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1
Q

What does helodermatine do? Vaso

A

Hypotensive effect

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2
Q

What does dopamine and noradrenalin do?

A

pain and vasodilation (leading to ischemia)

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3
Q

How can DOX generate radicals?

A

NADPH dependent reduction generate semi-quinone radicals. Lead to O2 radicals and H2O2.

Association with iron from ferritin generate OH radicals

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4
Q

Name 4 improvements on DOX

A

Epirubicin - faster elimination by glucuronidation

Idarubicin - Oral administration, increased fat solubility and cellular uptake

Mitoxantrone - very toxic and selective against cancer, use different mechanism

AQ4N - activates in hypoxic cells, target solid tumours.

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5
Q

Name the 11 chemicals in doxorubicin synthesis.

A
  1. CH3CH2COSCOA + HO2CCH2COSCOA 2. 12-deoxyaklanonic acid 3. aklanonic acid/methyl ester 4. aklaviketone 5. aklavinone 6. E-rhodomycinone 7. Rhodomycin D 8a/8b/9a 9b. Carminomycin 10. Daunorubicin 11. Doxorubicin
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6
Q

What does a sting from a honey bee cause?

A

Typically anaphylaxis, high dose lead to vomitting, fever, cramps and hypotension.

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7
Q

What do helokinestatins do? vaso

A

Inhibit bradykinin and its relaxant effect

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8
Q

What does helothermine do? recep.

A

Block ryanodine receptors and calcium receptors, blocking Ca induced Ca release - lethargy, hypothermia and paralysis

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9
Q

What is interesting about gila monster venom?

A

Defensive, from a modified salivery gland and chewing.

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10
Q

What do tachykinins do? What are they?

A

inflammatory, nociceptive

Substance P, Neurokinin A+B

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11
Q

What does secapin do? (Coag.)

A

Plasmin inhibitor, preventing clot degradation.

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12
Q

Which J coupling is important?

A

2-3 = meta

7-8 = ortho

7-9 = axial (sugar)
9-11 = equitorial (sugar)
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13
Q

What are the topics of the cell receptor paragraph?

A

Helothermine (GM)

Mipartoxin (Mm-8) (CS)

Micrurotoxins (MmTX1 and MmTX2) (CS)

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14
Q

What does helothermine do? ion

A

Affect K channels, affect Ia current and action potential

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15
Q

What are the topics of the ion channel block paragraph?

A

Mast cell degranuating peptide (HB)
Tertiapin (HB)
Helothermine (GM)

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16
Q

What are the 5 steps of topoisomerase II enzymes?

A
  1. Bind helix and ATP
  2. ATP hydrolysis and double-stranded cleavage.
  3. Second helix enter in-gate, go through cleavage, exit out-gate.
  4. Re-ligase
  5. Release ADP and reset the system
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17
Q

What does polarimetry tell us?

A

That there is a chiral centre

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18
Q

How does DOX enter the nucleus?

A
  1. Diffuse into cells
  2. Associate with proteasome
  3. translocate to nucleus
  4. Dissociate and intercalate with DNA
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19
Q

What are the topics if allergic paragraph?

A

Icarapin
Vitellogenin
Procamine
Royal jelly proteins
Histamine

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20
Q

Which UV peaks are important?

A

254 benzene

300 phenol, with shift in base

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21
Q

What natural products are of use from HB?

A

Adolapin - pain killer

Melittin - anti-arthritis/inflammatory

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22
Q

What does mast cell degranulating peptide do? Ion

A

Block voltage-gated ionic channels on mast cells, affecting histamine release

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23
Q

Give the structure of idarubicin.

A

Removal of MeO on first ring

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24
Q

What does Horridum toxin do? (Spread)

A

Haemorrhagic

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25
Q

What does a bite from a gila monster cause?

A

Vomitting, hypotension and chest/abdo pain.

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26
Q

Give the enzymes in order for doxorubicin synthesis.

A
  1. dps ABCD EFGH 2. dnrG/dnrC 3. dnrD 4. dnrE 5. dnrF 6. dnmS + TDP-L-daunosamine 7. dnrP 8. doxA 9. dnrK 10. doxA
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27
Q

What are the topics of the small molecule paragraph?

A

Serotonin (GM HB)

Dopamine/Noradrenalin (HB)

Histamine (HB)

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28
Q

What does C-type lectin do? (Coag.)

A

Inhibit prothrombinase cleavage, prevent fibrinogen cleavage

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29
Q

What does PLA2 do? (Spread.)

A

Release arachidonic acid, inflammation and vasodilation.

CS: myotoxic capability, less anticoagulant.

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30
Q

What do the DEPT shifts show with C NMR?

A

C = none none

CH = up up

CH2 = Down none

CH3 = Up none

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31
Q

What natural products are of use from CS?

A

Anti-coagulant

32
Q

If Streptomycin is grown on 1-14C-propionate or methyl-[14C]-methionine, which carbons are radiolabelled?

A

The 4th ring hydroxyl carbon.

33
Q

What is the nmr peaks for an anomeric carbon/hydrogen?

A

C = 100

H = 4.9

34
Q

What is the proteins and what percent make up CS venom?

A

60% - 3FT

30% - PLA2

35
Q

If Streptomycin is grown on 1-[13C]acetate, which carbons are radiolabelled?

A

The carbon linking the sugar, then every other one. Not including the 4th ring hydroxyl carbon.

