Cryptolepine | CAS# 480-26-2 | antimalarial and cytotoxic

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

MedKoo CAT#: 413359

CAS#: 480-26-2

Description: Cryptolepine is an alkaloid with antimalarial and cytotoxic properties. It is able to intercalate into DNA at the cytosine-cytosine sites.

Chemical Structure

Cryptolepine

CAS# 480-26-2

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 413359
Name: Cryptolepine
CAS#: 480-26-2
Chemical Formula: C10H11N
Exact Mass: 145.09
Molecular Weight: 145.210
Elemental Analysis: C, 82.72; H, 7.64; N, 9.65

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 394	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: Cryptolepine; CCRIS9019; CCRIS-9019; CCRIS 9019

IUPAC/Chemical Name: 5H-Quindoline, 5-methyl-

InChi Key: IUMFAHWKEMZVTO-UHFFFAOYSA-N

InChi Code: InChI=1S/C10H11N/c1-8-4-2-6-10-9(8)5-3-7-11-10/h2-8,11H,1H3

SMILES Code: CC1C2=CC=CNC2=CC=C1

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

More Info:

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	TBD
In vitro activity:	Cryptolepine inhibited the growth of HepG2 cells in a dose- and time-dependent fashion (Fig. 1A). IC50 values at 48 and 72 h post-cryptolepine treatment were 6.8 and 3.8 μM, respectively. Reference: BMC Complement Med Ther. 2021; 21: 161. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8170807/
In vivo activity:	Monitoring of the estimated volume of the tumor xenografts indicated that the average tumor growth/size in terms of total tumor volume/mouse was significantly lower (68%, P < 0.001) in the cryptolepine-treated group than the group of mice administered vehicle alone (Fig. 7a). As shown in Fig. 7b, the average wet weight of the tumor at the termination of the experiment in the mice that were treated with cryptolepine was significantly lower than that of tumors from vehicle-treated control mice (61%, P < 0.001). Reference: Sci Rep. 2017; 7: 1498. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5431443/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	Soluble in DMSO	0.0	100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 145.21 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. Domfeh SA, Narkwa PW, Quaye O, Kusi KA, Awandare GA, Ansah C, Salam A, Mutocheluh M. Cryptolepine inhibits hepatocellular carcinoma growth through inhibiting interleukin-6/STAT3 signalling. BMC Complement Med Ther. 2021 Jun 2;21(1):161. doi: 10.1186/s12906-021-03326-x. PMID: 34078370; PMCID: PMC8170807. 2. Pal HC, Prasad R, Katiyar SK. Cryptolepine inhibits melanoma cell growth through coordinated changes in mitochondrial biogenesis, dynamics and metabolic tumor suppressor AMPKα1/2-LKB1. Sci Rep. 2017 May 4;7(1):1498. doi: 10.1038/s41598-017-01659-7. PMID: 28473727; PMCID: PMC5431443.
In vitro protocol:	1. Domfeh SA, Narkwa PW, Quaye O, Kusi KA, Awandare GA, Ansah C, Salam A, Mutocheluh M. Cryptolepine inhibits hepatocellular carcinoma growth through inhibiting interleukin-6/STAT3 signalling. BMC Complement Med Ther. 2021 Jun 2;21(1):161. doi: 10.1186/s12906-021-03326-x. PMID: 34078370; PMCID: PMC8170807. 2. Pal HC, Prasad R, Katiyar SK. Cryptolepine inhibits melanoma cell growth through coordinated changes in mitochondrial biogenesis, dynamics and metabolic tumor suppressor AMPKα1/2-LKB1. Sci Rep. 2017 May 4;7(1):1498. doi: 10.1038/s41598-017-01659-7. PMID: 28473727; PMCID: PMC5431443.
In vivo protocol:	1. Pal HC, Prasad R, Katiyar SK. Cryptolepine inhibits melanoma cell growth through coordinated changes in mitochondrial biogenesis, dynamics and metabolic tumor suppressor AMPKα1/2-LKB1. Sci Rep. 2017 May 4;7(1):1498. doi: 10.1038/s41598-017-01659-7. PMID: 28473727; PMCID: PMC5431443.

