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PHRM 501 > Lecture 1: Chemical Properties + Lecture 2: Intro to biochemical principles > Flashcards

Lecture 1: Chemical Properties + Lecture 2: Intro to biochemical principles Flashcards

1
Q

Water can form hydrogen bonds:

A

-between water and alcohol, between water and amino acids and between water and sugar

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2
Q

Hydrophilic

A
  • Water loving
  • Drugs that are hydrophilic(soluble in water) tend to stay in the blood circulation and surrounding interstitial tissue
  • Polar molecules ( not = sharing of e-)
  • Molecules with a lot of hydroxyl groups
  • more soluble in body fluids
  • Ex: Glucose
  • will have trouble passing through lipid membranes
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3
Q

Hydrophobic

A
  • Water fearing
  • Drugs that are hydrophobic tend to get trapped inside the tissue and are slowly eliminated
  • Non polar molecules (= sharing of e-
  • less soluble in body fluids but can pass lipid membrane
  • Ex: Benzene
  • can pass through lipid membranes
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4
Q

Ion channels are

A

Hydrophobic on the outside and hydrophilic on the inside

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5
Q

Lipid Bilayer in water has

A

Hydrophilic heads and hydrophobic tails

- aqueous around

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6
Q

pH =

A
  • log [H+]

- pKa + Log [A-] / [HA]

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7
Q

A low pH means

A
  • more hydrogen ions

- more acidic

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8
Q

A high pH means

A
  • less hydrogen ions

- more basic

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9
Q

Ka

A

Dissociation constant

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10
Q

pKa

A
  • log [Ka]
  • Tells you how strong the acid is
  • pH at which conc. of acid HA equals that of its conjugated base A-
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11
Q

The stronger the acid

A
  • the larger Ka value
  • easier to dissociate and fully dissociates in sltn

–the smaller the pKa and pH

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12
Q

The weaker the acid

A
  • a smaller Ka value
  • harder to dissociate (partially dissociates)

–the larger the pKa and pH

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13
Q

If pH=pKa

A

the charged species = uncharged species

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14
Q

if pH is lowered

A

molecule becomes more protonated

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15
Q

If pH is raised

A

molecule becomes more de-protonated

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16
Q

pKa of amide is

pKa of carboxylic acid

A

9-10

4-5

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17
Q

Partition coefficient

A
  • Describes the extent to which an uncharged compound dissolves in an aqueous solvent versus organic solvent
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18
Q

Water phase vs octanol phase

A

Hydrophilic molecules will partition more into water phase. Hydrophobic molecules will partition more into octanol phase

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19
Q

Small molecule drugs are

A

less than 500 Daltons. Large molecule drugs are over 500 Daltons

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20
Q

For acids,

A

pH > pKa charge is negative

pH < pKa charge is neutral

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21
Q

For bases,

A

pH > pKa charge is neutral

pH < pKa charge is positive

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22
Q

Lowering pH

A

shifts equilibrium to the left

-More of the carboxylic acid becomes protonated and is in its neutral form

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23
Q

Raising pH

A

shifts equilibrium to the right

- More of the carboxylic acid dissociates and forms a negatively charged species

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24
Q

Strength of interactions

A
  1. Covalent
  2. Ionic
  3. Hydrophobic
  4. Hydrogen
  5. Van der waals
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25
Q

Tertiary proteins have

A

non-covalent bonds and disulfide bridges

26
Q

Buffer solutions

A

-resist pH change following the addition of a strong acid or base

27
Q

Physiologic buffers

A

include bicarbonate, orthophosphate, and proteins

28
Q

Ion

A

when an atom loses or gains an electron

29
Q

Anion

A

negatively charged ions

gains an electron

30
Q

Cation

A

loses an electron

becomes positively chaged

31
Q

The charge of the nucleus of an atom

A

positively charged

32
Q

Covalent bonds

A

sharing of electrons between atoms

- very strong bonds

33
Q

Electronegativity

A

tendency for an atom to attract a bonding pair of electrons
- atoms affinity for electrons
Trend is F>O>N»>C>H

34
Q

Polar vs nonpolar molecules

A

Polar: Unequal sharing of electrons

Non-polar: electrons are shared equally between carbon atoms in a carbon bond

35
Q

Dipole-Dipole

A

attractive forces between the positive end of one polar molecule and the negative end of another polar molecule
- weak, distance dependent interactions

36
Q

Hydrogen bonding

A

when a H atom is attached to a highly electronegative element such as N or O that is in proximity to another electronegative atom with a lone pair of e-

37
Q

Charge on Amines and Carboxylic Acids

A

An amine can gain a proton to become positively charged (NH2→ NH3
+)

A carboxylic acid can lose a proton to become negatively charged (COOH→ COO-)

38
Q

What is an acid?

