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MedKoo Cat#: 562129 | Name: Clitocine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Clitocine is a potent and efficacious readthrough agent. It acts by inducing the production of p53 protein in cells harboring p53 nonsense-mutated alleles.

Chemical Structure

Clitocine
Clitocine
CAS#105798-74-1

Theoretical Analysis

MedKoo Cat#: 562129

Name: Clitocine

CAS#: 105798-74-1

Chemical Formula: C9H13N5O6

Exact Mass: 287.0866

Molecular Weight: 287.23

Elemental Analysis: C, 37.63; H, 4.56; N, 24.38; O, 33.42

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Clitocine;
IUPAC/Chemical Name
(2R,3R,4S,5R)-2-[(6-Amino-5-nitropyrimidin-4-yl)amino]-5-(hydroxymethyl)oxolane-3,4-diol
InChi Key
OHEMBWZZEKCBAS-UUOKFMHZSA-N
InChi Code
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
SMILES Code
O[C@H]1[C@H](NC2=NC=NC(N)=C2[N+]([O-])=O)O[C@H](CO)[C@H]1O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 287.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Friesen WJ, Trotta CR, Tomizawa Y, Zhuo J, Johnson B, Sierra J, Roy B, Weetall M, Hedrick J, Sheedy J, Takasugi J, Moon YC, Babu S, Baiazitov R, Leszyk JD, Davis TW, Colacino JM, Peltz SW, Welch EM. The nucleoside analog clitocine is a potent and efficacious readthrough agent. RNA. 2017 Apr;23(4):567-577. doi: 10.1261/rna.060236.116. Epub 2017 Jan 17. PubMed PMID: 28096517; PubMed Central PMCID: PMC5340919. 2: Sun JG, Ruan F, Zeng XL, Xiang J, Li X, Wu P, Fung KP, Liu FY. Clitocine potentiates TRAIL-mediated apoptosis in human colon cancer cells by promoting Mcl-1 degradation. Apoptosis. 2016 Oct;21(10):1144-57. doi: 10.1007/s10495-016-1273-y. PubMed PMID: 27421828. 3: Sun JG, Xiang J, Zeng XL, Li X, Wu P, Fung KP, Liu FY. Clitocine induces apoptosis and enhances the lethality of ABT-737 in human colon cancer cells by disrupting the interaction of Mcl-1 and Bak. Cancer Lett. 2014 Dec 28;355(2):253-63. doi: 10.1016/j.canlet.2014.09.024. Epub 2014 Oct 7. PubMed PMID: 25304383. 4: Sun JG, Li H, Li X, Zeng X, Wu P, Fung KP, Liu FY. Clitocine targets Mcl-1 to induce drug-resistant human cancer cell apoptosis in vitro and tumor growth inhibition in vivo. Apoptosis. 2014 May;19(5):871-82. doi: 10.1007/s10495-014-0969-0. PubMed PMID: 24563182. 5: Sun J, Yeung CA, Co NN, Tsang TY, Yau E, Luo K, Wu P, Wa JC, Fung KP, Kwok TT, Liu F. Clitocine reversal of P-glycoprotein associated multi-drug resistance through down-regulation of transcription factor NF-κB in R-HepG2 cell line. PLoS One. 2012;7(8):e40720. doi: 10.1371/journal.pone.0040720. Epub 2012 Aug 22. PubMed PMID: 22927901; PubMed Central PMCID: PMC3425549. 6: Ren G, Zhao YP, Yang L, Fu CX. Anti-proliferative effect of clitocine from the mushroom Leucopaxillus giganteus on human cervical cancer HeLa cells by inducing apoptosis. Cancer Lett. 2008 Apr 18;262(2):190-200. doi: 10.1016/j.canlet.2007.12.013. Epub 2008 Jan 25. PubMed PMID: 18222036. 7: Fortin H, Tomasi S, Delcros JG, Bansard JY, Boustie J. In vivo antitumor activity of clitocine, an exocyclic amino nucleoside isolated from Lepista inversa. ChemMedChem. 2006 Feb;1(2):189-96. PubMed PMID: 16892351. 8: Varaprasad CV, Habib Q, An H, Hong Z. Solid-phase synthesis of 5'-deoxy-5'-amino-clitocine analogues. Nucleosides Nucleotides Nucleic Acids. 2006;25(1):61-72. PubMed PMID: 16440986. 9: Lee CH, Daanen JF, Jiang M, Yu H, Kohlhaas KL, Alexander K, Jarvis MF, Kowaluk EL, Bhagwat SS. Synthesis and biological evaluation of clitocine analogues as adenosine kinase inhibitors. Bioorg Med Chem Lett. 2001 Sep 17;11(18):2419-22. PubMed PMID: 11549437. 10: Bacchelli C, Condom R, Patino N, Aubertin AM. Synthesis and biological activities of new carbaacyclonucleosides and 1'-oxaacyclonucleosides related to clitocine. Nucleosides Nucleotides Nucleic Acids. 2000 Mar;19(3):567-84. PubMed PMID: 10843493. 11: Moss RJ, Petrie CR, Meyer RB Jr, Nord LD, Willis RC, Smith RA, Larson SB, Kini GD, Robins RK. Synthesis, intramolecular hydrogen bonding, and biochemical studies of clitocine, a naturally occurring exocyclic amino nucleoside. J Med Chem. 1988 Apr;31(4):786-90. PubMed PMID: 3351857.