Natural and Synthetic Drugs

Molecules are synthesized and broken down by reactions involving

enzymes in biological system (lock-and-key mechanism).

Enzyme systems will tend to produce a single optical isomer that could
work perfectly.

Some Compounds with Physiological Activity

Taxol, an anti-cancer drug, is originally obtained

from the bark of the Pacific yew tree. naproxen

Its complex structure made it difficult to

synthesize initially.
Sometimes, natural products need to be
modified to reduce side effects.

causes serious mouth irritation painkiller

non-competitive
inhibitor
Pharmaceutical synthesis often requires the production of just one optical
isomer.
 one optical isomer usually works better than the other The use of computers
 the other optical isomer may cause dangerous side effects and molecular
modelling made drug
 laboratory reactions usually produce both optical isomers
development more
 naturally occurring reactions usually produce just one optical isomer efficient.

(S)-(+)-naproxen is used to treat arthritis pain but

(R)-(–)-naproxen causes liver poisoning with no (S,S)-(+)-ethambutol is used to treat tuberculosis
analgesic effect but (R,R)-(–)-ethambutol causes blindness.
Ways of preparing pure
enantiomers
 optical resolution
 using optically active starting materials
 using a chiral catalyst
Reasons for producing drugs consisting of a single
active isomer:
 It lowers the chances of undesirable side-effects due to
the other isomers.
 It is cheaper in the long-run, because it is a waste of
money and materials producing a drug half of which (or
more) is of no use.
 The patient can be given smaller doses if all the drug is
active.

DRUG DISCOVERY AND DEVELOPMENT

PROCESS
7-min video: https://youtu.be/3Gl0gAcW8rw
 Oral: takes time, ester and amide groups occurring in drugs are
Drug Delivery hydrolyzed under acidic conditions which in turn reduces its efficacy
Injection: injecting drugs directly into the blood gets a faster response,
the patient doesn't have to be conscious, and you can use smaller doses.

USE of liposomes, hydrogels, and

PEG

There is an -OH group at either end of the polymer

molecule, it is where drug molecules can get
attached. Each PEG molecule can carry two drug
molecules.

Hydrogels are like liposomes except that the

A liposome is like a little bubble which can carry
drugs around. The outside of the bubble consists
of a double layer of molecules known as
phospholipids. The head is hydrophilic, the tail
is hydrophobic.
PEG (polyethylene glycol) is a polymer used to coat
nano-cages (or liposomes) where the drug is
enclosed. The PEG dissolves in water when it gets
hot, releasing the drug from the nano-cage.
PEG is made from monomers of epoxyethane
drug was held in a thick-walled bubble made
from a network of polymer chains.
Hydrogels swell and absorb water at a rate
depending on the pH of the solution around
them. As the hydrogel swells, it releases the
drug.
Cisplatin an anti-cancer drug containing two ammine ligands and two chloro
ligands oriented in a cis planar configuration around the central
platinum ion

Cisplatin binds to the N7 reactive center on purine residues and causes DNA damage in
cancer cells, blocking cell division and resulting in apoptotic cell death.

Mechanism:
https://youtu.be/Wq_up2uQRDo
https://www.sciencedirect.com/topics/chemistry/cisplatin
Topics: Structure and Properties of Polymers
Nanotechnology: The Nanoscale
Uses of Nanoparticles

LEARNING OBJECTIVES ASSESSMENT CRITERIA

 know a range of properties of polymers and  relate the properties of polymers to its structure
understand how these are related to their
 understand the principles of nanotechnology
structure
 identify common examples of nanomaterials and state
 appreciate the nanoscale
its use
 know and understand in outline the structure
 understand the structure and properties of nanoscale
of some carbon-based nanoparticles (e.g.
materials and its application in nanotechnology-based
buckminsterfullerene, graphene, nanotubes)
research and industries
 know some uses of nanoparticles
Polymerization
A process in which small molecules called monomers join into large molecules
consisting of repeating units.

BASIC TYPES
ADDITION – all the atoms in the monomer are used to form the polymer
CONDENSATION – monomers join up the with expulsion of small molecules
not all the original atoms are present in the polymer
CONDENSATION
Polymer

ESTER LINK AMIDE LINK

Structure and Property of some Polymers
Thermosoftening plastics are ones which soften, and eventually melt, on heating. Typical examples include poly(ethene),
PET (poly(ethylene terephthalate) - a polyester) and nylon.

