Alpha oxidaiton of Phytanic acid
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Human liver homogenate was incubated to study the α-oxidation pathway of phytanic acid. Gas chromatography analysis identified pristanal as the product of the decarboxylation of 2-hydroxyphytanoyl-CoA. Pristanal was converted to pristanic acid in a NAD+-dependent reaction in human liver, demonstrating that pristanal is an intermediate in the production of pristanic acid from phytanoyl-CoA. Deficiencies in α-oxidation enzymes can lead to the accumulation of phytanic acid and cause Refsum's disease.
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ARTEMISININ presentation .pptx
Content:
Introduction
History
Chemistry of artemisinin
Structural activity relationship of artemisinin
Mechanism of action
Drug interactions
Malaria is a very common disease. This probably originated in Africa around 30 million years ago.
In 1600s first treatment to malaria was recorded in Peru where native tribes used bitter bark of cinchona, to reduce the fever and pain.
In 1897 Sir Ronald Ross described female anopheles mosquito as the vector of the disease.
In 1950s the disease rebounded largely due to emergence of parasites resistant to drugs like chloroquine.
In 1967 a plant screening research program code named “Project 523” was set up in China by the People’s liberation army ordered by Mao Zedong at the request of North Vietnamese.
Under able leadership of Dr. Y. Tu more than 2000 herbs preparations were investigated . Out of which 640 herbs were hits.
The turning point came when Sweet wormwood extract showed a promising degree of inhibition in mouse model.
Although the progress was not smooth as the observation was not reproducible in subsequent experiments.
During cultural revolution no clinical trials were performed so Dr. Tu bravely volunteered to the first trials.
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Encouraged by this outcome, she moved on to investigate and isolated the pure compound of Artemisia.
In 1972 a colorless crystalline substance with a mol wgt. of 282 Da, having molecular formula of C15H22O5 was isolated. The molecule was named as Qinghau su (Artemisinin) from the leaves of Sweet wormwood scientifically known as Artemisia annua, family Compositae.
Dr. Y. Tu was awarded with Lasker DeBakey clinical medical research award in 2011 and finally the Nobel Prize in physiology and medicine of artemisinin in 2015.
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Tetracyclic structure with a trioxane ring and a lactone ring.
Trioxane ring contains a peroxide bridge, the active moiety of the molecule.
MOL. FORMULA: C15H22O5; MOL .MASS: 282.332
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Reduction of artemisinin to dihydroartemisinin gives rises to a chiral centre that may ultimately lead to the formation of prodrugs.
Artemisinin is a poorly soluble in oils and water so it is administered through oral, IM or rectal route.
Semi synthetic like artesunate, artemether arteether and hemisuccinate ester were produced because of poor bioavailability and limit of its effectiveness.
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Content:
Introduction
History
Chemistry of artemisinin
Structural activity relationship of artemisinin
Mechanism of action
Drug interactions
Malaria is a very common disease. This probably originated in Africa around 30 million years ago.
In 1600s first treatment to malaria was recorded in Peru where native tribes used bitter bark of cinchona, to reduce the fever and pain.
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In 1950s the disease rebounded largely due to emergence of parasites resistant to drugs like chloroquine.
In 1967 a plant screening research program code named “Project 523” was set up in China by the People’s liberation army ordered by Mao Zedong at the request of North Vietnamese.
Under able leadership of Dr. Y. Tu more than 2000 herbs preparations were investigated . Out of which 640 herbs were hits.
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In Hainan first official trials happened on malaria patients. The patients showed much better result than chloroquine (Test samples).
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In 1972 a colorless crystalline substance with a mol wgt. of 282 Da, having molecular formula of C15H22O5 was isolated. The molecule was named as Qinghau su (Artemisinin) from the leaves of Sweet wormwood scientifically known as Artemisia annua, family Compositae.
Dr. Y. Tu was awarded with Lasker DeBakey clinical medical research award in 2011 and finally the Nobel Prize in physiology and medicine of artemisinin in 2015.
SAR OF ARTEMISININ
Tetracyclic structure with a trioxane ring and a lactone ring.
Trioxane ring contains a peroxide bridge, the active moiety of the molecule.
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Presence of a ‘Trioxane’ moiety which consists of the endoperoxide & doxepin oxygens that is evidently displayed by a simplified version of 3- aryltrioxanes.
Modification of 10th position ‘C’ gives a powerful derivative compared to the original compound.
Reduction of artemisinin to dihydroartemisinin gives rises to a chiral centre that may ultimately lead to the formation of prodrugs.
