. Author manuscript; available in PMC: 2018 Sep 6.

Published in final edited form as: Toxicol Res (Camb). 2017 Sep 6;6(6):740–754. doi: 10.1039/c7tx00223h

Table 2.

Formation of covalent o-quinone-DNA adducts

Quinone	Treatment Conditions	Structure of Adduct	Method of Detection	Reference
Estrone-2,3-dione	2-OHE1 + MnO₂ + dG + acetic acid/water	2-OH-E1-6-N²-dG	NMR	Stack et al.⁷²
	2-OHE1 + MnO₂ + dA + acetic acid/water	2-OH-E1-6-N⁶-dA
Estradiol-2.3-dione	2-OHE2 + MnO₂ + Ade + acetic acid/water	2-OH-E2-6-N3-adenine	NMR	Zahid et al.⁷¹
	2-OHE2 + peroxidase + Calf thymus DNA	2-OH-E2-6-N3-adenine	HPLC
			³²P-post-labeling
Estrogen-3,4-dione	4-OHE1/E2 + MnO₂ dG + acetic acid/water	4-OH-E1-1-N7-guanine	NMR	Stack et al.⁷²
		4-OH-E2-1-N7-guanine
Estrogen-3,4-dione	4-OHHE2/E1 + MnO₂ + Ade + acetic acid/water	4-OH-E1(E2)-1-N3-adenine	NMR	Zahid et al.⁷¹
	4-OHE2/E1 + Peroxidase + Calf thymus DNA	4-OH-E1(E2)-1-N3-adenine	NMR	Li et al.⁷³
	4-OHE2 or E-3,4-dione	4-OH-E1(E2)-1-N7-guanine	LC-MS
	ACI Rat Mammary Gland	4-OH-E2-1-N3-adenine	HPLC
		4-OH-E2-1-N7-guanine	³²P-post-labeling
4-OHEN	4-OHEN in MetOH	2-N1,3-(N²-dG)-1,3-Dihydroxy-5,7,9(10)-estratriene-4,17-dione.	¹H-NMR, ¹³C-NMR and LC/MS	Shen et al.¹⁸
	dG, dA or dC	1-N⁶,3-C2-dA-2,3-Dihydroxy-5,7,9(10)-estratriene-4,17-dione
	KPO4 buffer pH 7.4, 37 °C for 7 h or Calf-thymus DNA	1-N3,3-(N⁴-dC)-2,3-Dihydroxy-5,7,9(10)-estratriene-4,17-dione.
4-OHEN	4-OHEN or 4-OHEN-diacetate + MCF7 cells	1-N⁶,3-C2-dA-2,3-Dihydroxy-5,7,9(10)-estratriene-4,17-dione	SID-LC-MS/MS	Wang⁷⁶
		N3,3-(N⁴-dC)-2,3-Dihydroxy-5,7,9(10)-estratriene-4,17-dione.
4-OHEN	4-OHEN + SD rat mammary gland injection	2-N1,3-(N²-dG)-1,3-Dihydroxy-5,7,9(10)-estratriene-4,17-dione	LC-MS/MS	Zhang et al.⁴⁰
		1-N⁶,3-C2-dA-2,3-Dihydroxy-5,7,9(10)-estratriene-4,17-dione
NQ	dG/dA acetic acid/water/DMF	1,2-Dihydroxy-naphthalene-4-N7-gaunine	UPLC/MS	Saeed et al.⁶⁹
	dG/acetic acid : water	1,2-Dihydroxy-naphthalene-4-N3-adenine	UPLC/MS	Saeed et al⁶⁹
		Naphthalene-1,2-dion-4-yl-N7-guanine	NMR/MS	McCoull et al.⁷⁰
PQ	dG/acetic acid : water or Calf Thymus DNA	Phenanthrene-1,2-dion-4-yl-N7-guanine	NMR/MS	McCoull et al.⁷⁰
BPQ	dG /acetic acid : water	Benzo[a]pyrene-7,8-dion-10-yl-N7-guanine	NMR/MS	McCoull et al.⁷⁰
BPQ	dG or dA/DMF/55 °C/pH 7.0	10-(N²-dG)-9,10-dihydro-9-hydroxy-B[a]P-7,8-dione	NMR	Balu et al.¹⁹
		8-N1,9-(N²-dG)-8,10-Dihydroxy-9,10-dihydro-B[a]P-7(8H)-one
		8-N⁶,10-N1-dA-8,9-Dihydroxy-9,10-dihydro-B[a]P-7(8H)-one
BPQ	A549 cells and HBEC-tk cells incubated with	6-(N²-dG)-9,10-Dihydro-10-hydroxy-B[a]P-7,8-dione	LC-MS/MS	Huang et al.⁴⁴
	2 μM B [a]P-7,8-dione in HBSS + pyruvate	10-(N¹-dG)-9,10-Dihydro-9-hydroxy-B[a]P-7,8-dione	LC-MS/MS	Huang et al.⁴⁴
		10-(N⁶-dGA)-9,10-Dihydro-9-hydroxy-B[a]P-7,8-dione	LC-MS/MS	Huang et al.⁴⁴
		10-(N³-dA)-9,10-Dihydro-9-hydroxy-B[a]P-7,8-dione	LC-MS/MS	Huang et al.⁴⁴
		10-(N³-dA)-B[a]P-7,8-dione	LC-MS/MS	Huang et al.⁴⁴

4OHEN = 4-hydroxyequilenin; NQ = naphthalene-1,2-dione; PQ = phenanthrene-9.10-dione; BPQ = benzo[a]pyrene-7,8-dione.