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Synthesis and in vitro evaluation of manganese(II)-porphyrin modified with chitosan oligosaccharides as potential MRI contrast agents

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Abstract

Mn-TCPP-CS n (n=6, 11, 20) as a type of potential magnetic resonance imaging(MRI) contrast agents were synthesized via manganese(II) meso-tetra(4-carboxyphenyl) porphyrin(Mn-TCPP) modified with chitosan oligosaccharides(CS n ). Experimental data of infared(IR), UV-Vis, MS, inductively coupled plasma-atomic emission spectrometer(ICP-AES) and size exclusion chromatography evidenced the formation of Mn-TCPP-CS n . The stability results show that Mn-TCPP-CS n in aqueous solution was stable enough to prevent Mn(II) ions from leaking. The magnetic properties in vitro indicate that Mn-TCPP-CS20 possesses higher longitudinal relaxivity(r 1=10.38 L·mmol−1·s−1) in aqueous solution than unmodified porphyrin Mn-TCPPNa4[manganese(II) meso-tetra(4-carboxyphenyl) porphyrin, tetrasodium salt](r 1=5.10 L·mmol−1·s−1) and the commercial contrast agent Gd-DTPA(r 1=4.05 L·mmol−1·s−1). The preliminary T 1-weighted flash image studies in vitro show that the contrast and the imaging signal of Mn-TCPP-CS n were superior to those of Mn-TCPPNa4 and Gd-DTPA under the same conditions. The 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide(MTT) assay shows that Mn-TCPP-CS n has a good biocompatibility. In addition, the thermodynamical parameters(ΔH<0, ΔS<0, ΔG<0) of Mn-TCPP-CS n bound to bovine serum albumin(BSA) show that Mn-TCPP-CS n could bind to BSA spontaneously, where the binding complex was stabilized mainly by van der Waals interactions and hydrogen bonds. These results suggest that Mn-TCPP-CS n have the advantage of becoming a potential MRI contrast agent.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, P. R. China

    Yun Liu, Yan Huang, Peter Osei Boamah, Qi Zhang, Yuanyuan Liu & Mingqing Hua

  2. Hainan Provincial Key Lab of Fine Chemistry, Hainan University, Haikou, 570228, P. R. China

    Qi Zhang

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  1. Yun Liu
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  2. Yan Huang
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  3. Peter Osei Boamah
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  4. Qi Zhang
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  5. Yuanyuan Liu
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  6. Mingqing Hua
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Correspondence to Qi Zhang.

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Supported by the National Natural Science Foundation of China(Nos.21261008, 21302071, 21171076), and the Cooperation Project of Hainan International Science and Technology, China(No.KJHZ2014-05).

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Liu, Y., Huang, Y., Boamah, P.O. et al. Synthesis and in vitro evaluation of manganese(II)-porphyrin modified with chitosan oligosaccharides as potential MRI contrast agents. Chem. Res. Chin. Univ. 30, 549–555 (2014). https://doi.org/10.1007/s40242-014-4015-0

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  • DOI: https://doi.org/10.1007/s40242-014-4015-0

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