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2'-Deoxyguanosine monohydrate

CAS No.312693-72-4
Chemical Name:2'-Deoxyguanosine monohydrate
CBNumber:CB0209021
Molecular Formula:C10H15N5O5
Formula Weight:285.26
MOL File:312693-72-4.mol

2'-Deoxyguanosine monohydrate Property

Melting point >300 °C (dec.)(lit.)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility NH₄OH 1 M: 50 mg/mL, clear to very faintly turbid, yellow to brown
form powder
pka pK1:2.5(+1) (25°C,μ=0.1)
color White to Off-White
biological source synthetic (organic)
BRN 39814
InChI InChI=1/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5+,6+/s3
InChIKey LZSCQUCOIRGCEJ-FPKZOZHISA-N
SMILES OC[C@H]1O[C@@H](N2C3=C(C(NC(=N3)N)=O)N=C2)C[C@@H]1O |&1:2,4,17,r|
FDA UNII G9481N71RO
UNSPSC Code 41106305
NACRES NA.75

Safety

Hazard Codes :Xn,T
Risk Statements :22-25
Safety Statements :45
WGK Germany :3
F :10-23
TSCA :Yes
HS Code :2934999090

NFPA 704:

	0
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H302
Precautionary statements P264b-P270-P301+P312-P330-P403-P501c

2'-Deoxyguanosine monohydrate Price More Price(11)

Brand: Sigma-Aldrich(India)
Product number: D7145
Product name : 2′-Deoxyguanosine monohydrate
Purity: 99-100%
Packaging: 25MG
Price: ₹4037.73
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: D7145
Product name : 2′-Deoxyguanosine monohydrate
Purity: 99-100%
Packaging: 100MG
Price: ₹11009.03
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: D7145
Product name : 2′-Deoxyguanosine monohydrate
Purity: 99-100%
Packaging: 1G
Price: ₹58649.85
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: D7145
Product name : 2′-Deoxyguanosine monohydrate
Purity: 99-100%
Packaging: 5G
Price: ₹113835.7
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: D0901
Product name : 2′-Deoxyguanosine monohydrate
Purity: powder, BioReagent, suitable for cell culture, 99-100%
Packaging: 100MG
Price: ₹12318.85
Updated: 2022/06/14
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2'-Deoxyguanosine monohydrate Chemical Properties,Usage,Production

Description 2''-Deoxyguanosine is a purine nucleoside with diverse biological activities. It inhibits the clonogenic growth of HL-60 and K562 leukemia cells (IC₅₀s = 80 and 100 μM, respectively). 2''-Deoxyguanosine inhibits the growth of MOLT-4 T cells and MGL-8 B cells by 99.8 and 68.3%, respectively, when used at a concentration of 50 μM. It increases the number of binucleated cells, a marker of inhibited cytokinesis, in A. sativum meristems. 2''-Deoxyguanosine (>1 μM) also induces relaxation of precontracted isolated bovine lingual artery.
Chemical Properties White to Off-White Solid. Soluble in NH4OH 1 M: 50 mg/mL, clear to very faintly turbid.
Uses 2′-Deoxyguanosine monohydrate has been used in stromal cell purification. It has also been used for the quantification of whole cell dNTP (deoxyribonucleotide triphosphate).
Definition ChEBI: 2'-Deoxyguanosine monohydrate is a purine 2'-deoxyribonucleoside having guanine as the nucleobase. It has a role as a Saccharomyces cerevisiae metabolite, a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a purines 2'-deoxy-D-ribonucleoside and a purine 2'-deoxyribonucleoside. It is functionally related to a guanosine.
Application 2′-Deoxyguanosine monohydrate has been used as a nucleoside supplement:
to study its effect on mitochondrial DNA copy number in deoxyguanosine kinase (dguok) mutant zebrafish,
in tissue culture medium for deoxyribonucleotide triphosphate (dNTP) synthesis,
in RPMI (Roswell Park Memorial Institute)-1640 medium to eliminate the endogenous thymocytes.
Biological Functions lu et al. found that 2'-Deoxyguanosine (2-dG) is a key immune signaling molecule in plant–microbe interactions and that Arabidopsis VENOSA4 (VEN4) is essential for plant immunity. 2-dG is the immunoreactive component in ZhiNengCong (ZNC). This compound induced classical immune responses, including ROS production, allose accumulation and MPKs phosphorylation, and upregulated the expression of plant immunity-associated genes. In addition, 2-dG-induced plant immunity requires salicylic acid (SA) receptor NPR1 (but not SA), ethylene (ET) signaling, pattern-recognition receptors/coreceptors (PRRs/coreceptors) and the ATP receptor P2K1[1]. VEN4 was involved in 2-dG biosynthesis and could convert dGTP to 2-dG.
Biochem/physiol Actions Deoxyguanosine (dG) is a purine nucleoside that upon sequential phosphorylation (kinases) forms deoxyguanosine triphosphate (dGTP) which is used by DNA polymerases and reverse transcriptases to synthesize DNA(s). Deoxyguanosine is the most electron-rich of the four canonical bases and includes many nucleophilic sites which are susceptible to oxidative damage. This makes deoxyguanosine and its oxidized derivatives useful reagents to study mechanisms of oxidative damage to nucleosides and nucleotides.
References [1] Chongchong Lu . “Discovery of a novel nucleoside immune signaling molecule 2′-deoxyguanosine in microbes and plants.” Journal of Advanced Research 46 (2023): Pages 1-15.