Ultrasmall particle of iron oxide - RGD peptidomimetic conjugate: synthesis and characterization

[en] Ultrasmall particles of iron oxide (USPIOs) coated with 3,3'-bis(phosphonate)propionic acid were covalently coupled to a home-made Arg-Gly-Asp (RGD) peptidomimetic molecule via a short oligoethyleneglycol (OEG) spacer. The conjugation rate was measured by X-ray photoelectron spectroscopy (XPS). The particle size and magnetic characteristics were kept. Our novel conjugate targeted efficiently Jurkat cells (increase of 229% versus the control).

Research center :

CMMI - Centre de Recherche en Microscopie et Imagerie Médicale

Disciplines :

Radiology, nuclear medicine & imaging
Chemistry

Author, co-author :

Rerat, Vincent

Laurent, Sophie ; Université de Mons > Faculté de Médecine et de Pharmacie > Chimie générale, organique et biomédicale

Burtea, Carmen ; Université de Mons > Faculté de Médecine et de Pharmacie > Chimie générale, organique et biomédicale

Driesschaert, Benoît

Pourcelle, Vincent

Vander Elst, Luce ; Université de Mons > Faculté de Médecine et de Pharmacie > Chimie générale, organique et biomédicale

Muller, Robert ; Université de Mons > Faculté de Médecine et de Pharmacie > Chimie générale, organique et biomédicale

Marchand-Brynaert, Jacqueline

Language :

English

Title :

Ultrasmall particle of iron oxide - RGD peptidomimetic conjugate: synthesis and characterization

Publication date :

15 March 2010

Journal title :

Bioorganic and Medicinal Chemistry Letters

ISSN :

0960-894X

Publisher :

Elsevier, United Kingdom

Volume :

Issue :

Pages :

1861-1865

Peer reviewed :

Peer Reviewed verified by ORBi

Research unit :

M108 - Chimie générale, organique et biomédicale

Research institute :

R550 - Institut des Sciences et Technologies de la Santé
R100 - Institut des Biosciences

Available on ORBi UMONS :

since 21 December 2010

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Bibliography

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Coupling protocol: USPIO material was received from Guerbet laboratories (Aulnay-sous-Bois, France). The particles feature carboxylated groups on their surface according to Ref. 18. They are suspended in water in order to obtain the [Fe] concentration of 0.407 M. USPIO (1 mL, 0.407 mmol) was introduced in a flask previously washed with 37% HCl, milliQ water, acetone, and ether, and gently stirred with a magnetic bar. Lysine (8.13 × 10-2 mL of a solution of 4.5 mg Lys·HCl in 25 mL milliQ water; 0.0814 mmol) and water soluble carbodiimide (WSC, 54 mg, 0.28 mmol) were successively added, very slowly. The mixture was left under stirring at 20 °C or 40 °C, for 1 h to 6 h (see Table 1). After dialysis against milliQ water (membrane of 12-14,000) during 48 h, the suspension was freeze-dried, and the resulting powder analyzed by XPS (see Supplementary data for the table of results). The so-called blank samples were similarly prepared, but with omitting the carbodiimide. Control samples were similarly prepared but with omitting the lysine. These samples were also analyzed by XPS (see Supplementary data). For the coupling of peptidomimetic 6b, we used USPIO (0.5 mL, 0.203 mmol), a 10-3 M solution of 6b in water-DMSO, 95:5 (4.06 × 10-2 mL) and WSC (27 mg, 0.14 mmol); the mixture was reacted for 2 h at 20 °C and dialyzed during 24 h. For the coupling of GRGDS peptide, we applied the above protocol with a 10-3 M solution of peptide in water.
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Calculation of derivatization rate (%) from XPS data: The simplified atomic formula of USPIO surface derivatized with lysine is: xC3 + yC9N2, considering the native surface (C3) and the modified fraction (C9N2); accordingly x + y = 100. Thus the atomic ratio N/C = 2y/(3x + 9y). For instance, 10% of grafting (y = 10; x = 90) gives the calculated N/C atomic ratio of: N/C = (10 × 2)/[(90 × 3) + (10 × 9)] = 20/(270 + 90) = 0.0555. The percentages of derivatization are deduced from the N/C experimental values. The formula considered for USPIO grafted with 6b and GRGDS are respectively: xC3 + yC44N5F3 and xC3 + yC20N8. Accordingly, for 6b, N/C = 5y/(3x + 44y) and F/C = 3y/(3x + 44y) and for GRGDS, N/C = 8y/(3× + 20y).
Calculation of the number (Nbr) of grafted molecules per particle: Magnetite is considered as a crystalline system with a unit cell volume of 0.592 nm3. The surface of a USPIO particle (sphere with r = 10 nm) and of a magnetite unit cell being respectively 1256 nm2 and 0.71 nm2, the number of unit cell faces displayed on one particle is 1,256/0.71 = 1769. Assuming the presence of 2 iron atoms per unit cell face, we calculate that one particle surface features about 3538 Fe atoms. With an organic covering of 1.6%, we can determine the average number of 56 bis-(phosphonate)propionic acid molecules per particle. The number of grafted molecules per particle is thus given by the percentage of surface derivatization (% from XPS) × 0.56.
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