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Dye and Fluorescence Labeled Peptides

Molecular imaging techniques play a critical role in modern clinical and experimental diagnostics. Fluorescently labeled reporter molecules can provide biological information at the molecular level in living systems, enable visualization of the specific molecular events in disease process, and monitor therapeutic responses. As an important molecular imaging technology, fluorescent imaging has specific advantages over other imagaing techiques, such as high sensitivity, use of nonradioactive materials, and easy detection by lower cost instruments.

Dye Chemistry

Dye and fluorescence labeled molecular tags can be incorporated at variety of positions of a peptide, including the (1) N-terminus, (2) C-terminus, and (3) side-chains of amino acids such as Lysine, Glutamic Acid, and Asparatic Acid.

Custom fluorescein labeled peptides

Carboxyfluorescein (abbreviated, FAM) is the one of the most popular fluorescent tags for peptides. FAM conjugations often out performs in stability over its counter part, fluorescein-isothiocyanate (FITC). FAM carboxamide conjugates are generally more stable to hydrolysis than are FITC conjugates.

Peptide Dye Labels Abz EDANS MCA AMC Peptide Dyes Cy5 and Cy3
Dye-labeled custom peptides

Warren, Andrew D., et al. "Disease detection by ultrasensitive quantification of microdosed synthetic urinary biomarkers." Journal of the American Chemical Society 136.39 (2014): 13709-13714.

Dye and Fluorescence Labeled Peptide Citations

"The 5-TAMRA (5-carboxytetramethylrhodamine) peptide was generated by CPCScientific consisting of the sequence 5-TAMRA-YPYDVPDYAIREIVSRNKRRYQEDG.."

1. Kategaya, Lorna, et al. "USP7 small-molecule inhibitors interfere with ubiquitin binding." Nature 550.7677 (2017): 534.Learn More »

"All peptides were synthesized by CPC Scientific. For recombinant enzyme studies and ABNz, intramoleculary quenched peptides were used: MMP substrate, 5-FAM–GGPLGVRGKK(CPQ2)–PEG2–C; thrombin substrate, 5-FAM–GGfPRSGGGK(CPQ2)–PEG2–C; where 5-FAM is the 5-carboxyfluorescein fluorophore, CPQ2 is the quencher, PEG2 is the linker polyethylene glycol, and lower case letters indicate the d-stereoisomer of the residue. In vivo protease-sensitive substrates were synthesized to contain a urinary reporter comprised of a protease-resistant d-stereoisomer of glutamatefibrinopeptide B with a near-infrared dye for urinary detection (biotin–CGPLGVRGKK(Cy7)eGvndneeGffsar; Cy7 is cyanine7). Targeting peptides were synthesized and cyclized: LyP1, C–K(5-FAM)–C6–CGNKRTRGC; iRGD, C–PEG2–CRGDKGPDC; where C6 is the 6-aminohexanoic acid linker and there is a disulfide bridge between Cysteines 2 and 3."

2. Kwon, Ester J., Jaideep S. Dudani, and Sangeeta N. Bhatia. "Ultrasensitive tumour-penetrating nanosensors of protease activity." Nature Biomedical Engineering 1 (2017): 0054.Learn More »

"The 7-amido-4-thifluoromethylcoumarin (AFC) containing fluorescence substrate, CH3SO2-cyclohexyl-Gly-Gly-Arg-AFC (cyclohexylG-G-R-AFC) was custom synthesized by CPC Scientific (Sunnyvale, CA, USA)"

3. Barbieri, Christopher M., et al. "Factor XIIa as a novel target for thrombosis: target engagement requirement and efficacy in a rabbit model of microembolic signals." Journal of Pharmacology and Experimental Therapeutics 360.3 (2017): 466-475.Learn More »

"ASY*-FITC was synthesized using good manufacturing practice (GMP) methods (CPC Scientific, Inc.). Stability was evaluated on high-performance liquid chromatography (HPLC) and mass spectrometry. Aliquots of peptide (0.8 mg) were stored at −20 °C as lyophilized powder in single-use amber vials for protection from light."

