Quinones
Anas taifour
(201610274)
Section : 63
Quinones importance in cells
Oxidation of hydroquinone to make p-benzoquinones is
carried with Mild oxidizing agent, this leads to removing of
two Electrons and two protons to form the p-benzoquinone
However, mild reducing agent may reverse the Reaction. The
cells in body benefit from this reaction to transport a pair of
electrons from a substrate to Another in reactions that are
enzyme-catalyzed.
But what got the mitochondria to do in this respect ?
In the mitochondria there are compound called ubiquinones(
coenzyme Q) that is important part of the electron transport
chain.
• These has side chains that is nonpolar, thus more soluble in
the membranes of the mitochondria so lateral diffusion is
easier for them from one unit of ET chain to the other
• And they carry 2 protons and electrons, thus became
hydroquinone that carry electrons from one part of electron-
transport-chain to the next acceptor.
Resources:
• Quinones and Quinone Enzymes
• www.sciencedirect.com
• en.wikipedia.org/wiki/Bombardier beetle
• Organic Chemistry (11th edition) by T.W. Graham
Solomon
They are a class of organic compounds derived from aromatic compounds by the conversion of an even
number of –CH= groups into –C(=O)- groups. And are alpha, beta Unsaturated ketones.
Quinone enzymes
Quinone reductases are enzymes that catalyze the reduction
of quinones. two major quinone reductase catalyze the formation
of hydroquinone from quinone by reduction. In cancer treatment
NQO1 and NQO2 are a major target because of their high levels
in human cancers in combination with their ability to bioactivate a
wide-range of quinone antitumor drugs.
• quinones undergoes bio reductive activation by NQO1 that
result in the formation of hydroquinone's which undergoes
internal rearrangement that cause DNA alkylation and DNA
crosslinking's.
• HSP90 stabilizes a number of proteins required for tumor
growth, so Hsp90 inhibitors are investigated as anti-cancer
drugs.
• This ability of NQO1 in bioactivating the anti-cancer drugs
made it an important consideration in cancer chemotherapy.
Ubiquinone (coenzyme Q)
Dyes and quinones The Bombardier Beetle’s Noxious
Spray
• The chemistry of quinone dyes was reviewed
thoroughly by Venkatraman in 1971.
• Quinone molecules are well known as electron
acceptors and emit virtually no light in the visible
region. The bombardier beetle defends itself by
spraying a jet stream of hot (100 8C), noxious p-
• Providing the quinone nucleus with electron donors
benzoquinones at an attacker
and/or acceptors will produces visible absorption
produces visible absorption with intramolecular When the beetle feels threatened it opens a valve
charge-transfer character. which allows the aqueous solution from the
reservoir to reach the vestibule. The catalases lining
• l,4-Naphthoquinone and 9,10- anthraquinone are the
the vestibule wall facilitate the decomposition of
main chromophores for the colorants.
hydrogen peroxide into oxygen gas and water
• The reaction
• This reaction is very exothermic, and the
• Reduction of p-benzoquinone to hydroquinone form a
released energy raises the temperature of the mixture
colored intermediate known as Quinhydrone. This
to near 100 °C
intermediate is believed to be a charge-transfer
• New research, published in the journal Science in 2015,
complex formed from the quinone (acting as electron
acceptor) and hydroquinone (electron donor) and is
revealed how the bombardier beetle can survive while a
boiling mix of chemicals is brewing inside its abdomen.
stabilized by hydrogen bonding
• If X-ray was used to take a picture for the two abdomens
we will see this pathway as membrane and valve.
• When these insects feel threaten they release a burst of
benzoquinone, after releasing this pressure the membrane
relaxes allowing the valve to reopen and the refill.