Artemisinin is a poorly soluble in oils and water so it is administered through oral, IM or rectal route.
Semi synthetic like artesunate, artemether arteether and hemisuccinate ester were produced because of poor bioavailability and limit of its effectiveness.
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DIURETICS
Diuertics are the drugs used to increase the urine output by excretion of Na+ and water from the kidney.
Primary effect: Reduce absorption of sodium and chlorine ions from the filtrate.
Secondary effect: Increased water loss along with the excretion of sodium and chlorine.
CLASSIFICATION
Based on mechanism of action and site of action
Acting on PCT
a. Carbonic anhydrase inhibitor
Acetazolamide
Dorazolamide
Metazolamide
b. Xanthine derivative
Aminophylline
Theophylline
2. Act on loop of Henlee
a. Osmotic Diuretic
Mannitol
Glycerin
Urea
b. Loop diuretic/ High ceiling
Furosemide
Torsemide
Ethacrynic acid
3. Drug acting on DCT
a. Thaizide diuretic
Chlorthiazide
Hydrochlorthiazide
Hydroflumethazide
Bendroflumethazide
Benzthiazide
Cyclopenthiazide
b. Thiazide like diuretic
Chlorthalidone
Indapamide
Metolazine
4. Drugs acting on collecting duct
a. Aldosterone antagonist
Spironolactone
b. Directly acting
Amiloride
Triamterine
Major application of diuretics ;
Used in congestive heart failure
Essential hypertension
Acute and chronic heart failure
Currently used screening methods are based on effect of drug on water and electrolyte metabolism in rats.
SCREENING METHODS
IN VIVO METHODS :
Diuretic activity in rats [LIPSCHITZ TEST]
Saluretic and diuretic activity in dogs
Saluretic activity in rats
Clearance methods
Stop flow technique
Micro puncture technique in rat.
IN VITRO METHODS :
Carbonic anhydrase inhibition in vitro
Patch clamp technique in kidney cells
Isolated perfused kidney
Perfusion of isolated kidney tubules
1. CARBONIC ANHYDRASE INHIBITION IN-VITRO
PURPOSE AND RATIONALE
Carbonic anhydrase is a Zn containing enzyme.
H2CO3 H20+CO2
Inhibition of CARBONIC anhydrase in PCT causes
● Decreased H+ ion formation
● Decreased Na+/H+ antiport
●Increased Na+and HCO3- in lumen
●increased excretion of Na+HCO3-
●Increased production of alkaline urine
PROCEDURE
The analytical method is based on the catalysis of the conversion of CO2 to H2CO3 by the enzyme , with resulting decrease in pH being monitored colorimetrically.
ASSAY
■ CO2 flow rate is adjusted to 30 to 45 ml/min
■ 400 µl phenol red indicator solution
■ 100µ l enzyme.
■ 200 µl H2O or appropriate drug concentration after 3min of equilibriation.
■ 100 µl carbonate/bicarbonate buffer is added.
■ The following parameters are determined in duplicate samples :
Tu = [uncatalysed time]=time for the colour change to occur in the absence of enzyme.
Te =[Catalysed time]=time for the colour change to occur in presence of enzyme.
Tu – Te = enzyme rate
Ti = enzyme rate in the presence of various concentrations of inhibitor.
EVALUATION
Percentage inhibition of carbonic anhydrase is evaluated
% evaluation =1
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DIURETICS
Diuertics are the drugs used to increase the urine output by excretion of Na+ and water from the kidney.
Primary effect: Reduce absorption of sodium and chlorine ions from the filtrate.
Secondary effect: Increased water loss along with the excretion of sodium and chlorine.
CLASSIFICATION
Based on mechanism of action and site of action
Acting on PCT
a. Carbonic anhydrase inhibitor
Acetazolamide
Dorazolamide
Metazolamide
b. Xanthine derivative
Aminophylline
Theophylline
2. Act on loop of Henlee
a. Osmotic Diuretic
Mannitol
Glycerin
Urea
b. Loop diuretic/ High ceiling
Furosemide
Torsemide
Ethacrynic acid
3. Drug acting on DCT
a. Thaizide diuretic
Chlorthiazide
Hydrochlorthiazide
Hydroflumethazide
Bendroflumethazide
Benzthiazide
Cyclopenthiazide
b. Thiazide like diuretic
Chlorthalidone
Indapamide
Metolazine
4. Drugs acting on collecting duct
a. Aldosterone antagonist
Spironolactone
b. Directly acting
Amiloride
Triamterine
Major application of diuretics ;
Used in congestive heart failure
Essential hypertension
Acute and chronic heart failure
Currently used screening methods are based on effect of drug on water and electrolyte metabolism in rats.
