MedKoo Cat#: 462688 | Name: Dihydrosanguinarine
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Description:

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

Dihydrosanguinarine is an alkaloid and a metabolite of the alkaloid sanguinarine that has diverse biological activities, including anticancer, fungicidal, and antiprotozoal properties. It inhibits proliferation of PANC-1, SW 1990, and HPDE6c7 cancer cells when used at concentrations of 10, 20, and 30 µM. It also reduces the levels of phosphorylated ERK and C-RAF, halts the cell cycle at the G0/G1 and G2/M phases, and induces apoptosis in PANC-1 cells. Dihydrosanguinarine inhibits spore germination of the phytopathogenic fungi B. cinerea and E. graminis in vitro. It has protective and curative effects against B. cinerea and E. graminis when applied as a spray to plants either before or after infection, respectively, at concentrations of 100 and 500 µg/ml. Dihydrosanguinarine is also effective against I. multifiliis infestation in S. curriculus with an LC50 value of 13.3 mg/L.

Chemical Structure

Dihydrosanguinarine
CAS#3606-45-9

Theoretical Analysis

MedKoo Cat#: 462688

Name: Dihydrosanguinarine

CAS#: 3606-45-9

Chemical Formula: C20H15NO4

Exact Mass: 333.1001

Molecular Weight: 333.34

Elemental Analysis: C, 72.06; H, 4.54; N, 4.20; O, 19.20

Price and Availability

Size Price Availability Quantity
5mg USD 500.00 2 Weeks
10mg USD 800.00 2 Weeks
25mg USD 1,300.00 2 Weeks
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Related CAS #
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Synonym
DHSA; 13,14-Dihydrosanguinarine; Dihydrosanguinarine; Hydrosanguinarine; Dihydrosanquinarine
IUPAC/Chemical Name
13-methyl-13,14-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridine
InChi Key
CIUHLXZTZWTVFL-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H15NO4/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/h2-7H,8-10H2,1H3
SMILES Code
CN1CC2=C(C=CC3=C2OCO3)C4=C1C5=C(C=C4)C=C6OCOC6=C5
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
Biological target:
Dihydrosanguinarine is a natural compound isolated from the leaves of Macleaya microcarpa; has antifungal and anticancer activity.
In vitro activity:
The results showed that DHSA (dihydrosanguinarine) treatment inhibited cell proliferation, migration and invasion in a time- and dose-dependent manner and led to induction of cell cycle arrest and apoptosis. These findings offer the novel perspective that DHSA inhibits pancreatic cancer cells through a bidirectional regulation between mut-p53/-Ras and WT-p53/-Ras to restore the dynamic balance by Ras and p53 proteins. Reference: Phytomedicine. 2019 Jun;59:152895. https://pubmed.ncbi.nlm.nih.gov/30913453/
In vivo activity:
TBD
Solvent mg/mL mM comments
Solubility
DMSO 5.2 15.60
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 333.34 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. Wu SZ, Xu HC, Wu XL, Liu P, Shi YC, Pang P, Deng L, Zhou GX, Chen XY. Dihydrosanguinarine suppresses pancreatic cancer cells via regulation of mut-p53/WT-p53 and the Ras/Raf/Mek/Erk pathway. Phytomedicine. 2019 Jun;59:152895. doi: 10.1016/j.phymed.2019.152895. Epub 2019 Mar 16. PMID: 30913453. 2. Fuchino H, Kawano M, Mori-Yasumoto K, Sekita S, Satake M, Ishikawa T, Kiuchi F, Kawahara N. In vitro leishmanicidal activity of benzophenanthridine alkaloids from Bocconia pearcei and related compounds. Chem Pharm Bull (Tokyo). 2010 Aug;58(8):1047-50. doi: 10.1248/cpb.58.1047. PMID: 20686258.
