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C2 > Metals In Medicine 🩺 > Flashcards

Metals In Medicine 🩺 Flashcards

1
Q

What does an s orbital look like?

How many p orbital shapes?

How many d orbital shapes?

How many f orbital shapes?

A

spherical

like 2xS, 3

5

7

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2
Q

What do s block elements have?

A

their electron of highest energy level in the s block

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3
Q

What are 5 characteristics of s-block elements?

far left: H, Li,…

A
  • Most abundant metal ions in biology - occur in most cells at high concentrations (~mM)
  • Difficult to monitor
  • Trigger wide range of biochem processes (Ca, Mg)
  • Activators of enzyme action (K, Mg)
  • Stabilisers of biomolecular structures (Mg, Ca)
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4
Q

What are the 5 s-block elements essential for life?

A

H, Na, K, Ca, Mg

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5
Q

What are 2 characteristics of p-block elements?

A
  • Constituents of living matter

- C, H , N, and O comprise 99% of human body

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6
Q

Characteristics of d-block elements:

  • Usually prevalent in _____ quantities
  • ____er to monitor
  • Highly relevant in the function of metalloproteins
  • Key participants in e_______transfer reactions, r__________ chain, _2 storage and transport
A
  • Usually prevalent in trace quantities
  • Easier to monitor
  • Highly relevant in the function of metalloproteins
  • Key participants in electron transfer reactions, respiratory chain, O2 storage and transport
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7
Q

What are 4 chemical interactions?

A
  • covalent bond
  • ionic bond
  • Hydrogen bond
  • Van der Waals
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8
Q

What is a covalent bond? Name 2 examples

A

sharing of electrons

  • peptide bonds
  • ligand to metal bonds
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9
Q

What is an ionic bond? Name 2 examples

A

Association of positively and negatively charged species

  • salt bridges
  • association of hard cations
    and hard ligands
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10
Q

What is a hydrogen bond? Name 2 examples

A

H atom shared between two highly electronegative atoms

  • Base-base interactions in DNA
  • α-helixes in proteins
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11
Q

What are Van der Waals forces? Name 1 example

A

Large number of atoms reinforcing transient weak polarising effects
- Intercalation between DNA base pairs

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12
Q

What type of bond exists between a metal centre and ligands?

A

coordinative/dative bond

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13
Q

6 questions to cover when dealing with ligands and qs?

A
  • type of bond
  • Oxi state
  • Any ligands?
  • What ligands?
  • Hm ligands?
  • Shape?
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14
Q

What is a coordinative/dative bond?

A

Covalent bond in which both electrons come from the same “donor” atom/ligand

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15
Q
  1. Where is the coordinate/dative bond coming from in [Co(NH₃)₆]Cl₃?
A

coordinate/dative bond comes from NH₃

Co -:N

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16
Q
  1. How do you determine the oxidation state of the metal centre?
A
  • Determine the overall charge of the complex
  • Assign charges to the ligands (most are usually neutral, can be -)
  • Determine the difference in charge between
    the overall cation and the ligands
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17
Q

e.g. Determine the oxidation state of Co in [Co(NH₃)₆]Cl₃.

A
  • Cl₃ = 3- charge outside
  • inside must add up to 3+ to balance
  • NH₃ are neutral
  • therefore Co = 3+
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18
Q

Determine the oxidation state of Fe in [Fe(CN)₆]4⁻.

A
  • Entire complex adds up to -4
  • 6 Ligands that are single negative (CN-) = -6
  • therefore Fe must be +2
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19
Q

Determine the oxidation state of Co in [Co(SO₄)(NH₃)₅]Cl.

no pic

A
  • Entire complex adds up to +1, as outside is balanced by Cl (-1)
  • 5 neutral NH₃ ligands
  • 1 SO₄ = -2
  • Cobalt must therefore = +3
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20
Q

Oxygen atoms from what compounds can act as donor centres/ligands?

A
  • H₂O
  • OH⁻
  • OR⁻
  • NO₃⁻
  • RCO₂⁻ (including side-chains of glu, asp, tyr, ser, thr)
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21
Q

What can act as donor centres/ligands? (4)

A
  • O atoms
  • Single charged anions
  • Neutral ligands
  • Sulphur atoms
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22
Q

Name 3 single charged anions that can act as donor centres/ligands

A

Cl⁻, F⁻, CN⁻

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23
Q

Name 2 examples of neutral ligands

A

NH₃, CO

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24
Q

Sulphur atoms from residues like what compounds can act as donor centres/ligands?

