Nitidine chloride | CAS#13063-04-2 | 6872-57-7 | topisomerase I inhibitor

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

MedKoo CAT#: 407364

CAS#: 13063-04-2 (chloride)

Description: Nitidine is a benzophenanthridine alkaloid found in species of the genus Zanthoxylum , notably in Zanthoxylum nitidum. This compound has an anti-malarial activity. Nitidine increased CNS tissue sparing and improved functional recovery by attenuating reactive microgliosis, suggestive of the potential therapeutic benefit for CNS injury. Nitidine chloride induces apoptosis and inhibits tumor cell proliferation via suppressing ERK signaling pathway in renal cancer. Nitidine chloride inhibits renal cancer cell metastasis via suppressing AKT signaling pathway. Nitidine chloride inhibits ovarian cancer cell migration and invasion by suppressing MMP-2/9 production via the ERK signaling pathway. Nitidine chloride induces apoptosis, cell cycle arrest, and synergistic cytotoxicity with doxorubicin in breast cancer cells.

Chemical Structure

Nitidine chloride

CAS# 13063-04-2 (chloride)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 407364
Name: Nitidine chloride
CAS#: 13063-04-2 (chloride)
Chemical Formula: C21H18ClNO4
Exact Mass: 0.00
Molecular Weight: 383.828
Elemental Analysis: C, 65.71; H, 4.73; Cl, 9.24; N, 3.65; O, 16.67

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 240
25mg	USD 610
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.

Related CAS #: 6872-57-7 (Nitidine cation); 13063-04-2 (chloride)

Synonym: Nitidine; NSC 146397; NSC-146397; NSC146397.

IUPAC/Chemical Name: (1,3)-Benzodioxolo(5,6-c)phenanthridinium, 2,3-dimethoxy-12-methyl-, chloride

InChi Key: QLDAACVSUMUMOR-UHFFFAOYSA-M

InChi Code: InChI=1S/C21H18NO4.ClH/c1-22-10-13-7-17(23-2)18(24-3)8-15(13)14-5-4-12-6-19-20(26-11-25-19)9-16(12)21(14)22;/h4-10H,11H2,1-3H3;1H/q+1;/p-1

SMILES Code: C[N+]1=CC2=CC(OC)=C(OC)C=C2C(C=CC3=C4)=C1C3=CC5=C4OCO5.[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: >2 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

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Product Data:

Product Data

Instruction:

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Biological target:	Nitidine is an anti-malarial activity.
In vitro activity:	This study demonstrated that Nitidine Chloride (NC) could inhibit breast cancer cells migration and invasion both in vitro and in vivo. Meanwhile, the protrusion formation and partial proteolytic activity of MMP-9 and MMP-2 were attenuated by NC in a dose-dependent manner in MDA-MB-231 cells. Furthermore, addition NC to cells significantly decreases PDGF induced phosphorylation of c-Src, FAK, MAPKs, activation of RhoA, Rac1 and AP-1 transcriptional activity. Reference: Cancer Lett. 2011 Dec 27;313(2):181-91. https://pubmed.ncbi.nlm.nih.gov/21959111/
In vivo activity:	Nitidine chloride (NC), a natural bioactive alkaloid derived from Zanthoxylum nitidum (Roxb) DC, has been shown to have inhibitory effects on various tumors. Consistently, the xenograft model performed in nude mice exhibited reduced tumor growth with NC treatment. Mechanically, this study presented that NC significantly decreased phosphorylation of ERK and Akt, accompanied by up-regulation of P53, Bax, cleavage caspase-3 and cleavage PARP, downregulation of Bcl-2, caspase-3 and PARP. Reference: Food Chem Toxicol. 2014 Apr;66:210-6. https://pubmed.ncbi.nlm.nih.gov/24508476/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	2.5	6.51