In vitro protocol:
1. Wu SZ, Xu HC, Wu XL, Liu P, Shi YC, Pang P, Deng L, Zhou GX, Chen XY. Dihydrosanguinarine suppresses pancreatic cancer cells via regulation of mut-p53/WT-p53 and the Ras/Raf/Mek/Erk pathway. Phytomedicine. 2019 Jun;59:152895. doi: 10.1016/j.phymed.2019.152895. Epub 2019 Mar 16. PMID: 30913453. 2. Fuchino H, Kawano M, Mori-Yasumoto K, Sekita S, Satake M, Ishikawa T, Kiuchi F, Kawahara N. In vitro leishmanicidal activity of benzophenanthridine alkaloids from Bocconia pearcei and related compounds. Chem Pharm Bull (Tokyo). 2010 Aug;58(8):1047-50. doi: 10.1248/cpb.58.1047. PMID: 20686258.
In vivo protocol:
TBD
1: Wu SZ, Xu HC, Wu XL, Liu P, Shi YC, Pang P, Deng L, Zhou GX, Chen XY. Dihydrosanguinarine suppresses pancreatic cancer cells via regulation of mut-p53/WT-p53 and the Ras/Raf/Mek/Erk pathway. Phytomedicine. 2019 Jun;59:152895. doi: 10.1016/j.phymed.2019.152895. Epub 2019 Mar 16. PMID: 30913453. 2: Chow YL, Iwata Y, Sato F. Dihydrosanguinarine Enhances Glucose Uptake in Mouse 3T3-L1 Cells. ACS Omega. 2017 Oct 31;2(10):6916-6925. doi: 10.1021/acsomega.7b01134. Epub 2017 Oct 19. PMID: 29202114; PMCID: PMC5705173. 3: Vrba J, Dolezel P, Vicar J, Ulrichová J. Cytotoxic activity of sanguinarine and dihydrosanguinarine in human promyelocytic leukemia HL-60 cells. Toxicol In Vitro. 2009 Jun;23(4):580-8. doi: 10.1016/j.tiv.2009.01.016. Epub 2009 Feb 3. PMID: 19346183. 4: Romo-Pérez A, Miranda LD, Chávez-Blanco AD, Dueñas-González A, Camacho-Corona MDR, Acosta-Huerta A, García A. Mild C(sp3)-H functionalization of dihydrosanguinarine and dihydrochelerythrine for development of highly cytotoxic derivatives. Eur J Med Chem. 2017 Sep 29;138:1-12. doi: 10.1016/j.ejmech.2017.06.021. Epub 2017 Jun 13. PMID: 28641156. 5: Yao JY, Zhou ZM, Li XL, Yin WL, Ru HS, Pan XY, Hao GJ, Xu Y, Shen JY. Antiparasitic efficacy of dihydrosanguinarine and dihydrochelerythrine from Macleaya microcarpa against Ichthyophthirius multifiliis in richadsin (Squaliobarbus curriculus). Vet Parasitol. 2011 Dec 29;183(1-2):8-13. doi: 10.1016/j.vetpar.2011.07.021. Epub 2011 Jul 20. PMID: 21813242. 6: Fossati E, Ekins A, Narcross L, Zhu Y, Falgueyret JP, Beaudoin GA, Facchini PJ, Martin VJ. Reconstitution of a 10-gene pathway for synthesis of the plant alkaloid dihydrosanguinarine in Saccharomyces cerevisiae. Nat Commun. 2014;5:3283. doi: 10.1038/ncomms4283. PMID: 24513861. 7: Xie H, Yang J, Feng S, Cheng P, Zeng J, Xiong X. Simultaneous quantitative determination of sanguinarine, chelerythrine, dihydrosanguinarine and dihydrochelerythrine in chicken by HPLC-MS/MS method and its applications to drug residue and pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Mar 15;985:124-30. doi: 10.1016/j.jchromb.2015.01.001. Epub 2015 Jan 12. PMID: 25681643. 8: Feng G, Zhang J, Liu YQ. Inhibitory activity of dihydrosanguinarine and dihydrochelerythrine against phytopathogenic fungi. Nat Prod Res. 2011 Jul;25(11):1082-9. doi: 10.1080/14786419.2010.487187. PMID: 21500094. 