Sanguinarine chloride | CAS# 5578-73-4 | Alkaloid

MedKoo Cat#: 461769 | Name: Sanguinarine chloride

Description:

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

Sanguinarine chloride is discontinued. Sanguinarine is a plant alkaloid with anti-proliferative effects against cancers, including pancreatic cancer.

Chemical Structure

Sanguinarine chloride

CAS#5578-73-4 (chloride)

Theoretical Analysis

MedKoo Cat#: 461769

Name: Sanguinarine chloride

CAS#: 5578-73-4 (chloride)

Chemical Formula: C20H14ClNO4

Exact Mass: 367.0600

Molecular Weight: 367.78

Elemental Analysis: C, 65.32; H, 3.84; Cl, 9.64; N, 3.81; O, 17.40

Price and Availability

This product was removed for the commercial reasons.

Related CAS #

2447-54-3 (cation) 5578-73-4 (chloride) 8006-58-4 (sulfate) 4752-86-7 (nitrate) 1099738-80-3 (chloride hydrate)

Synonym

SANGUINARINE; 2447-54-3; Pseudochelerythrine; Sanguinarin; Sangvinarin; SANGUINARIUM; Veadent; Sanguiritrin;

IUPAC/Chemical Name

13-methyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-13-ium chloride

InChi Key

GIZKAXHWLRYMLE-UHFFFAOYSA-M

InChi Code

InChI=1S/C20H14NO4.ClH/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21;/h2-8H,9-10H2,1H3;1H/q+1;/p-1

SMILES Code

C[N+]1=CC2=C3C(OCO3)=CC=C2C(C=CC4=C5)=C1C4=CC6=C5OCO6.[Cl-]