A

An acid is a proton donor
• Example: Hydrochloric acid (HCl), acetic acid (CH3COOH)
• Hydrochloric acid: HCl→H+ + Cl-

39
Q

What is a base?

A
  • A base is a proton acceptor
  • Example: Sodium hydroxide (NaOH), ammonia (NH3)
  • Ammonia: NH3 + H2O→ NH4+ + OH-
40
Q

What is meant by a weak versus strong acid/base in terms of dissociation

A

A strong acid/base fully dissociates in solution
Hydrochloric acid: HCl→H+ + Cl-

A weak acid/base only partially dissociates in solution
Some of the acid/base will separate and form ions
• Some of the acid/base will remain as a neutral complex
• acetic acid CH3COOH →H+ + CH3COO-

41
Q

Reversibility

A

Gain and loss of protons on weak acids/bases are are reversible reactions and there exists an equilibrium between the charged and neutral forms
Ex: A neutral carboxylic acid can lose a proton (+) to become negatively charged (COOH→ COO-)
• A negatively charged carboxylic acid can gain a proton(+) to become neutral (COO- → COOH

42
Q

pH

A
  • based on hydrogen ion conc.
  • -log[H+]
  • can be changed by adding acid/base
43
Q

If we protonate an amine, it becomes

A

positively charged

44
Q

Intermolecular Interactions

A

dictate various properties of a molecule, including its solubility and interaction with biological drug targets

45
Q

• Drug A: 1 g/100 mL water
• Drug B: 10 g/100 mL water
Which drug is more soluble?

A

Drug B

We can get more of a mass into a lower volume of water

46
Q

Solubility

A

How much of a solute can be dissolved in a solvent

to make a solution

47
Q

Biochemistry

A

the study of chemical process in living

organisms

48
Q

Drugs that are hydrophilic

A

tend to stay in the blood circulation and surrounding interstitial tissue

49
Q

Drugs that are hydrophobic

A

tend to get trapped

inside the tissue and are slowly eliminated

50
Q

Why is it that water can easily break apart
NaCl but can not cleave an amide bond
without the help of a catalyst?

A

The water molecule has greater electronegativity than Cl

  • bc of ionic interactions
51
Q

Nucelophile

A

electron rich molecules

  • negatively charged or that has lone pairs of electrons
52
Q

Electrophile

A

electron poor molecules

  • attracts electron rich molecules
  • positively charged or neutral w no one pairs of e-
53
Q

Pepsin

A

an enzyme that degrades proteins into smaller

peptides in the stomach and digestive system

54
Q

Water can act both as

A

an acid and as a base, an equilibrium between hydronium ion (H3O+) and a hydroxide ion (OH−)
- water has the ability to ionize

55
Q

pOH

A

-log [OH-]

56
Q

Kw=

A

[H+] [OH-] = 10^-14

pH + pOH = 14

57
Q 
To calculate the pH of a NaOH solution you need to know its
A. Molarity
B. Density
C. Volume
D. All the above
A

A. Molarity

58
Q

Buffer solutions

A

they resist to pH change because of the presence of an equilibrium
between the acid HA and its conjugate base A−

  • the ability to resist a change following addition
    of a strong acid or base
59
Q

What helps to maintain pH of plasma (blood) around 7.4

A

Carbonic acid (H2CO3) and Bicarbonate ( HCO3-)

60
Q

Hydrogen bond donors vs. Hydrogen bond acceptors

A

Donors: O or N that is covalently bonded to H

Acceptors: H bonds

Water can serve as a donor and acceptor

PHRM 501 (21 decks)

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