Synthesis, spectroscopic, physicochemical and structural characterization of tetrandrine-based macrocycles functionalized with acridine and anthracene groups: DNA binding and anti-proliferative activity

Calvillo-Páez, Viviana; Sotelo‐Mundo, Rogerio R.; Leyva-Peralta, Mario Alberto; Gálvez-Ruíz, Juan Carlos; Corona-Martínez, David Octavio; Moreno-Corral, Ramón; Escobar-Picos, Raymundo Enrique; Höpfl, Herbert; Juárez-Sánchez, J. Octavio; Lara, Karen Ochoa

doi:10.1016/j.cbi.2018.02.013

Cited by 24 publications

(29 citation statements)

References 36 publications

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“…[65] The developed receptors for nucleotides can also find applicationsa sa nti-proliferative agents for different cancer cell lines in the near future. [66]…”

Section: Application Of Receptors and Probes For Nucleotidesmentioning

confidence: 99%

“…An interesting work has been reported, in which the synthetic receptor can bind selectively specific trinucleotide repeats in RNA (CUG) reversing myotonia disease or in DNA (CCG) . The developed receptors for nucleotides can also find applications as anti‐proliferative agents for different cancer cell lines in the near future …”

Section: Application Of Receptors and Probes For Nucleotidesmentioning

confidence: 99%

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Molecular Receptors for Recognition and Sensing of Nucleotides

Agafontsev

Ravi

Shumilova

et al. 2018

Chemistry A European J

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Nucleotides are constituents of nucleic acids and they have a variety of functions in cellular metabolism. Synthetic receptors and sensors are required to reveal the role of nucleotides in living organisms and mechanisms of signal transduction events. In recent years, a large number of nucleotide‐selective synthetic receptors have been devised, which utilize different molecular designs and sensing mechanisms. This Minireview presents recent progress in the design of synthetic molecular receptors for selective recognition of nucleotides in aqueous solution. The binding properties of receptors and the origins of their selectivity for a particular nucleotide are discussed.

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“…[65] The developed receptors for nucleotides can also find applicationsa sa nti-proliferative agents for different cancer cell lines in the near future. [66]…”

Section: Application Of Receptors and Probes For Nucleotidesmentioning

confidence: 99%

Section: Application Of Receptors and Probes For Nucleotidesmentioning

confidence: 99%

Molecular Receptors for Recognition and Sensing of Nucleotides

Agafontsev

Ravi

Shumilova

et al. 2018

Chemistry A European J

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“…This work has inspired other groups to evaluate interactions between cyclophanes and nucleotides in aqueous solution . These macrocycles have also been found to interact with G‐quadruplex and show antiproliferative activity . Interestingly, bis‐naphthaline‐derived macrocycles and bis‐anthracene receptor 2 containing 2,2′‐oxybis(ethylamine) as linker can recognize thymine‐thymine mismatches in DNA (Figure ) .…”

Section: Introductionmentioning

confidence: 99%

“…[23][24][25][26][27][28][29] These macrocycles have also been found to interact with G-quadruplex [30] and showa ntiproliferativea ctivity. [31] Interestingly,b is-naphthaline-derived macrocycles and bis-anthracene receptor 2 containing 2,2'-oxybis(ethylamine) as linker can recognize thymine-thymine mismatches in DNA ( Figure 1). [11,26,32] Detailed studies have demonstrated that the fluorescenceo fr eceptor 2 is quenched after coordination to a single mismatched thymine residue in duplexes containing 16 AT and GC base pairs.…”

Section: Introductionmentioning

confidence: 99%

Anthracene‐Based Cyclophanes with Selective Fluorescent Responses for TTP and GTP: Insights into Recognition and Sensing Mechanisms

Agafontsev

Shumilova

Rüffer

et al. 2019

Chemistry A European J

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Three anthracene‐based cyclophanes were synthesized and their binding properties towards nucleoside triphosphates were studied. A new polycyclic amine derived from dearomatized anthracene was identified as a major side product in the cyclization reaction between 9,10‐anthracenedicarboxaldehyde and diethylenetriamine. Its structure was determined by single‐crystal X‐ray analysis. The cyclophanes were found to form 1:1 complexes with all nucleoside triphosphates as well as with pyrophosphate in a buffered aqueous solution at pH 6.2. A turn‐on fluorescence response was observed for all nucleotides except for GTP, which demonstrated strong fluorescence quenching. The strongest turn‐on fluorescence was observed for the largest receptor 3 in the presence of thymidine triphosphate (TTP). Based on the NMR and fluorescence experiments, two major binding modes for nucleotide complexes were identified.

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“…Significant examples include compounds such as amonafide 3, mitonafide 4, and DMP 840-bisnafide 5 (Figure 2) [6]. is encourages our strong interest in modifying acridine ring or naphthalimide, for identifying potential novel antitumor drugs [7,8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Some 1,8-Naphthalimide-Acridinyl Hybrids

Chen

Yuan

Jaiswal

et al. 2020

Journal of Chemistry

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In the present study, the synthesis of three 1,8-naphthalimide-acridinyl hybrids (2a, 2b, and 5b) using N-amido-1,8-naphthalimides (1 and 4) and acridinyl isothiocyanates is reported. The newly synthesized hybrids were evaluated for their anticancer activity in six human cancer cell lines (HL-60, MT-4, HepG2, HeLa, SK-OV-3, and MCF-7). Their inhibition activity against DNA-topoisomerase I (Topo I) and Electrophorus electricus acetylcholinesterase (AChE) was also studied. The results indicate that 2b displayed good cytotoxicity for MT-4, HepG2, HeLa, and SK-OV-3 with the IC50 values of 14.66 ± 0.31, 27.32 ± 2.67, 17.51 ± 0.34, and 32.26 ± 1.74 μM, respectively. All compounds, especially 2b, exhibited obvious bands corresponding to DNA fragments at 0.5 mM concentration, further confirming the pharmacological mechanism related to the Topo I inhibitory activities. In addition, compound 2a exhibited higher inhibition activity against AChE than 2b and 5b, with IC50 values of 0.32 ± 0.04 mM, and the acridinyl ring may contribute to the activity of 2a.

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Synthesis, spectroscopic, physicochemical and structural characterization of tetrandrine-based macrocycles functionalized with acridine and anthracene groups: DNA binding and anti-proliferative activity

Cited by 24 publications

References 36 publications

Molecular Receptors for Recognition and Sensing of Nucleotides

Molecular Receptors for Recognition and Sensing of Nucleotides

Anthracene‐Based Cyclophanes with Selective Fluorescent Responses for TTP and GTP: Insights into Recognition and Sensing Mechanisms

Synthesis and Biological Evaluation of Some 1,8-Naphthalimide-Acridinyl Hybrids

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