2'-Deoxy-7,8-dihydro-8-oxoguanosine - ≥95%(HPLC) , CAS No.88847-89-6

CAS: 88847-89-6 Cat. No.: H136806 Molecular Weight: 283.24

GRADE & PURITY ≥95%(HPLC)

Synonyms

7,8-Dihydro-2'-deoxy-8-oxoguanosine | SR-01000946628-1 | 8-oxo-2'-dG | CID 5287560 | Guanosine, 7,8-dihydro-2'-deoxy-8-oxo- | HMS3649O10 | 2-amino-8-hydroxy-9-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one | UNII-4RGB38T3I

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

8-Hydroxy-2'-deoxyguanosine (8-Oxo-dG) is a marker compound typically indicative of DNA damage associated with mutagenesis and carcinogenesis.
A useful marker for indication of DNA damage via mutagenesis and carcinogenesis.

Specifications

Synonyms

7, 8-Dihydro-2'-deoxy-8-oxoguanosine | SR-01000946628-1 | 8-oxo-2'-dG | CID 5287560 | Guanosine, 7, 8-dihydro-2'-deoxy-8-oxo- | HMS3649O10 | 2-amino-8-hydroxy-9-((2R, 4S, 5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one | UNII-4RGB38T3I

Specifications & Purity

≥95%(HPLC)

Biochemical and Physiological Mechanisms

A marker compound typically indicative of DNA damage associated with mutagenesis and carcinogenesis.Oxidative stress biomarker. A predominant form of free radical-induced oxidative lesions in nuclear and mitochondrial DNA. Oxidized deoxyguanosine derivati

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥95%(HPLC)

Names and Identifiers

• Pubchem Sid: 504773317
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504773317
• Canonical Smiles: C1C(C(OC1N2C3=C(C(=O)NC(=N3)N)NC2=O)CO)O
• IUPAC Name: 2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,7-dihydropurine-6,8-dione
• InChIKey: HCAJQHYUCKICQH-VPENINKCSA-N
• INCHI: 1S/C10H13N5O5/c11-9-13-7-6(8(18)14-9)12-10(19)15(7)5-1-3(17)4(2-16)20-5/h3-5,16-17H,1-2H2,(H,12,19)(H3,11,13,14,18)/t3-,4+,5+/m0/s1
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C3=C(C(=O)NC(=N3)N)NC2=O)CO)O
• WGK Germany: 3
• Molecular Weight: 283.24
• Reaxy-Rn: 10576465
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=10576465&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class Purine nucleosides
      • Subclass Purine 2'-deoxyribonucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: Purine nucleosides
• Subclass: Purine 2'-deoxyribonucleosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Purine 2'-deoxyribonucleosides
• Alternative Parents: Purines and purine derivatives Hydroxypyrimidines N-substituted imidazoles Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Oxacyclic compounds Azacyclic compounds Primary alcohols Organopnictogen compounds Organonitrogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Purine 2'-deoxyribonucleoside - Imidazopyrimidine - Purine - Hydroxypyrimidine - N-substituted imidazole - Pyrimidine - Tetrahydrofuran - Heteroaromatic compound - Azole - Imidazole - Secondary alcohol - Oxacycle - Azacycle - Organoheterocyclic compound - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Organonitrogen compound - Alcohol - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. These are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2.
• External Descriptors: guanosines

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

HL-60 (67320 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

RAW264.7 (28094 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (partly miscible), DMSO (19.60-20.40 mg/ml), and 0.1 M HCl (10 mg/ml).
• Molecular Weight: 283.240 g/mol
• XLogP3: -2.600
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 283.092 Da
• Monoisotopic Mass: 283.092 Da
• Topological Polar Surface Area: 150.000 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 544.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Rong-Fa Xu, Hang Mei, Li Chen, Bin Tang, Qi-Yuan Lu, Feng-Shan Cai, Xiao Yan, Jing Zheng, Xian-Tao Shen, Yun-Jiang Yu.  (2023)  Development and validation of an HPLC-MS/MS method for the simultaneous analysis of volatile organic compound metabolites, hydroxylated polycyclic aromatic hydrocarbons, and 8-hydroxy-2′-deoxyguanosine in human urine.  JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES,      [PMID:37725852] [10.1016/j.jchromb.2023.123885]

2. Songtao Xiang, Yuxiang Lan, Zhiliang Mai, Feng Tian, Hua Mao.  (2022)  Dynamic monitoring of bacteriostatic process by SERS analysis based on a simple but effective detection strategy.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:35988511] [10.1016/j.saa.2022.121611]

3. Yingying Sheng, Yifu Zhu, María Luisa Cerón, Yufu Yi, Peng Liu, Peng Wang, Ting Xue, María Belén Camarada, Yangping Wen.  (2021)  A stable nanosilver decorated phosphorene nanozyme with phosphorus-doped porous carbon microsphere for intelligent sensing of 8-hydroxy-2′-deoxyguanosine.  JOURNAL OF ELECTROANALYTICAL CHEMISTRY,      [PMID:] [10.1016/j.jelechem.2021.115522]

4. Guojun Cao, Can Wu, Yong Tang, Chidan Wan.  (2019)  Ultrasmall HKUST-1 nanoparticles decorated graphite nanosheets for highly sensitive electrochemical sensing of DNA damage biomarker 8-hydroxy-2’-deoxyguanosine.  ANALYTICA CHIMICA ACTA,      [PMID:30851856] [10.1016/j.aca.2019.01.031]

5. Tong Ren, Zhen Feng, Fang Jiang, Xingtong Liu, Tingting Chen, Yanli Guo, Lei Tian, Xiao-Feng Kang, Fujun Yao.  (2024)  Nanopore detection of guanine derivatives based on vacancy G-quadruplex DNA.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2024.112366]