TETROQUINONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H4O6
Molecular Weight	172.0924
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=C(O)C(=O)C(O)=C(O)C1=O

InChI

InChIKey=DGQOCLATAPFASR-UHFFFAOYSA-N

InChI=1S/C6H4O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h7-8,11-12H

HIDE SMILES / InChI

Molecular Formula	C6H4O6
Molecular Weight	172.0924
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29298374
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19476355 | https://www.ncbi.nlm.nih.gov/pubmed/8721612

Tetroquinone (Tetrahydroxy-1,4-benzoquinone, tetrahydroxy-p-benzoquinone, tetrahydroxybenzoquinone) is cyclohexadiene derivative with four hydroxyl groups and two ketone groups in opposite (para) positions, with potent prooxidant activity. The exposure of exponentially growing cultures to Tetroquinone, in the presence of Ca2+, caused a dose-dependent inhibition of cell growth and DNA synthesis. The chemical reactivity of Tetroquinone is strongly similar to those of physiological polyphenols, such as catechols and catecholamines. Despite their physiological and pharmacological roles, these compounds may, in addition, present toxicological properties due to their ability to autoxidize generating ROS and quinones Similar to catechols, the OH-substituents confer to Tetroquinone the ability to autoxidize readily in neutral aqueous solutions generating intermediate superoxide anion radicals, semiquinone radicals, and the corresponding quinone. The compound can be synthesized from glyoxal or from myo-inositol (phytic acid), a natural compound widely present in plants.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Hydroxyquinones are competitive non-peptide inhibitors of HIV-1 proteinase.	1995-11-15	7492599

Patents

Sample Use Guides

In Vivo Use Guide

Daphnia magna and zebra fish (Brachydanio rerio) were exposured for 2, 4, 6, and 24 h at 1, 3.5, 10, 35, and 100 mg/L.

Route of Administration: Oral

In Vitro Use Guide

V79 Chinese hamster lung fibroblasts cell line was used for activity evaluation. Assays were performed with cells in exponential phase of growth. Cells were seeded in 24-well plates (from Coming), at a density of 3 x l0^4 cells/well, and incubated in complete medium for 44 h. Exposure to Tetroquinone was performed in phosphate-buffered saline (PBS) alone, or containing 1.0 mM CaCl, (PBS/Ca2+), for 30 min at 37°C. THQ solutions were prepared at the desired concentrations immediately before addition to cultures. After treatment, cells were washed twice with PBS and incubated in fresh medium for a further 24-h period. At the end of this growth period cells were lysed with 0.5 M NaOH ( 1.0 ml/well). Cell population was determined by measuring lysate absorbance at 260 nm, a parameter directly correlated with cell number, in the range of 10^5-l0^6 cells.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:49:06 GMT 2025` Edited by `admin` on `Mon Mar 31 17:49:06 GMT 2025`
Record UNII	U7L4P6H0SU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TETROQUINONE

Official Name

English

HPEK-1

Preferred Name

English

THQ

Code

English

TETROQUINONE [MI]

Common Name

English

NSC-112931

Code

English

TETROQUINONE [USAN]

Common Name

English

tetroquinone [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C796