CNDAC hydrochloride

• CAT Number: M112349
• CAS Number: 134665-72-8
• Molecular Formula: C10H13ClN4O4
• Molecular Weight: 288.69
• Purity: ≥95%
• Synonyms: (2R,3S,4S,5R)-2-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolane-3-carbonitrile;hydrochloride
• InChI: InChI=1S/C10H12N4O4.ClH/c11-3-5-8(16)6(4-15)18-9(5)14-2-1-7(12)13-10(14)17;/h1-2,5-6,8-9,15-16H,4H2,(H2,12,13,17);1H/t5-,6+,8-,9+;/m0./s1
• InChIKey: PKGUOXDXRLGZBN-KUAPJGQRSA-N
• SMILES: C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)C#N.Cl

CNDAC hydrochloride is a metabolite of the orally active agent Sapacitabine (HY-16445), and a nucleoside analog. CNDAC hydrochloride induces DNA damage and apoptosis[1][2].
CNDAC has a unique mechanism of action: after incorporation into DNA, it induces single-strand breaks (SSBs) that are converted into double-strand breaks (DSBs) when cells go through a second S phase[1].
Lack of Rad51D and XRCC3 sensitizes cells to CNDAC (0-1 μM; 24 h)[1].
CNDAC (0-100 μM; 3 days) inhibits proliferation of HL-60 and THP-1 cells[2].
CNDAC (0-10 μM; 3-6 days) induces apoptosis in HL-60 and THP-1 cells[2].
CNDAC (6 μM; 48 h) induces cell cycle arrest in the G2 phase following a delayed S phase in HCT116 cells[3].
CNDAC (20mg/kg; i.p.; daily for 10 days) shows antitumor activity in mice[4].

Reference

[1]. Liu XJ, et al. Sapacitabine, the prodrug of CNDAC, is a nucleoside analog with a unique action mechanism of inducing DNA strand breaks. Chin J Cancer. 2012 Aug;31(8):373-80.
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[2]. Jagan S, et al. Bone Marrow and Peripheral Blood AML Cells Are Highly Sensitive to CNDAC, the Active Form of Sapacitabine. Adv Hematol. 2012;2012:727683.
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[3]. Serova M, et al. Antiproliferative effects of sapacitabine (CYC682), a novel 2′-deoxycytidine-derivative, in human cancer cells. Br J Cancer. 2007 Sep 3;97(5):628-36.
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[4]. Azuma A, et al. Nucleosides and nucleotides. 122. 2′-C-cyano-2′-deoxy-1-beta-D-arabinofuranosylcytosine and its derivatives. A new class of nucleoside with a broad antitumor spectrum. J Med Chem. 1993 Dec 24;36(26):4183-9.
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