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MedKoo Cat#: 112196 | Name: Dihydrochelerythrine
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Description:

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

Dihydrochelerythrine inhibits secretion of the hepatitis B virus (HBV) antigens HBsAg and HBeAg from HepG2 2.2.15 cells and is cytotoxic to HCT8, BGC-823, and A2780 cancer cells.

Chemical Structure

Dihydrochelerythrine
CAS#6880-91-7

Theoretical Analysis

MedKoo Cat#: 112196

Name: Dihydrochelerythrine

CAS#: 6880-91-7

Chemical Formula: C21H19NO4

Exact Mass: 349.1314

Molecular Weight: 349.39

Elemental Analysis: C, 72.19; H, 5.48; N, 4.01; O, 18.32

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 650.00 2 Weeks
25mg USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
Dihydrochelerythrine; 12,13-Dihydrochelerythrine;
IUPAC/Chemical Name
1,2-dimethoxy-12-methyl-12,13-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine
InChi Key
ALZAZMCIBRHMFF-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H19NO4/c1-22-10-16-13(6-7-17(23-2)21(16)24-3)14-5-4-12-8-18-19(26-11-25-18)9-15(12)20(14)22/h4-9H,10-11H2,1-3H3
SMILES Code
CN1CC2=C(C(OC)=CC=C2C3=C1C4=CC5=C(C=C4C=C3)OCO5)OC
Appearance
To be determined
Purity
>95% (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

Preparing Stock Solutions

The following data is based on the product molecular weight 349.39 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
1: Qiu BL, Wang LY, Xia GY, Zhang JF, Wu YZ, Li R, Xiao BB, Zhong WC, Lin PC, Lin S. [Study on structural conversion of dihydrochelerythrine in different solvents]. Zhongguo Zhong Yao Za Zhi. 2018 Aug;43(16):3315-3321. Chinese. doi: 10.19540/j.cnki.cjcmm.20180511.002. PMID: 30200735. 2: 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. 3: Malhotra R, Rarhi C, Diveshkumar KV, Barik R, D'cunha R, Dhar P, Kundu M, Chattopadhyay S, Roy S, Basu S, Pradeepkumar PI, Hajra S. Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents. Bioorg Med Chem. 2016 Jul 1;24(13):2887-2896. doi: 10.1016/j.bmc.2016.04.059. Epub 2016 Apr 29. PMID: 27234888. 4: Vrba J, Dolezel P, Vicar J, Modrianský M, Ulrichová J. Chelerythrine and dihydrochelerythrine induce G1 phase arrest and bimodal cell death in human leukemia HL-60 cells. Toxicol In Vitro. 2008 Jun;22(4):1008-17. doi: 10.1016/j.tiv.2008.02.007. Epub 2008 Feb 15. PMID: 18358694. 5: Fotie J, Bohle DS, Olivier M, Adelaida Gomez M, Nzimiro S. Trypanocidal and antileishmanial dihydrochelerythrine derivatives from Garcinia lucida. J Nat Prod. 2007 Oct;70(10):1650-3. doi: 10.1021/np0702281. Epub 2007 Sep 20. PMID: 17880175. 6: 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. 7: Silva TCC, de Faria Lopes GP, de J Menezes-Filho N, de Oliveira DM, Pereira E, Pitanga BPS, Dos Santos Costa R, da Silva Velozo E, Freire SM, Clarêncio J, Borges HL, Rehen SK, Moura-Neto V, Costa SL. Specific Cytostatic and Cytotoxic Effect of Dihydrochelerythrine in Glioblastoma Cells: Role of NF-κB/β-catenin and STAT3/IL-6 Pathways. Anticancer Agents Med Chem. 2018;18(10):1386-1393. doi: 10.2174/1871520618666180412122101. PMID: 29651966. 8: 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. 9: Vacek J, Papoušková B, Kosina P, Galandáková A, Ulrichová J. Mass spectrometric investigation of chelerythrine and dihydrochelerythrine biotransformation patterns in human hepatocytes. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Dec 15;941:17-24. doi: 10.1016/j.jchromb.2013.09.037. Epub 2013 Oct 2. PMID: 24184831. 10: 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. 11: Lin Q, Ma C, Guan H, Chen L, Xie Q, Cheng X, Wang C. Metabolites identification and reversible interconversion of chelerythrine and dihydrochelerythrine in vitro/in vivo in rats using ultra-performance liquid chromatography combined with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. J Pharm Biomed Anal. 2020 Sep 10;189:113462. doi: 10.1016/j.jpba.2020.113462. Epub 2020 Jul 7. PMID: 32659571. 12: Klejdus B, Lojková L, Kosina P, Ulrichová J, Simánek V, Kubán V. Liquid chromatographic/electrospray mass spectrometric determination (LC/ESI-MS) of chelerythrine and dihydrochelerythrine in near-critical CO(2) extracts from real and spiked plasma samples. Talanta. 2007 Jun 15;72(4):1348-56. doi: 10.1016/j.talanta.2007.01.055. Epub 2007 Feb 2. PMID: 19071768.

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