Benz[c,d]indolium-containing Monomethine Cyanine Dyes: Synthesis and Photophysical Properties

Soriano, Eduardo; Holder, Cory; Levitz, Andrew; Henary, Maged

doi:10.3390/molecules21010023

Cited by 28 publications

(35 citation statements)

References 70 publications

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“…General Procedure for Obtaining Title Compounds, Using 5a as Example The known intermediate 2 was prepared by a conventional method using concentrated nitric acid in glacial acetic acid (Gryshchenko et al, 2015;Soriano et al, 2016). A solution containing 3 (1 mmol) in CH 3 CN (5 mL) at 0 • C was added to a solution of 2 (1 mmol) and K 2 CO 3 in CH 3 CN (10 mL).…”

Section: Methodsmentioning

confidence: 99%

“…We also established the detail on the feasible routes of the linkers 3 and 8 in the Supporting Information. We prepared known intermediate 2 by a conventional method using concentrated nitric acid in glacial acetic acid (Gryshchenko et al, 2015;Soriano et al, 2016). Generated intermediate 2 reacted with diverse protected polyamines 3 and 8 to give compounds 4 and 9.…”

Section: Synthesis and Characterization Of Polyamine-based Naphthalimidementioning

confidence: 99%

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A Polyamine-Based Dinitro-Naphthalimide Conjugate as Substrates for Polyamine Transporters Preferentially Accumulates in Cancer Cells and Minimizes Side Effects in vitro and in vivo

et al. 2020

Front. Chem.

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Naphthalimides, such as amonafide and mitonafide in clinical trials, have been developed as antitumor agents for orthotopic tumor. However, the serious side effects in cancer patients limit their applications. Herein, a new class of polyamine-based naphthalimide conjugates 5a-5c, 7a-7b, and 11a-11b with and without the alkylation of the distant nitrogen in the polyamine chain were synthesized and the mechanism was determined. Compared with amonafide, dinitro-naphthalimide conjugate 5c with a 4,3-cyclopropyl motif preferentially accumulates in cancer cells and minimizes side effects in vitro and in vivo. More importantly, 5c at the dosage of as low as 3 mg/kg (57.97%) displays better antitumor effects than the positive control amonafide (53.27%) at 5 mg/kg in vivo. And a remarkably elevated antitumor activity and a reduced toxicity are also observed for 5c at 5 mg/kg (65.90%). The upregulated p53 and the apoptotic cells (73.50%) indicate that the mechanism of 5c to induce apoptosis may result from its enhanced DNA damage. Further investigation indicates that in addition to target DNA, 5c can modulate the polyamine homeostasis by upregulating polyamine oxidase (PAO) in a different way from that of amonafide. And also by targeting PTs overexpressed in most of cancer cells, 5c downregulates the contents of Put, Spd, and Spm, which are in favor of suppressing fast-growing tumor cells. Our study implies a promising strategy for naphthalimide conjugates to treat hepatic carcinoma with notable activities and reduced toxicities at a low dosage.

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Section: Methodsmentioning

confidence: 99%

Section: Synthesis and Characterization Of Polyamine-based Naphthalimidementioning

confidence: 99%

A Polyamine-Based Dinitro-Naphthalimide Conjugate as Substrates for Polyamine Transporters Preferentially Accumulates in Cancer Cells and Minimizes Side Effects in vitro and in vivo

et al. 2020

Front. Chem.

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“…The synthesis, properties and applications of cyanine dyes reflect the important and vital position of these dyes in the chemistry of dyes and pigments (Shindy et al, 2015;Soriano et al, 2016;Shindy 2017a;Shindy et al, 2017;Shindy 2016a;Shindy et al, 2016;Shindy et al, 2016a;Shindy et al, 2016b;Shindy et al, 2016c;Shindy et al, 2017a;Komljenovic et al, 2016;Zhang et al, 2016;Chen et al, 2016;Arjona et al, 2016;Shindy 2018;Shindy 2018a;Shindy et al, 2018;Shindy et al, 2018a;Shindy et al, 2019;Shindy et al, 2020).…”

Section: Synthesis Of Different Classes Of Five/six Membered Heterocymentioning

confidence: 99%

Synthesis of different classes of five/six membered heterocyclic cyanine dyes: A review

Int¹

2019

Preprint

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In this paper, synthesis of different classes of five/six membered heterocyclic cyanine dyes has been reviewed. In this paper review detailed synthesis steps were represented via equations. The synthesis covers, monomethine cyanine dyes (simple cyanine dyes), dimethine cyanine dyes, trimethine cyanine dyes (carbocyanine dyes), styryl cyanine dyes (hemicyanine dyes), aza-styryl cyanine dyes (aza-hemicyanine dyes and/or aza-cyanine dyes), merocyanine dyes (acyclic merocyanine dyes and cyclic merocyanine dyes) and apocyanine dyes. Besides, in the introduction section of this review paper some light is focused on the uses, applications and properties of cyanine dyes. This review paper is informative, useful and very readable for synthetic dye chemists, researchers and students who look for the different methods in the synthesis and preparation of various classes of five/six membered heterocyclic cyanine dyes with special emphasize in the field of heterocyclic and/or cyanine dyes chemistry. This specific type of collective review in the synthesis of different classes of only five/six membered heterocyclic cyanine dyes has been paid little attention and has great importance in the chemistry literature.

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“…One of the main factors that defines the intermolecular interaction is the chemical structure of molecule, which can be tuned to drive the structure of the condensed film overall and to change its physical properties, respectively. Monomethincyanine dyes belong to polymethine dyes serving as convenient model objects that allow one to understand how slight variation in the molecular structure can influence formation of the aggregate or bulk structure [4][5][6][7]. These dyes have relatively short length and are stable upon thermal evaporation in vacuum [8].…”

Section: Introductionmentioning

confidence: 99%

Tuned aggregation and film self-assembly of monomethincyanine dyes through variation of their monomer structure

Sieryk¹

2019

Semicond. Phys. Quantum Electron. and Optoelectron.

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Formation of condensed films and solution aggregates of four different monomethincyanine dyes have been studied using optical absorption spectroscopy and simulation methods, depending on variation of the dye monomer structure. The structure of molecular dimer as a basic unit for formation of the condensed state was found to be largely dependent on heteroatoms in the dye structure and the presence of end hydrocarbon groups. The above factors mainly determine the mutual position of molecules in the dimer. It has been found that mutual orientation, intermolecular distance and overlap of the adjacent molecules are the major factors influencing absorption spectra of dye aggregates. The dimer geometry that plays the primary role in film nucleation, however, has been shown to undergo changes depending on the temperature conditions or film thickness.

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Benz[c,d]indolium-containing Monomethine Cyanine Dyes: Synthesis and Photophysical Properties

Cited by 28 publications

References 70 publications

A Polyamine-Based Dinitro-Naphthalimide Conjugate as Substrates for Polyamine Transporters Preferentially Accumulates in Cancer Cells and Minimizes Side Effects in vitro and in vivo

A Polyamine-Based Dinitro-Naphthalimide Conjugate as Substrates for Polyamine Transporters Preferentially Accumulates in Cancer Cells and Minimizes Side Effects in vitro and in vivo

Synthesis of different classes of five/six membered heterocyclic cyanine dyes: A review

Tuned aggregation and film self-assembly of monomethincyanine dyes through variation of their monomer structure

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