Zebularin

Zebularin
	1-(β-D-Ribofuranozil)-2(1H)-pirimidinon
Drugi nazivi	Pirimidin-2-on β-D-ribofuranozid
Identifikacija
CAS registarski broj	3690-10-6
PubChem	100016
ChemSpider	90372
Jmol-3D slike	Slika 1
SMILES
	O=C1/N=C\C=C/N1[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO
InChI
	InChI=1S/C9H12N2O5/c12-4-5-6(13)7(14)8(16-5)11-3-1-2-10-9(11)15/h1-3,5-8,12-14H,4H2/t5-,6-,7-,8-/m1/s1 ; Kod: RPQZTTQVRYEKCR-WCTZXXKLSA-N InChI=1/C9H12N2O5/c12-4-5-6(13)7(14)8(16-5)11-3-1-2-10-9(11)15/h1-3,5-8,12-14H,4H2/t5-,6-,7-,8-/m1/s1; Kod: RPQZTTQVRYEKCR-WCTZXXKLBP
Svojstva
Molekulska formula	C9H12N2O5
Molarna masa	228.2 g mol−1
	; ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Zebularin je nukleozidni analog citidina. On je inhibitor citidinske deaminaze (analog prelaznog stanja) koji deluje putem vezivanja za aktivno mesto kao kovalentni hidrat. Takođe je poznato da inhibira DNK metilaciju i rast tumora in vitro i in vivo.^[4]

U jednoj maloj studiji na miševima sa defektivnim APC genom, oralna administracija zebularina kod mužjaka nije imala efekta na sveukupnu metilaciju DNK, niti na broj polipa, dok je kod ženki prosečan broj poliba bio redukovan sa 58 no 1.^[5] Stoga je izveden zaključak da je ovaj lek prototip epigenetičke terapije za hemoprevenciju kancera.^[6]


Zebularin (levo) je blisko srodan sa citidinom (desno), ali mu nedostaje 4'-amino grupa.

Reference[uredi | uredi kod]

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ „pyrimidin-2-one beta-ribofuranoside - Compound Summary”. PubChem/National Center for Biotechnology Information.
↑ Christine B. Yoo et al. (2008-09-01). „Long-term Epigenetic Therapy with Oral Zebularine Has Minimal Side Effects and Prevents Intestinal Tumors in Mice”. Cancer Prev Res 1: 233.
↑ Laird, Peter W. (2005-04-15). „Cancer epigenetics”. Hum. Mol. Genet. 14 (suppl 1): R65-R76.

Vanjske veze[uredi | uredi kod]

Portal Hemija

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] „pyrimidin-2-one beta-ribofuranoside - Compound Summary”. PubChem/National Center for Biotechnology Information.

[5] Christine B. Yoo et al. (2008-09-01). „Long-term Epigenetic Therapy with Oral Zebularine Has Minimal Side Effects and Prevents Intestinal Tumors in Mice”. Cancer Prev Res 1: 233.

[6] Laird, Peter W. (2005-04-15). „Cancer epigenetics”. Hum. Mol. Genet. 14 (suppl 1): R65-R76.

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Zebularin

Reference[uredi | uredi kod]

Vanjske veze[uredi | uredi kod]

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