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 367.78 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: Rosen J, Landriscina A, Adler BL, Krauz A, Doerner J, Navati M, Musaev T, Gravekamp C, Nosanchuk J, Friedman AJ. Characterization and assessment of nanoencapsulated sanguinarine chloride as a potential treatment for melanoma. J Drugs Dermatol. 2015 May;14(5):453-8. PubMed PMID: 25942662. 2: Singh CK, Kaur S, George J, Nihal M, Pellitteri Hahn MC, Scarlett CO, Ahmad N. Molecular signatures of sanguinarine in human pancreatic cancer cells: A large scale label-free comparative proteomics approach. Oncotarget. 2015 Apr 30;6(12):10335-48. PubMed PMID: 25929337; PubMed Central PMCID: PMC4496359. 3: Çeçen E, Erçetin P, Kırkım G, Pamukoğlu A, Aktaş S, Altun Z, Doğan E, Olgun N. Apoptotic Effects of Sanguinarine on the Organ of Corti 1 Cells: Comparison with Cisplatin. J Int Adv Otol. 2015 Apr;11(1):19-22. doi: 10.5152/iao.2015.484. PubMed PMID: 26223712. 4: Chan WH. Hazardous effects of sanguinarine on maturation of mouse oocytes, fertilization, and fetal development through apoptotic processes. Environ Toxicol. 2015 Jul 8;30(8):946-55. doi: 10.1002/tox.21969. Epub 2014 Feb 21. PubMed PMID: 24677673. 5: Webster I, Smith A, Lochner A, Huisamen B. Sanguinarine non- versus re-circulation during isolated heart perfusion--a Jekyll and Hyde effect? Cardiovasc Drugs Ther. 2014 Oct;28(5):489-91. doi: 10.1007/s10557-014-6543-8. PubMed PMID: 25022545. 6: Cecen E, Altun Z, Ercetin P, Aktas S, Olgun N. Promoting effects of sanguinarine on apoptotic gene expression in human neuroblastoma cells. Asian Pac J Cancer Prev. 2014;15(21):9445-51. PubMed PMID: 25422239. 7: Zhang DS, Li YY, Chen XJ, Li YJ, Liu ZY, Xie WJ, Sun ZL. BCL2 promotor methylation and miR-15a/16-1 upregulation is associated with sanguinarine-induced apoptotic death in rat HSC-T6 cells. J Pharmacol Sci. 2015 Jan;127(1):135-44. doi: 10.1016/j.jphs.2014.11.012. Epub 2015 Jan 2. PubMed PMID: 25704029. 8: Park SY, Jin ML, Kim YH, Lee SJ, Park G. Sanguinarine inhibits invasiveness and the MMP-9 and COX-2 expression in TPA-induced breast cancer cells by inducing HO-1 expression. Oncol Rep. 2014 Jan;31(1):497-504. doi: 10.3892/or.2013.2843. Epub 2013 Nov 12. PubMed PMID: 24220687. 9: Kalogris C, Garulli C, Pietrella L, Gambini V, Pucciarelli S, Lucci C, Tilio M, Zabaleta ME, Bartolacci C, Andreani C, Giangrossi M, Iezzi M, Belletti B, Marchini C, Amici A. Sanguinarine suppresses basal-like breast cancer growth through dihydrofolate reductase inhibition. Biochem Pharmacol. 2014 Aug 1;90(3):226-34. doi: 10.1016/j.bcp.2014.05.014. Epub 2014 May 27. PubMed PMID: 24875448. 10: Park SY, Jin ML, Kim YH, Kim CM, Lee SJ, Park G. Involvement of heme oxygenase-1 in neuroprotection by sanguinarine against glutamate-triggered apoptosis in HT22 neuronal cells. Environ Toxicol Pharmacol. 2014 Nov;38(3):701-10. doi: 10.1016/j.etap.2014.08.022. Epub 2014 Sep 21. PubMed PMID: 25299846. 11: Hamoud R, Reichling J, Wink M. Synergistic antibacterial activity of the combination of the alkaloid sanguinarine with EDTA and the antibiotic streptomycin against multidrug resistant bacteria. J Pharm Pharmacol. 2015 Feb;67(2):264-73. doi: 10.1111/jphp.12326. Epub 2014 Dec 10. PubMed PMID: 25495516. 12: Deng W, Fang Y, Liu Y, Zhou H, Cheng Z, Zhang Y, Sun D, He M, Lin Y, Zhang R, Zhang J, Li W, Tang Q. Sanguinarine protects against pressure overload induced cardiac remodeling via inhibition of nuclear factor-κB activation. Mol Med Rep. 2014 Jul;10(1):211-6. doi: 10.3892/mmr.2014.2206. Epub 2014 May 2. PubMed PMID: 24804701. 13: Lee TK, Park C, Jeong SJ, Jeong MJ, Kim GY, Kim WJ, Choi YH. Sanguinarine Induces Apoptosis of Human Oral Squamous Cell Carcinoma KB Cells via Inactivation of the PI3K/Akt Signaling Pathway. Drug Dev Res. 2016 Aug;77(5):227-40. doi: 10.1002/ddr.21315. Epub 2016 Jul 1. PubMed PMID: 27363951. 14: Hamoud R, Reichling J, Wink M. Synergistic antimicrobial activity of combinations of sanguinarine and EDTA with vancomycin against multidrug resistant bacteria. Drug Metab Lett. 2014;8(2):119-28. PubMed PMID: 25692301. 15: Ying L, Li G, Wei SS, Wang H, An P, Wang X, Guo K, Luo XJ, Gao JM, Zhou Q, Li W, Yu Y, Li YG, Duan JL, Wang YP. Sanguinarine inhibits Rac1b-rendered cell survival enhancement by promoting apoptosis and blocking proliferation. Acta Pharmacol Sin. 2015 Feb;36(2):229-40. doi: 10.1038/aps.2014.115. Epub 2014 Dec 29. PubMed PMID: 25544362; PubMed Central PMCID: PMC5424477. 16: Verma P, Khan SA, Mathur AK, Ghosh S, Shanker K, Kalra A. Improved sanguinarine production via biotic and abiotic elicitations and precursor feeding in cell suspensions of latex-less variety of Papaver somniferum with their gene expression studies and upscaling in bioreactor. Protoplasma. 2014 Nov;251(6):1359-71. doi: 10.1007/s00709-014-0638-8. Epub 2014 Mar 28. PubMed PMID: 24677097. 17: Kollárová R, Oblozinský M, Kováciková V, Holková I, Balazová A, Pekárová M, Hoffman P, Bezáková L. Lipoxygenase activity and sanguinarine production in cell suspension cultures of California poppy (Eschscholtzia californica CHAM.). Pharmazie. 2014 Aug;69(8):637-40. PubMed PMID: 25158577. 18: Du XH, Huang S, Feng HR, Chen LL, Yang S, Lu LF. [Inhibition of sanguinarine on S180 subcutaneously implanted tumors in mice]. Zhong Yao Cai. 2014 Oct;37(10):1830-3. Chinese. PubMed PMID: 25895393. 19: Bojjireddy N, Sinha RK, Panda D, Subrahmanyam G. Sanguinarine suppresses IgE induced inflammatory responses through inhibition of type II PtdIns 4-kinase(s). Arch Biochem Biophys. 2013 Sep 15;537(2):192-7. doi: 10.1016/j.abb.2013.07.017. Epub 2013 Jul 27. PubMed PMID: 23899475. 20: Burgeiro A, Bento AC, Gajate C, Oliveira PJ, Mollinedo F. Rapid human melanoma cell death induced by sanguinarine through oxidative stress. Eur J Pharmacol. 2013 Apr 5;705(1-3):109-18. doi: 10.1016/j.ejphar.2013.02.035. Epub 2013 Mar 13. PubMed PMID: 23499690.