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Seminar OnSeminar On
MutagensMutagens
andand
Their ActionsTheir Actions
Mutation
Heritable changes in DNA or gene
Mutagen
Chemical Mutagens
Radiation
Biological Mutagens
Conclusion
Introduction
The process that produces an
inheritable alteration in
DNA Structure
 Chromosome Structure
There are two types of mutations
Spontaneous Mutation
Induced Mutation
A.Spontaneous Mutation
Natural error during DNA replication or
recombination.
Caused by background radiation.
Arise randomly as a result in cells.
NO ARTIFICIAL TREATMENT
Spontaneous Mutation vs. Induced
Mutation
Induced Mutation
Caused by exposure to known mutagenic
agents
Mutagens
A natural or human-made agent which
can alter the structure or sequence of
genetic material and induce
There are three main types of mutagens
classifying by their sources:
Chemical Mutagens
Radiation
Biological Mutagens
Chemical Mutagens:
 Base analogs
 Chemical modification agents
 Intercalating agents
Radiation:
Ionizing Radiation
UV Radiation
Biological Mutagens:
Transposable element
Chemical Mutagens:
 First discovery of a chemical mutagen was made by
Charlotte Auerbach
Base Analogs:
Chemicals with structures similar to that of any of the four
standard bases of DNA
DNA polymerases cannot distinguish these analogs
They may be incorporated into newly synthesized DNA
molecules
5-Bromouracil(5-BU)
2-Aminopurine(2-AP)
5-bromouracil
an analog of thymine
N
N
1
2
3
6
5
4
O
O
5BU
Br N
N
1
2
3
6
5
4
CH₃
T
O
O
5-Bromouracil: analog of a pyrimidine
Resembles Thymine(T) .
has Br atom at C-5 instead of methyl group as
in T.
can incorporate into DNA and pair with either
A or G due to tautomerization.
5-Bromouracil: analog of a pyrimidine
TAUTOMERIZATION –spontaneous structural
alternations between 2 forms, ketoform and enolform
N
N
1
2
3
6
5
4
Br
O
5BU
O
N
N
1
2
3
6
5
4
Br
O
5BU
OH
Keto
pairs with A
Enol
mispair with G
T
A
5dBU
A
5dBU
5dBU
G
C
G
TRANISITION
T C
A G
GAC
CTG
Strand
seperation
3’
5’ 3’
5’
GAC
3’ 5’
CTG
5’ 3’
GAC
3’
5’
CBG
5’
3’
CTG
5’
3’
GAC
3’
5’
GAC
3’ 5’
CBG
5’ 3’
GAC
3’ 5’
CTG
5’ 3’
CBG
5’ 3’
GGC
3’ 5’
CBG
5’ 3’
GGC
3’ 5’
CBG
5’ 3’
GAC
3’ 5’
GGC
3’
5’
CCG
5’
3’replication
Incorporated error
G
C
5dBU
5dBU
G
5dBU
A
A
T
TRANISITION
G A
C T
2-amino purine (P)
 Base analog of adenine
 Normally pairs with thymine
 May mispair with cytosine
 Causes a transition mutation
GTC
CAG
Strand
separation
3’
5’ 3’
5’
GTC
3’
5’
CAG
5’
3’
GTC
3’ 5’
CPG
5’ 3’
CAG
5’ 3’
GTC
3’ 5’
GTC
3’ 5’
CPG
5’ 3’
GTC
3’ 5’
CAG
5’ 3’
CPG
5’ 3’
GCC
3’ 5’
CPG
5’ 3’
GCC
3’ 5’
CAG
5’ 3’
GTC
3’ 5’
GCC
3’ 5’
CGG
5’ 3’
replication
Incorporated error
T.A C.G
T
A
2AP
2AP
T
C
2AP
C
G
TRANISITION
T C
A G
C
G
2AP
2AP
C
T
2AP
T
A
TRANISITION
C T
G A
Both base analogs produce transition
mutations
Mutations by base analogs can be
reversed by treatment with the same
analog or different analog
Alkylating agents:
Chemicals that donate alkyl groups e.g.
ehylmethanesulfonate(EMS)
It adds an ethyl group to guanine and produces 6-
ethylguanine, which pairs with thymine and leads to
CG:TA transitions
Also adds an ethyl group to thymine to produce 4-
ethylthymine, which then pairs with guanine, leading to a
TA:CG transition
Mutations produced by EMS can be reversed by
additional treatment with EMS.
Mustard gas is another alkylating agent.
Modify the normal bases by adding alkyl
groups.
Common alkylatingagents
Ethylmethanesulfonate(EMS)
Nitrosoguanidine(NG)
Di-(2-chloroethyl) sulfide (Sulfur mustard)
Di-(2-chloroethyl) methylamine (Nitrogen
mustard)
Alkylating agents
Ethylmethanesulfonate(EMS)
Mechanism of Ethylmethanesulfonate(EMS)
Ethylatebase’s 7-N & 6-O positions
Mechanism of
Ethylmethanesulfonate(EMS)
Ethylatebase’s 7-N & 6-O positions
C
G
EMS
6EG
T
T
A
T
A
EMS
G
4ET
C
G
Deaminating agents
Nitrous acid (HNO2) is one of
common deaminatingagents
Convert the amino group (-NH2) into
ketogroup (=O).
