Cryptolepine

Last updated
Cryptolepine
Cryptolepine.svg
Names
Preferred IUPAC name
5-Methyl-5H-indolo[3,2-b]quinoline
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C16H12N2/c1-18-15-9-5-2-6-11(15)10-14-16(18)12-7-3-4-8-13(12)17-14/h2-10H,1H3
    Key: KURWKDDWCJELSV-UHFFFAOYSA-N
  • N2=C1C(C=CC=C1)=C4C2=Cc3ccccc3N4C
Properties
C16H12N2
Molar mass 232.286 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cryptolepine is an alkaloid with antimalarial and cytotoxic properties, in vitro and in mice. It is able to intercalate into DNA at the cytosine-cytosine sites. [1] [2] Because of its toxicity, Cryptolepine is not considered appropriate for use as an anti-malarial drug in humans. [3]

Cryptolepine can be found in the roots of the West African plant, Cryptolepis sanguinolenta . [1]

References

  1. 1 2 Wright, C. W.; Addae-Kyereme, J.; Breen, A. G.; Brown, J. E.; Cox, M. F.; Croft, S. L.; Gökçek, Y.; Kendrick, H.; Phillips, R. M.; Pollet, P. L. (2001). "Synthesis and evaluation of cryptolepine analogues for their potential as new antimalarial agents". Journal of Medicinal Chemistry. 44 (19): 3187–3194. doi:10.1021/jm010929+. PMID   11543688.
  2. ↑ Onyeibor, O.; Croft, S. L.; Dodson, H. I.; Feiz-Haddad, M.; Kendrick, H.; Millington, N. J.; Parapini, S.; Phillips, R. M.; Seville, S.; Shnyder, S. D.; Taramelli, D.; Wright, C. W. (2005). "Synthesis of Some Cryptolepine Analogues, Assessment of Their Antimalarial and Cytotoxic Activities, and Consideration of Their Antimalarial Mode of Action". Journal of Medicinal Chemistry. 48 (7): 2701–2709. doi:10.1021/jm040893w. hdl: 2434/17291 . PMID   15801861.
  3. ↑ Gopalan, Rajendran C.; Emerce, Esra; Wright, Colin W.; Karahalil, Bensu; Karakaya, Ali E.; Anderson, Diana (December 2011). "Effects of the anti-malarial compound cryptolepine and its analogues in human lymphocytes and sperm in the Comet assay". Toxicology Letters. 207 (3): 322–325. doi:10.1016/j.toxlet.2011.09.010. PMID   21946165.


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