Squaraine Dyes as Fluorescent Turn-on Probes for Mucins: A Step Toward Selectivity
Journal
Photochemistry and photobiology
ISSN: 1751-1097
Titre abrégé: Photochem Photobiol
Pays: United States
ID NLM: 0376425
Informations de publication
Date de publication:
03 2023
03 2023
Historique:
received:
15
07
2022
accepted:
15
09
2022
medline:
31
3
2023
pubmed:
18
9
2022
entrez:
17
9
2022
Statut:
ppublish
Résumé
Mucins are a family of long polymeric glycoproteins which can be overexpressed in several types of cancers, and over recent years, great attention was addressed to identify mucins as an important biomarker of adverse prognosis. Fluorometric detection mediated by fluorescent probes could represent a winning strategy in the early diagnosis of different pathologies. Among promising biological fluorescent probes, squaraines are gaining particular attention, thanks to their sharp and intense absorption and emission in the NIR region. In this contribution, three squaraine dyes bearing different substituents and with different lipophilicity have been investigated for their ability to detect mucin. The turn-on response upon the addition of mucin has been investigated by means of absorbance and fluorescence spectroscopy. After a preliminary screening, the squaraine (S6) bearing bromine as a substituent and C4 aliphatic chains showed the highest fluorescence turn-on and highest affinity for mucin than albumin. To further highlight the selectivity of S6 for mucin, the fluorescence response has been evaluated in the presence of serum and site-specific proteins different than albumin. Absorption spectroscopy was used to characterize the binding mechanism of squaraine to mucin.
Substances chimiques
Fluorescent Dyes
0
squaraine
0
Mucins
0
Albumins
0
Cyclobutanes
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
562-569Informations de copyright
© 2022 The Authors. Photochemistry and Photobiology published by Wiley Periodicals LLC on behalf of American Society for Photobiology.
Références
Srinitha, B. (2021) Biomarkers and disease diagnosis. Prim. Heal. Care Open Access 11, 375.
Broza, Y. Y., X. Zhou, M. Yuan, D. Qu, Y. Zheng, R. Vishinkin, M. Khatib, W. Wu and H. Haick (2019) Disease detection with molecular biomarkers: From chemistry of body fluids to nature-inspired chemical sensors. Chem. Rev. 119, 11761-11817. https://doi.org/10.1021/acs.chemrev.9b00437
Füzéry, A. K., J. Levin, M. M. Chan and D. W. Chan (2013) Translation of proteomic biomarkers into FDA approved cancer diagnostics: Issues and challenges. Clin. Proteomics 10, 13. https://doi.org/10.1186/1559-0275-10-13
Ma, J., B. K. Rubin and J. A. Voynow (2018) Mucins, mucus, and goblet cells. Chest 154, 169-176. https://doi.org/10.1016/j.chest.2017.11.008
Petrou, G. and T. Crouzier (2018) Mucins as multifunctional building blocks of biomaterials. Biomater. Sci. 6, 2282-2297. https://doi.org/10.1039/c8bm00471d
Kufe, D. W. (2009) Mucins in cancer: Function, prognosis and therapy. Nat. Rev. Cancer 9, 874-885. https://doi.org/10.1038/nrc2761
Hollingsworth, M. A. and B. J. Swanson (2004) Mucins in cancer: Protection and control of the cell surface. Nat. Rev. Cancer 4, 45-60. https://doi.org/10.1038/nrc1251
Bhatia, R., S. K. Gautam, A. Cannon, C. Thompson, B. R. Hall, A. Aithal, K. Banerjee, M. Jain, J. C. Solheim, S. Kumar and S. K. Batra (2019) Cancer-associated mucins: Role in immune modulation and metastasis. Cancer Metastasis Rev. 38, 223-236. https://doi.org/10.1007/s10555-018-09775-0
Wi, D. H., J. H. Cha and Y. S. Jung (2021) Mucin in cancer: A stealth cloak for cancer cells. BMB Rep. 54, 344-355. https://doi.org/10.5483/BMBRep.2021.54.7.064
Behrens, M. E., P. M. Grandgenett, J. M. Bailey, P. K. Singh, C. H. Yi, F. Yu and M. A. Hollingsworth (2010) The reactive tumor microenvironment: MUC1 signaling directly reprograms transcription of CTGF. Oncogene 29, 5667-5677. https://doi.org/10.1038/onc.2010.327
Wang, S., L. You, M. Dai and Y. Zhao (2020) Mucins in pancreatic cancer: A well-established but promising family for diagnosis, prognosis and therapy. J. Cell. Mol. Med. 24, 10279-10289. https://doi.org/10.1111/jcmm.15684
Croce, M. V., M. T. Isla-Larriain, S. O. Demichelis, J. R. Gori, M. R. Price and A. Segal-Eiras (2003) Tissue and serum MUCl mucin detection in breast cancer patients. Cancer Res. Treat. 81, 195-207.
