Literature DB >> 31365819

Squaraine Dyes: Molecular Design for Different Applications and Remaining Challenges.

Kristina Ilina1, William M MacCuaig2, Matthew Laramie1, Jannatun N Jeouty1, Lacey R McNally2, Maged Henary1,3.   

Abstract

Squaraine dyes are a class of organic dyes with strong and narrow absorption bands in the near-infrared. Despite high molar absorptivities and fluorescence quantum yields, these dyes have been less explored than other dye scaffolds due to their susceptibility to nucleophilic attack. Recent strategies in probe design including encapsulation, conjugation to biomolecules, and new synthetic modifications have seen squaraine dyes emerging into the forefront of biomedical imaging and other applications. Herein, we provide a concise overview of (1) the synthesis of symmetrical and unsymmetrical squaraine dyes, (2) the relationship between structure and photophysical properties of squaraine dyes, and (3) current applications of squaraine dyes in the literature. Given the recent successes at overcoming the limitations of squaraine dyes, they show high potential in biological imaging, in photodynamic and photothermal therapies, and as molecular sensors.

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Year:  2019        PMID: 31365819      PMCID: PMC7845514          DOI: 10.1021/acs.bioconjchem.9b00482

Source DB:  PubMed          Journal:  Bioconjug Chem        ISSN: 1043-1802            Impact factor:   4.774


  70 in total

Review 1.  Life sciences require the third dimension.

Authors:  Philipp J Keller; Francesco Pampaloni; Ernst Hk Stelzer
Journal:  Curr Opin Cell Biol       Date:  2006-01-04       Impact factor: 8.382

2.  An Aggregating Amphiphilic Squaraine: A Light-up Probe That Discriminates Parallel G-Quadruplexes.

Authors:  Vincenzo Grande; Filippo Doria; Mauro Freccero; Frank Würthner
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-19       Impact factor: 15.336

3.  Aggregation-induced near-infrared absorption of squaraine dye in an albumin nanocomplex for photoacoustic tomography in vivo.

Authors:  Fei-Fei An; Zi-Jian Deng; Jun Ye; Jin-Feng Zhang; Yin-Long Yang; Chang-Hui Li; Cai-Jun Zheng; Xiao-Hong Zhang
Journal:  ACS Appl Mater Interfaces       Date:  2014-10-01       Impact factor: 9.229

4.  Oxidative cleavage of DNA by pentamethine carbocyanine dyes irradiated with long-wavelength visible light.

Authors:  Carla T Mapp; Eric A Owens; Maged Henary; Kathryn B Grant
Journal:  Bioorg Med Chem Lett       Date:  2013-11-25       Impact factor: 2.823

5.  Synthesis of squaraine-N-hydroxysuccinimide esters and their biological application as long-wavelength fluorescent labels.

Authors:  E Terpetschnig; H Szmacinski; A Ozinskas; J R Lakowicz
Journal:  Anal Biochem       Date:  1994-03       Impact factor: 3.365

6.  Synthesis, spectral properties, and detection limits of reactive squaraine dyes, a new class of diode laser compatible fluorescent protein labels.

Authors:  B Oswald; L Patsenker; J Duschl; H Szmacinski; O S Wolfbeis; E Terpetschnig
Journal:  Bioconjug Chem       Date:  1999 Nov-Dec       Impact factor: 4.774

Review 7.  Fluorescence imaging of tumors in vivo.

Authors:  Byron Ballou; Lauren A Ernst; Alan S Waggoner
Journal:  Curr Med Chem       Date:  2005       Impact factor: 4.530

Review 8.  Near-infrared light-mediated nanoplatforms for cancer thermo-chemotherapy and optical imaging.

Authors:  Zhenjiang Zhang; Jing Wang; Chunying Chen
Journal:  Adv Mater       Date:  2013-06-06       Impact factor: 30.849

9.  Real-time identification of liver cancers by using indocyanine green fluorescent imaging.

Authors:  Takeaki Ishizawa; Noriyoshi Fukushima; Junji Shibahara; Koichi Masuda; Sumihito Tamura; Taku Aoki; Kiyoshi Hasegawa; Yoshifumi Beck; Masashi Fukayama; Norihiro Kokudo
Journal:  Cancer       Date:  2009-06-01       Impact factor: 6.860

10.  Synthesis and Optical Properties of Pentamethine Cyanine Dyes With Carboxylic Acid Moieties.

Authors:  Tyler L Dost; Michael T Gressel; Maged Henary
Journal:  Anal Chem Insights       Date:  2017-05-30
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  16 in total

Review 1.  Development of Multispectral Optoacoustic Tomography as a Clinically Translatable Modality for Cancer Imaging.