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1: Tudu CK, Bandyopadhyay A, Kumar M, Radha, Das T, Nandy S, Ghorai M, Gopalakrishnan AV, Proćków J, Dey A. Unravelling the pharmacological properties of cryptolepine and its derivatives: a mini-review insight. Naunyn Schmiedebergs Arch Pharmacol. 2023 Feb;396(2):229-238. doi: 10.1007/s00210-022-02302-7. Epub 2022 Oct 17. PMID: 36251044; PMCID: PMC9574835.

2: Zheng Z, Xu T, Liu Z, Tian W, Jiang ZH, Zhu GY, Li T, Gao J, Bai LP. Cryptolepine suppresses breast adenocarcinoma via inhibition of HIF-1 mediated glycolysis. Biomed Pharmacother. 2022 Sep;153:113319. doi: 10.1016/j.biopha.2022.113319. Epub 2022 Jun 23. PMID: 35753261.

3: Domfeh SA, Narkwa PW, Quaye O, Kusi KA, Awandare GA, Ansah C, Salam A, Mutocheluh M. Cryptolepine inhibits hepatocellular carcinoma growth through inhibiting interleukin-6/STAT3 signalling. BMC Complement Med Ther. 2021 Jun 2;21(1):161. doi: 10.1186/s12906-021-03326-x. PMID: 34078370; PMCID: PMC8170807.

4: Quarshie JT, Fosu K, Offei NA, Sobo AK, Quaye O, Aikins AR. Cryptolepine Suppresses Colorectal Cancer Cell Proliferation, Stemness, and Metastatic Processes by Inhibiting WNT/β-Catenin Signaling. Pharmaceuticals (Basel). 2023 Jul 19;16(7):1026. doi: 10.3390/ph16071026. PMID: 37513937; PMCID: PMC10383422.

5: Amissah JN, Alorvor FE, Okorley BA, Asare CM, Osei-Safo D, Appiah-Opong R, Addae-Mensah I. Mineral Fertilization Influences the Growth, Cryptolepine Yield, and Bioefficacy of Cryptolepis sanguinolenta (Lindl.) Schlt. Plants (Basel). 2022 Jan 1;11(1):122. doi: 10.3390/plants11010122. PMID: 35009125; PMCID: PMC8747327.

6: Mante PK, Adomako NO, Antwi P, Kusi-Boadum NK, Osafo N. Solid-lipid nanoparticle formulation improves antiseizure action of cryptolepine. Biomed Pharmacother. 2021 May;137:111354. doi: 10.1016/j.biopha.2021.111354. Epub 2021 Feb 6. PMID: 33561642.

7: Mensah KB, Benneh C, Forkuo AD, Ansah C. Cryptolepine, the Main Alkaloid of the Antimalarial Cryptolepis sanguinolenta (Lindl.) Schlechter, Induces Malformations in Zebrafish Embryos. Biochem Res Int. 2019 Jul 8;2019:7076986. doi: 10.1155/2019/7076986. PMID: 31360547; PMCID: PMC6644280.

8: Shnyder SD, Wright CW. Recent Advances in the Chemistry and Pharmacology of Cryptolepine. Prog Chem Org Nat Prod. 2021;115:177-203. doi: 10.1007/978-3-030-64853-4_4. PMID: 33797643.

9: Wright CW. Recent developments in naturally derived antimalarials: cryptolepine analogues. J Pharm Pharmacol. 2007 Jun;59(6):899-904. doi: 10.1211/jpp.59.6.0017. PMID: 17637183.

