Cryptolepine

Cryptolepine
Names
	Preferred IUPAC name 5-Methyl-5H-indolo[3,2-b]quinoline
Identifiers
CAS Number	480-26-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:3930;
ChEMBL	ChEMBL92129;
ChemSpider	74137;
KEGG	C09142;
PubChem CID	82143;
UNII	OF1UIT4RDH ;
CompTox Dashboard (EPA)	DTXSID6037645 ;
	InChI 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;
	SMILES N2=C1C(C=CC=C1)=C4C2=Cc3ccccc3N4C;
Properties
Chemical formula	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). Infobox references

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

^ ^a ^b 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.
^ 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.
^ 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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[Wright-1] 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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