Nanotexaphyrin: One-Pot Synthesis of a Manganese Texaphyrin-Phospholipid Nanoparticle for Magnetic Resonance Imaging

The discovery and synthesis of novel multifunctional organic building blocks for nanoparticles is challenging. Texaphyrin macrocycles are capable and multifunctional chelators. However, they remain elusive as building blocks for nanoparticles because of the difficulty associated with synthesis of te...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-05, Vol.55 (21), p.6187-6191
Main Authors: Keca, Joseph M., Chen, Juan, Overchuk, Marta, Muhanna, Nidal, MacLaughlin, Christina M., Jin, Cheng S., Foltz, Warren D., Irish, Jonathan C., Zheng, Gang
Format: Article
Language:English
Subjects:
Assembly
Chelating agents
Head
Head and neck
Lymph nodes
Lymphatic drainage
Magnetic resonance imaging
Manganese
metal chelation
Metallography
nano-assembly
Nanoparticles
NMR
Nuclear magnetic resonance
Phospholipids
Resonance
Structural stability
Synthesis
texaphyrin
Tumors
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Summary:The discovery and synthesis of novel multifunctional organic building blocks for nanoparticles is challenging. Texaphyrin macrocycles are capable and multifunctional chelators. However, they remain elusive as building blocks for nanoparticles because of the difficulty associated with synthesis of texaphyrin constructs capable of self‐assembly. A novel manganese (Mn)‐texaphyrin‐phospholipid building block is described, along with its one‐pot synthesis and self‐assembly into a Mn‐nanotexaphyrin. This nanoparticle possesses strong resilience to manganese dissociation, structural stability, in vivo bio‐safety, and structure‐dependent T1 and T2 relaxivities. Magnetic resonance imaging (MRI) contrast enhanced visualization of lymphatic drainage is demonstrated with respect to proximal lymph nodes on the head and neck VX‐2 tumors of a rabbit. Synthesis of 17 additional metallo‐texaphyrin building blocks suggests that this novel one‐pot synthetic procedure for nanotexaphyrins may lead to a wide range of applications in the field of nanomedicines. Contrast and compare: A one‐pot synthesis and self‐assembly method is described for preparation of Mn‐texaphyrin‐phospholipids, allowing facile self‐assembly of Mn‐nanotexaphyrins. Each Mn‐nanotexaphyrin constitutes a stable 1:1 porphyrin:metal chelation, equating to 8×104 MnII ions. The newly prepared contrast agent was applied to magnetic resonance imaging (MRI) of lymphatic metastasis drainage, revealing drainage from the tumor site to the adjacent metastatic lymph node.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201600234