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Medicinal Chemistry: Technetium and Nuclear Medicine. ICIS - CNR - Padova, Italy. Group 7 metals relevant to Nuclear Medicine - 1. 4. 5. 6. 7. 8. 9. 10. 11. Ti. V. Cr. Mn. Fe. Co. Ni. Cu. 1st row. Ag. Zr. Nb. Tc. Pd. Rh. Ru. Mo. 2nd row. Ir. Hf. Ta. W. Re. Os. Pt.

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Medicinal chemistry technetium and nuclear medicine l.jpg
Medicinal Chemistry:Technetium and Nuclear Medicine

ICIS - CNR - Padova, Italy


Group 7 metals relevant to nuclear medicine 1 l.jpg
Group 7 metals relevant to Nuclear Medicine - 1

4

5

6

7

8

9

10

11

Ti

V

Cr

Mn

Fe

Co

Ni

Cu

1st row

Ag

Zr

Nb

Tc

Pd

Rh

Ru

Mo

2nd row

Ir

Hf

Ta

W

Re

Os

Pt

Au

3rd row

transition metals


Group 7 metals relevant to nuclear medicine 2 l.jpg

  • radiodiagnosis

  • 99mTct1/2 = 6.0 h

  • Eg = 142 keV

  • inorganic chemistry

  • 99Tct1/2 = 2.12x105 y

  • Eb- = 292 keV

  • inorganic chemistry

  • ’cold’ 185/187Re

Group 7 metals relevant to Nuclear Medicine - 2


Inorganic chemistry vs nuclear medicine l.jpg
Inorganic Chemistry vs Nuclear Medicine

  • inorganic chemistry:10-3 – 10-5 M (millimolar conc)

  • Conventional physico-chemical characterization

  • NMR, IR, UV-vis spectroscopies

  • Mass spectrometry (EI, ESI)

  • X-ray crystal structure determination

  • TLC & HPLC chromatography

  • nuclear medicine:10-7 – 10-9 M (micro/nanomolar conc)

  • Radiometric characterization

  • TLC & HPLC chromatography


The 99 mo 99m tc generator l.jpg
The 99Mo/99mTc generator

99Mo

t1/2 = 66.7 h;

Eb- = 1.37 MeV

99mTc

t1/2 = 6 h;

Eg- = 142 KeV

99Tc


The bifunctional approach in mixed nitrido tc heterocomplexes l.jpg
The bifunctional approach in mixed nitrido-Tc heterocomplexes

O

H

H

N

N

N

P

S

O

Tc

P

O

N

S

N

H

O

MW = 913


The substitution inert tc n pxp synthon l.jpg

N

N

Tc

Tc

P

P

Cl

Y

Cl

P

P

Z

X

X

The substitution-inert [Tc(N)(PXP] synthon

Bolzati et al.,J. Am. Chem. Soc. 124, 2002, 11468


Slide19 l.jpg

Crystal structure of [Re(N)(dedc)(pnp2)]+

  • pseudo-octahedron

  • cis-P co-ordination

  • P(1)-Re-P(2) = 101.2(1)°

  • trans-N co-ordination

  • N(1)-Re-N(2) = 164.5(5)°

  • Re-N(2) = 2.73(1) Å


From aryl to alkyl diphosphines l.jpg

S

P

P

N

N

S

O

dedc

pnp2

O

O

O

P

P

S

O

N

O

N

S

O

O

dbodc

pnp5

From aryl- to alkyl-diphosphines


Esi ms of 99 tc dbodc pnp5 l.jpg

846.6

100

95

90

85

[Tc(N)Cl2(PPh3)2]

