A triphenylamine terpyridine manganese complex with dual functions of two-photon imaging and magnetic resonance imaging and its synthesis method

Abstract

A triphenylamine terpyridine manganese complex having double functions including two-photon development and magnetic resonance development and a synthetic method thereof are disclosed. The structure formula of the complex is shown in the description. The complex has a two-photon development function and a magnetic resonance development function, and can be adopted as a contrast medium for double modes. Compared with a commercial nuclear magnetic contrast medium that is Gd-DTPA, the complex can be ingested by cells well so that magnetic resonance signals are enhanced.

Description

technical field

[0001] The invention relates to a triphenylamine terpyridine manganese complex with dual functions of two-photon imaging and magnetic resonance imaging and a synthesis method thereof, which can be applied to the dual-mode imaging functions of two-photon microscopic imaging and magnetic resonance imaging of living cells in biology. It has obvious commercial application value. Background technique

[0002] Magnetic resonance imaging (MRI) is a relatively new medical imaging technique, and it is attracting more and more attention for medical diagnosis. In 1945, two research groups headed by E.M.Purcell of Harvard University and F.Bloch of Stanford University observed the phenomenon of nuclear magnetic resonance almost simultaneously, and they both won the 1952 Nobel Prize in Physics. In 1953, Varian Corporation of the United States successfully developed the world's first commercial nuclear magnetic resonance instrument. As research on contrast agents has deve...

Examples

Embodiment 1

[0044] Ligand L 1 (0.202g, 0.400mmol) was dissolved in 20mL of absolute ethanol and placed in a 50mL round-bottomed flask, added with Mn(OAc) 2 4H 2 O (0.049g, 0.200mmol) in 20mL ethanol solution, heated to reflux for 4h, after the reaction, the reaction solution was cooled to room temperature, and then NH 4 PF 6 (0.082g, 0.500mmol), continue heating to reflux reaction for 2h, precipitate a red solid, filter while it is hot, collect the filter cake by filtration under reduced pressure, and recrystallize with absolute ethanol to obtain the target product Mn10.206g as a red solid, the yield 75.90% (calculated based on the amount of ligand, the same below).

[0045] M.P.: 232℃. 1 H NMR (400MHz, d 6 -DMSO,ppm):δ8.72(d,J=31.1Hz,12H),8.04(s,4H),7.86(s,4H),7.52(s,4H),7.34(s,8H),7.11( s,14H),5.15(s,2H),4.49(s,4H).IR(cm -1):3421(m),3063(m),2922(m),1587(vs),1512(s),1475(s),1417(m),1329(s),1288(m),1196(s ),1017(m),844(s),792(s),760(m),698(m),658(m),640(m),558(s),522(m).ESI-MS :m...

Embodiment 2

[0047] Ligand L 2 (0.214g, 0.400mmol) was dissolved in 20mL of absolute ethanol and placed in a 50mL round-bottomed flask, added with Mn(OAc) 2 4H 2 O (0.049g, 0.200mmol) in 20mL ethanol solution, heated to reflux for 4h, after the reaction, the reaction solution was cooled to room temperature, and then NH 4 PF 6 (0.082g, 0.500mmol), continue heating to reflux reaction for 2h, precipitate a red solid, filter while hot, collect the filter cake by filtration under reduced pressure, and recrystallize with absolute ethanol to obtain the target product Mn20.211g, which is a red solid, yield 74.45% (calculated based on the amount of ligand, the same below).

[0048] M.P.: 236℃. 1 H NMR (400MHz, d 6 -DMSO,ppm):δ8.72(d,J=30.9Hz,12H),8.03(s,4H),7.85(s,4H),7.52(s,4H),7.32(s,8H),7.09( s,13H),5.15(s,4H),4.49(s,8H).IR(cm -1 ):3393(m),3063(m),2922(m),2872(m),1593(vs),1510(s),1475(s),1417(m),1327(s),1288(m ),1197(s),1016(s),844(vs),791(s),731(m),671(m),658(m),639(m),558(s),521(m ).E...

technical field

[0001] The invention relates to a triphenylamine terpyridine manganese complex with dual functions of two-photon imaging and magnetic resonance imaging and a synthesis method thereof, which can be applied to the dual-mode imaging functions of two-photon microscopic imaging and magnetic resonance imaging of living cells in biology. It has obvious commercial application value. Background technique

[0002] Magnetic resonance imaging (MRI) is a relatively new medical imaging technique, and it is attracting more and more attention for medical diagnosis. In 1945, two research groups headed by E.M.Purcell of Harvard University and F.Bloch of Stanford University observed the phenomenon of nuclear magnetic resonance almost simultaneously, and they both won the 1952 Nobel Prize in Physics. In 1953, Varian Corporation of the United States successfully developed the world's first commercial nuclear magnetic resonance instrument. As research on contrast agents has deve...

Examples

Embodiment 1

[0044] Ligand L 1 (0.202g, 0.400mmol) was dissolved in 20mL of absolute ethanol and placed in a 50mL round-bottomed flask, added with Mn(OAc) 2 4H 2 O (0.049g, 0.200mmol) in 20mL ethanol solution, heated to reflux for 4h, after the reaction, the reaction solution was cooled to room temperature, and then NH 4 PF 6 (0.082g, 0.500mmol), continue heating to reflux reaction for 2h, precipitate a red solid, filter while it is hot, collect the filter cake by filtration under reduced pressure, and recrystallize with absolute ethanol to obtain the target product Mn10.206g as a red solid, the yield 75.90% (calculated based on the amount of ligand, the same below).

[0045] M.P.: 232℃. 1 H NMR (400MHz, d 6 -DMSO,ppm):δ8.72(d,J=31.1Hz,12H),8.04(s,4H),7.86(s,4H),7.52(s,4H),7.34(s,8H),7.11( s,14H),5.15(s,2H),4.49(s,4H).IR(cm -1):3421(m),3063(m),2922(m),1587(vs),1512(s),1475(s),1417(m),1329(s),1288(m),1196(s ),1017(m),844(s),792(s),760(m),698(m),658(m),640(m),558(s),522(m).ESI-MS :m...

Embodiment 2

[0047] Ligand L 2 (0.214g, 0.400mmol) was dissolved in 20mL of absolute ethanol and placed in a 50mL round-bottomed flask, added with Mn(OAc) 2 4H 2 O (0.049g, 0.200mmol) in 20mL ethanol solution, heated to reflux for 4h, after the reaction, the reaction solution was cooled to room temperature, and then NH 4 PF 6 (0.082g, 0.500mmol), continue heating to reflux reaction for 2h, precipitate a red solid, filter while hot, collect the filter cake by filtration under reduced pressure, and recrystallize with absolute ethanol to obtain the target product Mn20.211g, which is a red solid, yield 74.45% (calculated based on the amount of ligand, the same below).

[0048] M.P.: 236℃. 1 H NMR (400MHz, d 6 -DMSO,ppm):δ8.72(d,J=30.9Hz,12H),8.03(s,4H),7.85(s,4H),7.52(s,4H),7.32(s,8H),7.09( s,13H),5.15(s,4H),4.49(s,8H).IR(cm -1 ):3393(m),3063(m),2922(m),2872(m),1593(vs),1510(s),1475(s),1417(m),1327(s),1288(m ),1197(s),1016(s),844(vs),791(s),731(m),671(m),658(m),639(m),558(s),521(m ).E...

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