Heterocycles Seminar: Purines

Presented by:
-Manuel Andres Marin
-Andrea Aristizabal
Pharmaceutical Chemistry
Teacher: Jorge Emilio Parra
2024
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 PURINE
Purines are molecules of great interest along with pyrimidines because they are constituents of DNA or RNA. Most purines found in
nature have structures such as adenine, guanine and hypoxanthine.

Furthermore, as nucleotides and

nucleosides they act as hormones
and neurotransmitters and are
present in some coenzymes. Some
examples are: adenosine,
guanosine, inosine and ATP.

The xanthine nucleus is found in caffeine and uric acid

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SÍNTESIS DE LOS NUCLEÓTIDOS DE PURINA. (2016, 25
noviembre). Bioquímica
 MAIN USES OF PURINES IN PHARMACEUTICAL AND INDUSTRIAL USES

Purines are structurally flat,

heterocyclic molecules,
formed by the fusion of two
rings: one with six atoms
and the other with five. The
main molecules that include
purines are nucleotides,
which are the building
blocks of nucleic acids.

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Purinas en el ADN. Fuente: Basquetteur, BruceBlaus, CC BY-SA 3.0
PHARMACEUTICAL USES
Purines play a crucial role in
many metabolic and signaling
processes within the
compounds guanosine
monophosphate (GMP) and
adenosine monophosphate
(AMP). Medications called
“xanthine oxidase inhibitors”
(XOIs), such as allopurinol
(Aloprim, Lopurin, Zyloprim)
and febuxostat (Uloric), limit
the amount of uric acid the
body makes. This can lower
the level of uric acid in the
blood and reduce the risk of
gout.

SÍNTESIS DE LOS NUCLEÓTIDOS DE PURINA. (2016, 25 4

noviembre). Bioquímica
 INDUSTRIAL USES
Purines are found in high
concentrations in meat
and meat products,
especially in internal
organs such as the liver
and kidneys. Therefore,
purines are used in the
food industry to improve
the taste of foods.

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cuál es la función de las purinas. (s. f.). https://aleph.org.mx/cual-es-la-funcion-de-las-purina
 ORGANIC REACTIONS FOR THE FORMATION OF PURINES
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The word "purina" (from Latin:pura urina 'pure urine') was coined by the German chemist
Emil Fischer in 1884 when he proposed its structure. It was first synthesized by Fischer in
1899. The starting material for the reactive sequence was uric acid (8), which had been
isolated from kidney stones by Scheele in 1776.
Chloride
of iodide
phosphorus(V) hydrogen Reducing agent

Phosphonium
Salt

2,6,8-tricloropurina 2,6-diiodopurina

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cuál es la función de las purinas. (s. f.). https://aleph.org.mx/cual-es-la-funcion-de-las-purina
 ORGANIC REACTIONS FOR THE FORMATION OF PURINES
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The Traube reaction, also known as the Traube purine synthesis, is a method for synthesizing
purine derivatives from 4-amino-6-hydroxypyrimidine or 4,6-diaminopyrimidine.

sulfide 4-amino-6-diaminopirimidina
Nitrosación of
ammonium formic acid

4,6-diaminopirimidina
chlorocarbon ester
4-nitroso-6-diaminopirimidina

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cuál es la función de las purinas. (s. f.). https://aleph.org.mx/cual-es-la-funcion-de-las-purina
 IMPORTANCE OF PURINES
Structural blocks of nucleic acids: Purines, specifically adenine and guanine, are fundamental
components of nucleic acids, DNA and RNA. Nucleic acids are responsible for storing genetic
information and orchestrating the protein synthesis process.

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cuál es la función de las purinas. (s. f.). https://aleph.org.mx/cual-es-la-funcion-de-las-purina
 IMPORTANCE OF PURINES
Energy storage molecules: Nucleoside triphosphates, particularly ATP (adenosine triphosphate),
are energy-rich molecules. Purines are involved in many processes of cellular metabolism and
also in protein synthesis.

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cuál es la función de las purinas. (s. f.). https://aleph.org.mx/cual-es-la-funcion-de-las-purina
 IMPORTANCE OF PURINES
Neurotransmitters: Some purines act as neurotransmitters, participating in the
transmission of signals in the nervous system.

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cuál es la función de las purinas. (s. f.). https://aleph.org.mx/cual-es-la-funcion-de-las-purina
 IMPORTANCE OF PURINES
Regulation of blood pH and energy production: Purines are necessary for a large
number of biological processes, including cellular respiration, regulation of blood
pH and energy production.

SÍNTESIS DE LOS NUCLEÓTIDOS DE

PURINA. (2016, 25 noviembre). Bioquímica 11
 Purine nucleoside phosphorylase and the enzymatic antioxidant
defense system in breast milk from women with different levels of
arsenic exposure
Autores: Ramón Gaxiola-Robles1,2, Vanessa Labrada-Martagón1 , Oscar Kurt Bitzer-
Quintero3 , Tania ZentenoSavín1 and Lía Celina Méndez-Rodríguez1 .

