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Journal articles on the topic 'Pentamethine cyanine dyes'

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Published: 4 June 2025

Last updated: 1 August 2025

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1

Hassan, Abazied Shindy, Abdallah El-Maghraby Mohamed, Mubark Goma Maha, and Abdelrahman Harb Nemat. "Dicarbocyanine and tricarbocyanine dyes: Novel synthetic approaches, photosensitization evaluation and antimicrobial screening." Chemistry International 6, no. 1 (2020): 30–41. https://doi.org/10.5281/zenodo.2631739.

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Novel dicarbocyanine dyes (pentamethine cyanine dyes), bis dicarbocyanine dyes (bis pentamethine cyanine dyes), tricarbocyanine dyes (heptamethine cyanine dyes) and bis tricarbocyanine dyes (bis heptamethine cyanine dyes) derived from the nucleus of furo[(3,2-d)pyrazole; (3',2'-d)oxazole] were prepared using novel synthetic approaches. The electronic visible absorption spectra were investigated in 95% ethanol to evaluate the photosensitization properties. The cyanine dyes were better photosensitizers in visible light to initiate the electronic transitions at higher wavelength bands (ba

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2

Slavicek, Petr, Šárka Paušová, and Karel Bouzek. "Thermal Truncation of Heptamethine Cyanine Dyes." Journal of the American Chemical Society 146, no. 29 (2024): 19768–81. https://doi.org/10.1021/jacs.4c02116.

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Cyanine dyes are a class of organic, usually cationic molecules containing two nitrogen centers linked through conjugated polymethine chains. Unlike phototruncation, the thermal truncation (chain-shortening) reaction is a phenomenon that has rarely been described for these important fluorophores. Here, we present a systematic investigation of the truncation of heptamethine cyanines (Cy7) to pentamethine (Cy5) and trimethine (Cy3) cyanines via homogeneous, acid-base catalyzed nucleophilic exchange reactions. We demonstrate how different substituents at the C3′ and C4′ positions of t

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3

Chapman, Gala, Maged Henary, and Gabor Patonay. "The Effect of Varying Short-Chain Alkyl Substitution on the Molar Absorptivity and Quantum Yield of Cyanine Dyes." Analytical Chemistry Insights 6 (January 2011): ACI.S6568. http://dx.doi.org/10.4137/aci.s6568.

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The effect of varying short-chain alkyl substitution of the indole nitrogens on the spectroscopic properties of cyanine dyes was examined. Molar absorptivities and fluorescence quantum yields were determined for a set of pentamethine dyes and a set of heptamethine dyes for which the substitution of the indole nitrogen was varied. For both sets of dyes, increasing alkyl chain length resulted in no significant change in quantum yield or molar absorptivity. These results may be useful in designing new cyanine dyes for analytical applications and predicting their spectroscopic properties.

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4

Dost, Tyler L., Michael T. Gressel, and Maged Henary. "Synthesis and Optical Properties of Pentamethine Cyanine Dyes With Carboxylic Acid Moieties." Analytical Chemistry Insights 12 (January 1, 2017): 117739011771193. http://dx.doi.org/10.1177/1177390117711938.

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Cyanine dyes possessing carboxylic acid groups have been used in many different fields of study. The acid groups can act as handles for bioconjugation or as metal chelators. Several pentamethine cyanine dyes with propionic acid handles were synthesized and their optical properties were studied to determine their usefulness as fluorescent probes. The optical properties studies performed include the absorbance and emission maxima values as well as the calculation of quantum yield and molecular brightness levels. Molecular models were also calculated to help analyze the dyes’ behavior and were co

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5

Aristova, D., G. Volynets, S. Chernii, et al. "Far-red pentamethine cyanine dyes as fluorescent probes for the detection of serum albumins." Royal Society Open Science 7, no. 7 (2020): 200453. http://dx.doi.org/10.1098/rsos.200453.

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Benzothiazole based cyanine dyes with bridged groups in the pentamethine chain were studied as potential far-red fluorescent probes for protein detection. Spectral-luminescent properties were characterized for unbound dyes and in the presence of serum albumins (bovine (BSA), human (HSA), equine (ESA)), and globular proteins (β-lactoglobulin, ovalbumin). We have observed that the addition of albumins leads to a significant increase in dyes fluorescence intensity. However, the fluorescent response of dyes in the presence of other globular proteins was notably lower. The value of fluorescence qua

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6

Rozovsky, Alex, Leonid Patsenker, and Gary Gellerman. "Bifunctional reactive pentamethine cyanine dyes for biomedical applications." Dyes and Pigments 162 (March 2019): 18–25. http://dx.doi.org/10.1016/j.dyepig.2018.09.064.