10: Qin LQ, Liang CJ, Zhou Z, Qin QP, Wei ZZ, Tan MX, Liang H. Mitochondria- localizing curcumin-cryptolepine Zn(II) complexes and their antitumor activity. Bioorg Med Chem. 2021 Jan 15;30:115948. doi: 10.1016/j.bmc.2020.115948. Epub 2020 Dec 19. PMID: 33360578.

11: Zhou Z, Du LQ, Huang XM, Zhu LG, Wei QC, Qin QP, Bian H. Novel glycosylation zinc(II)-cryptolepine complexes perturb mitophagy pathways and trigger cancer cell apoptosis and autophagy in SK-OV-3/DDP cells. Eur J Med Chem. 2022 Dec 5;243:114743. doi: 10.1016/j.ejmech.2022.114743. Epub 2022 Sep 8. PMID: 36116236.

12: Domfeh SA, Narkwa PW, Quaye O, Kusi KA, Addy BS, Lant S, Sumner RP, Maluquer de Motes C, Awandare GA, Ansah C, Mutocheluh M. The Pharmacologically Active Alkaloid Cryptolepine Activates a Type 1 Interferon Response That Is Independent of MAVS and STING Pathways. J Immunol Res. 2022 Jul 26;2022:8873536. doi: 10.1155/2022/8873536. PMID: 35928633; PMCID: PMC9345703.

13: Olajide OA, Ajayi AM, Wright CW. Anti-inflammatory properties of cryptolepine. Phytother Res. 2009 Oct;23(10):1421-5. doi: 10.1002/ptr.2794. PMID: 19288476.

14: Forkuo AD, Ansah C, Mensah KB, Annan K, Gyan B, Theron A, Mancama D, Wright CW. In vitro anti-malarial interaction and gametocytocidal activity of cryptolepine. Malar J. 2017 Dec 28;16(1):496. doi: 10.1186/s12936-017-2142-z. PMID: 29282057; PMCID: PMC5745596.

15: Ansah C, Mensah KB. A review of the anticancer potential of the antimalarial herbal cryptolepis sanguinolenta and its major alkaloid cryptolepine. Ghana Med J. 2013 Sep;47(3):137-47. PMID: 24391229; PMCID: PMC3875281.

16: Olajide OA, Heiss EH, Schachner D, Wright CW, Vollmar AM, Dirsch VM. Synthetic cryptolepine inhibits DNA binding of NF-kappaB. Bioorg Med Chem. 2007 Jan 1;15(1):43-9. doi: 10.1016/j.bmc.2006.10.018. Epub 2006 Oct 24. PMID: 17064915.

17: Pal HC, Prasad R, Katiyar SK. Cryptolepine inhibits melanoma cell growth through coordinated changes in mitochondrial biogenesis, dynamics and metabolic tumor suppressor AMPKα1/2-LKB1. Sci Rep. 2017 May 4;7(1):1498. doi: 10.1038/s41598-017-01659-7. PMID: 28473727; PMCID: PMC5431443.

18: Olajide OA, Bhatia HS, de Oliveira AC, Wright CW, Fiebich BL. Inhibition of Neuroinflammation in LPS-Activated Microglia by Cryptolepine. Evid Based Complement Alternat Med. 2013;2013:459723. doi: 10.1155/2013/459723. Epub 2013 May 8. PMID: 23737832; PMCID: PMC3662116.

19: Mehraj U, Qayoom H, Shafi S, Farhana P, Asdaq SMB, Mir MA. Cryptolepine Targets TOP2A and Inhibits Tumor Cell Proliferation in Breast Cancer Cells - An In vitro and In silico Study. Anticancer Agents Med Chem. 2022;22(17):3025-3037. doi: 10.2174/1871520622666220419135547. PMID: 35440335.

20: Sawer IK, Berry MI, Ford JL. The killing effect of cryptolepine on Staphylococcus aureus. Lett Appl Microbiol. 2005;40(1):24-9. doi: 10.1111/j.1472-765X.2004.01625.x. PMID: 15612998.

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