1 Centro de Investigaciones Biológicas del Noroeste, S.C. Instituto Politécnico Nacional 195, Playa Palo de Santa Rita Sur, La Paz, Baja
California Sur, C.P. 23096. 2 Hospital General de Zona No.1. Instituto Mexicano del Seguro Social. 5 de febrero y Héroes de la Independencia,
Centro, La Paz Baja California Sur, C.P. 23000. 3 Centro de Investigación Biomédica de Occidente (CIBO), Instituto Mexicano del Seguro
Social (IMSS), Sierra Mojada 800, Colonia Independencia, CP: 44340, Guadalajara, Jalisco. México. - Nutr Hosp. 2015;31(5):2289-2296

Fecha de publicación: 10 de marzo 2015

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Gaxiola-Robles et al. (2015)
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Gaxiola-Robles et al. (2015)
 Purine nucleoside phosphorylase

It is an enzyme that in humans is encoded by the NP gene. [2] Catalyzes the

chemical reaction.
purine nucleoside + phosphate ⇌ purine + alpha-D-ribose 1-phosphate
Thus, the two substrates of this enzyme are a purine nucleoside and a
phosphate, while its products are a purine and an alpha-D-ribose 1-phosphate.

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Gaxiola-Robles et al. (2015)
Methods:
Purine nucleoside
phosphorylase (PNP,
Sampling Total arsenic concentration
70% nitric acid (HNO3 ) and 30% hydrogen peroxide (H2 O2 ) EC. 2.4.2.1) activity

DATE: Sampling was

performed between
July and December
2011

NUMBER OF 108
SAMPLES
COLLECTED:

POPULATION: Mexican Women

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Antioxidant enzyme activity
Glutathione S-transferase (GST, EC
2.5.1.18) activity
In a cuvette, working solution (sodium
carbonate 50 mM; xanthine 0.1 mM; nitro
blue tetrazolium (NBT) 0.025 mM;
ethylenediaminetetraacetic acid (EDTA) 0.1
mM), XO (1 U mL-1 in 2 M ammonium
sulfate), and the breast milk sample were
mixed. The change in absorbance was
registered every 30 s during 5 min at 560
nm.
GST activity was determined by measuring
the change in absorbance caused by the
synthesis of thioether glutathione
dinitrobenzene complex as a product of the
reaction between GSH and 1-chloro-2,4-
dinitrobenzene (CDNB)28. Working solution
(0.1 M phosphate buffer, 10 mM GSH, 60
mM EDTA), CDNB (10 mM) and sample
were mixed in a cuvette. Change in
absorbance was measured every 30 s
during 6 min at 340 nm. Enzyme activity
was expressed in units mg-1 of protein.
One unit of GST activity is defined as the
amount of enzyme that catalyzes the
production of 1 µmol of CDNB per min.
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 Association between PNP activity and covariates.
Results:
The GLM contributes to explaining the variability of PNP activity in breast milk in association
Data grouped by purine nucleoside phosphorylase (PNP) with [TA], antioxidant enzyme activities and GSH concentration. The analysis started with the
maximum model with k=7 (k= number of parameters), PNP activity (intercept), SOD, GST,
activity level GPx, GR and CAT activities, GSH concentration and [TA] (β=-3.302 Standard error = 0.4703,
p<0.01, scale 1.767, residual deviation = 114.560), where 6 of the 7 parameters were not
In 30 of the 52 (58%) breast milk samples analyzed, PNP activity levels significant. The simplification of the initial model was achieved by using
were <0.003 U mg-1 protein. Data for SOD, CAT, GST, GPx and GR
activities, GSH concentration and [TA], grouped according to PNP activity,
are summarized in Table I. SOD and GPx activities were lower (85.7%
and 80.0%, respectively p<0.01) in the group with PNP activity >0.003 U
mg-1 of protein than in the group with PNP activity <0.003 U mg-1 of
protein. The activities of GST, GR and CAT were 50.0%, 50.0% and
44.3% less, respectively, in the group with PNP activity >0.003 U mg-1 of
protein than in the group with PNP activity <0.003 U mg-1 protein
(p>0.05). GSH levels were 2.1% higher in the PNP activity >0.003 U mg-1
protein than in the PNP activity <0.003 U mg-1 protein group (p>0.05).
[TAs] was 11500% higher in the group with PNP activity >0.003 U mg-1
protein than in the group with PNP activity <0.003 U mg-1 protein;
however, this difference was not statistically significant (p=0.32).

Data are shown as median. P10-P90, 10th and 90th percentile;*compared group; **statistical significance using the
Mann-Whitney test; PNP, purine nucleoside phosphorylase activity U mg-1 protein; n.d., not detectable; SOD,
superoxide dismutase activity, protein U mg-1; GSH, glutathione concentration, nmol mg-1 protein; GST, glutathione
S-transferase activity, protein U mg-1; GPx, glutathione peroxidase activity, mU mg-1 protein; GR, glutathione 18
reductase activity, mU mg-1 protein; CAT, catalase activity, U mg-1 protein; [TAs], total arsenic concentration, µg L-1.
Gaxiola-Robles et al. (2015)
THANK YOU

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 BIBLIOGRAPHY

1. https://www.lifeder.com/purinas/
2. https://academia-lab.com/enciclopedia/purina/
3. https://aleph.org.mx/que-son-las-purinas-y-para-que-sirven
4. PURINA NUCLEÓSIDO FOSFORILASA Y EL SISTEMA DE DEFENSA ANTIOXIDANTE ENZIMÁTICO EN
LECHE MATERNA DE MUJERES CON DIFERENTES NIVELES DE EXPOSICIÓN A ARSÉNICO. articulo
cientifico. Nutr Hosp. 2015;31(5):2289-2296

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