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Kirstys Flashcards > BMP: Drug targets (carbohydrates) > Flashcards

BMP: Drug targets (carbohydrates) Flashcards

1
Q

What are primary, secondary, tertiary and quaternary amines?

A

CH3-NH2

(CH3)2NH

(CH3)3N

(CH3)4N+

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2
Q

What is a quaternary Amine also known as?

A

Catinoic salt

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3
Q

What is the dominant factor determining boiling point?

Which of these bonds are strongest?

A

Hydrogen bonding

O—-H bonding stronger than N — H binds

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4
Q

What are nitrogen containing functional groups?

A
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5
Q

What properties of AA is there?

A
  • Amphoteric - act as acids and bases
  • a-carbon chiral centre
    *
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6
Q

What AA are:

  • Basic
  • Acidic
  • Hydrophobic
  • Aromatic
A
  • Basic
    • arginine, histidine, lysine
  • Acidic
    • aspartic acid, glutamic acid
  • Hydrophobic
    • alanine, glycine, isoleucine, leucine, proline, valine
  • Aromatic
    • phenylalanine, tryptophan, tyrosine
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7
Q

What are primary, secondary, teritary, quaternary alcohols?

A
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8
Q

Discuss phenol properites

A
  • Phenols are about a million times more acidic than alcohols
  • Practical consequence – phenols are soluble in NaOH
  • More acidic due to resonance stabilised phenoxide anion
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9
Q

What do EWG do to the anion?

A

•Electron-withdrawing groups stabilise the alkoxide

form by spreading the charge over a larger volume

making the alcohol more acidic.

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10
Q
A
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11
Q

What do carbohydrates play an important role in?

A

Cell recoginisation, regulation and growth

  • Energy storage - glycogen
  • Structure - cellulose and starch
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12
Q

What does glycomics mean?

A

The study of carbohydrates/ glycomes as drug targets or drugs themselves

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13
Q

What substances is glucose the monomer for?

A

Glycogen, starch, cellulose

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14
Q

What is an example of carbohydrates play in there role of cell regonition, regulation and growth?

A

Bacteria and viruses are microgorganisms which must recoginize the host cells before infecting them. The carbohydrate molecules/ structures play a role in recoginition. Blocking these recognition sites will hopefully prevent microganisms from recognising them and infecting cells

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15
Q

What are examples of glycoconjugates?

Why are these useful?

A

Glycoproteins and proteoglycans

Rather than just carbohydrates involed in the recoginition process it normally involves glycoproteins instead.

Glycoproteins benefically compared to AA as rather than only 2 sites on the AA avialbe to react (-COOH/NH2) there is multiple -OH groups available for esterifcation reactions on the carbohydrate. This gives rise to greater stuctural diversity

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16
Q

What are carbohydrates and lipids known as

A

GLycolipids

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17
Q

What is an antigen?

A

A substance which when recognized as non-self by the adaptive immune system triggers an immune response where antibodies are produced specififcallt against it to react with it

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18
Q

What are antibodies?

A

Proteins which indentify with forgin cells/macrophages and mark them for destruction. Also can be used to carry specific drug targets

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19
Q

What are AB produced by?

A

B lymphocytes

20
Q

What are the problems with AB?

How is this problem over come?

A

The body produces Anti-AB to the AB

Using part human, part rat (66% human/ Rat)

21
Q

What are examples of AB that reach the clinic?

A

Omalizumab - targets imuglobin E and treatment for allergic ahstma

Adalimumab - first fully human AB. USed for rheumatoid arthritis and works by binding to inflam molecule cytokine-TNF-a

22
Q

Describe Reversible competitive inhibiton, include examples

A
  • The inhibitor binds to the active site of the enzyme by intermolecular forces (e.g. H-bond, hydrophobic interactions, Van der Waals) so the inhibition is reversbile
  • The drug binds to the active site and then is released and binds again
  • As the concentration of the natural substrate increases, the inhibtor competes more effectively with the drug for the active site - making the drug less effective
  • Competetive inhibitor - Rosuvastatin
  • ethanol can be used as a competitive inhibitor for anti-freeze posioning
23
Q

Describe the irreversible inhibition

A
  • These bind to the active site irreversibly and block the enzyme permanently. This is usually effected by the alkylation of nucleophilic R groups within the active site, e.g. the OH or SH of Serine and cysteine.
  • The majority of this type of inhibitor are, by their very nature, highly toxic. There are, however, exceptions e.g. Disulfuram, some proton pump inhibitors and anti-obesity drug Orlistat.
24
Q
  • Describe allosteric binding
  • What is good about allosteric binding?
A
  • Allosteric binding sites are different sites to the active site. Here agents which control enzyme activity bind
  • When the inhibitor binds here it causes the acitve site and allosteric site to change shape. The AS is no longer recogonizable to the substrate molecule, therefore its action is inhibited
  • This gives rise to 2 sites for drug targeting
25
Q

What is an example of an allosteric inhibitor?

