Cryptolepine

• CAT Number: I025230
• CAS Number: 480-26-2
• Molecular Formula: C10H11N
• Molecular Weight: 145.21
• Purity: 98%
• Synonyms: Cryptolepine; CCRIS9019; CCRIS-9019; CCRIS 9019
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 5H-Quindoline, 5-methyl-
• InChI: InChI=1S/C10H11N/c1-8-4-2-6-10-9(8)5-3-7-11-10/h2-8,11H,1H3
• InChIKey: IUMFAHWKEMZVTO-UHFFFAOYSA-N
• SMILES: CC1C2=CC=CNC2=CC=C1

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

Reference

1: 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.
2: Mariz IFA, Pinto S, Lavrado J, Paulo A, Martinho JMG, Maçôas EMS. Cryptolepine and quindoline: understanding their photophysics. Phys Chem Chem Phys. 2017 Apr 19;19(16):10255-10263. doi: 10.1039/c7cp00455a. PMID: 28265616.
3: Nuthakki VK, Mudududdla R, Sharma A, Kumar A, Bharate SB. Synthesis and biological evaluation of indoloquinoline alkaloid cryptolepine and its bromo- derivative as dual cholinesterase inhibitors. Bioorg Chem. 2019 Sep;90:103062. doi: 10.1016/j.bioorg.2019.103062. Epub 2019 Jun 12. PMID: 31220673.
4: 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.
5: 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.
6: 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.
7: Stell JG, Wheelhouse RT, Wright CW. Metabolism of cryptolepine and 2-fluorocryptolepine by aldehyde oxidase. J Pharm Pharmacol. 2012 Feb;64(2):237-43. doi: 10.1111/j.2042-7158.2011.01408.x. Epub 2011 Nov 18. PMID: 22221099.
8: Yuan JM, Wei K, Zhang GH, Chen NY, Wei XW, Pan CX, Mo DL, Su GF. Cryptolepine and aromathecin based mimics as potent G-quadruplex-binding, DNA-cleavage and anticancer agents: Design, synthesis and DNA targeting-induced apoptosis. Eur J Med Chem. 2019 May 1;169:144-158. doi: 10.1016/j.ejmech.2019.02.072. Epub 2019 Mar 4. PMID: 30875505.
9: Forkuo AD, Ansah C, Pearson D, Gertsch W, Cirello A, Amaral A, Spear J, Wright CW, Rynn C. Identification of cryptolepine metabolites in rat and human hepatocytes and metabolism and pharmacokinetics of cryptolepine in Sprague Dawley rats. BMC Pharmacol Toxicol. 2017 Dec 22;18(1):84. doi: 10.1186/s40360-017-0188-8. PMID: 29273084; PMCID: PMC5741962.
10: Ameyaw EO, Asmah KB, Biney RP, Henneh IT, Owusu-Agyei P, Prah J, Forkuo AD. Isobolographic analysis of co-administration of two plant-derived antiplasmodial drug candidates, cryptolepine and xylopic acid, in Plasmodium berghei. Malar J. 2018 Apr 4;17(1):153. doi: 10.1186/s12936-018-2283-8. PMID: 29618354; PMCID: PMC5885295.