Preparing Stock Solutions

The following data is based on the product molecular weight 383.83 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:	1. Bouquet J, Rivaud M, Chevalley S, Deharo E, Jullian V, Valentin A. Biological activities of nitidine, a potential anti-malarial lead compound. Malar J. 2012 Mar 9;11:67. doi: 10.1186/1475-2875-11-67. PMID: 22404785; PMCID: PMC3325168. 2. Pan X, Han H, Wang L, Yang L, Li R, Li Z, Liu J, Zhao Q, Qian M, Liu M, Du B. Nitidine Chloride inhibits breast cancer cells migration and invasion by suppressing c-Src/FAK associated signaling pathway. Cancer Lett. 2011 Dec 27;313(2):181-91. doi: 10.1016/j.canlet.2011.09.001. Epub 2011 Sep 10. PMID: 21959111. 3. Fang Z, Tang Y, Jiao W, Xing Z, Guo Z, Wang W, Xu Z, Liu Z. Nitidine chloride induces apoptosis and inhibits tumor cell proliferation via suppressing ERK signaling pathway in renal cancer. Food Chem Toxicol. 2014 Apr;66:210-6. doi: 10.1016/j.fct.2014.01.049. Epub 2014 Feb 5. PMID: 24508476. 4. Chen J, Wang J, Lin L, He L, Wu Y, Zhang L, Yi Z, Chen Y, Pang X, Liu M. Inhibition of STAT3 signaling pathway by nitidine chloride suppressed the angiogenesis and growth of human gastric cancer. Mol Cancer Ther. 2012 Feb;11(2):277-87. doi: 10.1158/1535-7163.MCT-11-0648. Epub 2011 Dec 27. PMID: 22203730.
In vitro protocol:	1. Bouquet J, Rivaud M, Chevalley S, Deharo E, Jullian V, Valentin A. Biological activities of nitidine, a potential anti-malarial lead compound. Malar J. 2012 Mar 9;11:67. doi: 10.1186/1475-2875-11-67. PMID: 22404785; PMCID: PMC3325168. 2. Pan X, Han H, Wang L, Yang L, Li R, Li Z, Liu J, Zhao Q, Qian M, Liu M, Du B. Nitidine Chloride inhibits breast cancer cells migration and invasion by suppressing c-Src/FAK associated signaling pathway. Cancer Lett. 2011 Dec 27;313(2):181-91. doi: 10.1016/j.canlet.2011.09.001. Epub 2011 Sep 10. PMID: 21959111.
In vivo protocol:	1. Fang Z, Tang Y, Jiao W, Xing Z, Guo Z, Wang W, Xu Z, Liu Z. Nitidine chloride induces apoptosis and inhibits tumor cell proliferation via suppressing ERK signaling pathway in renal cancer. Food Chem Toxicol. 2014 Apr;66:210-6. doi: 10.1016/j.fct.2014.01.049. Epub 2014 Feb 5. PMID: 24508476. 2. Chen J, Wang J, Lin L, He L, Wu Y, Zhang L, Yi Z, Chen Y, Pang X, Liu M. Inhibition of STAT3 signaling pathway by nitidine chloride suppressed the angiogenesis and growth of human gastric cancer. Mol Cancer Ther. 2012 Feb;11(2):277-87. doi: 10.1158/1535-7163.MCT-11-0648. Epub 2011 Dec 27. PMID: 22203730.

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1: Yuan Y, Zhu F, Pu Y, Wang D, Huang A, Hu X, Qin S, Sun X, Su Z, He C. Neuroprotective effects of nitidine against traumatic CNS injury via inhibiting microglia activation. Brain Behav Immun. 2015 Aug;48:287-300. doi: 10.1016/j.bbi.2015.04.008. PubMed PMID: 25900440.

2: Bouquet J, Rivaud M, Chevalley S, Deharo E, Jullian V, Valentin A. Biological activities of nitidine, a potential anti-malarial lead compound. Malar J. 2012 Mar 9;11:67. doi: 10.1186/1475-2875-11-67. PubMed PMID: 22404785; PubMed Central PMCID: PMC3325168.

3: Praveena C, Veeresham C. Multiple shoot regeneration and effect of sugars on growth and nitidine accumulation in shoot cultures of Toddalia asiatica. Pharmacogn Mag. 2014 Aug;10(Suppl 3):S480-6. doi: 10.4103/0973-1296.139777. PubMed PMID: 25298663; PubMed Central PMCID: PMC4189261.

4: Chen J, Wang J, Lin L, He L, Wu Y, Zhang L, Yi Z, Chen Y, Pang X, Liu M. Inhibition of STAT3 signaling pathway by nitidine chloride suppressed the angiogenesis and growth of human gastric cancer. Mol Cancer Ther. 2012 Feb;11(2):277-87. doi: 10.1158/1535-7163.MCT-11-0648. PubMed PMID: 22203730.

5: Xu Q, Li ZX, Ye ZM. [Nitidine chloride-induced apoptosis of human osteosarcoma cells and its mechanism]. Nan Fang Yi Ke Da Xue Xue Bao. 2011 Feb;31(2):361-4. Chinese. PubMed PMID: 21354931.

6: Cesari I, Grisoli P, Paolillo M, Milanese C, Massolini G, Brusotti G. Isolation and characterization of the alkaloid Nitidine responsible for the traditional use of Phyllanthus muellerianus (Kuntze) Excell stem bark against bacterial infections. J Pharm Biomed Anal. 2015 Feb;105:115-20. doi: 10.1016/j.jpba.2014.11.051. PubMed PMID: 25546028.

7: Li Y, Zhang Z, Zhang Y, Deng D, Luo L, Han B, Fan C. Nitidine chloride-assisted bio-functionalization of reduced graphene oxide by bovine serum albumin for impedimetric immunosensing. Biosens Bioelectron. 2016 May 15;79:536-42. doi: 10.1016/j.bios.2015.12.076. PubMed PMID: 26748371.

