Dihydrochelerythrine | CAS#6880-91-7 | Cytotoxic

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

MedKoo CAT#: 112196

CAS#: 6880-91-7

Description: 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

Instruction

Theoretical Analysis

MedKoo Cat#: 112196
Name: Dihydrochelerythrine
CAS#: 6880-91-7
Chemical Formula: C21H19NO4
Exact Mass: 349.13
Molecular Weight: 349.390
Elemental Analysis: C, 72.19; H, 5.48; N, 4.01; O, 18.32

Price and Availability

Size	Price	Availability
1mg	USD 250	2 Weeks
5mg	USD 560	2 Weeks
10mg	USD 880	2 Weeks
25mg	USD 1250	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: 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: >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

Biological target:
In vitro activity:
In vivo activity:

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.

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:
In vitro protocol:
In vivo protocol:

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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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