8-Oxodeoxyguanosine is an established marker of oxidative DNA damage. It can be induced by TNF-alpha. It is a prominent indicator of oxidative stress and has been well-characterized as a premutagenic lesion in mammalian cells and putative initiator of the carcinogenic process.

Synonyms: 8-Hydroxy-2'-deoxyguanosine; 8-OH-dG; 8-Oxodeoxyguanosine

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Quality Control of 2'-Deoxy-8-oxoguanosine Purity: 96% SDS Specification

COA

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NMR

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Product Details of 2'-Deoxy-8-oxoguanosine

CAS No. :	88847-89-6
Formula :	C₁₀H₁₃N₅O₅
M.W :	283.24
SMILES Code :	O=C1N=C(N)NC2=C1NC(N2[C@@H]3O[C@H](CO)[C@@H](O)C3)=O
Synonyms :	8-Hydroxy-2'-deoxyguanosine; 8-OH-dG; 8-Oxodeoxyguanosine
MDL No. :	MFCD03788705
InChI Key :	HCAJQHYUCKICQH-VPENINKCSA-N
Pubchem ID :	135440064

Safety of 2'-Deoxy-8-oxoguanosine

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of 2'-Deoxy-8-oxoguanosine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 88847-89-6 ]

[ 88847-89-6 ] Synthesis Path-Downstream 1~54

1
[ 961-07-9 ]
[ 142559-87-3 ]
[ 137608-88-9 ]
[ 88847-89-6 ]

References: [1]Journal de Chimie Physique et de Physico-Chimie Biologique,1991,vol. 88,p. 1053 - 1060.

2
[ 961-07-9 ]
[ 142559-87-3 ]
[ 137608-88-9 ]
[ 88847-89-6 ]
[ 152785-98-3 ]

References: [1]Journal de Chimie Physique et de Physico-Chimie Biologique,1991,vol. 88,p. 1069 - 1076.

3
[ 88847-89-6 ]
3-(2-deoxy-β-D-erythro-pentofuranosyl)tetrahydro-2,4,6-trioxo-1,3,5-triazine-1(2H)-carboximidamide [ No CAS ]

References: [1]Journal of the American Chemical Society,1996,vol. 118,p. 1892 - 1898.

4
[ 88847-89-6 ]
[ 137608-88-9 ]
[ 152785-98-3 ]

References: [1]Journal of the American Chemical Society,1996,vol. 118,p. 9233 - 9238.
[2]Journal of the American Chemical Society,1996,vol. 118,p. 9233 - 9238.

5
[ 88847-89-6 ]
[ 152785-98-3 ]

References: [1]Journal of the American Chemical Society,1996,vol. 118,p. 9233 - 9238.
[2]Chemical Research in Toxicology,2000,vol. 13,p. 1199 - 1207.

6
[ 961-07-9 ]
[ 137608-88-9 ]
[ 88847-89-6 ]
N-[(1R,9R,10S)-10-Hydroxy-4-oxo-7,12-dioxa-2,5-diaza-tricyclo[7.2.1.0^2,6]dodec-(3E)-ylidene]-guanidine [ No CAS ]
[ 137608-89-0 ]
[ 137608-90-3 ]

References: [1]Journal of the American Chemical Society,1997,vol. 119,p. 719 - 723.

7
[ 961-07-9 ]
[ 137608-88-9 ]
[ 88847-89-6 ]
[ 152785-98-3 ]

References: [1]Photochemistry and Photobiology,1996,vol. 63,p. 768 - 778.

8
[ 961-07-9 ]
[ 88847-89-6 ]

References: [1]Journal of the American Chemical Society,1997,vol. 119,p. 11373 - 11380.
[2]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2141 - 2144.
[3]Photochemistry and Photobiology,2000,vol. 72,p. 619 - 624.
[4]Chemical Research in Toxicology,1999,vol. 12,p. 270 - 277.
[5]Chemical Research in Toxicology,2002,vol. 15,p. 426 - 432.
[6]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3627 - 3631.
[7]Journal of Organic Chemistry,2011,vol. 76,p. 720 - 723.

9
[ 961-07-9 ]
[ 137608-88-9 ]
[ 88847-89-6 ]
[ 152785-98-3 ]
N-[(1R,9R,10S)-10-Hydroxy-4-oxo-7,12-dioxa-2,5-diaza-tricyclo[7.2.1.0^2,6]dodec-(3E)-ylidene]-guanidine [ No CAS ]

References: [1]Journal of the American Chemical Society,1998,vol. 120,p. 3549 - 3559.

