Influence of charge transfer on the isomerisation of stilbene derivatives for application in cancer therapy

Holzmann, Nicole; Bernasconi, Leonardo; Bisby, Roger H.; Parker, Anthony W.

doi:10.1039/c8cp05375h

Cited by 7 publications

(7 citation statements)

References 66 publications

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“…Upon photoexcitation, the donor–acceptor coupling can lead to significant charge transfer (CT) character in the electronic excited states. Increasing the push–pull effect leads to greater charge separation and twisted intramolecular CT, as demonstrated in previous investigations. , …”

Section: Introductionsupporting

confidence: 80%

“…Increasing the push−pull effect leads to greater charge separation and twisted intramolecular CT, as demonstrated in previous investigations. 18,19 One interesting example of a strong push−pull stilbene derivative is 4-(N,N-dimethylamino)-4′-nitrostilbene (DANS, see Figure 1). 17,20 The dipole moment of DANS changes significantly from the electronic ground to the excited states, making its emissive and nonradiative properties rather sensitive to its surrounding.…”

Section: Introductionmentioning

confidence: 99%

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Adsorption of 4-(N,N-Dimethylamino)-4′-nitrostilbene on an Amorphous Silica Glass Surface

Vörös,

Angeletti,

Franchini

et al. 2023

J. Phys. Chem. C

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Stilbenes are a compelling class of organic photoswitches with a high degree of tunability that sensitively depend on their environment. In this study, we investigate the adsorption properties of 4-(N,N-dimethylamino)-4′-nitrostilbene (DANS), a push–pull stilbene, on amorphous silica glass. Plane-wave density functional theory (DFT) calculations are used to understand how the trans and cis isomers of DANS interact with the amorphous surface and which are the most preferred modes of adsorption. Our calculations revealed that the O–H···O hydrogen bonds between the nitro group and hydroxyl groups of the silica surface dominate the intramolecular interaction. In addition to hydrogen bonding, O–H···π interactions with the aromatic ring and double bond play a critical role in adsorption, whereas C–H···O interactions are present, but contribute little. Therefore, both isomers of DANS favor parallel orientations such that not only the functional groups but also the aromatic parts can strongly interact with the glass surface.

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Section: Introductionsupporting

confidence: 80%

Section: Introductionmentioning

confidence: 99%

Adsorption of 4-(N,N-Dimethylamino)-4′-nitrostilbene on an Amorphous Silica Glass Surface

Vörös,

Angeletti,

Franchini

et al. 2023

J. Phys. Chem. C

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“…For this reason, extensive research efforts have been devoted to understanding the photosensitizing side effects of light on them [17,18,19] . Note that the existence of low‐lying charge transfer states can influence their isomerization, their applications, or their inhibition properties [20,21,22] . Finally, molecules presenting absorption in particular excitation wavelengths can be used as photosensitizers and even they could be candidates as photosensitizers in photodynamic therapy (PDT) [21–23] …”

Section: Introductionmentioning

confidence: 99%

“…[17,18,19] Note that the existence of low-lying charge transfer states can influence their isomerization, their applications, or their inhibition properties. [20,21,22] Finally, molecules presenting absorption in particular excitation wavelengths can be used as photosensitizers and even they could be candidates as photosensitizers in photodynamic therapy (PDT). [21][22][23] Mycro 3 presents an interesting bioactivity having exhibited promising results in in vivo studies against pancreatic cancer.…”

Section: Introductionmentioning

confidence: 99%

“…[20,21,22] Finally, molecules presenting absorption in particular excitation wavelengths can be used as photosensitizers and even they could be candidates as photosensitizers in photodynamic therapy (PDT). [21][22][23] Mycro 3 presents an interesting bioactivity having exhibited promising results in in vivo studies against pancreatic cancer. Its analogues inhibit the MYC oncoprotein by interfering with the MYC-MAX dimerization, [1,23,24,25] highlighting the need for data regarding the geometry of minima energy structures for both trans and cis isomers of mycro 3, as well as their isomerization energy path.…”

Section: Introductionmentioning

confidence: 99%

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A DFT Study towards the Amide cis‐trans Isomerization Process of the Myc‐Max Inhibitor Mycro 3 and Its Photophysical Properties; Synthesis and NMR Studies of the trans‐Conformation

et al. 2022

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Mycro 3 is a synthetic pyrazolo[1,5-a]pyrimidine amide with interesting bioactivity having exhibited promising results in in vivo studies against pancreatic cancer. Even though it is a known compound, no data concerning its conformations have been reported before. The aim of this work is to investigate the formation of its trans-and cis-isomers, the photophysical processes of the isomerization, and the solvent effect via a DFT study. We found that this isomerization is a thermodynamically favourable reaction, having a small barrier of 10.3 kcal/mol in DMSO. Additionally, the calculated 1 H and 13 C NMR spectra of the two isomers revealed measurable differences. Furthermore, the S 0 !S 1 excitation was found in vis area at 413 nm (transisomer), while the S 2 !S 0 and S 1 !S 0 excitations are charge transfer (CT) and partially CT state in near-infrared and vis spectra, showing that mycro 3 also has the potential to be used as a photosensitizer. Finally, its synthesis and its NMR analysis revealed a good agreement with the proposed trans conformation.

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A Photoisomerizable Zinc (II) Complex Inhibits Microtubule Polymerization for Photoactive Therapy

Cao

Wang

et al. 2023

Angewandte Chemie

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The photoisomerization-induced cytotoxicity in photopharmacology provides a unique pathway for phototherapy because it is independent of endogenous oxygen. In this study, we developed a biosafe photoisomerizable zinc(II) complex (Zn1), which releases its trans ligand (trans-L1) after being irradiated with blue light. This causes the complex to undergo photoisomerization and produce the toxic cis product (cis-L1) and generate singlet oxygen ( 1 O 2 ). The resulting series of events caused impressive phototoxicity in hypoxic A431 skin cancer cells, as well as in a tumor model in vivo. Interestingly, Zn1 was able to inhibit tumor microtubule polymerization, while still showing good biocompatibility and biosafety in vivo. This photoisomerizable zinc(II) complex provides a novel strategy for addressing the oxygen-dependent limitation of traditional photodynamic therapy.

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Influence of charge transfer on the isomerisation of stilbene derivatives for application in cancer therapy

Abstract: The photoisomerisation of non-toxic trans-combretastatin CA4 to its cytotoxic cis isomer demonstrates the high potential of this and similar compounds for localised cancer therapy.

Cited by 7 publications

References 66 publications

Adsorption of 4-(N,N-Dimethylamino)-4′-nitrostilbene on an Amorphous Silica Glass Surface

Adsorption of 4-(N,N-Dimethylamino)-4′-nitrostilbene on an Amorphous Silica Glass Surface

A DFT Study towards the Amide cis‐trans Isomerization Process of the Myc‐Max Inhibitor Mycro 3 and Its Photophysical Properties; Synthesis and NMR Studies of the trans‐Conformation

A Photoisomerizable Zinc (II) Complex Inhibits Microtubule Polymerization for Photoactive Therapy

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