An anti-aggregation NIR-II heptamethine-cyanine dye with a stereo-specific cyanine for imaging-guided photothermal therapy

J Mater Chem B. 2021 Mar 21;9(11):2688-2696. doi: 10.1039/d1tb00018g. Epub 2021 Mar 5.

Abstract

Due to the hydrophobicity of the cyanine dye and the huge conjugated plane, the cyanine dye is prone to H-aggregation in aqueous solution, and the ultraviolet absorption is blue-shifted. Here, a hydrophilic quaternary stereo-specific cyanine (HQS-Cy) dye has been synthesized and polypeptide based nanoparticles have been prepared, which improve the water solubility of the cyanine in two aspects. First, at the molecular level, the sulfonic acid group increases the water solubility of the dye molecule while the dimethyl-ammonium functional group repels the molecule through the charge-charge interaction, destroying the planar characteristics of the cyanine structure, increasing the molecular distance between the dye molecules, and preventing the accumulation of cyanine. Secondly, at the nano-micelle level, the use of amphiphilic polypeptide blocks to encapsulate the dye increases the water solubility of the dye while also increasing its biocompatibility. The HQS-Cy@P NPs prepared by the above methods exhibit the maximum absorption at 985 nm and maximum fluorescence emission at 1050 nm in aqueous solution. HQS-Cy@P exhibits good photothermal stability and significant photothermal conversion efficiency of about 35.5%, and both in vitro and in vivo studies revealed that it is an efficient system for NIR-II imaging-guided photothermal therapy of cancer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Breast Neoplasms / diagnostic imaging
  • Breast Neoplasms / drug therapy*
  • Carbocyanines / chemical synthesis
  • Carbocyanines / chemistry
  • Carbocyanines / pharmacology*
  • Cell Line
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Coloring Agents / chemical synthesis
  • Coloring Agents / chemistry
  • Coloring Agents / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Female
  • Humans
  • Infrared Rays
  • Mammary Neoplasms, Experimental / diagnostic imaging
  • Mammary Neoplasms, Experimental / drug therapy
  • Mice
  • Mice, Inbred BALB C
  • Molecular Structure
  • Optical Imaging
  • Photothermal Therapy*
  • Solubility
  • Uterine Cervical Neoplasms / diagnostic imaging
  • Uterine Cervical Neoplasms / drug therapy*

Substances

  • Antineoplastic Agents
  • Carbocyanines
  • Coloring Agents
  • heptamethine cyanine dye