A

RSH

R₂S (including cys and met)

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25
Q

Mg²⁺ cation prefers what type of donor centre? Name an example

A

O donors strongly preferred e.g. phosphate groups in DNA, RNA

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26
Q

Ca²⁺ prefers what type of donor centre? Name an example

A

Only O donors e.g. Ca binding proteins

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27
Q

Zn²⁺ prefers what type of donor centre? Name an example

A

N, O, S favours his, glu, asp, cys

e.g. Zn-dependent endopeptidases, metallothionein

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28
Q

What is the coordination number?

A

Number of ligands surrounding a metal centre in a complex

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29
Q

What does the coordination number determine?

A

the complex geometry and spatial distribution

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30
Q

What is the geometry of a metal with 3 ligands?

A

trigonal planar

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31
Q

What are the potential geometries of a metal with 4 ligands?

A

tetrahedral or square planar

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32
Q

What is the geometry of a metal with 6 ligands?

A

octahedral

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33
Q

What are the potential geometries of a metal with 5 ligands?

A

trigonal bipyramid or square pyramid

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34
Q

What is a trace element?

A

a dietary element that is needed for the proper

growth, development, and physiology of the organism.

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35
Q

How does the biological function of an organism change with the concentration of that element in diet?

A

Death->deficient->optimum->toxic->death

rise then fall

always have optimum window

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36
Q

What is an example of a metalloprotein that transports O2? Describe the structure

A

Haemoglobin:
metal centre = Fe
4 big units which each contain a central Fe atom which holds O2, allowing it to be transported in respiration events

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37
Q

What happens when there’s too little and too much Fe?

A

Too little = anaemia

Too much = damage to heart + liver

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38
Q

What happens when there’s too little Zn?

A

growth failure, scaly skin inflammation, reproductive failure, impaired immunity

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39
Q

What happens when there’s too much Cu?

A

damage to liver, discolouration of skin, hair, hyperactivity in children

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40
Q

State the following of haemoglobin:

Metal centre, ligands, geometry, structure (how many units, what group?), function

A
  • metal centre: Fe(II)/Fe(III)
  • ligands: 4xN on the plane,1xN histidine below, 1xO₂ above
  • geometry: octahedral when O₂ bound
  • structure: 4 subunits, each including a haeme group (heterocyclic porphyrin)
  • function: O₂ transport, gases transport: CO₂, NO
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41
Q

State the following of cytochrome P450:

Metal centre, ligands, geometry, structure (what group?), function

A
  • metal centre: Fe(II)/Fe(III)
  • ligands: 4xN on the plane,1xN histidine below, 1 active site above
  • geometry: octahedral
  • structure: a haeme group (heterocyclic porphyrin)
  • function: metabolic oxidation
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42
Q

State the following of cobalamin vitamin B12:

Metal centre, ligands, geometry, structure (what ring?), function

A
  • metal centre: Co
  • ligands: 4xN on the plane,1xN dimethylbenzimidazole, 1 active site above (X = -CN, -OHM
  • geometry: octahedral
  • structure: corrin ring
  • function: coenzyme for isomerases, methyl-transferases and dehalogenases; key in synthesis of myelin, DNA synthesis!!, amino acid metabolism

X could be -CN, -OH, -CH₃

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43
Q

State the following of carbonic anhydrase:

Metal centre, ligands, geometry, function

A
  • metal centre: Zn
  • ligands: 3xN histidine side chains, 1x active site above
  • geometry: tetrahedral
  • function: catalyses conversion of CO₂ and water to bicarbonate
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44
Q

State the following of superoxide dismutase:

Metal centre, ligands, geometry, struture (how many subunits in each form?) function

A
  • metal centre: Cu/Zn (SOD1), Mn (SOD2)
  • ligands: 3xN histidine side chains, 1xO from water, 1xO carboxilate
  • geometry: trigonal bypry
  • structure: SOD1 = 2 subunits, SOD2 = 4 subunits
  • function: antioxidant in cells, turning O₂ radical into H₂O₂
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45
Q

Where are the 2 forms of superoxide dismutase found?

A

SOD1: cytoplasm
SOD2: mitochondria

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46
Q

What are 4 different mechanisms of reactions that can occur in metal centres

A
  • Substitution reactions (Ligand exchange)
  • Addition reactions
  • Elimination reactions
  • Oxidative/reductive addition
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47
Q

What happens in a substitution reaction w a metal centre?

A

1 step
In an octahedral with 5 ligands = L and 1 = X, X could be substituted for Y

       ? ML5X -> ML5Y
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48
Q

What are 2 types of substitution reactions that can occur?

