花菁 [荧光标记试剂]

Cyanine dyes, including Cyanine3, Cyanine5, Cyanine5.5, Cyanine 7 and Indocyanine Green (ICG) [I0535] are important compounds in biological applications. Among them, ICG, which is a heptamethine cyanine dye, has an absorption wavelength and an emission wavelength in the near-infrared window (about 800 nm), and is used for ophthalmic angiography and examining cardiac output, hepatic function, gaster/liver bloodstream. But ICG is nonspecific and cannot stain a certain tissue. Alternatively, researchers have been trying to utilize conjugates of heptamethine cyanine dye, which has functional group, with proteins including antibodies for diagnosis of a specific disease, drug release in a specific tissue, or fluorescence-guided surgery.^1-6) In particular, NIR fluorophore-mAb conjugates, which are complexes with monoclonal antibodies (mAbs), are useful as contrast agents for tumor targeting. As a near-infrared dye that can be conjugated with such antibodies, we introduce a cyanine dye that was added a carboxyl group into the polymethine structure of ICG.^7,8) ICG Carboxylic Acid [O0574] can be expected to be used as a material with characteristics that are close to but different from ICG, such as solubility and specific reactivity with biomolecules. For example, a probe for cellular hypoxia imaging that can "turn on" fluorescence with nitroreductase has been reported.⁹⁾

We offer ICG Carboxylic Acid at a lower price than ICG. We have 1 g and 5 g packages, and will be happy to discuss bulk synthesis requests.

In addition to ICG Carboxylic Acid, we also offer IR 754 Carboxylic Acid [C3693], IR 775 Chloride [I1026] and IR 783 [I1031]. IR 783 can be used for conjugation with proteins such as antibodies because the functional group that can be conjugated with alcohol, amine, thiol and phenylboronic acid can be introduced into the chlorine moiety of the polymethine chain.^2,10)

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References

• 1) A Biliary Tract-Specific Near-Infrared Fluorescent Dye for Image-Guided Hepatobiliary Surgery
  • M. P. Luciano, J. M. Namgoong, R. R. Nani, S. H. Nam, C. Lee, H. Shin, M. J. Schnermann, J. Cha, Mol. Pharmaceutics 2019, 16, 3253.
• 2) Two new, near-infrared, fluorescent probes as potential tools for imaging bone repair
  • C. C. Lin, W. Chang, T. M. Cheng, L. H. Chiu, Y. H. Wang, C. A. Lin, Y. S. Ho, C. Zuo,Y. M. Wang, W. F. Lai, Sci. Rep. 2020, 10, 2580.
• 3) Near-IR Light-Mediated Cleavage of Antibody–Drug Conjugates Using Cyanine Photocages
  • R. R. Nani, A. P. Gorka, T. Nagaya, H. Kobayashi, M. J. Schnermann, Angew. Chem. Int. Ed. 2015, 54, 13635.
• 4) Alkaline Phosphatase-Triggered Self-Assembly of Near-Infrared Nanoparticles for the Enhanced Photoacoustic Imaging of Tumors
  • C. Wu, R. Zhang, W. Du, L. Cheng, G. Liang, Nano Lett. 2018, 18, 7749.
• 5) Electrophile integrating smiles rearrangement provides previously inaccessible C4-O-alkyl heptamethine cyanine fluorophores
  • R. R. Nani, J. B. Shaum, A. P. Gorka, M. J. Schnermann, Org. Lett. 2015, 17, 302.
• 6) Selective imaging of solid tumours via the calcium-dependent high-affinity binding of a cyclic octapeptide to phosphorylated Annexin A2
  • D. Shen, B. Xu, K. Liang, R. Tang, G. Sudlow, C. Egbulefu, K. Guo, A. Som, R. Gilson, D. Maji, S. Mondal, L. Habimana-Griffin, W. Akers, S. Li, Y. Liu, S. Bloch, S. Kurkure, Z. Nussinov, A. Seidel, S. Achilefu, Nat. Biomed. Eng. 2020, 4, 298.
• 7) Approach to a Substituted Heptamethine Cyanine Chain by the Ring Opening of Zincke Salts
  • L. Štacková, P. Štacko, P. Klán, J. Am. Chem. Soc. 2019, 141, 7155.
• 8) Deciphering the Structure–Property Relations in Substituted Heptamethine Cyanines
  • L. Štacková, E. Muchová, M. Russo, P. Slavíček, P. Štacko, P. Klán, J. Org. Chem. 2020, 85, 9776.
• 9) Generalizable synthesis of bioresponsive near-infrared fluorescent probes: sulfonated heptamethine cyanine prototype for imaging cell hypoxia
  • K. Atkinson, J. Morsby, S. Kommidi, B. Smith, Org. Biomol. Chem. 2021, 19, 4100.
• 10) A near-infrared probe for non-invasively monitoring cerebrospinal fluid flow by 18F-positron emitting tomography and fluorescence
  • H. Guo, H. Kommidi, C. C. Lekaye, J. Koutcher, M. S. Judenhofer, S. R. Cherry, A. P. Wu, O. Akin, M. M. Souweidane, O. Aras, Z. Zhu, R. Ting, EJNMMI Res. 2020, 10, 37.
• 11) A Method for the High Efficiency of Water-Soluble Carbodiimide-Mediated Amidation
  • D. Sehgal, I. K. Vijay, Anal. Biochem. 1994, 218, 87.
• 12) Monosaccharide analog, molecular probe comprising the same and its application in preparing reagents for labeling cells, bacteria and virus and tracking and developing living body
  • L. Cai, L. Wenjun, X. Meng, H. Pan, P. Gong, Y. Ma, S. Li, G. Deng, CN109553643A 2019.

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