Thermosetting plastics tend to char (blacken) but remain solid on heating. Examples of this include Bakelite (one of the
first plastics) and epoxy resins

In the production of thermosetting plastics, covalent bonds are made between the original polymer chains to give a cross-
linked structure which is essentially one huge molecule.
The effect of side-chains in polythene
Polymers which conduct
electricity

The presence of the delocalized electrons over the

whole chain enables it to conduct electricity.
Kevlar is a very tough polyamide. It is made by polymerizing
benzene-1,4-dicarboxylic acid and 1,4-diaminobenzene.
The sulfur bridges between
polymer chains make rubber more
resilient

dotted lines represent hydrogen bond

why condensation polymers like proteins show a
wider range of properties than addition polymers
 Proteins are made from a wide range of combinations of amino acids leading to a wide range of properties.
 Proteins have side-chains which contain a range of functional groups.
 Bonding involving the side-chains leads to differences in the secondary and tertiary structures (and so the functions) of
proteins. By contrast, addition polymers have a very limited range of bonds and side-chains.
 Stronger interactions such as hydrogen bonding involving either the chains or the side-groups are much rarer in addition
polymers.
Nanotechnology
 The prefix ‘nano’ was
derived from the Latin
nanus, meaning "dwarf".
 Used primarily with the
metric system denoting a
factor of 10−9 or
0.000000001.
 Nanoparticle are particles
between 1 and 100
nanometers (nm) in size
with a surrounding
interfacial layer.
 Nanotechnology is
manipulation of matter on
an atomic, molecular, and
supramolecular scale.
Bio Nanoparticles
• Nanobiotechnology is a discipline in which tools
from nanotechnology are developed and applied to
study biological phenomena. Nanoparticles can
serve as probes, sensors or vehicles for biomolecule
delivery in cellular systems.

Buckyball
• An allotrope of carbon, discovered by Harry Kroto,
Robert Curl, and Richard Smalley in 1985

Buckyball: in Medicine
• Fullerenes are active molecules; can be used as an
antioxidant because it can easily react with radicals
due to the high affinity of the electron.
• Fullerene is used as an anti-aging and anti-damage
agent in the cosmetic sector.
• Fullerenes are used as antiviral agents. This use is
provided by its unique molecular structure,
antioxidant effect and biological compatibility.
Endohedral Fullerene
• Aside from medical application, it can be used to make the
most accurate clocks.

• A miniature of an atomic clock on a mobile chip could

increase GPS accuracy to 1 millimeter which could, in turn,
prevent accidents within a millimeter scale – it can
revolutionize the future of self-driving cars.
145 - 300 million US Dollars per
gram
Carbon Nanotubes (CNTs)
• are tubes made of carbon with diameters typically measured
in nanometers.
• Single-wall carbon nanotubes are one of the allotropes of
carbon, intermediate between fullerene cages and flat
graphene.
• can act as antennas for radios and other electromagnetic
devices
• can lead to significant improvements in the mechanical
properties of biodegradable polymeric nanocomposites for
applications in tissue engineering and in electronic devices
and circuitry
Graphene
Is an allotrope of carbon in the form of a single layer of atoms
in a two-dimensional hexagonal lattice in which one atom forms
each vertex. It is the basic structural element of other allotropes,
including graphite, charcoal, carbon nanotubes and fullerenes.

Interesting 7-min video about

graphene!
https://youtu.be/IesIsKMjB4Y
Uses
Nitinol
is a nickel-titanium alloy distinguished from other materials by
its shape memory and super elastic characteristics
Nitinol tubing is commonly used in catheters, stents, and super
elastic needles.

Ceramic Coating
 Industrial sectors Nanoparticles
silver, titanium dioxide, gold, carbon, zinc oxide, silicon dioxide, clay, sodium
cosmetics
silicate, kojic acid and hydroxy acid
electronics silver, aluminum, silicon dioxide and palladium
environment silver, titanium dioxide, clay, gold, selenium
food silver, clay, titanium dioxide, gold, silicon dioxide, calcium

medicine silver, gold, hydroxyapatite, clay, titanium dioxide, silicon dioxide, zirconium dioxide

titanium, clay, palladium, tungsten disulfide, graphite, silicon dioxide,  zirconium(IV)

renewable energies oxide-yttria stabilized, nickel(II) oxide, rhodium, sm-doped-cerium(IV)
oxide, and silver

textile silver, carbon, titanium dioxide, polyethylene terephthalate copper sulfide, clay, gold, 

