38819-10-2 Usage
Description
9-(BETA-D-ARABINOFURANOSYL)GUANINE, also known as Ara-G, is a purine nucleoside analog of guanosine and an active metabolite of nelarabine. It is characterized by the attachment of guanine to arabinofuranose via a beta-N9-glycosidic bond. Ara-G plays a significant role in inhibiting DNA synthesis and causing cell death, making it a promising candidate for various therapeutic applications.
Uses
Used in Anticancer Applications:
9-(BETA-D-ARABINOFURANOSYL)GUANINE is used as an inducer of apoptosis and an inhibitor of DNA synthesis for its antineoplastic properties. It is particularly effective against malignant T-lymphoid cells, where it accumulates and is phosphorylated to produce ara-GTP, which is then incorporated into the DNA. This process leads to a 92% inhibition of DNA replication in CEM cells, a model for human T lymphoblasts, after 30 minutes when used at a concentration of 50 μM. Additionally, Ara-G halts the cell cycle at the sub-G1 phase and induces apoptosis in these cells.
Used in Preclinical Models:
In syngeneic bone marrow containing 6C3HED tumor cells, treatment with ara-G (100 mM) ex vivo prior to transplantation increases the survival of lethally irradiated mice and induces reconstitution of lymphoid, myeloid, and erythroid cell linages.
Used in Pharmaceutical Industry:
9-(BETA-D-ARABINOFURANOSYL)GUANINE is used as an antimetabolite for the development of novel therapeutic agents targeting cancer cells. Its unique mechanism of action and ability to inhibit DNA synthesis make it a valuable compound in the search for new cancer treatments.
Used in Research and Development:
Ara-G is used as a research tool for studying the mechanisms of DNA synthesis inhibition, cell cycle regulation, and apoptosis induction in various cell types, particularly those involved in cancer progression. This knowledge can be applied to develop more targeted and effective cancer therapies.
Check Digit Verification of cas no
The CAS Registry Mumber 38819-10-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,8,8,1 and 9 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 38819-10:
(7*3)+(6*8)+(5*8)+(4*1)+(3*9)+(2*1)+(1*0)=142
142 % 10 = 2
So 38819-10-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6+,9-/m1/s1
38819-10-2Relevant articles and documents
Synthesis of 2'-iodo- and 2'-bromo-ATP and GTP analogues as potential phasing tools for X-ray crystallography
Gruen, Mathias,Becker, Christian,Beste, Andrea,Siethoff, Christoph,Scheidig, Axel J.,Goody, Roger S.
, p. 137 - 151 (1999)
Ara-adenosine (adenine 9-β-D-arabinofuranoside) and ara-guanosine (guanine 9-β-D-arabinofuranoside) are converted into 2' halogenated ATP and GTP analogues by triflation and subsequent inversion of configuration at C- 2'. For the commercially unavailable ara-guanosine a short synthesis starting from guanosine is presented. The nucleotide analogues could serve for the preparation of heavy atom derivatives of ATP- and GTP-binding proteins useful for protein crystal structure determination by MIR/MAD phasing.
MODIFIED OLIGONUCLEOTIDES AND METHODS OF USE IN TAUOPATHIES
-
, (2019/10/04)
Oligonucleotides comprising modifications at the 2' and/or 3' positions(s) along with methods of 5 making and use against Alzheimer disease and other tauopathies are disclosed.
MODIFIED OLIGONUCLEOTIDES AND METHODS OF USE
-
, (2018/04/12)
Modified oligonucleotides comprising modifications at the 2' and/or 3' positions(s) along with methods of making and use, e.g., against HBV are disclosed.
Synthesis of 9-β-d-arabinofuranosylguanine by combined use of two whole cell biocatalysts
Medici, Rosario,Iribarren, Adolfo M.,Lewkowicz, Elizabeth S.
scheme or table, p. 4210 - 4212 (2010/04/05)
Unlike the preparation of other purine nucleosides, transglycosylation from a pyrimidine nucleoside and guanine is difficult because of the low solubility of this base. Thus, another strategy, based on the coupled action of two whole cell biocatalyzed reactions, transglycosylation and deamination, was used. Enterobacter gergoviae and Arthrobacter oxydans were employed to synthesize 9-β-d-arabinofuranosylguanine (AraG), an efficient anti leukemic drug.