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7

Lange, Natalia, Wojciech Szlasa, Jolanta Saczko, and Agnieszka Chwiłkowska. "Potential of Cyanine Derived Dyes in Photodynamic Therapy." Pharmaceutics 13, no. 6 (2021): 818. http://dx.doi.org/10.3390/pharmaceutics13060818.

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Photodynamic therapy (PDT) is a method of cancer treatment that leads to the disintegration of cancer cells and has developed significantly in recent years. The clinically used photosensitizers are primarily porphyrin, which absorbs light in the red spectrum and their absorbance maxima are relatively short. This review presents group of compounds and their derivatives that are considered to be potential photosensitizers in PDT. Cyanine dyes are compounds that typically absorb light in the visible to near-infrared-I (NIR-I) spectrum range (750–900 nm). This meta-analysis comprises the current s

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8

Ndaleh, David, Cameron Smith, Mahesh Loku Yaddehige, et al. "Shortwave Infrared Absorptive and Emissive Pentamethine-Bridged Indolizine Cyanine Dyes." Journal of Organic Chemistry 86, no. 21 (2021): 15376–86. http://dx.doi.org/10.1021/acs.joc.1c01908.

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9

Mehranpour, Abdolmohammad, Sedigheh Hashemnia, Fereshteh Azamifar, and Elham Bashiri. "Synthesis and Characterization of New Quinoline Bounded Pentamethine Cyanine Dyes." Organic Preparations and Procedures International 52, no. 5 (2020): 458–62. http://dx.doi.org/10.1080/00304948.2020.1780881.

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10

Mehranpour, A. M., S. Hashemnia та R. Maghamifar. "Synthesis and Characterization of New γ-Substituted Pentamethine Cyanine Dyes". Synthetic Communications 40, № 24 (2010): 3594–602. http://dx.doi.org/10.1080/00397910903457290.

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11

Zhytniakivska, Olga, Uliana Tarabara, Kateryna Vus, Valeriya Trusova, and Galyna Gorbenko. "Simultaneous Docking of Antiviral Drugs and Cyanine Dyes with Proteins Using Multiple Ligand Approach." East European Journal of Physics, no. 4 (December 2, 2023): 318–25. http://dx.doi.org/10.26565/2312-4334-2023-4-42.

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The protein-based nanosystems for targeted drug delivery of a wide array of substances, ranging from small drugs and therapeutic proteins to nucleic acids and genes, attract increasing attention due to their biocompatibility and biodegradability, extraordinary binding capacity for different ligands, accessibility from natural sources, effective drug protection and gentle encapsulation conditions. Due to the multitude of binding pockets and functional groups on the protein surface, these nanocarriers seem to be highly efficient multifunctional nanotheranostic systems that could incorporate both

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12

Hassan, Naglaa, Sara Gamea, Reda Abd El-Aal, Ahmed Koraiem, and Hussein El-Damarany. "Novel Eco-Friendly Curcumin Pentamethine Cyanine Dyes as Photosensitizers and Antitumor." Aswan University Journal of Environmental Studies 5, no. 3 (2024): 351–71. http://dx.doi.org/10.21608/aujes.2024.298048.1256.

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13

Abd El-Aal, R. M., N. M. Saber, S. M. Mina, and Z. M. Essam. "Synthesis and physicochemical studies of some new quinolinoxazine pentamethine cyanine dyes." Arabian Journal of Chemistry 10, no. 1 (2017): 82–90. http://dx.doi.org/10.1016/j.arabjc.2012.06.003.

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14

Nanjunda, Rupesh, Eric A. Owens, Leah Mickelson, et al. "Halogenated pentamethine cyanine dyes exhibiting high fidelity for G-quadruplex DNA." Bioorganic & Medicinal Chemistry 20, no. 24 (2012): 7002–11. http://dx.doi.org/10.1016/j.bmc.2012.10.008.

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15

Mehranpour, A. M., S. Hashemnia та R. Maghamifar. "ChemInform Abstract: Synthesis and Characterization of New δ-Substituted Pentamethine Cyanine Dyes." ChemInform 42, № 16 (2011): no. http://dx.doi.org/10.1002/chin.201116199.

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16

Ciubini, Betty, Sonja Visentin, Loredana Serpe, Roberto Canaparo, Andrea Fin, and Nadia Barbero. "Design and synthesis of symmetrical pentamethine cyanine dyes as NIR photosensitizers for PDT." Dyes and Pigments 160 (January 2019): 806–13. http://dx.doi.org/10.1016/j.dyepig.2018.09.009.

