Block 5 (Test 1)

Question 1

what is a bioisostere?

Answer 1

a substituent or functional group with similar chemical/physical properties and which produces broadly similar biological properties

Question 2

List examples of classical monovalent bioisosteres

Answer 2

CH3 OH NH2 S

Question 3

list examples of classical divalent bioisosteres

Answer 3

R-O-R, R-NH-R, R-CH2-R

Question 4

List examples of classical trivalent bioisosteres

Answer 4

R-N=R, R-CH=R

Question 5

List examples of classical tetravalent bioisosteres

Answer 5

R=C=R, R=N=R, R=P=R

Question 6

what are non-classical bioisosteres?

Answer 6

they do not have the same number of atoms and do not fit steric or electronic rules of classical isosteres, but they have similar biological activity

Question 7

boronic acid is a bioisostere of _______. what is the result of using this bioisostere?

Answer 7

carboxylic acid boronic acid forms a covalent bond instead of a hydrogen bond (how COOH works), thus making it a suicide inhibitor

Question 8

what is a prodrug?

Answer 8

an inactive compound that is converted (either chemically or enzymatically) to the active form (once in the body)

Question 9

what are the two main considerations when making a prodrug?

Answer 9

effective conversion to active drug in the blood stream the prodrug “shield” group is not toxic when released

Question 10

describe the function of ester prodrugs

Answer 10

carboxylic acids are excellent HBA and HBD, but they ionize too easily which can be a problem in crossing membranes a prodrug is used to protect the acid function by making it an ester. the less polar ester can cross the membrane and be hydrolyzed to the acid by an esterase enzyme

Question 11

how do prodrugs aid in circumventing metabolism?

Answer 11

they are often designed to be slowly converted into the active metabolite in order to prolong plasma levels

Question 12

give an example of how prodrugs mask toxicity

Answer 12

ex. salicylic acid is known to cause GI bleeding due to its phenolic group. by making it a prodrug (masking the phenol), the active drug is only exposed by esterases once it enters the bloodstream

Question 13

what is the most common activation pathway of a prodrug?

Answer 13

hydrolysis with esterase

Question 14

the major objectives of prodrugs are

Answer 14

improved bioavailability improved aqueous solubility improved passive intestinal absorption

Question 15

NMR stands for

Answer 15

nuclear magnetic resonance

Question 16

___________ provides a direct link between the genetic alterations and a disease phenotype. _______ identified this way are more likely to be the cause rather than a consequence.

Answer 16

phenotypic screening genes

Question 17

phenotypic screening is a whole organism (or cell) approach that speeds up ______________.

Answer 17

physicochemical property optimization

Question 18

iPSC stands for

Answer 18

induced pluripotent stem cells

Question 19

_____ can be differentiated into neurons (or other cell types) that harbor the same genetic mutation as the patient

Answer 19

iPSCs

Question 20

describe theranostics

Answer 20

the combination of diagnostics and therapeutics using the same molecular scaffold

Question 21

what is chemical biology (chemical genetics)

Answer 21

using a chemical to probe to learn about biological functions (usually a signaling pathway)

Question 22

_______ enables identification of the biomolecular targets of efficacious agents with unknown mechanisms of action

Answer 22

Reverse Pharmacology

Question 23

______ is a technique that is used with chemical biology approach to understand which proteins are impacted by the process

Answer 23

proteomics

Question 24

organic elements include

Answer 24

H, C, O, N

Question 25

essential macronutrients include

Answer 25

Na, K, Mg, Ca, P, S, Cl, Si, Fe

Question 26

the most important class of inorganic chemical therapeutics by far is

Answer 26

cisplantin (platinum) acts by forming a covalent “complex” with guanine that leads to cytotoxicity and apoptosis

Question 27

the three approved platinum based treatments for cancer include

Answer 27

carboplatin, oxaliplatin, and cisplatin

Question 28

why are metals good for structural scaffolds?

Answer 28

they have greater valency and can accommodate more bonds

Question 29

what useful property does boron possess?

Answer 29

it can exist as both tri and tetra valent it is also non-toxic

Question 30

_________ was the first non-platinum based chemotherapeutic approved since the approval of platinum

Answer 30

velcade

Question 31

imaging agents are designed to

Answer 31

provide more information about internal organs or processes

Question 32

a vast majority of imaging agents have a _______ that acts as a delivery vehicle to deliver the _______ to the site of action you want to image

Answer 32

organic scaffold inorganic element

Question 33

fluorodeoxyglucose is used in association with

Answer 33

PET scans

Question 34

________ looks at physiologic parameters of the body (glucose metabolism, protein composition, etc.)

Answer 34

PET scans

Question 35

SPECT is used for

Answer 35

visualizing vasculature

Question 36

What is the difference between target validation via gene knockout and via the RNAi method?

Answer 36

Gene knockout inhibits protein expression fully and RNAi results in partial inhibition of protein expression.

Question 37

Define medicinal chemistry.

Answer 37

The science that deals with the discovery/design of new therapeutic agents and their development into useful medications