MHI-148 Chemical Properties

storage temp. 

Store at -20°C

solubility 

DMF: 20 mg/ml
DMSO: 20 mg/ml
Ethanol: 10 mg/mlPBS (pH 7.2): 1 mg/ml

form 

Solid

color 

Light green to green

InChIKey

SBSLCJXMLMGYFH-UHFFFAOYSA-N

SMILES

C(N1C(C(C)(C)C2=CC=CC=C12)=CC=C1CCCC(C=CC2C(C3=CC=CC=C3[N+]=2CCCCCC(=O)O)(C)C)=C1Cl)CCCCC(=O)O.[Br-]

MHI-148 Usage And Synthesis

Description

MHI-148 ((2-[2-[2-Chloro-3-[2-[1,3-dihydro-3,3-dimethyl-1-(5-carboxypentyl)-2H-indol-2-ylidene]-ethylidene]-1-cyclohexen-1-yl]-ethenyl]-3,3-dimethyl-1-(5-carboxypentyl)-3H-indolium bromide)) is a near-infrared heptamethine cyanine dye with tumour-targeting properties for cancer detection, diagnosis and research. MHI-148 is immediately taken up and accumulated by the lysosomes and mitochondria of tumour cells but not in the lysosomes and mitochondria of normal cells.

Uses

The heptamethine cyanine dye MHI-148 is an analogue of IR-783, which was initially synthesized as an optical imaging agent to detect human kidney cancer. MHI-148 dye-conjugated porous Gd silicate nanoparticles were developed as a NIRF-MRI dual-modal contrast agent for LLC/LL2 tumours. In another work, an MHI-148-based PET imaging probe labelled with Cu64 was developed as a tumour-targeting agent. These studies showed that the MHI-148 dye has active tumour-targeting properties and enhanced accumulation in tumours compared to control groups. NIRF dye MHI-148 can be used for effective imaging with good stability and specificity in different types of tumour cell lines and tumour xenografts, such as kidney cancer, prostate cancer and lung cancer. Thomas et al. have also used MHI-148 as a tumour-targeting agent conjugated to nanoparticles for breast cancer treatment[1].

References

[1] Jian Song. “Near-infrared fluorescence imaging of hepatocellular carcinoma cells regulated by β-catenin signaling pathway.” Frontiers in Oncology 13 (2023): 1140256.
[2] XIUYING CHEN. Photostabilities of novel heptamethine 3H-indolenine cyanine dyes with different N-substituents[J]. Journal of Photochemistry and Photobiology A-chemistry, 2006, 181 1: Pages 79-85. DOI: 10.1016/j.jphotochem.2005.11.004
[3] ATHIRA RAVEENDRAN. Heptamethine Cyanine Dye MHI-148-Mediated Drug Delivery System to Enhance the Anticancer Efficiency of Paclitaxel.[J]. International Journal of Nanomedicine, 2021: 7169-7180. DOI: 10.2147/ijn.s325322
[4] JIA P, JI H, LIU S, et al. Integration of IR-808 and thiol-capped Au–Bi bimetallic nanoparticles for NIR light mediated photothermal/photodynamic therapy and imaging†[J]. Journal of Materials Chemistry B, 2020, 1: 101-111. DOI: 10.1039/d0tb02378g