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17

Kovalska, V. B., M. Yu Losytskyy, O. I. Tolmachev та ін. "Tri- and Pentamethine Cyanine Dyes for Fluorescent Detection of α-Synuclein Oligomeric Aggregates". Journal of Fluorescence 22, № 6 (2012): 1441–48. http://dx.doi.org/10.1007/s10895-012-1081-x.

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18

Ahoulou, Effibe O., Kaitlyn K. Drinkard, Kanchan Basnet, et al. "DNA Photocleavage in the Near-Infrared Wavelength Range by 2-Quinolinium Dicarbocyanine Dyes." Molecules 25, no. 12 (2020): 2926. http://dx.doi.org/10.3390/molecules25122926.

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Here, we report the syntheses of two pentamethine cyanine dyes containing quinolinium rings and substituted with either hydrogen (3) or bromine (4) at the meso carbon. The electron withdrawing bromine atom stabilizes dye 4 in aqueous buffer, allowing complex formation to occur between the dye and double-helical DNA. UV–visible, CD, and fluorescence spectra recorded at low DNA concentrations suggest that dye 4 initially binds to the DNA as a high-order aggregate. As the ratio of DNA to dye is increased, the aggregate is converted to monomeric and other low-order dye forms that interact with DNA

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19

Meguellati, Kamel, Martin Spichty, and Sylvain Ladame. "Reversible Synthesis and Characterization of Dynamic Imino Analogues of Trimethine and Pentamethine Cyanine Dyes." Organic Letters 11, no. 5 (2009): 1123–26. http://dx.doi.org/10.1021/ol802913b.

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20

Biaggne, Austin, William B. Knowlton, Bernard Yurke, Jeunghoon Lee, and Lan Li. "Substituent Effects on the Solubility and Electronic Properties of the Cyanine Dye Cy5: Density Functional and Time-Dependent Density Functional Theory Calculations." Molecules 26, no. 3 (2021): 524. http://dx.doi.org/10.3390/molecules26030524.

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The aggregation ability and exciton dynamics of dyes are largely affected by properties of the dye monomers. To facilitate aggregation and improve excitonic function, dyes can be engineered with substituents to exhibit optimal key properties, such as hydrophobicity, static dipole moment differences, and transition dipole moments. To determine how electron donating (D) and electron withdrawing (W) substituents impact the solvation, static dipole moments, and transition dipole moments of the pentamethine indocyanine dye Cy5, density functional theory (DFT) and time-dependent (TD-) DFT calculatio

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21

Abed El-Aal, R. M., and A. I. M. Koraiem. "Synthesis and photophysics in organic solvents of mesosubstituted pentamethine and related metal complexes cyanine dyes." Dyes and Pigments 54, no. 2 (2002): 121–29. http://dx.doi.org/10.1016/s0143-7208(02)00034-7.

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22

Sun, Ru, Bao-Long Yan, Jian-Feng Ge, et al. "Third-order nonlinear optical properties of unsymmetric pentamethine cyanine dyes possessing benzoxazolyl and benzothiazolyl groups." Dyes and Pigments 96, no. 1 (2013): 189–95. http://dx.doi.org/10.1016/j.dyepig.2012.07.007.

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23

Losytskyy, M. Yu, K. D. Volkova, V. B. Kovalska, et al. "Fluorescent Properties of Pentamethine Cyanine Dyes with Cyclopentene and Cyclohexene Group in Presence of Biological Molecules." Journal of Fluorescence 15, no. 6 (2005): 849–57. http://dx.doi.org/10.1007/s10895-005-0002-7.

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24

Owens, Eric A., Nicholas Bruschi, Joseph G. Tawney, and Maged Henary. "A microwave-assisted and environmentally benign approach to the synthesis of near-infrared fluorescent pentamethine cyanine dyes." Dyes and Pigments 113 (February 2015): 27–37. http://dx.doi.org/10.1016/j.dyepig.2014.07.035.

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25

Mehranpour, A. M., S. Hashemnia та F. Azamifar. "Synthesis and Characterization of γ-Heteroaryl-substituted Pentamethine Cyanine Dyes with Carboxy or Methoxycarbonyl Substituents at the Two Heterocyclic End Groups". Journal of Heterocyclic Chemistry 51, № 5 (2014): 1457–62. http://dx.doi.org/10.1002/jhet.1816.