8: Liu H, Ye D, Huang H, Wang X, Li D. [Studies on pharmacokinetics of nitidine chloride in rabbits]. Zhongguo Zhong Yao Za Zhi. 2009 Jun;34(11):1406-9. Chinese. PubMed PMID: 19771873.

9: Fang Z, Tang Y, Jiao W, Xing Z, Guo Z, Wang W, Xu Z, Liu Z. Nitidine chloride induces apoptosis and inhibits tumor cell proliferation via suppressing ERK signaling pathway in renal cancer. Food Chem Toxicol. 2014 Apr;66:210-6. doi: 10.1016/j.fct.2014.01.049. PubMed PMID: 24508476.

10: Fang Z, Tang Y, Jiao W, Xing Z, Guo Z, Wang W, Shi B, Xu Z, Liu Z. Nitidine chloride inhibits renal cancer cell metastasis via suppressing AKT signaling pathway. Food Chem Toxicol. 2013 Oct;60:246-51. doi: 10.1016/j.fct.2013.07.062. PubMed PMID: 23911800.

11: Wang Z, Jiang W, Zhang Z, Qian M, Du B. Nitidine chloride inhibits LPS-induced inflammatory cytokines production via MAPK and NF-kappaB pathway in RAW 264.7 cells. J Ethnopharmacol. 2012 Oct 31;144(1):145-50. doi: 10.1016/j.jep.2012.08.041. PubMed PMID: 22971898.

12: Jia CP, Feng F. Optimization of the separation and determination of nitidine and chelerythrine in Zanthoxylum nitidum by high-performance liquid chromatography with fluorescence detection. J Chromatogr Sci. 2014 Feb;52(2):164-8. doi: 10.1093/chromsci/bmt003. PubMed PMID: 23390024.

13: Sun X, Lin L, Chen Y, Liu T, Liu R, Wang Z, Mou K, Xu J, Li B, Song H. Nitidine chloride inhibits ovarian cancer cell migration and invasion by suppressing MMP-2/9 production via the ERK signaling pathway. Mol Med Rep. 2016 Apr;13(4):3161-8. doi: 10.3892/mmr.2016.4929. PubMed PMID: 26935265.

14: Zhai H, Hu S, Liu T, Wang F, Wang X, Wu G, Zhang Y, Sui M, Liu H, Jiang L. Nitidine chloride inhibits proliferation and induces apoptosis in colorectal cancer cells by suppressing the ERK signaling pathway. Mol Med Rep. 2016 Mar;13(3):2536-42. doi: 10.3892/mmr.2016.4827. PubMed PMID: 26847477; PubMed Central PMCID: PMC4768981.

15: Ou X, Lu Y, Liao L, Li D, Liu L, Liu H, Xu H. Nitidine chloride induces apoptosis in human hepatocellular carcinoma cells through a pathway involving p53, p21, Bax and Bcl-2. Oncol Rep. 2015 Mar;33(3):1264-74. doi: 10.3892/or.2014.3688. PubMed PMID: 25530218.

16: Liu N, Li P, Zang S, Liu Q, Ma D, Sun X, Ji C. Novel agent nitidine chloride induces erythroid differentiation and apoptosis in CML cells through c-Myc-miRNAs axis. PLoS One. 2015 Feb 3;10(2):e0116880. doi: 10.1371/journal.pone.0116880. PubMed PMID: 25647305; PubMed Central PMCID: PMC4315404.

17: Sun M, Zhang N, Wang X, Cai C, Cun J, Li Y, Lv S, Yang Q. Nitidine chloride induces apoptosis, cell cycle arrest, and synergistic cytotoxicity with doxorubicin in breast cancer cells. Tumour Biol. 2014 Oct;35(10):10201-12. doi: 10.1007/s13277-014-2327-9. PubMed PMID: 25027404.

18: Lin J, Shen A, Chen H, Liao J, Xu T, Liu L, Lin J, Peng J. Nitidine chloride inhibits hepatic cancer growth via modulation of multiple signaling pathways. BMC Cancer. 2014 Sep 30;14:729. doi: 10.1186/1471-2407-14-729. PubMed PMID: 25266147; PubMed Central PMCID: PMC4190448.

19: Li L, Tu M, Yang X, Sun S, Wu X, Zhou H, Zeng S, Jiang H. The contribution of human OCT1, OCT3, and CYP3A4 to nitidine chloride-induced hepatocellular toxicity. Drug Metab Dispos. 2014 Jul;42(7):1227-34. doi: 10.1124/dmd.113.056689. PubMed PMID: 24778366.

20: Kang M, Ou H, Wang R, Liu W, Tang A. The effect of nitidine chloride on the proliferation and apoptosis of nasopharyngeal carcinoma cells. J BUON. 2014 Jan-Mar;19(1):130-6. PubMed PMID: 24659654.

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