9: Kim DH, Lee JH, Park S, Oh SS, Kim S, Kim DW, Park KH, Kim KD. 6-Acetonyl-5,6-dihydrosanguinarine (ADS) from Chelidonium majus L. triggers proinflammatory cytokine production via ROS-JNK/ERK-NFκB signaling pathway. Food Chem Toxicol. 2013 Aug;58:273-9. doi: 10.1016/j.fct.2013.04.051. Epub 2013 May 6. PMID: 23659910. 10: Vrublova E, Vostalova J, Vecera R, Klejdus B, Stejskal D, Kosina P, Zdarilova A, Svobodova A, Lichnovsky V, Anzenbacher P, Dvorak Z, Vicar J, Simanek V, Ulrichova J. The toxicity and pharmacokinetics of dihydrosanguinarine in rat: a pilot study. Food Chem Toxicol. 2008 Jul;46(7):2546-53. doi: 10.1016/j.fct.2008.04.013. Epub 2008 Apr 15. PMID: 18495316. 11: Psotová J, Klejdus B, Vecera R, Kosina P, Kubán V, Vicar J, Simánek V, Ulrichová J. A liquid chromatographic-mass spectrometric evidence of dihydrosanguinarine as a first metabolite of sanguinarine transformation in rat. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Jan 2;830(1):165-72. doi: 10.1016/j.jchromb.2005.10.030. Epub 2005 Nov 8. PMID: 16280262. 12: Gao L, Schmitz HJ, Merz KH, Schrenk D. Characterization of the cytotoxicity of selected Chelidonium alkaloids in rat hepatocytes. Toxicol Lett. 2019 Sep 1;311:91-97. doi: 10.1016/j.toxlet.2019.04.031. Epub 2019 May 1. PMID: 31054355. 13: Tatton MR, Simpson I, Donohoe TJ. New methods for the synthesis of naphthyl amines; application to the synthesis of dihydrosanguinarine, sanguinarine, oxysanguinarine and (±)-maclekarpines B and C. Chem Commun (Camb). 2014 Oct 7;50(77):11314-6. doi: 10.1039/c4cc05209a. PMID: 25116797. 14: Zhao ZM, Shang XF, Lawoe RK, Liu YQ, Zhou R, Sun Y, Yan YF, Li JC, Yang GZ, Yang CJ. Anti-phytopathogenic activity and the possible mechanisms of action of isoquinoline alkaloid sanguinarine. Pestic Biochem Physiol. 2019 Sep;159:51-58. doi: 10.1016/j.pestbp.2019.05.015. Epub 2019 May 25. PMID: 31400784. 15: SARKAR SM. Isolation from argemone oil of dihydrosanguinarine and sanguinarine; toxicity of sanguinarine. Nature. 1948 Aug 14;162(4111):265. doi: 10.1038/162265a0. PMID: 18877104. 16: Tyler RT, Eilert U, Rijnders CO, Roewer IA, Kurz WG. Semi-continuous production of sanguinarine and dihydrosanguinarine by Papaver somniferum L. cell suspension cultures treated with fungal homogenate. Plant Cell Rep. 1988 Oct;7(6):410-3. doi: 10.1007/BF00269525. PMID: 24240257. 17: Sandor R, Slanina J, Midlik A, Sebrlova K, Novotna L, Carnecka M, Slaninova I, Taborsky P, Taborska E, Pes O. Sanguinarine is reduced by NADH through a covalent adduct. Phytochemistry. 2018 Jan;145:77-84. doi: 10.1016/j.phytochem.2017.10.010. Epub 2017 Nov 5. PMID: 29107809. 18: Dvorák Z, Simánek V. Metabolism of sanguinarine: the facts and the myths. Curr Drug Metab. 2007 Feb;8(2):173-6. doi: 10.2174/138920007779815959. PMID: 17305495. 19: Hu NX, Chen M, Liu YS, Shi Q, Yang B, Zhang HC, Cheng P, Tang Q, Liu ZY, Zeng JG. Pharmacokinetics of sanguinarine, chelerythrine, and their metabolites in broiler chickens following oral and intravenous administration. J Vet Pharmacol Ther. 2019 Mar;42(2):197-206. doi: 10.1111/jvp.12729. Epub 2018 Oct 22. PMID: 30350369. 20: Huang P, Xia L, Liu W, Jiang R, Liu X, Tang Q, Xu M, Yu L, Tang Z, Zeng J. Hairy root induction and benzylisoquinoline alkaloid production in Macleaya cordata. Sci Rep. 2018 Aug 10;8(1):11986. doi: 10.1038/s41598-018-30560-0. PMID: 30097605; PMCID: PMC6086913.