indocyanine green maleimide icg maleimide

ICG maleimide

 170.00 1090.00

Labeling via free thiol chemistry

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Introduction

The non-invasive near-infrared (NIR) fluorescence imaging dye Indocyanine green (ICG) is approved by the United States Food and Drug administration (FDA) for ophthalmologic angiography to determine cardiac output and liver blood flow and function. This dye is also used in cancer patients for the detection of solid tumors, localization of lymphnodes, and for angiography during reconstructive surgery, visualization of retinal and choroidal vasculature, and photodynamic therapy1-3. In cancer diagnostics and therapeutics, ICG could be used as both an imaging dye and a hyperthermia agent.

ICG is a tricarbocyanine-type dye with NIR-absorbing properties (peak absorption around 800 nm) and emission maximum at 807 nm (10% v/vDMSO/PBS). Little absorption in the visible range accounts for the low autofluorescence, tissue absorbance, and scattering at NIR wavelengths (700-900 nm).

The maleimide of the ICG dye offers the opportunity to develop optimal conjugates. Maleimide active group provides an efficient and convenient way to selectively link ICG dye to sulfhydryl groups (free thiol, R-SH) on various substrates (antibodies[1], peptides, proteins, oligonucleotides, small molecule drugs etc.) at neutral (physiological) pH without any activation. Maleimides have very low reactivity with amines, alcohols, and phenols (incl. tyrosine and histidine) and do not react with histidine and methionine thus providing very high labeling selectivity.

It has been reported that conjugation to some antibodies may cause decrease in fluorescence intensity of ICG bound to antibody due to the formation of H-dimers4. However, fluorescence is restored after cell binding and internalization, which can be used to design an activatable NIR fluorescent probe. Fluorescence intensity of the unbound ICG-antibody conjugate can be dramatically increased (up to 50-fold) by addition of SDS and β-mercaptoethanol, which diminishes π- π stacking5.

Material Amount Storage Stability
ICG maleimide 1 mg
  • -20° C
  • Desiccate
  • Protect from light
When stored as directed, reactive probes are stable for at least 3 months
5 mg
10 mg

Immediately before use, dissolve the ICG maleimide dye in anhydrous dimethylsulfoxide (DMSO). Once reconstituted, this reactive probe solution is somewhat unstable, especially in presence of moisture that can slowly hydrolyze the ICG maleimide to the non-reactive derivatives.

  1. Schaafsma B.E. The clinical use of indocyanine green as a near-infrared fluorescent contrast agent for image-guided oncologic surgery. Surg. Oncol. 2011, 104, 323-332
  2. Saxena V, Sadoqi M, Shao J. Degradation kinetics of indocyanine green in aqueous solution. Pharm. Sci. 2003, 92, 2090
  3. Yaseen MA, Yu J, Wong MS, Anvari B. Stability assessment of indocyanine green within dextran-coated mesocapsules by absor- bance spectroscopy. Biomed. Opt. 2007, 12, 064031
  4. Ogawa, M., Kosaka, N., Choyke, P. L., Kobayashi, H. H-Type Dimer Formation of Fluorophores: A Mechanism of Activatable In Vivo Optical Molecular Imaging ACS Chem. Biol. 2009, 4(7), 535-546
  5. Ogawa, M., Kosaka, N., Choyke, P. L., Kobayashi, H. In vivo Molecular Imaging of Cancer with a Quenching Near-Infrared Florescent Probe Using Conjugates of Monoclonal Antibodies and Indocyanine Green Cancer Res. 2009, 69(4), 1268-1272
Color

Dark green powder

Label

Maleimide

Product Size

1 kit

Detection Method

Fluorescence, optoacoustic

Excitation Class

Near infrared, NIR

Excitation/Emission maximum (nm)

790/830

Molecular Weight

853.09 g.mol-1

Formula

C51H56N4O6S

Shipping Condition

RT

Regulatory Statement

For Research Use Only. Not for use in diagnostic procedures.

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