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Modified norcyanines enable ratiometric pH imaging beyond 1000 nm.
Usama, Syed Muhammad; Caldwell, Donald R; Shrestha, Pradeep; Luciano, Michael P; Patel, Nimit L; Kalen, Joseph D; Ivanic, Joseph; Schnermann, Martin J.
Affiliation
  • Usama SM; Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, Frederick, MD, 21702, United States.
  • Caldwell DR; Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, Frederick, MD, 21702, United States.
  • Shrestha P; Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, Frederick, MD, 21702, United States.
  • Luciano MP; Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, Frederick, MD, 21702, United States.
  • Patel NL; Small Animal Imaging Program, Frederick National Laboratory for Cancer Research, Leidos Biomedical Research Inc, Frederick, MD, 21702, United States.
  • Kalen JD; Small Animal Imaging Program, Frederick National Laboratory for Cancer Research, Leidos Biomedical Research Inc, Frederick, MD, 21702, United States.
  • Ivanic J; Advanced Biomedical Computational Science, Frederick National Laboratory for Cancer Research, Leidos Biomedical Research Inc, Frederick, MD, 21702, United States.
  • Schnermann MJ; Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, Frederick, MD, 21702, United States. Electronic address: martin.schnermann@nih.gov.
Biosens Bioelectron ; 217: 114610, 2022 Dec 01.
Article in En | MEDLINE | ID: mdl-36137483
Activatable fluorophores with emission beyond 1000 nm have the potential to enable high contrast imaging in complex in vivo settings. However, there are few scaffolds that can be applied to this challenge. Here we detail the synthesis and evaluation of benzo[c,d]indole-substituted norcyanines that enable pH responsive fluorescence imaging in the long wavelength (>1150 nm) range. A key component of our molecular design is the installation of a hydrophilic substituted quaternary amine in the central dihydropyridine ring system. A compound with a C4'-phenyl substituent, but not the C4'-protio homologue, exhibits absorbance maxima of 740 nm and 1130 nm in basic and acidic media, respectively, with evidence of J-aggregate-like properties. These two distinct absorbances enabled ratiometric imaging of probe internalization in a tumor model. Overall, these studies provide a new class of activatable long-wavelength responsive fluorophores with promising photophysical properties.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Dihydropyridines / Biosensing Techniques Language: En Journal: Biosens Bioelectron Journal subject: BIOTECNOLOGIA Year: 2022 Document type: Article Affiliation country: United States Country of publication: United kingdom

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Dihydropyridines / Biosensing Techniques Language: En Journal: Biosens Bioelectron Journal subject: BIOTECNOLOGIA Year: 2022 Document type: Article Affiliation country: United States Country of publication: United kingdom