VIDEO Summary on Nanotechnology: https://youtu.be/dQhhcgn8YZo

Topics: Environment and Energy
Efficient use of Natural Resources
LEARNING OBJECTIVES
 know and understand how chemistry can
help to solve some environmental
problems
 know and understand how chemistry can
help to use natural resources more
efficiently
ASSESSMENT CRITERIA
 identify an environmental problem and suggest
ways on mitigating the problem
 understand the underlying principles of green
chemistry
 identify renewable sources of energy, principles
behind recycling, and alternative ways to replace
hazardous materials
Environmental
Problems

Suggest a way on how

these problems can be
mitigated or reduced.
Consequence of increased UV light exposure due to Ozone layer depletion
• increased risk of sunburn, faster ageing of our skin, more skin cancer
• damage to our eyes, such as cataracts
• reduced resistance to some disease
• disruption of plant photosynthesis (and hence disrupted food chains).

Prevention / Mitigation
• Banning the use of CFCs
• Use of HFCs (hydrofluorocarbons). Have no effect on the ozone layer. They tend to be
broken down in the lower atmosphere by reaction with hydroxyl radicals, OH.
Water Pollution i.e. Oil spills
Spillage of oil at sea obviously causes major environmental damage when it occurs.

Ways of dealing with Oil spills

• Simple physical methods (use of fibrous brooms)
• Use of detergents to break up oil (detergents can pose environmental problems)
• Bioremediation – use of organisms (bacteria) and plants
• Use of sorbents (porous materials which soak up oil) like hydrophobic aerogels (light, very porous
material that can absorb as much as 200 times its own weight of liquid)

Soil Pollution i.e. Heavy metal contamination

• Bioremediation aids in the removal of toxic metals

Ground Water Contaminated with Heavy Metals

• Heavy metals can be precipitated (use of nanosized particles to increase contact with pollutants)
• Bioremediation
 • encourages environmentally conscious behavior
Green Chemistry • reduces and prevents pollution
• reduces the destruction of the planet

Explaining Principle 1: https://youtu.be/X9GHBdyYcyo

• better to prevent waste than to treat it afterwards

• aim for maximum atom economy
• use processes which require fewer chemicals
• don’t make products that are toxic to human health
• don’t make products that are toxic to the environment
• reduce the energy requirements of processes
• use alternative energy resources
• use renewable raw materials, not finite resources
• use catalysts where possible
• waste products should be designed to be biodegradable
• reduce the risk of explosions and fires
RENEWABLE RESOURCES AND ENERGY
Renewable Resources
• can be replenished by natural processes
• their rate of replenishment is equal or greater
than the rate of consumption
• often do not contribute to global warming
• often far more environmentally friendly
• lead to more sustainable use of materials;
resources can be used indefinitely
Renewable Energy
• plant-based substances such as wood
• solar energy
• tidal energy
• Biomass
• hydro-electric power
• wind power
Energy Sources
• Fuel Cells
• Biofuels – bioethanol and biodiesel
RECYCLING
• world resources are running out and are non-renewable
• we need to reduce the waste of valuable resources
• reduces the expense of disposal
• reduces expense of making things from raw materials
• avoids environmental problems posed by waste
Glass is made mainly from silicon dioxide (from sand). Making
glass uses lots of energy; recycling glass saves that energy.
Steel (a form of iron) is made from iron ores which are
reasonably plentiful, but making it uses lots of energy, and mining
the ore is also energy-intensive. The main reason is therefore to
save energy.
Plastics (and Polymers) are recycled because they come from
crude oil - a valuable and finite resource.
Aluminium is recycled because extracting it from its ore uses
huge amounts of electricity.
Paper is recycled to save energy
CATALYSTS
• can be used to lower the energy required for a reaction to
take place
• can reduce the CO2 emissions from burning of fossil fuels
• can give a better atom economy

SOLVENTS (replaces hazardous solvents)

Supercritical CO2
• critical point is at 31°C and 73 atm; supercritical CO 2 is
where the gas is at higher temperatures or pressures than
this
• behaves as if it has properties of both a gas and a liquid.

Ionic liquids (pure ionic compounds that are liquid at room

temperature)
• excellent solvents for all sorts of different things - ionic
and covalent.
• can be used to extract oil from oil shales, or to clean up oil
spills on beaches
• will also dissolve otherwise insoluble things like copper
oxide or uranium oxide.