Change H-bonding potential of the modified
bases.
Nitrous acid: causes deamination
Cytosine Uracil
N
N
CYTOSINE
1
2
3
6
5
4
NH2
O
H
N
N
1
2
3
6
5
4
O
o
HNo2
URACIL
H
U
G
U
G
U
A
GC
U A
U
A AT
C.G TA
C
G
HNO2
5’ 3’
3’ 5’
5’ 3’
3’ 5’
5’ 3’
3’ 5’
5’ 3’
3’ 5’
3’ 5’
5’ 3’
5’ 5’
3’
3’3’
5’
5’ 3’
3’ 3’5’
5’
H
T
H
T
H
C
A
T
H C
H
C G
C
A.T G.C
A
T HNO2
5’ 3’
3’ 5’
5’ 3’
3’ 5’
5’ 3’
3’ 5’
5’ 3’
3’ 5’
3’ 5’
5’ 3’
5’ 5’
3’
3’3’
5’
5’ 3’
3’ 3’5’
5’
Adenine changes into Hypoxanthin which then pairs with Cytosine
Guanine (G) →Xanthine
Mechanism of Nitrous acid
X
C
X
C
X
T
C
G
X T
X
T A
T
A.TG.C
G
C HNO2
5’ 3’
3’ 5’
5’ 3’
3’ 5’
5’ 3’
3’ 5’
5’ 3’
3’ 5’
3’ 5’
5’ 3’
5’ 5’
3’
3’3’
5’
5’ 3’
3’ 3’5’
5’
Guanine changes into Xanthin which pairs with Cytosine. Xanthin can
also pair with Thymine
 Nitrous acid produces exclusively
transition mutations
 Both C.G T.A & T.A C.G transitions
are produced
 Thus mutations can be reversed with the
nitrous acid
Hydroxl amine
 Specific base modifying mutagen which adds a
hydroxyl group to cytosine producing hydroxlamine
cytosine which pairs with adenine instead of guanine
 This Leads to C.G T.A tranisitions
 Acts only on cytosine thus can not revert the
mutation produced
hC
G
hC
G
hC
A
G
C
hC
A
hC
A T
A
T.AC.G
C
G
5’ 3’
3’ 5’
5’ 3’
3’ 5’
5’ 3’
3’ 5’
5’ 3’
3’ 5’
3’ 5’
5’ 3’
5’ 5’
3’
3’3’
5’
5’ 3’
3’ 3’5’
5’
Cytosine changes into hydroxlamine Cytosine which pairs
with Adenine instead of Guanine
NH₂OH
Oxidative reactions:
 Reactive forms of oxygen like superoxide radicals,
hydrogen peroxide and hdroxyl radicals produced in
the course of normal aerobic metabolism or by
radiation, ozone, peroxides, and certain drugs Cause
damage to DNA & induce mutations by chemical
changes
 Oxidation converts guanine into 8-oxy-7,8-
dihydrodeoxyguanine which mispairs with adenine
leading to G.C T.A transversion
Intercalating agents
 Proflavin, acridine orange, ethidium bromide,
and dioxin
 They are about the same size as a nucleotide
 They produce mutations by sandwiching
themselves (intercalating) between adjacent
bases in DNA
 They distort the three-dimensional structure of
the helix and cause single-nucleotide insertions
and deletions in replication
 These insertions and deletions frequently
produce frameshift mutations
Common intercalating
agents
2,8-Diamino acridine(proflavin)
Acridineorange
Physical Mutagens
Ionising radiation
e.g. x rays, γrays, cosmic rays
Non-ionising radiation
e.g. UV radiation
Ionizing Radiation
(high energy and penetrating)
Effects
Organelle failure
Cell division blockage
Cell death
Interaction with DNA
Breaks in one or both strands
(can lead to rearrangements, deletions,
chromosome loss death if unrepaired)
Damage to/loss of bases (mutation)
Crosslinkingof DNA to itself or proteins
Non-Ionizing Radiation
(Less energy, Non-penetrating)
Take UV radiationas an example
Its wavelengths are preferentially
absorbed by bases of DNA and by aromatic
amino acids of proteins.
Normally classified in terms of its
wavelengths: UV-A, UV-B, UV-C (in
decreasing order of wavelengths)
UV Radiation,
Pyrimidine dimers
5’--CCGAATTCAG--3’
3’--GGCTTAAGTC--5’
©2001 Lee Bardwell
tt
Thymine Dimer
T
T
Mutation rates
 The frequency with which a gene changes from the
wild type to a mutant is reffered to as the mutation
rate.
 Expressed as the number of mutations per biological
unit i.e. mutations per cell division, per gamete per
round of replication
e.g. mutation rate for achondroplasia (hereditary
dwarfism) is about 4 mutations per 100,000 gametes
Mutation frequency:
Incidence of a specific type of mutation with in a
group of individual organism
e.g. for achondroplasia, the mutation frequency
in united states is about 2x10⁻⁴
Principles of Genetics
An Introduction of Genetic Analysis
DNA replication
http://pharmacology.unmc.edu/cancer/a
ntibio.htm
References
Hemant

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