Synthesis and in vitro Evaluation of Manganese(II)-porphyrin Modified with Chitosan Oligosaccharides as Potential MRI Contrast Agents

doi:10.1007/s40242-014-4015-0

高等学校化学研究 ›› 2014, Vol. 30 ›› Issue (4): 549-555.doi: 10.1007/s40242-014-4015-0

Synthesis and in vitro Evaluation of Manganese(II)-porphyrin Modified with Chitosan Oligosaccharides as Potential MRI Contrast Agents

LIU Yun¹, HUANG Yan¹, BOAMAH Peter Osei¹, ZHANG Qi^1,2, LIU Yuanyuan¹, HUA Mingqing¹

1. School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, P. R. China;
2. Hainan Provincial Key Lab of Fine Chemistry, Hainan University, Haikou 570228, P. R. China

出版日期:2014-08-01 发布日期:2014-04-14
通讯作者: ZHANG Qi E-mail:qzhang@ujs.edu.cn
基金资助:
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).

Synthesis and in vitro Evaluation of Manganese(II)-porphyrin Modified with Chitosan Oligosaccharides as Potential MRI Contrast Agents

LIU Yun¹, HUANG Yan¹, BOAMAH Peter Osei¹, ZHANG Qi^1,2, LIU Yuanyuan¹, HUA Mingqing¹

1. School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, P. R. China;
2. Hainan Provincial Key Lab of Fine Chemistry, Hainan University, Haikou 570228, P. R. China

Online:2014-08-01 Published:2014-04-14
Contact: ZHANG Qi E-mail:qzhang@ujs.edu.cn
Supported by:
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).

摘要/Abstract

摘要：

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(r₁=10.38 L·mmol^-1·s^-1) in aqueous solution than unmodified porphyrin Mn-TCPPNa₄[manganese(II) meso-tetra(4-carboxyphenyl) porphyrin, tetrasodium salt](r₁=5.10 L·mmol^-1·s^-1) and the commercial contrast agent Gd-DTPA(r₁=4.05 L·mmol^-1·s^-1). The preliminary T₁-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.

关键词: MRI contrast agent, Porphyrin, Chitosan oligosaccharide, Relaxivity, T₁-Weighted flash image

Abstract:

Key words: MRI contrast agent, Porphyrin, Chitosan oligosaccharide, Relaxivity, T₁-Weighted flash image

LIU Yun, HUANG Yan, BOAMAH Peter Osei, ZHANG Qi, LIU Yuanyuan, HUA Mingqing. Synthesis and in vitro Evaluation of Manganese(II)-porphyrin Modified with Chitosan Oligosaccharides as Potential MRI Contrast Agents[J]. 高等学校化学研究, 2014, 30(4): 549-555.

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Synthesis and in vitro Evaluation of Manganese(II)-porphyrin Modified with Chitosan Oligosaccharides as Potential MRI Contrast Agents

Synthesis and in vitro Evaluation of Manganese(II)-porphyrin Modified with Chitosan Oligosaccharides as Potential MRI Contrast Agents

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