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26

Habashi, Fatemeh, Abdolmohammad Mehranpour та Enayatollah Bahman Jahromi. "Synthesis and characterization of new derivatives of bis(1,4‐diazepinium) salts and bis(γ‐substituted pentamethine cyanine(dyes using vinamidinium salt". Journal of Heterocyclic Chemistry 57, № 6 (2020): 2428–32. http://dx.doi.org/10.1002/jhet.3958.

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27

Kurutos, Atanas, Olga Ryzhova, Valeriya Trusova, Galyna Gorbenko, Nikolay Gadjev, and Todor Deligeorgiev. "Symmetric Meso-Chloro-Substituted Pentamethine Cyanine Dyes Containing Benzothiazolyl/Benzoselenazolyl Chromophores Novel Synthetic Approach and Studies on Photophysical Properties upon Interaction with bio-Objects." Journal of Fluorescence 26, no. 1 (2015): 177–87. http://dx.doi.org/10.1007/s10895-015-1700-4.

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28

KOGURE, Kentaro, Hironori SASSA, Kazutoyo ABE, et al. "Inhibitory Effects of Pentamethine Trinuclear Cyanine Dyes on ADP/Fe2+-Induced Lipid Peroxidation in Rat Liver Mitochondria: Changes in the Mode of Action with the Hydrophobic Nature of the Dyes." Biological & Pharmaceutical Bulletin 21, no. 2 (1998): 180–83. http://dx.doi.org/10.1248/bpb.21.180.

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29

Zhytniakivska, Olga, Uliana Tarabara, Pylyp Kuznietsov, Kateryna Vus, Valeriya Trusova, and Galyna Gorbenko. "Molecular Docking Study of the Interactions Between Cyanine Dyes And DNA." East European Journal of Physics, no. 2 (June 2, 2023): 335–40. http://dx.doi.org/10.26565/2312-4334-2023-2-39.

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Among the various fluorescent probes currently used for biomedical and biochemical studies, significant attention attracts cyanine dyes possessing advantageous properties upon their complexation with biomolecules, particularly nucleic acids. Given the wide range of cyanine applications in DNA studies, a better understanding of their binding mode and intermolecular interactions governing dye-DNA complexation would facilitate the synthesis of new molecular probes of the cyanine family with optimized properties and would be led to the development of new cyanine-based strategies for nucleic acid d

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30

Azamifar, Fereshteh, M. Reza Naimi-Jamal, Oleg M. Demchuk, and Agnieszka Szmagara. "Efficient synthesis and characterization of meso-substituted bis(benzothiazolium) pentamethine cyanine dyes and investigation of the impact of meso-substitution on water solubility and the structural rigidity to improve photophysical properties and fluorescent brightness." Dyes and Pigments 218 (October 2023): 111519. http://dx.doi.org/10.1016/j.dyepig.2023.111519.

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31

Buß, Volker, та Christian Reichardt. "Chiral dimers of a chiral pentamethine cyanine dye and of an achiral pentamethine cyanine dye in γ-cyclodextrin as chiral host". J. Chem. Soc., Chem. Commun., № 22 (1992): 1636–38. http://dx.doi.org/10.1039/c39920001636.

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32

Reimann, Louise Kommers, Daniela de Souza Fortes, Fabiano da Silveira Santos, et al. "Near-Infrared-Emitting Meso-Substituted Heptamethine Cyanine Dyes: From the Synthesis and Photophysics to Their Use in Bioimaging." Chemosensors 11, no. 1 (2023): 47. http://dx.doi.org/10.3390/chemosensors11010047.

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Heptamethine cyanine dyes were synthesized in good yields by the reaction between quaternary indoles and a pentamethinic salt, under mild reaction conditions minimizing photooxidation. These compounds were used as precursors to prepare meso-substituted derivatives. The cyanine dye precursors presented UV-Vis absorption, related to fully allowed electronic transitions and fluorescence emission in the NIR region, without any evidence of aggregation in both ground and excited states. The substitution at the meso position showed a fundamental role in their photophysics, with the main absorption in

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33

Zhang, Xiu-Fu, Jun-Long Zhao, Wei-Bin Bi, Dan-Dan Zhang, Zhi-Yuan Yang, and Lan-Ying Wang. "Synthesis, Crystal Structure, Spectral and Thermodynamic Properties of One Benzoindole Pentamethine Cyanine Dye." Journal of the Chinese Chemical Society 60, no. 5 (2013): 503–10. http://dx.doi.org/10.1002/jccs.201200405.

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34

Yao, Hiroshi, and Tomoki Enseki. "Size-dependent spectral linewidth narrowing of H-bands in organic nanoparticles of pentamethine cyanine dye." Journal of Photochemistry and Photobiology A: Chemistry 271 (November 2013): 124–29. http://dx.doi.org/10.1016/j.jphotochem.2013.08.013.