Ding, Y., J. Ling, H. Wang, J. Zou, K. Wang, X. Xiao and M. Yang (2015) Fluorescent detection of mucin 1 protein based on aptamer functionalized biocompatible carbon dots and graphene oxide. Anal. Methods 7, 7792-7798. https://doi.org/10.1039/c5ay01680k
Wang, W., Y. Wang, H. Pan, S. Cheddah and C. Yan (2019) Aptamer-based fluorometric determination for mucin 1 using gold nanoparticles and carbon dots. Microchim. Acta 186, 544. https://doi.org/10.1007/s00604-019-3516-4
He, Y., Y. Lin, H. Tang and D. Pang (2012) A graphene oxide-based fluorescent aptasensor for the turn-on detection of epithelial tumor marker mucin 1. Nanoscale 4, 2054-2059. https://doi.org/10.1039/c2nr12061e
Barbero, N., C. Butnarasu, S. Visentin and C. Barolo (2019) Squaraine dyes: Interaction with bovine serum albumin to investigate supramolecular adducts with aggregation-induced emission (AIE) properties. Chem. Asian J. 14, 896-903. https://doi.org/10.1002/asia.201900055
Xie, S., A. Y. H. Wong, S. Chen and B. Z. Tang (2019) Fluorogenic detection and characterization of proteins by aggregation-induced emission methods. Chem. Eur. J. 25, 5824-5847. https://doi.org/10.1002/chem.201805297
Butnarasu, C., N. Barbero, C. Barolo and S. Visentin (2020) Squaraine dyes as fluorescent turn-on sensors for the detection of porcine gastric mucin: A spectroscopic and kinetic study. J. Photochem. Photobiol. B Biol. 205, 111838. https://doi.org/10.1016/j.jphotobiol.2020.111838
Butnarasu, C., N. Barbero, C. Barolo and S. Visentin (2021) Interaction of squaraine dyes with proteins: Looking for more efficient fluorescent turn-on probes. Dye. Pigment. 184, 108873. https://doi.org/10.1016/j.dyepig.2020.108873
Serpe, L., S. Ellena, N. Barbero, F. Foglietta, F. Prandini, M. P. Gallo, R. Levi, C. Barolo, R. Canaparo and S. Visentin (2016) Squaraines bearing halogenated moieties as anticancer photosensitizers: Synthesis, characterization and biological evaluation. Eur. J. Med. Chem. 113, 187-197. https://doi.org/10.1016/j.ejmech.2016.02.035
Chinigò, G., A. Gonzalez-Paredes, A. Gilardino, N. Barbero, C. Barolo, P. Gasco, A. Fiorio Pla and S. Visentin (2022) Polymethine dyes-loaded solid lipid nanoparticles (SLN) as promising photosensitizers for biomedical applications. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 271, 120909. https://doi.org/10.1016/j.saa.2022.120909
Matsui, M., M. Fukushima, Y. Kubota, K. Funabiki and M. Shiro (2012) Solid-state fluorescence of squarylium dyes. Tetrahedron 68, 1931-1935. https://doi.org/10.1016/j.tet.2011.12.067
Barbero, N., C. Magistris, J. Park, D. Saccone, P. Quagliotto, R. Buscaino, C. Medana, C. Barolo and G. Viscardi (2015) Microwave-assisted synthesis of near-infrared fluorescent indole-based Squaraines. Org. Lett. 17, 3306-3309. https://doi.org/10.1021/acs.orglett.5b01453
Käsdorf, B. T., F. Weber, G. Petrou, V. Srivastava, T. Crouzier and O. Lieleg (2017) Mucin-inspired lubrication on hydrophobic surfaces. Biomacromolecules 18, 2454-2462. https://doi.org/10.1021/acs.biomac.7b00605