SCREENING METHODS
IN VIVO METHODS :
Diuretic activity in rats [LIPSCHITZ TEST]
Saluretic and diuretic activity in dogs
Saluretic activity in rats
Clearance methods
Stop flow technique
Micro puncture technique in rat.
IN VITRO METHODS :
Carbonic anhydrase inhibition in vitro
Patch clamp technique in kidney cells
Isolated perfused kidney
Perfusion of isolated kidney tubules
1. CARBONIC ANHYDRASE INHIBITION IN-VITRO
PURPOSE AND RATIONALE
Carbonic anhydrase is a Zn containing enzyme.
H2CO3 H20+CO2
Inhibition of CARBONIC anhydrase in PCT causes
● Decreased H+ ion formation
● Decreased Na+/H+ antiport
●Increased Na+and HCO3- in lumen
●increased excretion of Na+HCO3-
●Increased production of alkaline urine
PROCEDURE
The analytical method is based on the catalysis of the conversion of CO2 to H2CO3 by the enzyme , with resulting decrease in pH being monitored colorimetrically.
ASSAY
■ CO2 flow rate is adjusted to 30 to 45 ml/min
■ 400 µl phenol red indicator solution
■ 100µ l enzyme.
■ 200 µl H2O or appropriate drug concentration after 3min of equilibriation.
■ 100 µl carbonate/bicarbonate buffer is added.
■ The following parameters are determined in duplicate samples :
Tu = [uncatalysed time]=time for the colour change to occur in the absence of enzyme.
Te =[Catalysed time]=time for the colour change to occur in presence of enzyme.
Tu – Te = enzyme rate
Ti = enzyme rate in the presence of various concentrations of inhibitor.
EVALUATION
Percentage inhibition of carbonic anhydrase is evaluated
% evaluation =1
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Alpha oxidaiton of Phytanic acid
- 1. Resolution of the Phytanic Acid 𝛼-Oxidation pathway: Identification of Pristanal as product of the decarboxylation of 2-Hydroxyphytanoyl-CoA N. M. Verhoeven, D. S. M. Schor, H. J. ten Brink, R. J. A. Wanders, and C. Jakobs Department of Clinical Chemistry, Free University Hospital, Amsterdam, The Netherlands; and Departments of Clinical Chemistry and Pediatrics, University of Amsterdam, Academic Medical Centre, Amsterdam, The Netherlands
- 2. • Phytanic cannot be metabolized by 𝛽-oxidation because of the methyl group on the 3-Carbon. • The product of 𝛼-oxidation is pristanic acid • Phytanoyl-CoA dioxygenase deficiency in 𝛼-oxidation leads to Refsum’s disease. In this study, Pristanal is produced from 2- hydroxyphytanoyl-CoA and undergoes NAD+ dependent oxidation to produce Pristanic acid in human liver is considered.
- 3. Methods • Homogenized human liver was incubation to produce pristanic acid • Each 200 𝜇l of NAD+ was added after 0, 10, 30, 60 and 120 minutes through incubation • Dodecylaldehyde was added as internal standard. • Then they were analyzed by gas chromatography (for pristanal-ethoxime m/z 326 was monitored, for dodecylaldehyde-ethoxime m/z 228 was monitor)
- 4. Mass fragmentogram of a standard solution containing pristanal- ethoxime and dodecylaldehyde-ethoxime as internal standard
- 5. Mass fragmentogram of an extract from the incubation medium of human liver homogenate incubated at t=0
- 6. Mass fragmentogram of an extract from the incubation medium of human liver homogenate incubated at t=100
- 7. When NAD+ is added, pristanal is absent and pristanic acid is present
- 8. 1. Phytanic acid is first catalyzed by phytanoyl- CoA ligase to form Phytanoyl-CoA 2. Phytanoyl-CoA is hydrolyzed by phytanoyl- CoA hydroxylase, in a process using Fe2+, to yield 2- hydroxyphytanoyl-CoA. 3. 2-hydroxyphytanoyl-CoA is cleaved by a lyase type of enzyme to form pristanal and formyl-CoA (in turn later broken down into formate) 4. Pristanal is converted into pristanic acid in a NAD+ dependent reaction 5. Pristanic acid is further metabolised by peroxisomal 𝛽-oxidation.
- 9. Thank you for your attention