A
  • green: 2 separate steps where the intermediate ML₅ is formed and Y is added in second step
    SN1
  • blue: 1 step where XY coexist in a transition state
    SN2
49
Q

What does the energy profile look like for green (2 step) substitution reactions?

A 
2 peaks (transition states) in energy between reacs and products
trough between them = intermediate

X leaving as Y arriving

50
Q

What does the energy profile look like for blue (1 step) substitution reactions?

A

X leaves at same time Y arrives

1 peak/ transition state

51
Q

What is the most common example of a substitution reaction?

A

hydrolysis - Y ligand that replaces X is H₂O molecule

52
Q

in substitution reac, what is name of process occuring? (common when X=halogen)

A

acquation = hydrolisis

53
Q

Write a general addition reaction with M and L as the reactants

A

M + L → ML

54
Q

Write a general elimination reaction with ML₂ as the reactant

A

ML₂ → ML + L

55
Q

Write a general oxidative/reductive reaction with Y-ML₄-X as the reactant

A

aim of reaction is to bring X and Y close enough to they generate X-Y (M used as template)

Y-ML₄-X -> ML4 + X-Y

56
Q

Write the 2 equations summarising the changes in oxidation state between superoxide dismutase, oxygen and hydrogen in the catalysis of hydrogen peroxide

A

Mn³⁺+O₂⁻ → Mn²⁺+O₂

Mn²⁺+O₂⁻+2H⁺→Mn³⁺+H₂O₂

57
Q

3 considerations in M and L addition, elimination, oxi/red addition
reactions.

A

changes in oxi state
changes in geometry
charge of ligands

58
Q

Superoxide dismutase catalysis to hydrogen peroxide mechanism

A
  • Mn centre begins as +3, then goes to +2
  • Intermediate then can be oxidised back to +3 to complete catalytic circle
  • Mn at first has 5 ligands bound
  • Coordination number changes to 6, 6 ligands, octahedral shape
  • Then after loss of O₂, becomes pentacoordinated (to only 5 atoms)
59
Q

Mechanism of carbonic acid formation from carbonic anhydrase as catalytic enzyme

A
  • Tetrahedral to start with - what ligand is in top of zinc?
  • Water in first, OH- in second, then O- in final
  • Metal centre although doesn’t change its oxidation state, does change ligand in position at top
60
Q

What are 4 analytical techniques we can use to characterise metalloproteins?

A

UV-Vis
MS
EPR (instead of NMR)
RAMAN (instead of IR)

61
Q

Why can we use UV-Vis to characterise metalloproteins?

A

electrons can jump between different energy levels/orbitals

62
Q

What are the 3 types of electron jumps that can occur in metalloproteins?

A

1) intra-ligand where electrons start and end in ligand
2) metal-ligand/ligand-metal where electrons start in ligand, jump to higher energy state in metal orbital or vice versa
3) metal d-d bands where electrons can jump between occupied and unoccupied d-orbitals

63
Q

e- moving up or down orbital in M-L and L-M charge transfer in UV-Vis?

A

M-L: down

L-M: up

64
Q

what do metal d-d bands depend on? in UV-Vis

A

orbital e.g. d d-d jump orbs

characteristic of each metal

65
Q

How does the absorbance and wavelength of different electron jumps look like on a UV-vis spectra?

A

absorbance/wavelength nm

IL then ML and LM then d-d

66
Q

UV-Vis can only be done if you have….

A

chromophore

BUT metals most often solution coloured by d-d transition bands

67
Q

What type of electron jumps generate coloured spectra on a UV-vis spectrum?

A

d-d bands

68
Q

What about metals gives them a distinctive MS pattern?

A

the metal’s isotopes: the height of the signals of intensity of peaks next to them gives an indication of the number of isotopes

69
Q

What does EPR stand for?

A

electronic paramagnetic resonance

70
Q

What analytical technique does EPR correspond with?

A

NMR

71
Q

How do EPR and NMR compare?

A

NMR:

  • nuclei w spin can align in favour of magnetic field, reducing/inc its energy
  • this difference in energy is measured in relation to time

EPR:

  • instead of nuclei, unpaired e- can align with/against field
  • this difference in energy corresponding to time creates an EPR spectra
72
Q

Why are EPRs easier to read for metalloproteins than NMRs?

A
  • NMR has too many overlapping signals (hard read)

- EPR only has 2 signals generated by Fe atom, allowing differentiation between alpha and beta subunit

73
Q

Which analytical technique does RAMAN correspond with?

A

IR

74
Q

How do RAMAN and IR compare?

