WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H558352
CAS#: 27762-78-3
Description: Kethoxal is an antiviral that modifies guanine containing oligoribonucleotides by reacting selectively with guanine in polynucleotides.
Hodoodo Cat#: H558352
Name: Kethoxal
CAS#: 27762-78-3
Chemical Formula: C6H12O4
Exact Mass: 148.07
Molecular Weight: 148.160
Elemental Analysis: C, 48.64; H, 8.16; O, 43.19
This product is not in stock, which may be available by custom synthesis.
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Synonym: Kethoxal; Chetossale; Ketoxal; Ketoxalum;
IUPAC/Chemical Name: 2-Butanone, 3-ethoxy-1,1-dihydroxy-
InChi Key: YRCRRHNVYVFNTM-UHFFFAOYSA-N
InChi Code: InChI=1S/C6H12O4/c1-3-10-4(2)5(7)6(8)9/h4,6,8-9H,3H2,1-2H3
SMILES Code: CC(OCC)C(C(O)O)=O
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: >3 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: 2934.99.03.00
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 148.16 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.
| 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Iijima H, Patrzyc H, Bello J. Modification of amino acids and bovine pancreatic ribonuclease A by kethoxal. Biochim Biophys Acta. 1977 Mar 28;491(1):305-16. PubMed PMID: 14699.
2: Brow DA, Noller HF. Protection of ribosomal RNA from kethoxal in polyribosomes. Implication of specific sites in ribosome function. J Mol Biol. 1983 Jan 5;163(1):27-46. PubMed PMID: 6834429.
3: Akinsiku OT, Yu ET, Fabris D. Mass spectrometric investigation of protein alkylation by the RNA footprinting probe kethoxal. J Mass Spectrom. 2005 Oct;40(10):1372-81. PubMed PMID: 16237662.
4: Garrett RA, Noller HF. Structures of complexes of 5S RNA with ribosomal proteins L5, L18 and L25 from Escherichia coli: identification of kethoxal-reactive sites on the 5S RNA. J Mol Biol. 1979 Aug 25;132(4):637-48. PubMed PMID: 393829.
5: Iserentant D, Fiers W. Secondary structure of the 5' end of bacteriophage MS2 RNA Methoxyamine and kethoxal modification. Eur J Biochem. 1979 Dec 17;102(2):595-604. PubMed PMID: 118878.
6: UNDERWOOD GE, SIEM RA, GERPHEIDE SA, HUNTER JH. Binding of an antiviral agent (kethoxal) by various metabolites. Proc Soc Exp Biol Med. 1959 Feb;100(2):312-5. PubMed PMID: 13634123.
7: Noller HF, Chaires JB. Functional modification of 16S ribosomal RNA by kethoxal. Proc Natl Acad Sci U S A. 1972 Nov;69(11):3115-8. PubMed PMID: 4564202; PubMed Central PMCID: PMC389716.
8: Hogan JJ, Gutell RR, Noller HF. Probing the conformation of 26S rRNA in yeast 60S ribosomal subunits with kethoxal. Biochemistry. 1984 Jul 3;23(14):3330-5. PubMed PMID: 6380585.
9: The synthesis and antitumor activity of kethoxal bis-thiosemicarbazone and its related compounds. Chinas Med. 1967 Dec;12:879-89. PubMed PMID: 4969805.
10: Underwood GE, Nichol FR. Clinical evaluation of kethoxal against cutaneous herpes simplex. Appl Microbiol. 1971 Oct;22(4):588-92. PubMed PMID: 4331769; PubMed Central PMCID: PMC376368.
11: Noller HF, Garrett RA. Structure of 5 S ribosomal RNA from Escherichia coli: identification of kethoxal-reactive sites in the A and B conformations. J Mol Biol. 1979 Aug 25;132(4):621-36. PubMed PMID: 393828.
12: Sabina LR, Morrow DG, Szabo RA. Diminished virucidal activity of kethoxal against vesicular stomatitis virus pretreated with guanidinating reagent and proteases. Acta Virol. 1976 Apr;20(2):119-25. PubMed PMID: 5866.
13: Miura K, Tsuda S, Ueda T, Harada F, Kato N. Chemical modification of guanine residues of mouse 5 S ribosomal RNA with kethoxal. (Nucleosides and nucleotides 46). Biochim Biophys Acta. 1983 Apr 15;739(3):281-5. PubMed PMID: 6403036.
14: Sachsenmaier N, Handl S, Debeljak F, Waldsich C. Mapping RNA structure in vitro using nucleobase-specific probes. Methods Mol Biol. 2014;1086:79-94. doi: 10.1007/978-1-62703-667-2_5. PubMed PMID: 24136599.
15: Thweatt R, Lee JC. Yeast precursor ribosomal RNA. Molecular cloning and probing the higher-order structure of the internal transcribed spacer I by kethoxal and dimethylsulfate modification. J Mol Biol. 1990 Jan 20;211(2):305-20. PubMed PMID: 2407850.
16: Hogan JJ, Gutell RR, Noller HF. Probing the conformation of 18S rRNA in yeast 40S ribosomal subunits with kethoxal. Biochemistry. 1984 Jul 3;23(14):3322-30. PubMed PMID: 6205688.
17: Delihas N, Dunn JJ, Erdmann VA. The reaction of 5S RNA in 70S ribosomes with kethoxal. FEBS Lett. 1975 Oct 15;58(1):76-80. PubMed PMID: 773691.
18: Shapiro R, Cohen BI, Shiuey SJ, Maurer H. On the reaction of guanine with glyoxal, pyruvaldehyde, and kethoxal, and the structure of the acylguanines. A new synthesis of N2-alkylguanines. Biochemistry. 1969 Jan;8(1):238-45. PubMed PMID: 5777326.
19: Regelson W, Holland JF, Talley RW. Clinical pharmacologic study of kethoxal bis(thiosemicarbazone) [NSC-82116] in advanced cancer. Cancer Chemother Rep. 1967 Jun;51(3):171-7. PubMed PMID: 6043737.
20: Nishikawa K, Takemura S. Structure and function of 5S ribosomal ribonucleic acid from Torulopsis utilis. IV. Detection of exposed guanine residues by chemical modification with kethoxal. J Biochem. 1978 Aug;84(2):259-66. PubMed PMID: 568134.
