CHEM 1660 BETTERLIVINGTHROUGH

CHEMISTRY

PartIIIWonderDrugs_1
Dr.SusanY.LIANG
Email:ytliang@hkbu.edu.hk
Office:FSC702B

LongerLifeExpectancy
Inmanycultures,particularlybeforemodernmedicinewaswidely
available,thecombinationofhighinfantmortality()and
deathsinyoungadulthoodfromaccidents,diseases,epidemics(
,suchastheinfluenzain1918),wars,significantlylowersthe
overalllifeexpectancy.
Oneofthemainfactorsinlongerlifeexpectancyinmodernsociety
wastheintroductionofsyntheticdrugs,especiallyantibiotics.

theinfluenzain1918

FromHerbstoWonderDrugs

QuininefromCinchona tree

Chinesemedicineremedies

Penicillinfrommold
Aspirinfromwillowtree

Aspirin()
Aspirin,alsoknownasacetylsalicylicacid
(ASA,),isasalicylatedrug,
oftenusedasananalgesic()to
relieveminorachesandpains,asan
antipyretic() toreducefever,and
asanantiinflammatory()
medication.Aspirinwasfirstisolatedby
FelixHoffmann,achemistwiththe
GermancompanyBayerin1897.
Aspirin(brandname)

Acetylsalicylicacid(chemicalname)

Greekphysician
Hippocratesprescribes
thebarkandleavesof
thewillowtree(richina
substancecalledsalicin)
torelievepainandfever.

willowtree
Bayerdistributesaspirinpowder
tophysicianstogivetotheir
1899
patients.Aspirinissoonthe
numberonedrugworldwide.

400BC

Aspirin
(brandname)

1897
AGermanchemist
Chemist,FelixHoffmann,at
experimentswithsalicin and BayerinGermany,chemically
createssalicylicacid (SA).
synthesizesastableformof Acetylsalicylicacid
acetylsalicylicacid(ASA)
(chemicalname)
powderthatrelieveshis
father'srheumatism.The
compoundlaterbecomesthe
activeingredientinaspirin.
1832

salicylicacid

SynthesisofAspirin

Featuresofaspirin:
Reducetheacidityandirradianceto
stomachofsalicylicacid
Theacetylgroup (CH3C=O)canbe
cleavedunderslightlybasic()
environment(suchasinintestine,)
andkeepthemedicaleffectiveness
Thefirstsynthetic pharmaceutical,which
changingthepracticeofmedicine

Acetylsalicylicacidasawhite
powder

FatalBacterialInfection
Asmellcutwouldbefatal,ifinfected,
beforethedevelopmentofantibiotic
drug.
Thegreatinfluenzapandemicof1918
1919killedmorethan20million
peopleworldwide.Theinfluenzaitself
wasviral;theactualcauseofdeath
wasusuallyasecondaryinfectionof
50%ofsoldierswoundedduringthe
bacterialpneumonia().
AmericanCivilWardiedofbacterial
Bythe1940sfearofthedreaded
infections
childhoodduoofscarletfever()
anddiphtheria() hadrecededin
countrieswherevaccination()
programswereavailable.

OntheWaytoMagicBullet
PaulEhrlich,aGermandoctor,
proposedatermchemotherapy,
whichwasusingchemicalmolecules,
suchasdyes,tocurediseases.The
firstsuccessfulmagicbulletNumber
606wassalvarsan,whichwasused
totreatsyphilis().

Cellstainingbydye

Number606

salvarsan

Sulfanilamaid theFirstAntibiotic
Prontosil red,areddye,couldnotkill
bacteriainlaboratorybutshowedgood
antibacterialeffectinvivo(forexample
curingbacterialinfectedmice).
Sulfanilamaid (),themetabolite(
)ofprotosil red,isfirstantibiotic.

GerhardDogmak

SulfaDrugs
Thebacteriamistakenlyusesulfanilamaid ()asPABA,
whichsharessimilarchemicalstructure,andfailtosynthesis
folicacid(,B9).
Thosedrugscontainingthisspecificstructure
arecalledSulfadrug().

 InWorldWarI,solderswerelikelydead
frominjury.Oneofthereasonwasthe
infectionofbacteriaandgangrene().
Gasgangreneusuallydevelopedindeep
wounds.
Amputation ()wastheonlytreatment
inthosedays.
DuringWorldWarII,thanksto
antibioticsuchassulfadrugs,
thousandsofinjuredweresafe
fromamputationanddeath

TheMiracleMolecule Penicillin(/)
In1928,AlexanderFlemingwas
checkinghisculturedishofbacteria
andfoundthattherewasacolony
roundmolds.Itindicatedthatmold
wouldgeneratesomematerialsto
inhibitthegrowthofbacteria.
Henamedthismaterialpenicillin,
whichwasfromthemold
Penicillium notatum
()

AlexanderFleming

TimelineofPenicillin
1928,thediscoverybyFleming
1941,purificationandclinical
trialsbyChainandFlorey
1945,TheNobelPrizein
PhysiologyorMedicinewas
awardedtothethreepioneers
1946,confirmationofthe
structure
1945

1957,successfulsynthesis
http://www.youtube.com/watch?v=iXJhu1T3XQk

http://songshuhui.net/archives/76664

 Penicillinhasanoncommonstructure,a
fourmemberring()or-lactam,
whichisthemaincontributortothe
PenicillinG
antibioticeffect.
Thecauseofbacteriadeathissimple lysis ().Thecellwall
()ofbacteriaismadefromalotofpeptidoglycan()
byenzyme.Penicillincanbindtothisenzymeandinhibitthe
formationofcellwall,whichfinallyturnthebacteriadead.

http://www.youtube.com/watch?v=qBdYnRhdWcQ

http://songshuhui.net/archives/15875

PenicillinG

ampicillin

Amoxicillin

AntibioticsAbuse

AntibioticsResistance
"agenuinethreatofhumanityreturning
toanerawheremortalitydueto
commoninfectionsisrife".
Somebacteriaarenowsoresistant
thattheyarevirtuallyuntreatablewith
anyofthecurrentlyavailabledrugs
Superbacteria

https://www.youtube.com/watch?v=6sT5sz7cgBk

http://www.youtube.com/watch?v=zjR6L38yReE

https://www.youtube.com/watch?v=vYwypSLi
aTU

AntibioticResidue
Antibioticresiduesinmeat,milkandeggsduetotheproduction
patternofmodernfoodindustryraisehealthrisksintwoways:
onewhichproducespotentialthreattodirecttoxicityinhuman
secondiswhetherthelowlevelsofantibioticexposurewould
resultinalterationofmicroflora,causediseaseandthepossible
developmentofresistantstrains

https://www.youtube.com/watch?v=djfMg3anuI4&l
ist=PLF20C87E8ABAF78DF

http://v.youku.com/v_show/id_XNDkwMjk0Mjc2.html