A

IR:

  • stretching/bending/ movement of bonds/atoms generates polar changes
  • generates stretched signals seen in red spectra

RAMAN:

  • no changes in dipolar moments but atoms still making same usual movements as in IR
  • lower number of signals
75
Q

In NMR, what part of a molecule with a metal centre will produce the signals?

A

the ligands (¹H-NMR and ¹³C-NMR)

76
Q

What is required in a molecule with a metal centre for EPR to be used on it?

A

unpaired electrons !!! odd num

77
Q

What can the data obtained from an EPR allow for determination of?

A

oxidation state,

nature of ligands directly bound to metal centre

78
Q

Is fragmentation in MS for molecules with metal centres any different?

A

molecule will fragment as usual, the fragments that still contain the metal will show the isotope pattern characteristic of that metal

79
Q

How do RAMAN spectra normally compare to IR spectra in terms of signals?

A

normally have less than IR

80
Q

What are the 3 indications of lithium carbonate?

A
  • acute treatment of mania
  • prophylaxis in bipolar disorder
  • antidepressant augmentation in treatment of refractory recurrent depression
81
Q

How does lithium carbonate work?

A

selectively interferes with the inositol lipid cycle and relies on its similarities to Na/K/Ca/Mg, occupying their sites in several critical neuronal enz and NT receptors…

82
Q

What is therapeutic range of lithium carbonate?

A

narrow: 0.8-1.2mmol/L

therefore monitor levels

83
Q

How do we monitor lithium plasma levels?

A

atomic spectroscopy (as this a salt, not a metal centre surrounded by ligands)

  • signals are thin and don’t overlap with other signals
  • intensity relates to concentration
  • can use either absorption (find how much there is) or emission spectra (specific to each metal)

2 signals/sticks: absorption, emission

84
Q

What roles do metals place in CT and MRI scanning? Name examples for eacg

A

they act as contrast agents:

  • CT scan: tomographic images, X-ray based; iodine, barium, gallium based
  • MRI: NMR based technique mapping mostly water and fat; usually gallium based
85
Q

Describe the structure of gadolinium and its medical role

A
  • contrast agent for CT and MRI: allows for better diagnosis due to better image quality
  • 3 N ligand bands
  • 5 Os bound + additional O from addition of water molecule
  • can accept many ligands and has a high coordination sphere
86
Q

What arthritis treatment are gold based?

  • oral
  • IM
A
  • auranofin: has 2 ligands in linear shape: one is S, other is P
  • IM injection is myocrisin
87
Q

What is the Lipinski rule of 5?

A
  • no more than 5 HBDs
  • no more than 10 HBAs
  • molecular mass <500 Da
  • LogP not greater than 5
88
Q

Does auranofin and myocrisin comply with Lipinski’s rule of 5? What does this say about metal medicines’ compliance with the rule?

A
  • only myocrisin complies
  • metal centres ar every heavy meaning the MW tends to be high, breaking Lipinski’s rule
  • the logP changes as well due to the metal
89
Q

Auranofin: use and, hows it taken?

A

RA treatment. doesnt reduce pain but reduces inflamm

orally

90
Q

pharmacokinetics of auranofin?

A 
peak plasma time: 2 hrs
peak plasma conc: 0.025mcg/ml
onset of effects= 3-6mon
plasma half life=21-31 days
protein bound: 60% (mostly albumin)
excretion: urine. feces (after 55-80 days)
91
Q

how is auranofin metabolised?

A

phase 1: de-acetylation

92
Q

auranofin mechanism of action

A

inhib of red/oxi (redox) enzymes such as TrxR.

also appears to induce heme oxygenase 1(HO-1) mRNA- an inducible heme-degrading enz w anti-inflamm properties

93
Q

What are the 3 types of treatment available for cancer?

A
  • surgery
  • radiotherapy
  • chemotherapy
94
Q

In the selection of drugs used for cancer chemotherapy, what is the feature of the 1 common drug used?

A
  • it’s metal based (platinum - Pt)

- tends to be cisplatin

95
Q

50% of all chemotherapeutic regimes use what-based drugs?

A

platinum-based drugs

96
Q

What are 4 platinum-based drug examples?

A
  • cisplatin (original)
  • carboplatin
  • oxaliplatin
  • nedaplatin
97
Q

When developing an anticancer agent, two drug properties need to be measured. What are these?

A
  • the cytotoxicity of a drug
  • the drug uptake (important to know how much is getting into patient cells, can be determined using atomic spectroscopy)
98
Q

size of cisplatin and what 2 different ligands surround it?

A

small

NH₃ and Cl

99
Q

How is cisplatin synthesised from PtCl₄?

