Peptide and peptidomimetic

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What strategy can be used to increase resistance to proteolysis while retaining intended activity of peptides?

Using pseudo peptides

Replacing primary amide with secondary amides at key cleavage sites

Co-administering protease inhibitors and permeation enhancers

Replacing L-amino acids with their D-counterparts (correct)

Which route of administration for Leuprolide shows the highest percentage of dose absorbed?

Vaginal

Subcutaneous (correct)

Nasal

Rectal

What is a key advantage of using peptidomimetics in drug design?

Increased membrane permeation (correct)

Decreased bioavailability

Enhanced proteolysis of the drug

Reduced receptor binding

Which method is NOT a strategy to overcome the challenges posed by peptides as drug candidates?

Increasing primary amides at cleavage sites (D) Signup and view all the answers

In nasal delivery, what aids in the effective administration of peptides?

Co-administration of protease inhibitors and permeation enhancers (C) Signup and view all the answers

What is the main purpose of replacing non-pharmacophoric polar sections of a natural molecule with lipophilic moieties in peptidomimetics?

To increase membrane permeation (B) Signup and view all the answers

What is the natural target for designing inhibitors of HIV protease?

S3 protease cleavage site (A) Signup and view all the answers

Which amino acid residue in the protease mechanism forms a diol intermediate during the reaction?

Asp-25 (A) Signup and view all the answers

Which compound has the highest inhibitory potency (lowest IC50 value) among the Transition State Analogues mentioned?

CO2tBu (A) Signup and view all the answers

What is the role of Saquinavir in peptide drug design?

Decreasing Proteolysis (A) Signup and view all the answers

What is a key feature of Solid Phase Organic Synthesis relevant to Peptidomimetics?

Used in Combinatorial Chemistry (B) Signup and view all the answers

How can structural extension impact the affinity of a molecule towards its target binding site?

Increasing interactions with portions of the target binding site not reached by the natural substrate (A) Signup and view all the answers

Why is blocking the binding of fibrinogen to its receptor valuable in the treatment of stroke and heart attacks?

It prevents platelet aggregation (B) Signup and view all the answers

What is the significance of using a Glucose scaffold analogue for a cyclic peptide agonist in inhibiting Growth Hormone (GH)?

It displays effective GH inhibition in cultured rat anterior pituitary cells (B) Signup and view all the answers

Why are unnatural amino acids used in designing peptidomimetic drugs?

To increase affinity to target binding sites (C) Signup and view all the answers

In peptidomimetic design, what does conformational restriction along the peptide backbone aim to achieve?

Enhance specificity and mimic secondary structures (D) Signup and view all the answers

How does mimicking secondary structure contribute to peptidomimetic drug design?

Aids in improving the interaction with the target molecule (B) Signup and view all the answers

What is a common way to change a peptide backbone to improve its properties?

Pseudopeptides (D) Signup and view all the answers

How do peptidomimetics help overcome the limitations of using active peptides as drugs?

By improving hydrolytic stability and enhancing membrane penetration (B) Signup and view all the answers

In drug discovery, what approach aims to produce hundreds to thousands of new compounds using Solid Phase Organic Synthesis?

Combinatorial approach (D) Signup and view all the answers

What is a key advantage of peptoids in drug design?

Increased proteolysis resistance (D) Signup and view all the answers

Why are most peptides with significant biological activity not administered unchanged as drugs?

Due to adverse ADME profiles (A) Signup and view all the answers

Which strategy is employed by peptidomimetics to retain the activity of active peptides?

Appropriate display of binding subunits in 3-dimensional space (D) Signup and view all the answers

Which enzymatic cleavage would be a concern for a peptide with a C-terminal residue entering the gastrointestinal tract?

Carboxypeptidases (B) Signup and view all the answers

Why are full-sized proteins generally more resistant to enzymatic digestion than small proteins and polypeptides?

Their compact globular nature (D) Signup and view all the answers

Which enzyme would be most likely to cleave a peptide at the N-terminal end?

Aminopeptidases (A) Signup and view all the answers

In which part of the gastrointestinal tract would a peptide encounter trypsin, chymotrypsin, and elastase?