Authors:  William M MacCuaig; Meredith A Jones; Oshaani Abeyakoon; Lacey R McNally
Journal:  Radiol Imaging Cancer       Date:  2020-11-20

2.  Water-Soluble NIR Absorbing and Emitting Indolizine Cyanine and Indolizine Squaraine Dyes for Biological Imaging.

Authors:  William E Meador; Shane A Autry; Riley N Bessetti; Jacqueline N Gayton; Alex S Flynt; Nathan I Hammer; Jared H Delcamp
Journal:  J Org Chem       Date:  2020-02-21       Impact factor: 4.354

3.  Fast and Durable Intraoperative Near-infrared Imaging of Ovarian Cancer Using Ultrabright Squaraine Fluorophores.

Authors:  Takeshi Fukuda; Shinya Yokomizo; Stefanie Casa; Hailey Monaco; Sophia Manganiello; Haoran Wang; Xiangmin Lv; Amy Daniel Ulumben; Chengeng Yang; Min-Woong Kang; Kazumasa Inoue; Masahiro Fukushi; Toshiyuki Sumi; Cheng Wang; Homan Kang; Kai Bao; Maged Henary; Satoshi Kashiwagi; Hak Soo Choi
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-26       Impact factor: 15.336

Review 4.  Nanotheranostics for Image-Guided Cancer Treatment.

Authors:  Isabel S Dennahy; Zheng Han; William M MacCuaig; Hunter M Chalfant; Anna Condacse; Jordan M Hagood; Juan C Claros-Sorto; Wajeeha Razaq; Jennifer Holter-Chakrabarty; Ronald Squires; Barish H Edil; Ajay Jain; Lacey R McNally
Journal:  Pharmaceutics       Date:  2022-04-22       Impact factor: 6.525

5.  Rotaxane rings promote oblique packing and extended lifetimes in DNA-templated molecular dye aggregates.

Authors:  Matthew S Barclay; Simon K Roy; Jonathan S Huff; Olga A Mass; Daniel B Turner; Christopher K Wilson; Donald L Kellis; Ewald A Terpetschnig; Jeunghoon Lee; Paul H Davis; Bernard Yurke; William B Knowlton; Ryan D Pensack
Journal:  Commun Chem       Date:  2021-02-18

6.  Structural Engineering of Fluorescent Self-Threaded Peptide Probes for Targeted Cell Imaging.

Authors:  Cynthia L Schreiber; Canjia Zhai; Bradley D Smith
Journal:  Photochem Photobiol       Date:  2021-05-21       Impact factor: 3.421

Review 7.  Polymethine dyes for PDT: recent advances and perspectives to drive future applications.

Authors:  Degnet Melese Dereje; Carlotta Pontremoli; Maria Jesus Moran Plata; Sonja Visentin; Nadia Barbero
Journal:  Photochem Photobiol Sci       Date:  2022-02-01       Impact factor: 3.982

8.  Shortwave infrared-absorbing squaraine dyes for all-organic optical upconversion devices.

Authors:  Karen Strassel; Wei-Hsu Hu; Sonja Osbild; Daniele Padula; Daniel Rentsch; Sergii Yakunin; Yevhen Shynkarenko; Maksym Kovalenko; Frank Nüesch; Roland Hany; Michael Bauer
Journal:  Sci Technol Adv Mater       Date:  2021-04-13       Impact factor: 8.090

9.  Probing biotin receptors in cancer cells with rationally designed fluorogenic squaraine dimers.

Authors:  Kyong T Fam; Mayeul Collot; Andrey S Klymchenko
Journal:  Chem Sci       Date:  2020-07-09       Impact factor: 9.825

Review 10.  Near-infrared fluorescent probes: a next-generation tool for protein-labeling applications.

Authors:  Shahi Imam Reja; Masafumi Minoshima; Yuichiro Hori; Kazuya Kikuchi
Journal:  Chem Sci       Date:  2020-10-23       Impact factor: 9.825

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