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35

Han, Fuping, Syed Ali Abbas Abedi, Shan He, et al. "Aryl‐Modified Pentamethyl Cyanine Dyes at the C2’ Position: A Tunable Platform for Activatable Photosensitizers." Advanced Science, December 8, 2023. http://dx.doi.org/10.1002/advs.202305761.

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AbstractPentamethyl cyanine dyes are promising fluorophores for fluorescence sensing and imaging. However, advanced biomedical applications require enhanced control of their excited‐state properties. Herein, a synthetic approach for attaching aryl substituents at the C2’ position of the thio‐pentamethine cyanine (TCy5) dye structure is reported for the first time. C2’‐aryl substitution enables the regulation of both the twisted intramolecular charge transfer (TICT) and photoinduced electron transfer (PET) mechanisms to be regulated in the excited state. Modulation of these mechanisms allows th

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36

Laramie, Matthew D., Benjamin L. Fouts, William M. MacCuaig, et al. "Improved pentamethine cyanine nanosensors for optoacoustic imaging of pancreatic cancer." Scientific Reports 11, no. 1 (2021). http://dx.doi.org/10.1038/s41598-021-83658-3.

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AbstractOptoacoustic imaging is a new biomedical imaging technology with clear benefits over traditional optical imaging and ultrasound. While the imaging technology has improved since its initial development, the creation of dedicated contrast agents for optoacoustic imaging has been stagnant. Current exploration of contrast agents has been limited to standard commercial dyes that have already been established in optical imaging applications. While some of these compounds have demonstrated utility in optoacoustic imaging, they are far from optimal and there is a need for contrast agents with

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37

Uspenskaia, Anastasiia A., Irina A. Doroshenko, Kseniia A. Popovicheva, et al. "Pentamethine cyanine dyes with alkynyl group as perspective structure for conjugation with targeting moiety." Bioorganic & Medicinal Chemistry Letters, November 2024, 130025. http://dx.doi.org/10.1016/j.bmcl.2024.130025.

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38

REICHARDT, C., and U. BUDNIK. "ChemInform Abstract: Syntheses with Aliphatic Dialdehydes. Part 44. Chiral Pentamethine Cyanine Dyes and Heterocycles from Derivatives of (S)-(+)-2-sec-Butylmalonaldehyde." ChemInform 21, no. 51 (1990). http://dx.doi.org/10.1002/chin.199051345.

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39

Huang, Haiqiao, Qiang Liu, Jing‐Hui Zhu, et al. "Dimerized Pentamethine Cyanines for Synergistically Boosting Photodynamic/Photothermal Therapy." Aggregate, November 18, 2024. http://dx.doi.org/10.1002/agt2.706.

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ABSTRACTPhotodynamic therapy (PDT) and photothermal therapy (PTT) have emerged promising applications in both fundamental research and clinical trials. However, it remains challenging to develop ideal photosensitizers (PSs) that concurrently integrate high photostability, large near‐infrared absorptivity, and efficient therapeutic capabilities. Herein, we reported a sample engineering strategy to afford a benzene‐fused Cy5 dimer (Cy‐D‐5) for synergistically boosting PDT/PTT applications. Intriguingly, Cy‐D‐5 exhibits a tendency to form both J‐aggregates and H‐aggregates in phosphate‐buffered s

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40

Lin, Helen, Irene Lim, and Ellen May Sletten. "Counterion Exchange Enhances the Brightness and Photostability of a Fluorous Cyanine Dye." Chemistry – A European Journal, September 4, 2024. http://dx.doi.org/10.1002/chem.202402514.

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Fluorofluorophores are a unique class of fluorophores that can be solubilized in perfluorocarbons (PFCs) and used to study biological systems. However, because of the low dielectric constant and high oxygen solubility in the fluorous phase, the brightness and photostability of the fluorofluorophores are significantly diminished. Here, we leveraged the tight ion pairing in the fluorous phase to improve the photophysical properties of a fluorous soluble pentamethine dye (FCy5) via counterion exchange. We found that larger, softer, fluorinated, aryl borate counterions promote the ideal polymethin

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41

Shi, Tiancong, Xi Chen, Xiao Zhou, et al. "Azaindole-based asymmetric pentamethine cyanine dye for mitochondrial pH detection and near-infrared ratiometric fluorescence imaging of mitophagy." Chinese Chemical Letters, September 2024, 110408. http://dx.doi.org/10.1016/j.cclet.2024.110408.

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