;323(2):660-7. doi: 10.1016/j.bbrc.2004.08.135. PMID: 15369801. 14: Liu WJ, Jiang JF, Xiao D, Ding J. Down-regulation of telomerase activity via protein phosphatase 2A activation in salvicine-induced human leukemia HL-60 cell apoptosis. Biochem Pharmacol. 2002 Dec 15;64(12):1677-87. doi: 10.1016/s0006-2952(02)01424-7. PMID: 12445857. 15: Cai Y, Lu J, Miao Z, Lin L, Ding J. Reactive oxygen species contribute to cell killing and P-glycoprotein downregulation by salvicine in multidrug resistant K562/A02 cells. Cancer Biol Ther. 2007 Nov;6(11):1794-9. doi: 10.4161/cbt.6.11.4860. Epub 2007 Aug 12. PMID: 18032928. 16: Qing C, Jiang C, Zhang JS, Ding J. Induction of apoptosis in human leukemia K-562 and gastric carcinoma SGC-7901 cells by salvicine, a novel anticancer compound. Anticancer Drugs. 2001 Jan;12(1):51-6. doi: 10.1097/00001813-200101000-00007. PMID: 11272286. 17: Miao ZH, Tang T, Zhang YX, Zhang JS, Ding J. Cytotoxicity, apoptosis induction and downregulation of MDR-1 expression by the anti-topoisomerase II agent, salvicine, in multidrug-resistant tumor cells. Int J Cancer. 2003 Aug 10;106(1):108-15. doi: 10.1002/ijc.11174. PMID: 12794765. 18: Lu HR, Meng LH, Huang M, Zhu H, Miao ZH, Ding J. DNA damage, c-myc suppression and apoptosis induced by the novel topoisomerase II inhibitor, salvicine, in human breast cancer MCF-7 cells. Cancer Chemother Pharmacol. 2005 Mar;55(3):286-94. doi: 10.1007/s00280-004-0877-z. Epub 2004 Nov 16. PMID: 15592835. 19: Meng LH, He XX, Zhang JS, Ding J. DNA topoisomerase II as the primary cellular target for salvicine in Saccharomyces cerevisiae. Acta Pharmacol Sin. 2001 Aug;22(8):741-6. PMID: 11749849. 20: Lu HR, Zhu H, Huang M, Chen Y, Cai YJ, Miao ZH, Zhang JS, Ding J. Reactive oxygen species elicit apoptosis by concurrently disrupting topoisomerase II and DNA-dependent protein kinase. Mol Pharmacol. 2005 Oct;68(4):983-94. doi: 10.1124/mol.105.011544. Epub 2005 Jul 15. PMID: 16024664.