Small intestine (A) Signup and view all the answers

Which of the following is a strategy to overcome poor passage of hydrophilic peptides through lipid membranes?

Development of peptidomimetic drugs (B) Signup and view all the answers

Why can the enzymatic hydrolysis of peptide bonds in the gastrointestinal tract pose a challenge for oral administration of peptides?

Enzymes like pepsin and trypsin can degrade peptides (D) Signup and view all the answers

What is the role of Saquinavir in peptide drug design?

Saquinavir acts as an HIV protease inhibitor in drug design. Signup and view all the answers

How does mimicking secondary structure contribute to peptidomimetic drug design?

Mimicking secondary structure helps enhance the stability and activity of peptidomimetics. Signup and view all the answers

What strategy can be used to increase resistance to proteolysis while retaining intended activity of peptides?

One strategy is to replace non-pharmacophoric polar sections with lipophilic moieties. Signup and view all the answers

What is the natural target for designing inhibitors of HIV protease?

The natural target is the S3 protease cleavage site in viral polypeptides. Signup and view all the answers

Why are full-sized proteins generally more resistant to enzymatic digestion than small proteins and polypeptides?

Full-sized proteins have more complex structures and tertiary interactions that make them less susceptible to proteolysis. Signup and view all the answers

Peptide and peptidomimetic

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Questions and Answers

What strategy can be used to increase resistance to proteolysis while retaining intended activity of peptides?

Which route of administration for Leuprolide shows the highest percentage of dose absorbed?

What is a key advantage of using peptidomimetics in drug design?

Which method is NOT a strategy to overcome the challenges posed by peptides as drug candidates?

In nasal delivery, what aids in the effective administration of peptides?

What is the main purpose of replacing non-pharmacophoric polar sections of a natural molecule with lipophilic moieties in peptidomimetics?

What is the natural target for designing inhibitors of HIV protease?

Which amino acid residue in the protease mechanism forms a diol intermediate during the reaction?

Which compound has the highest inhibitory potency (lowest IC50 value) among the Transition State Analogues mentioned?

What is the role of Saquinavir in peptide drug design?

What is a key feature of Solid Phase Organic Synthesis relevant to Peptidomimetics?

How can structural extension impact the affinity of a molecule towards its target binding site?

Why is blocking the binding of fibrinogen to its receptor valuable in the treatment of stroke and heart attacks?

What is the significance of using a Glucose scaffold analogue for a cyclic peptide agonist in inhibiting Growth Hormone (GH)?

Why are unnatural amino acids used in designing peptidomimetic drugs?

In peptidomimetic design, what does conformational restriction along the peptide backbone aim to achieve?

How does mimicking secondary structure contribute to peptidomimetic drug design?

What is a common way to change a peptide backbone to improve its properties?

How do peptidomimetics help overcome the limitations of using active peptides as drugs?

In drug discovery, what approach aims to produce hundreds to thousands of new compounds using Solid Phase Organic Synthesis?

What is a key advantage of peptoids in drug design?

Why are most peptides with significant biological activity not administered unchanged as drugs?

Which strategy is employed by peptidomimetics to retain the activity of active peptides?

Which enzymatic cleavage would be a concern for a peptide with a C-terminal residue entering the gastrointestinal tract?

Why are full-sized proteins generally more resistant to enzymatic digestion than small proteins and polypeptides?

Which enzyme would be most likely to cleave a peptide at the N-terminal end?

In which part of the gastrointestinal tract would a peptide encounter trypsin, chymotrypsin, and elastase?

Which of the following is a strategy to overcome poor passage of hydrophilic peptides through lipid membranes?

Why can the enzymatic hydrolysis of peptide bonds in the gastrointestinal tract pose a challenge for oral administration of peptides?

What is the role of Saquinavir in peptide drug design?

How does mimicking secondary structure contribute to peptidomimetic drug design?

What strategy can be used to increase resistance to proteolysis while retaining intended activity of peptides?

What is the natural target for designing inhibitors of HIV protease?

Why are full-sized proteins generally more resistant to enzymatic digestion than small proteins and polypeptides?

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