36
Q

What does adolapin do? Inflam

A

Anti-inflammatory, inhibit cyclooxygenase

37
Q

How does DOX lead to double-stranded breaks?

A

Stabilities transition state of Topoisomerase II.

38
Q

What does helofensin do? Resp

A

inhibit direct electrical stimulation of isolated mouse hemi-draphragm

39
Q

What does the coral snake venom cause?

A

bilateral ptsosis and respiratory failure

40
Q

What does melittin do?

A

Haemorrhagic and increase cellular permeability (cell membrane lytic) by associating with bilayer and inhibiting PKC

41
Q

Give the structure of Mitoxantrone.

42
Q

Give the structure of AQ4N.

43
Q

What is the structure of helothermine?

A

16 cysteine residues

Cysteine rich secretory protein (CRISP)

44
Q

What does cardiopep do?

A

Beta-adrenergic and anti-arrhythmic effect

45
Q

What does Mast Cell Degranulating peptide do?

A

Inflammatory at low concentration

Anti-inflammatory at high concentration

46
Q

What does Gilatoxin do? (Coag.)

A

Degrade fibrinogen without producing clots

47
Q

What is mass spec peaks are important?

A

Odd number = odd number of nitrogens

48
Q

What is in the spreading factors paragraph?

A

Hyaluronidase (all)

L-AAO (CS and GM)

Horridum toxin (GM)

Melittin (HB)

49
Q

What does hyaluronidase do? (Spread)

A

Cleave hyaluronic acid, which is involved in repair, leading to inflammatory precursors and vasodilation.

50
Q

If Streptomycin is grown on 2-[13C]acetate, which carbons are radiolabelled?

A

The carbon NOT linking the sugar, then every other one. Not including the 4th ring hydroxyl carbon.

51
Q

What are the paragraph topics? (In order)

A

Introduction, coagulation, spreading factors, inflammation and allergy, ion channels, cell receptors, small signalling, vasodilators, respiratory system and conclusion.

52
Q

Why are cardiomyocytes more susceptible to DOX damage?

A

Cardiomyocytes have a higher reliance on oxidative substrate mechanisms.

53
Q

What are the topics of vasodilation paragraph?

A

Helokinestatins (GM)

Exendin-1/2/3/4 (GM)

Helodermatine (GM)

Tachykinins (HB)
Compound 48/80 (HB)

54
Q

If Streptomycin is grown on 14O labelled acetate, which oxygebs are radiolabelled?

A

The bottom five

55
Q

What does Serotonin do?

A

gut movement and happiness

Pain and convulsions of muscle

56
Q

What does melittlin do? Inflam

A

Anti-inflammatory

57
Q

What do exendins do? Vaso

A

Act like vasoactive intestinal peptides and increase cellular cAMP lead to hypotensive effect

58
Q

What is the strucure of 12-deoxyaklanonic acid?

59
Q

What natural products are of use from GM?

A

Exendin-4 led to Exenatide (GLP mimic)

60
Q

What are the 10 steps of doxorubicin synthesis?

A
  1. Form first compound 2. Top ketone 3. Make 4th ring (alcohol) 4. +Alcohol (3rd ring) 5. Add sugar 6. Remove ester (-me, -CO2H) 7. Add keto (+OH, +=O) 8. Add ester (1st ring) 9. Add OH (far right)
61
Q

Which proteins are involved in the coagulation paragraph? (Which species)

A

C-type lectin (CS)

Gilatoxin (GM)

Secapin (HB)

PLA2 (All)

62
Q

What do MmTX1/2 do? Recep

A

GABA receptors, increase susceptibility to agonist

Reduced activity -> seizures

63
Q

What does Mm-8 do? recep

A

Affect post-synaptic nicotinic receptors function

Reduced function -> respiratory failure and death

64
Q

What do L-AAOs do? (Spread)

A

Haemorrhagic and anti-coagulant.

65
Q

Which IR peaks are important?

A

Double at 1600 is aromatic

1700 is C=O

3500 is OH

66
Q

What does tertiapin and compoud 48/80 do? Inflam

A

Inflammatory and other roles.

67
Q

What are the topics if inflammatoryparagraph?

A

Melittin
Tachykinins (substance P, neurokin A+B)
Tertiapin
Compound 48/80
Mast cell degranulating peptide
Adolapin

68
Q

What does topoisomerase enzymes facilitate?

A

The unwinding and winding of supercoiled DNA, to allow DNA replication and transcription

69
Q

Give the structure of epirubicin.

A

Inverted hydroxyl on glycone.

70
Q

What is interesting about coral snake venom administration?

A

Cannot retract fangs, only small amount of venom, and bites/chews prey.

71
Q

What are the topics of the respiratory system paragraph?

A

Helofensin (GM)

Cardiopep (HB)

72
Q

What do radicals do?

A

Proton abstraction of DNA

Perioxidate lipids, lead to malondialdehyde-DNA

Lead to AMP-activated protein kinase activation
Leads to p53-induced cell death

73
Q

What does tertiapin do? (Ion)

A

Blocks potassium ion channels:

Calcium activated large conductance K - prolong AP + increase excitability

Inward rectifier K - shorten AP

Both on cardiac cells

74
Q

Why does DOX have dose-limiting cardiotoxicity?

A

Irreversible accumulation of 8-hydroxyguanosine adducts in cardiac mRNA.

75
Q

What does histmine do?

A

Inflammatory mediator

76
Q

What does PLA2 do? (Coag.)

A

Thrombokinase inhibitor

Natural Sciences Bath Final Year (5 decks)

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