What does it do?

A

6-mercaptopurine

Inhibits the firts enyzme involved in purine synthesis therefore blocks DNA synthesis and leads to cell death

26
Q

Describe non-competivie and uncompetive inhibitors

A
  • Rare
  • Tend to bind to enzyme-substrate complex as opposed to enzyme itself
27
Q

Describe transition-state analogues and give an example

Why are these difficult?

A
  • Renin inhibitors
  • These bind very potently (strongly) but not irreversbily
  • They mimic the transition state of the catalysed reaction
  • difficult because need to know the transition state and hard to mimic
28
Q

What is an example of a group which has optimum properties for a transition-state analogue? What are the properties?

What is a benefit of this group?

A

Hydroxyethylene - has the tetrahedral geometry and two hydorxyl groups required for optimum binding

stable to hydrolysis as no leaving group

29
Q

Describe suicide substrates

A
  • Agents that are designed to undergo anenzyme-catalyzed transformation which converts them into a highly reactive species, that binds irreversibly to the active site.
  • Example – Clavulanic acid.
  • Once bound undergoes biotransformation which posions the active site
30
Q

Describe isoenzymes and give examples

A

Isozymes are enzymes that differ in amino acid sequence but catalyze the same chemical reaction. Examples COX-1 and COX-2. This can be exploited for the treatment of rheumatoid arthritis, where COX-2 becomes activated, producing excess inflammatory prostaglandins.

Another example is the Monoamine Oxidase inhibitors.

31
Q

give examples of MAOIs

A

Two isozymes MAO-A and MAO-B. The isozyme MAO-A is selective for noradrenaline and serotonin, whereas MAO-B is selective for dopamine.

Clorgiline – antidepressant

Selegline and Levodopa – treatment for Parkinsons.

32
Q

bendfits of isoenyzme targeting?

A

Isozymes – targeting of these could lead to less side effects and more selective and effective drugs.

33
Q

NUCLEIC ACIDS

A
34
Q

What type of DNA binding is there?

A

3 reversible modes:

  • INTERCALATION – Major drug class
  • GROOVE BINDING
  • ELECTROSTATIC

Irreversible:

  • ALKYLATING AGENTS – Major drug class
35
Q

Describe intercalation binding

What is the stucture of intercalating drugs like?

A

Intercalating drugs tend to me planar or heteroaromatic (cationic) compounds which slide in between base pair layers of DNA.

They can have non-planar cationic or neutral parts to their structure which purdrude into a DNA groove

36
Q

Discuss specifciity in terms of intercalatinf drugs

A

Display no perefecnes for specific base pair binding or a slight GC prefercne

37
Q

Give an example of an intercalating anti-cancer drug

What properties are needed for an anti-tumour drug

A
  1. Actinomycin
  2. High levels of intercalating binding needed for anti-tumour activity but not all intercalating binding molecules have AT activity
38
Q

What are examples of intercalation drugs?

A
  1. Chloroquine and quine - antimalarial drugs
  2. Aminoacridines (proflavine) - antibacterials
  3. Doxorubican - chemotherpay drug
39
Q

What does Doxorubican do?

A

intercalattion prevents the normal function of topoimsomerases

40
Q

What is topoisomerase?

A

Enzymes which change the topological state of nucleic acids by disrupting the sugar-phosphate backbone of DNA

They are involved in metabolism of DNA and cell division

2 forms topo I and II - both targets for chemotherapeutic innervation

41
Q

Describe the general mechanism for groove bindiing

A

Involves direct interaction betwen the molecule and the edge of the base pair in wither the major or minor grooves

42
Q

Properties of groove binding drugs

A
  • Positive
  • Linked rather than fused aromatic or heteroaromatic rings
  • creasant shape
43
Q

what do the minor and major grooves differ in?

A
  • Electrostatic potential
  • Hydrogen bonding
  • hydration
  • Stearic interferance
44
Q

Examples of groove binding drugs

A
  • bis-imidazoles
  • Netropsin
  • distamycin

lead compounds with anticancer and antiviral properties

Minner groove binders

45
Q

Describe electrostatic binding

A
  • Generally non-specific interactions between cations and anions phosphate groups of DNA exterior backbone
  • ANy positive molecule can assoicate in this way
46
Q

Descibe alkylating agents

Examples

A
  • Highly electrophillic compounds which react with nucleophiles to form strong covalent bonds therefore this binding is irreversbile
  • nitrogen mustards, nitrosoureas, busulfan, cisplatin and mitomycin C.
47
Q
A

Kirstys Flashcards (116 decks)

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