Presentazione per inglese B2

TURMERIC

Curcumin is the main biological

Curcuma

active component of longa L.

This plant has been used since

ancient time for medical and

food purposes, for example in

Ayurvedic medicine

Turmeric is a good antioxidant,

anti-inflammatory, chemo-

protective, chemo-therapeutic

and antibacterial

Turmeric rhizome and powder

Turmeric flower

CURCUMIN

H Curcumin has high lipophilicity, this feature



N

O O

N allow the molecule to overcome critical

CH 3 barrier, like the blood-brain (BBB) one.

O CH

O 3 Is stable in a pH range of 2 – 5,



H

O OH decomposes slowly at pH<2 and rapidly at

OH alkaline pH

H O O O

CH H C

3 3 Pirazol-derivates of curcumin are more



Curcumin molecule

Pirazol-derivate of curcumin stable and bio-available than curcumin

itself

It can protect the brain from the formation

 of β-amyloid fibrils, that are the main

cause of Alzheimer disease, or it can bond

those fibrils selectively once they are

formed

This latter property is used in the design of

 radiopharmaceuticals for the diagnosis of

Alzheimer disease

ALZHEIMER

DISEASE

Alzheimer disease is a

 neurodegenerative disease

that affect the 25% of the

population between 80 and 85

years

It is associated with the

 deposit of β-amyloid fibrils on

the external part of neurons

and neurofibrillary tangles

(Tau protein’s insoluble

polymers) in the internal part

Dr. Alzheimer RADIO-

PHARMACEUTI

CALS

Radiopharmaceuticals

 are formed by:

- Radio-metal

- Chelating agent

- Linker

- Targeting vector

The targeting vector

 present high affinity with

a particular biological

tissue (target) and allow

the drug to selectively

concentrate in one area

of the body

Detecting the radio-

 metal is possible to

verify presence of the

target

SINTHESIS

Aim: sinthesis of new targeting vectors and linker derived from

 curcumin

REACTION PATH

In the first part, the linker is bound to the curcumin molecule via a

 nucleophilic substitution with SN2 mechanism

In the second part, the idrazine attack from the back a carbonyl

 portion of the molecule in acidic environment, and the intermediate

product cyclize to form the pirazol-derivate

The product is purified with chromatography and characterized with

 H-NMR and MS

1 H-NMR

1

CHARACTERIZATION

H1 H2 H3 H4 H5 H7 H8

6,54 6,80 6,99 7,04 3,82 6,71 6,90

Chemical shift of the protons (in ppm) relative to the analisys of the H-NMR spectra of the

1

pirazol-derivate of curcumin

H-NMR spectra of curcumin

1