80

75

i) pnp5

ii) dbodc

DCM

70

65

60

55

Relative Abundance

yellow oil

50

45

40

35

30

25

20

848.6

15

10

640.6

527.4

849.5

5

844.7

279.4

552.8

306.5

641.6

371.4

862.5

413.5

788.5

185.3

130.6

961.8

1049.9

1139.0

1183.9

1314.2

1401.2

1454.4

0

100

200

300

400

500

600

700

800

900

1000

1100

1200

1300

1400

1500

m/z

ESI - MS of [99Tc(dbodc)(pnp5)]+

M+

E. Marotta et al, RCM, 2003, submitted


Collisional experiments on 99 tc n bdodc pnp5 ms 2 l.jpg

640.3

100

95

90

85

80

75

70

65

641.3

60

55

Relative Abundance

50

45

40

35

30

847.4

25

668.2

20

846.4

15

669.3

553.2

10

569.2

527.2

405.1

348.0

582.3

608.3

5

813.3

406.1

844.3

297.1

775.3

276.0

318.0

452.3

496.1

758.2

714.5

868.9

0

250

300

350

400

450

500

550

600

650

700

750

800

850

900

950

1000

m/z

Collisional experiments on [99Tc(N)(bdodc)(pnp5)]+ -MS2

-

-


Collisional experiments on 99 tc n bdodc pnp5 ms 3 l.jpg

594.2

100

95

90

85

80

75

403.0

70

65

60

55

Relative Abundance

50

45

40

35

30

25

20

640.2

15

568.2

10

435.0

608.2

401.1

527.0

331.0

5

493.1

566.1

284.7

247.8

462.2

227.2

865.4

640.9

914.8

0

200

250

300

350

400

450

500

550

600

650

700

750

800

850

900

950

1000

m/z

Collisional experiments on [99Tc(N)(bdodc)(pnp5)]+ -MS3

-

-

-



1 h nmr of 99 tc n dbodc pnp5 l.jpg

99Tc-complex

1H NMR of [99Tc(N)(dbodc)(pnp5)]+

O

S

N

S

O

dbodc

O

O

P

P

O

N

O

O

pnp5


1 h 1 h cosy 45 of 99g tc n dbodc pnp5 l.jpg

dbodc

N-CH2-CH2-O-

dbodc

-O-CH2-CH3

pnp5

N-CH2-CH2-O-

pnp5

-O-CH2-CH3

1H-1H COSY-45 of [99gTc(N)(dbodc)(pnp5)]+


31 p and 13 c nmr of 99 tc n dbodc pnp5 l.jpg

-O-CH3

-C-CH3

various CH2

31P and 13C NMR of [99Tc(N)(dbodc)(pnp5)]+

30.2 ppm

impurity

oxidized pnp5


1 h 13 c hmqc of 99 tc n dbodc pnp5 l.jpg

C-CH3

C-C and P-C

N-C region

O-CH3

O-C region

1H - 13C HMQC of [99Tc(N)(dbodc)(PNP5)]+

+

O

O

N

O

O

P

S

N

Tc

O

O

S

P

N

O

P-…CH2-O-


Nitrido 99m tc v hetero complexes heart uptake in rats l.jpg

99mTc-DBODC5

99mTc-Cardiolite

99mTc-Myoview

Nitrido-99mTc(V) hetero-complexes:heart uptake in rats

6

5

%ID/g

4

3

2

1

2

5

10

20

30

60

120

time (min)

A. Boschi et al.,J. Nucl. Med. 2003, in press


Nitrido 99m tc v hetero complexes heart liver ratio in rats l.jpg

35

99mTc-DBODC5

30

99mTc-Cardiolite

25

h/l

99mTc-Myoview

20

15

10

5

2

5

10

20

30

60

120

Nitrido-99mTc(V) hetero-complexes:heart/liver ratio in rats

time (min)



Nitrido 99m tc v hetero complexes micro spet analysis l.jpg

Cardiolite®

by Dupont

NOEt

by Cis-Schering

Tc(N)DBODC5

by Nihon Medi-Physics

Nitrido-99mTc(V) hetero-complexes:micro-SPET analysis