4. Joshi, Bishnu P., et al. "Multimodal endoscope can quantify wide-field fluorescence detection of Barrett’s neoplasia." Endoscopy 48.02 (2016): A1-A13.Learn More »

"Myristoyl-transportan−LyP-1 tandem peptide was synthesized by CPC Scientific (sequence: myr-GGWTLNSAGYLLGKINLKALAALAKKIL-GGGG-CGNKRTRGC, Cys−Cys bridge). FAM-labeled LyP-1 bearing an azide (azidoacetyl-GGG-cyclo-(EGNKRTRGK)), FAM-labeled LyP-1 bearing a cysteine (C-K(5FAM)-C6-cyclo-(CGNKRTRGC)) and transportan bearing a C-terminal cysteine (myristic acid-GGWTLNSAGYLLGKINLKALAALAKKILC) were synthesized by CPC Scientific, Inc."

5. Lo, Justin H., et al. "A comparison of modular PEG incorporation strategies for stabilization of peptide-siRNA nanocomplexes." Bioconjugate Chemistry (2016): 27 (10), pp 2323–2331Learn More »

"D-CATH-2 (amino acid sequence: RFGRFLRKIRRFRPKVTITIQGSARF-NH2) and N-terminally FITC and TAMRA labeled peptides were generated by solid-phase synthesis using Fmoc-chemistry and purified to >95% purity by RP-HPLC by CPC Scientific Inc. (Sunnyvale, USA…"

6. Cuperus, Tryntsje, et al. "Protective effect of in ovo treatment with the chicken cathelicidin analog D-CATH-2 against avian pathogenic E. coli." Scientific Reports 6 (2016): 26622.Learn More »

"...protease activity are focused on functionalizing synthetic peptide substrates with reporters that emit ... In vivo, veiled nanosensors are selectively activated at the ..... sized by CPC Scientific, Inc. (V1: Biotin-PEG(5 kDa)-(KFAM)-..."

7. Dudani, Jaideep S., et al. "Photoactivated Spatiotemporally-Responsive Nanosensors of in Vivo Protease Activity." ACS Nano 9.12 (2015): 11708-11717.Learn More »

ABBREV. FULL FLUOROPHORE NAME EX/EM   λ
Abz 2-Aminobenzoyl or Anthraniloyl 320 nm
420 nm
N-Me-Abz N-Methyl-anthranilyl or N-Methyl-2-Aminobenzoyl 340-360 nm
440-450 nm
EDANS 5-((2-Aminoethyl)amino)naphthalene-1-sulfonic acid 340 nm
490 nm
5-FAM 5-Carboxyfluorescein 492 nm
517 nm
6-FAM 6-Carboxyfluorescein 492 nm
517 nm
FITC Fluorescein isocyanate 490 nm
520 nm
TAMRA 5-Carboxytetramethyl rhodamine 543 nm
572 nm
CP488 equivalent to Alexa Fluor™ 491 nm
518 nm
MCA 7-Methoxycoumarin-4-acetic acid 325 nm
392 nm
AMC 7-Amino-4-methylcoumarin 350 nm
450 nm
Dansyl 5-(Dimethylamino) naphthalene-1-sulfonyl 342 nm
562 nm
Cy3 1-(5-carboxypentyl)-3,3-dimethyl-2-((1E,3E)-3-(1,3,3-trimethylindolin-2-ylidene)prop-1-en-1-yl)-3H-indol-1-ium chloride 550 nm
570 nm
Cy5 1-(5-carboxypentyl)-3,3-dimethyl-2-((1E,3E,5E)-5-(1,3,3-trimethylindolin-2-ylidene)penta-1,3-dienyl)-3H-indolium chloride 550 nm
670 nm