3-Deazaadenosine

Category	Human immunodeficiency Virus (HIV)
CAS	6736-58-9
Description	3-Deazaadenosine (3-DZA) is an inhibitor of SAH hydrolase (Ki = 3.9 μM). 3-Deazaadenosine is a modified form of the nucleoside adenosine, where a nitrogen atom in the purine ring is replaced with a carbon atom. This modification results in the compound lacking the ability to form hydrogen bonds with complementary nucleotides, making it useful in studying the role of hydrogen bonding in nucleic acid structure and function. 3-Deazaadenosine has been investigated for its potential therapeutic applications, such as in the treatment of viral infections and cancer. It is also used as a biochemical tool in research to study RNA interactions and enzymatic mechanisms.

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Product Information

Synonyms	Deaza-Ado; (2R,3R,4S,5R)-2-(4-Amino-1H-imidazo[4,5-c]pyridin-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol; 3-Deaza-rA; 1-(beta-D-ribofuranosyl)-1H-imidazo[4,5-c]pyridin-4-amine; 4-Amino-1-(β-D-ribofuranosyl)-1H-imidazo(4,5)-pyridine
IUPAC Name	(2R,3R,4S,5R)-2-(4-aminoimidazo[4,5-c]pyridin-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Molecular Weight	266.26
Molecular Formula	C11H14N4O4
Canonical SMILES	C1=CN=C(C2=C1N(C=N2)C3C(C(C(O3)CO)O)O)N
InChI	InChI=1S/C11H14N4O4/c12-10-7-5(1-2-13-10)15(4-14-7)11-9(18)8(17)6(3-16)19-11/h1-2,4,6,8-9,11,16-18H,3H2,(H2,12,13)/t6-,8-,9-,11-/m1/s1
InChIKey	DBZQFUNLCALWDY-PNHWDRBUSA-N
Boiling Point	665.7±65.0°C (Predicted)
Melting Point	222-224°C
Flash Point	356.4±34.3 °C
Purity	≥97% by HPLC
Density	1.90±0.1 g/cm3 at 20°C, 760 Torr
Solubility	Soluble in DMSO (Slightly), Methanol (Slightly), Water (Slightly)
Appearance	Crystalline Solid
Storage	Store at -20°C
Complexity	334
Exact Mass	266.101501
Index Of Refraction	1.834
In Vitro	3-Deazaadenosine is an inhibitor of S-adenosylhomocysteine hydrolase, with a Ki of 3.9 µM. It shows anti-HIV effect, and inhibits p24 antigen in peripheral blood mononuclear (PBMCs) cells infected with HIV-1 isolates with IC50s of 0.15 and 0.20 µM, respectively. In addition, 3-Deazaadenosine (1-100 µM) inhibits LPS-induced expression of TNF-α mRNA, increases DNA binding activity of NF-κB, and causes proteolytic degradation of IκBα, but Not IκBβ in RAW 264.7 cells. 3-Deazaadenosine (100 µM) enhances nuclear translocation of NF-κB, but blocks LPS-induced NF-κB transcriptional activity, and such inhibition is augmented by the addition of homocysteine. 3-Deazaadenosine can inhibit the phosphorylation of Raf and ERK, protein-dependent kinase 1, protein kinase B (Akt), and forkhead transcription factor FoxO1a. 3-Deazaadenosine (50 µM) suppresses vascular smooth muscle cell (VSMC) proliferation via interfering with Ras signaling.
PSA	126.65000
Target	IC50: 0.15 (HIV-1, A012 isolate), 0.20 µM (HIV-1, A018 isolate)
Vapor Pressure	0.0±2.1 mmHg at 25°C
XLogP3-AA	-1.6