Cyanine5.5 maleimide

• CAT Number: I025340
• CAS Number: 1594414-90-0
• Molecular Formula: C46H49ClN4O3
• Molecular Weight: 741.373
• Purity: 98%
• Synonyms: Cyanine5.5 maleimide
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 2-((1E,3E,5E)-5-(3-(6-((2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl)amino)-6-oxohexyl)-1,1-dimethyl-1,3-dihydro-2H-benzo[e]indol-2-ylidene)penta-1,3-dien-1-yl)-1,1,3-trimethyl-1H-benzo[e]indol-3-ium chloride
• InChI: InChI=1S/C46H48N4O3.ClH/c1-45(2)38(48(5)36-25-23-32-16-11-13-18-34(32)43(36)45)20-8-6-9-21-39-46(3,4)44-35-19-14-12-17-33(35)24-26-37(44)49(39)30-15-7-10-22-40(51)47-29-31-50-41(52)27-28-42(50)53;/h6,8-9,11-14,16-21,23-28H,7,10,15,22,29-31H2,1-5H3;1H
• InChIKey: VNFHENZPAYHJJQ-UHFFFAOYSA-N
• SMILES: C[N+]1=C(/C=C/C=C/C=C2N(CCCCCC(NCCN3C(C=CC3=O)=O)=O)C4=C(C5=CC=CC=C5C=C4)C/2(C)C)C(C)(C)C6=C1C=CC7=CC=CC=C67.[Cl-]

Cyanine5.5 maleimide is a thiol reactive dye which is capable of selective labeling of sulfhydryl groups in proteins, an analog of Cy5.5® maleimide. Near infrared emission of Cyanine5.5 makes this dye suitable for bioimaging applications. Cyanine5.5 can replace Cy5.5®, Alexa Fluor 680, and DyLight 680.

Reference

1. Galstyan, A.; Chiechi, A.; Korman, A.J.; Sun, T.; Isreal, L.L.; Braubach, O.; Patil, R.; Shatalova, E.; Ljubimov, V.A.; Markman, J.; Grodzinski, Z.; Black, K.L.; Penichet, M.L.; Holler, E.; Ljubimov, A.V.; Ding, H.; Ljubimova, J.Y. Nano immunoconjugates crossing blood-brain barrier activate local brain tumor immune system for glioma treatment. bioRxiv, preprint. doi: 10.1101/466508
2. Gardinier, T.C.; Turker, M.Z.; Hinckley, J.A.; Katt, W.P.; DomNwachukwu, N.; Woodruff, F.; Hersh, J.; Wang, J.; Cerione, R.A.; Wiesner, U.B. Controlling Surface Chemical Heterogeneities of Ultrasmall Fluorescent Core–Shell Silica Nanoparticles as Revealed by High-Performance Liquid Chromatography. The Journal of Physical Chemistry C, 2019, 123(37), 23246–23254. doi: 10.1021/acs.jpcc.9b06905
3. Chen, C.; Corry, B.; Huang, L.; Hildebrandt, N. FRET-modulated multi-hybrid nanoparticles for brightness-equalized single-wavelength barcoding. Journal of the American Chemical Society, 2019, 141(28), 11123–11141. doi: 10.1021/jacs.9b03383
4. Guo, S.; Xiao, X.; Wang, X.; Luo, Q.; Zhu, H.; Zhang, H.; Li, H.; Gong, Q.; Luo, K. Reductive microenvironment responsive gadolinium-based polymers as potential safe MRI contrast agents. Biomaterials Science, 2019, 7(5), 1919–1932. doi: 10.1039/c8bm01103f