A
  • Cl atoms substituted by iodine atoms using excess KI
  • then 2 of the I atoms substituted by NH₃ atoms… intermediate
  • I-Pt bonds are hydrolysed and Cl atoms are added in place
100
Q

Which of cisplatin’s ligands have the key role in its mechanism of action? What does it do? Why is stereochemistry also important?

A
  • Cl binds to the N residues on a specific side
  • ## stereochemistry is important to ensure that it can bind both N residues, hence why transplatin is not cytotoxicCisplatin binds to DNA- platin both at same time
    can have Cl- Pt- Cl
101
Q

Why is cisplatin normally prepared in saline (NaCl) and administered by IV?

A
  • ensure we have enough Cl conc to keep eqm from being shifted + keeps molecule intact
  • once in blood, there’s enough Cl to prevent hydrolysis
  • if wasn’t admin with enough NaCl and was given hydrolysed, the non-DNA-proteins in the cell cytosol would bind it and deactivate it
102
Q

How does cisplatin enter cancer cells?

A

via a CTR1 transporter

responsible for 2/3 of total uptake

103
Q

After entering a cancer cell through the respective transporter, what happens to cisplatin?

A
  • begins to hydrolyse, losing both Cl atoms
  • this is due to the Cl conc dropping between the plasma and cytoplasm
  • this leaves the Pt in the nuclei
104
Q

Describe the mechanism of action of cisplatin (how it enters the cancer cell, how and what atoms are lost, what’s substituted for what from DNA)

A
  • enters cell via CTR1 transporter
  • hydrolysed due to Cl conc dropping from plasma to cytoplasm, leading to only Pt remaining and going on to nuclei
  • Cl atoms replace H₂O in hydrolysis, being substituted with N from DNA (hence why the stereochemistry is important)

where Cl lost, binds to DNA w 2 hands

105
Q

After being hydrolysed, what else could happen to cisplatin preventing it from carrying out its mechanism of action? (2)

A

could be:

  • kicked out via ATP channels: ATP7A/7B
  • conjugated with glutathione, where MRP2 will recognise its tag
106
Q

What are the two types of mechanisms of resistance that cancer cells have towards cisplatin?

A
  • inherent

- acquired

107
Q

What is meant by a tumour having inherent resistance?

A
  • it lacked sensitivity to a given drug from the start

- therefore doesn’t respond to treatment

108
Q

What is meant by a tumour having acquired resistance?

A

tumour originally responded to treatment, but effect lessens or stops entirely after time

  • due to development of cellular detoxification mechanisms such as an increased efflux, decreased influx and enhanced DNA repair
109
Q

How do cancer cells develop increased efflux?

A

generates higher glutathione levels that can bind cisplatin and export it through transporters

110
Q

How do cancer cells develop decreased influx?

A

downregulates things like CTR1 which transports cisplatin back in = less available to bind to DNA

111
Q

What do we do in terms of treatment when a cancer cell has all 3 forms of acquired resistance?

A

give a different drug

112
Q

How are carboplatin, oxaliplatin and nedaplatin better than cisplatin?

A
  • instead of 2 Cl ligands, 2 O ligands are used meaning hydrolysis is slower giving the drug a longer time to reach the nuclei and exert its anticancer effect
  • these all however also have a different side-effect, PK and hence administration profile
113
Q

How is oxaliplatin better than cisplatin?

A
  • instead of 2 NH₃ ligands, 2 NH₂ groups are linked to a ring
  • this causes a different type of DNA damage
  • as a result those cells with acquired resistance (that can only repair damages caused by cisplatin) are unable to repair DNA
114
Q

What are the 3 unwanted side-effects of platinum anti-cancer drugs?

A
  • nephrotoxicity
  • hepatic malfunction
  • ototoxicity
115
Q

A new drug called FM190 is being trialled for cancer. How does it work?

A
  • when shined on with light in a given wavelength, it is activated
  • Pt centre ends up adding directly to DNA, causing direct damage unlike cisplatin
  • due to its light activation, it can be non-toxic and have less side-effects
116
Q

A new drug called BBR3464 is being trialled for cancer. How does it work?

A
  • 3 Pt containing complexes are grouped together
  • this is so that the cell would intake 3 units
  • therefore if some hydrolysed, at least 1 unit will be able to make lesions on DNA
117
Q

cisplatin doses usually based on?

A

body surface area range of 20-140mg/m2

118
Q

hows cisplatin administered?

A

single dose, bolus injection/ blood infusion

infusions: reduces saline soln, dextrose and mannitol in IV drip

119
Q

pH of cisplatin?

A

3.5-4.5

C2 (5 decks)

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