Option D7 Flashcards

1
Q

How do chiral drugs exist?

A

They exist in 2 forms with different activities

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2
Q

How do enantiomers react in a chemical environment

A

Regardless of their similar chemical properties, they act in different ways

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3
Q

What does in vivo synthesis yield?

A

Biological synthesis reactions within cells (in vivo) produce only one enantiomeric
form.

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4
Q

What does in vitro fertilization yield

A

A mixture of enantiomers,
known as a racemate

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5
Q

What challenges do pharmaceutical companies face in this context?

A

Determining the effects of each enantiomer, in order to check whether to market the drug as racemate or single enantiomer

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6
Q

What was the reason for scientists to make these differentiation

A

Thalidomide incidence

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7
Q

Why was the thalidomide mixture a starting point for the scientists’ research?

A

It was sold in a racemic mixture form, however only the (R) isomer showed the effect of inducing sleep in women, while the (S) isomer was teratogenic

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8
Q

What are examples of racemic mixtures that are marketed as drugs

A

Ibuprofen and Prozac

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9
Q

What is chemotherapy

A

The treatment or control
of disease by chemical
agents. It is generally
used in the context of
cancer treatment.

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10
Q

What is Taxol

A

It is a powerful anti-cancer drug

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11
Q

What is Taxol known as and to what group does it belong?

A

Taxol is also known as Paclitaxel, and is part of taxoid group

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12
Q

How is Taxol used?

A

It is used
primarily in the treatment
of breast and ovarian
cancers.

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13
Q

How do the anti cancer properties of Taxol arise?

A

Due to its ability to bind to a protein known as tubulin

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14
Q

What is tubulin?

A

It is the main component of microtubules that makes up spindles during cell division

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15
Q

How does Taxol stop growth of tumor?

A

As Taxol binds to the tubulin, the microtubules will breakdown and halt the cell division therefore preventing the spread of tumor

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16
Q

How was Taxol first discovered?

A

Taxol was first isolated from the bark of Pacific yew trees (Taxus sp.) in the
1970s.

17
Q

Why did the practice of removing the Taxol from bark trees become controversial?

A

The process of stripping the bark kills the trees, which take 200 years to
mature and are part of a sensitive ecosystem

18
Q

What is asymmetric synthesis?

A

The production of a single enantiomer
of Taxol

19
Q

What challenges came with the synthesis of Taxol?

A

It is made of of 11 chiral centers with only one of them having therapeutic effects

20
Q

What is a strategy to synthesize Taxol?

A

The use of a chiral auxilary

21
Q

What is a chiral auxiliary?

A

This is a chiral molecule which binds to the reactant, physically blocking one reaction site through steric hindrance, so ensuring that the next step in the reaction can only take place from one side. This effectively forces the reaction to proceed with a specified stereochemistry.

22
Q

What happens to chiral auxiliary when the desired product is received

A

It is taken off and recycled

23
Q

What difficulties arose because of the complex structure of Taxol

A

Its synthesis from simple compounds took 30 steps, with a very poor yield

24
Q

What is considered to be a more efficient way to synthesize Taxol?

A

The extraction of a compound from the needles and leaves of yew trees which is similar to Taxol.

25
Q

Why is this considered to be more sustainable?

A

As it does not involve cutting down entire trees of yew

26
Q

What is the chemically related compound and what is its use?

A

10-DAB, and is used to form Taxol

27
Q

What is the process of synthesizing Taxol from 10-DAB known as?

A

Semi-synthetic as it begins with a precursor from nature