Sigurdsson, H. H., J. Kirch and C. M. Lehr (2013) Mucus as a barrier to lipophilic drugs. Int. J. Pharm. 453, 56-64. https://doi.org/10.1016/j.ijpharm.2013.05.040
Butnarasu, C., N. Barbero, D. Pacheco, P. Petrini and S. Visentin (2019) Mucin binding to therapeutic molecules: The case of antimicrobial agents used in cystic fibrosis. Int. J. Pharm. 564, 136-144. https://doi.org/10.1016/j.ijpharm.2019.04.032
Witten, J. and K. Ribbeck (2017) The particle in the spider's web: Transport through biological hydrogels. Nanoscale 9, 8080-8095. https://doi.org/10.1039/C6NR09736G
Butnarasu, C., G. Caron, D. Peneda Pacheco, P. Petrini and S. Visentin (2021) Cystic fibrosis mucus model to design more efficient drug therapies. Mol. Pharm. 19, 520-531. https://doi.org/10.1021/acs.molpharmaceut.1c00644
McShane, A., J. Bath, A. M. Jaramillo, C. Ridley, A. A. Walsh, C. M. Evans, D. J. Thornton and K. Ribbeck (2021) Mucus. Curr. Biol. 31, R938-R945. https://doi.org/10.1016/j.cub.2021.06.093
Frenkel, E. S. and K. Ribbeck (2015) Salivary mucins in host defense and disease prevention. J. Oral Microbiol. 7, 29759. https://doi.org/10.3402/jom.v7.29759
Skoog, E. C., Å. Sjöling, N. Navabi, J. Holgersson, S. B. Lundin and S. K. Lindén (2012) Human gastric mucins differently regulate Helicobacter pylori proliferation, gene expression and interactions with host cells. PLoS One 7, e36378.
Hansson, G. C. (2020) Mucins and the microbiome. Annu. Rev. Biochem. 89, 769-793. https://doi.org/10.1146/annurev-biochem-011520-105053
Pelosi, C., F. Saitta, C. Zerino, G. Canil, T. Biver, A. Pratesi, C. Duce, D. Fessas, C. Gabbiani and M. R. Tiné (2021) Thermodynamic evaluation of the interactions between anticancer Pt(II) complexes and model proteins. Molecules 26, 2376. https://doi.org/10.3390/molecules26082376
Thordarson, P. (2011) Determining association constants from titration experiments in supramolecular chemistry. Chem. Soc. Rev. 40, 1305-1323. https://doi.org/10.1039/C0CS00062K
Liu, T., X. Liu, W. Wang, Z. Luo, M. Liu, S. Zou, C. Sissa, A. Painelli, Y. Zhang, M. Vengris, M. V. Bondar, D. J. Hagan, E. W. Van Stryland, Y. Fang and K. D. Belfield (2018) Systematic molecular engineering of a series of aniline-based Squaraine dyes and their structure-related properties. J. Phys. Chem. C 122, 3994-4008. https://doi.org/10.1021/acs.jpcc.7b11997
Wang, G., W. Xu, Y. Guo and N. Fu (2017) Near-infrared squaraine dye as a selective protein sensor based on self-assembly. Sens. Actuators B 245, 932-937. https://doi.org/10.1016/j.snb.2017.01.172
Hendler, N., B. Belgorodsky, E. D. Mentovich, M. Gozin and S. Richter (2011) Efficient separation of dyes by mucin: Toward bioinspired white-luminescent devices. Adv. Mater. 23, 4261-4264. https://doi.org/10.1002/adma.201100529
Belgorodsky, B., E. Drug, L. Fadeev, N. Hendler, E. Mentovich and M. Gozin (2010) Mucin complexes of nanomaterials: First biochemical encounter. Small 6, 262-269. https://doi.org/10.1002/smll.200900637
Samad, T., J. Witten, A. J. Grodzinsky and K. Ribbeck (2022) Spatial configuration of charge and hydrophobicity tune particle transport through mucus. Biophys. J. 121, 277-287. https://doi.org/10.1016/j.bpj.2021.12.018