10
[ 961-07-9 ]
[ 137608-88-9 ]
[ 88847-89-6 ]
[ 137608-89-0 ]
[ 137608-90-3 ]

References: [1]Chemical Research in Toxicology,1995,vol. 8,p. 379 - 388.
[2]Chemical Research in Toxicology,1995,vol. 8,p. 379 - 388.
[3]Chemical Research in Toxicology,1995,vol. 8,p. 379 - 388.

11
[ 961-07-9 ]
[ 88847-89-6 ]
[ 137608-89-0 ]
[ 137608-90-3 ]

References: [1]Chemical Research in Toxicology,1995,vol. 8,p. 379 - 388.

12
[ 961-07-9 ]
[ 73-40-5 ]
[ 137608-88-9 ]
[ 88847-89-6 ]
2-amino-4-oxo-5-formamido-6-<N-(2'-deoxy-β-D-ribofuranosyl)>pyrimidine [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),1999,p. 1875 - 1880.

13
[ 961-07-9 ]
[ 88847-89-6 ]
[ 152785-98-3 ]

References: [1]Photochemistry and Photobiology,2000,vol. 71,p. 12 - 19.

14
3,4-dihydroxy-1,3,5-⁽¹⁰⁾,6,8-estrapentaen-17-one [ No CAS ]
Calf thymus DNA [ No CAS ]
[ 31077-24-4 ]
[ 88847-89-6 ]

References: [1]Chemical Research in Toxicology,1998,vol. 11,p. 1105 - 1111.

15
[ 96964-90-8 ]
[ 88847-89-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1677 - 1679.
[2]Journal of Organic Chemistry,2011,vol. 76,p. 720 - 723.

16
[ 88847-89-6 ]
8-oxo-7,8-dihydro-2'-deoxyguanosine radical cation [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2001,p. 210 - 213.

17
[ 961-07-9 ]
[ 88847-89-6 ]
[ 168701-80-2 ]
8-nitro-2'-deoxyguanosine [ No CAS ]

References: [1]Chemical Research in Toxicology,2001,vol. 14,p. 438 - 450.

18
[ 88847-89-6 ]
spiroiminodihydantoin deoxiribonucleoside [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4944 - 4947.
[2]Organic Letters,2002,vol. 4,p. 537 - 540.
[3]Chemical Research in Toxicology,2001,vol. 14,p. 1163 - 1169.
[4]Chemical Research in Toxicology,2001,vol. 14,p. 1163 - 1169.

19
[ 961-07-9 ]
[ 88847-89-6 ]
spiroiminodihydantoin deoxiribonucleoside [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 537 - 540.
[2]Organic Letters,2002,vol. 4,p. 537 - 540.
[3]Journal of Mass Spectrometry,2007,vol. 42,p. 1326 - 1332.

20
[ 961-07-9 ]
[ 73-40-5 ]
[ 88847-89-6 ]

References: [1]Journal of Physical Chemistry B,2002,vol. 106,p. 7704 - 7712.

21
[ 2082-76-0 ]
[ 88847-89-6 ]
3',5'-O-didecanoyl-8-oxo-2'-deoxyguanosine [ No CAS ]

References: [1]Journal of the American Chemical Society,2003,vol. 125,p. 14741 - 14749.

22
[ 961-07-9 ]
[ 88847-89-6 ]
[ 142559-87-3 ]
spiroiminodihydantoin deoxiribonucleoside [ No CAS ]
[ 444816-83-5 ]

References: [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 2157 - 2162.

23
[ 88847-89-6 ]
[ 142559-87-3 ]

References: [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 2157 - 2162.

24
[ 88847-89-6 ]
N¹-(β-D-erythro-pentofuranosyl)-5-guanidinohydantoin [ No CAS ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2003,vol. 46,p. 1269 - 1277.
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3627 - 3631.

25
[ 88847-89-6 ]
spiroiminodihydantoin-2'-deoxyribonucleoside [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3627 - 3631.

26
[ 961-07-9 ]
dehydro-guanidinohydantoin [ No CAS ]
[ 88847-89-6 ]
(5'R)-5',8-cyclo-2'-deoxyguanosine [ No CAS ]
N¹-(β-D-erythro-pentofuranosyl)-5-guanidinohydantoin [ No CAS ]

References: [1]Nucleosides, nucleotides and nucleic acids,2006,vol. 25,p. 259 - 278.

