Clitocine

Clitocine

Names
Preferred IUPAC name (2R,3R,4S,5R)-2-[(6-Amino-5-nitropyrimidin-4-yl)amino]-5-(hydroxymethyl)oxolane-3,4-diol
Identifiers
CAS Number	105798-74-1
3D model (JSmol)	Interactive image
ChEBI	CHEBI:178144
ChEMBL	ChEMBL304179
ChemSpider	114380
PubChem CID	129111
CompTox Dashboard (EPA)	DTXSID30909739
InChI InChI=1S/C9H13N5O6/c10-7-4(14(18)19)8(12-2-11-7)13-9-6(17)5(16)3(1-15)20-9/h2-3,5-6,9,15-17H,1H2,(H3,10,11,12,13)/t3-,5-,6-,9-/m1/s1 Key: OHEMBWZZEKCBAS-UUOKFMHZSA-N
SMILES C1=NC(=C(C(=N1)N[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)[N+](=O)[O-])N
Properties
Chemical formula	C9H13N5O6
Molar mass	287.232 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

Clitocine is a mushroom nucleoside isolate ^[1] with anticancer activity in vitro. ^{[2] [3] [4]}

References

1. Kubo, Isao; Kim, Mujo; Wood, William F.; Naoki, Hideo (1986). "Clitocine, A New Insecticidal Nucleoside From The Mushroom Clitocybe inversa". Tetrahedron Letters. 27 (36): 4277–4280. doi:10.1016/S0040-4039(00)94251-5.
2. Ren, Gang; Zhao, Yun-Peng; Yang, Lu; Fu, Cheng-Xin (April 2008). "Anti-proliferative effect of clitocine from the mushroom Leucopaxillus giganteus on human cervical cancer HeLa cells by inducing apoptosis". Cancer Letters. 262 (2): 190–200. doi:10.1016/j.canlet.2007.12.013. PMID   18222036.
3. Sun, Jianguo; Yeung, Chilam Au; Co, Ngai Na; Tsang, Tsun Yee; Yau, Esmond; Luo, Kewang; Wu, Ping; Wa, Judy Chan Yuet; Fung, Kwok-Pui; Kwok, Tim-Tak; Liu, Feiyan (2012). "Clitocine reversal of P-glycoprotein associated multi-drug resistance through down-regulation of transcription factor NF-κB in R-HepG2 cell line". PLOS ONE. 7 (8) e40720. Bibcode:2012PLoSO...740720S. doi: 10.1371/journal.pone.0040720 . PMC   3425549 . PMID   22927901.
4. Sun, Jian-guo; Li, Hua; Li, Xia; Zeng, Xueli; Wu, Ping; Fung, Kwok-Pui; Liu, Fei-yan (May 2014). "Clitocine targets Mcl-1 to induce drug-resistant human cancer cell apoptosis in vitro and tumor growth inhibition in vivo". Apoptosis. 19 (5): 871–82. doi:10.1007/s10495-014-0969-0. PMID   24563182. S2CID   14746593.