27
[ 961-07-9 ]
[ 88847-89-6 ]
[ 152785-98-3 ]
spiroiminodihydantoin deoxiribonucleoside [ No CAS ]

References: [1]Tetrahedron,2006,vol. 62,p. 10709 - 10715.

28
[ 403731-45-3 ]
[ 88847-89-6 ]
spiroiminodihydantoin deoxiribonucleoside [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 537 - 540.

29
[ 961-07-9 ]
[ 235439-61-9 ]
[ 142559-87-3 ]
[ 137608-88-9 ]
[ 88847-89-6 ]

References: [1]Photochemistry and Photobiology,2006,vol. 82,p. 191 - 199.

30
[ 88847-89-6 ]
[ 137608-88-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 2157 - 2162.

31
[ 13389-03-2 ]
[ 88847-89-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1677 - 1679.
[2]Journal of Organic Chemistry,2011,vol. 76,p. 720 - 723.

32
[ 106-44-5 ]
[ 88847-89-6 ]
[ 1042442-16-9 ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 10080 - 10081.

33
[ 537-55-3 ]
[ 88847-89-6 ]
[ 1042442-14-7 ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 10080 - 10081.

34
[ 902-04-5 ]
[ 73-40-5 ]
[ 5614-64-2 ]
[ 1186588-46-4 ]
[ 88847-89-6 ]
5'-monophosphate 2'-deoxy-7,8-dihydro-8-oxo-guanosine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4335 - 4338.

36
calf thymus DNA, γ-irradiated [ No CAS ]
[ 31077-24-4 ]
[ 105929-27-9 ]
[ 961-07-9 ]
[ 88847-89-6 ]
[ 117182-88-4 ]
(5'R)-5',8-cyclo-2'-deoxyadenosine [ No CAS ]
(5'R)-5',8-cyclo-2'-deoxyguanosine [ No CAS ]
[ 951-77-9 ]
[ 50-89-5 ]
[ 958-09-8 ]

References: [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 3211 - 3219.

37
[ 100-52-7 ]
[ 88847-89-6 ]
[ 1262310-95-1 ]
C₂₄H₂₅N₅O₅ [ No CAS ]

References: [1]Journal of Organic Chemistry,2011,vol. 76,p. 720 - 723.

38
[ 88847-89-6 ]
[ 1246662-17-8 ]

References: [1]Journal of Organic Chemistry,2011,vol. 76,p. 720 - 723.

39
[ 88847-89-6 ]
[ 1262310-96-2 ]

References: [1]Journal of Organic Chemistry,2011,vol. 76,p. 720 - 723.

40
[ 88847-89-6 ]
[ 1246662-18-9 ]

References: [1]Journal of Organic Chemistry,2011,vol. 76,p. 720 - 723.

41
[ 88847-89-6 ]
[ 1262310-97-3 ]

References: [1]Journal of Organic Chemistry,2011,vol. 76,p. 720 - 723.

42
[ 88847-89-6 ]
[ 123-38-6 ]
[ 1246662-16-7 ]
C₁₆H₂₅N₅O₅ [ No CAS ]

References: [1]Journal of Organic Chemistry,2011,vol. 76,p. 720 - 723.

43
[ 1003938-47-3 ]
[ 88847-89-6 ]
C₁₀H₁₃N₅O₅*C₃₇H₅₄N₄O₈Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; triethylamine; In chloroform; at 25℃;	General procedure: UV and fluorescent spectra were measured in CHCl3 solution at 25 °C using 3'-O- and 5'-O-TBDMS protected nucleosides. Fq and F0 in the fluorescence quenching ratio represent the fluorescence intensity of the 1:1 mixture of 8-oxoGclamp and 8-oxo-dG or dG and the fluorescence intensity of 8-oxoGclamp, respectively. Fluorescence titration was performed by the addition of a stock solution of the 3'-O-, 5'-O-di-TBDMS protected 2'-deoxynucleoside (0-10 muM final concentration) to a solution of the 8-oxoGclamp analog (1 muM) under the following conditions, A: CHCl3 solution containing 10 mM TEA and 2.7 mM AcOH, B: CHCl3 solution containing 0.33 mM TEA-AcOH, C: CHCl3 solution without addition of AcOH-TEA. The titration curve was analyzed by the non-linear curve fitting method based on the 1:1 complex ratio.