Abstract
Chemotherapy is still the most important method of cancer treatment. To make this method more effective and safe, new drugs to destroy cancer cells are needed. Some bis-naphthalimide derivatives show potential anticancer activity via an intercalation mechanism. A higher degree of DNA intercalation corresponds to better therapeutic effects. The degree of intercalation of naphthalimides depends on their structure, molecular dynamics and intermolecular interactions with DNA. In order to apply any active substance as a drug, its molecular dynamics as well as possible interactions with target molecules have to be examined in exhaustive details. This paper describes a practical preparation of some novel bis-naphthalimide derivatives with different functional groups and their FTIR and 1H- and 13C-NMR spectral characteristics. To determine the molecular dynamics of the obtained compounds the temperature, their 1H-NMR spectra were measured. It has been clearly proven in this paper that the unusual temperature-dependent 1H-NMR behavior of the aromatic protons of phthalimide derivatives, previously described in the literature as “hypersensitivity” and explained by n-π interactions and molecular motions of aromatic amide rings, is a result of temperature driven changes of the geometry of carbonyl groups.
Highlights
Introduction1,8-Naphthalimide derivatives are a very important class of compounds. Their photophysical properties are useful in many applications as organic light-emitting diodes, [1] fluorescent dyes for solar energy collectors, [2] laser active media, [3] potential photosensitive biologically active units, [4]
Chemotherapy is still the most important method of cancer treatment
In our paper we have very proven precisely, without any doubts, that no n-π interactions are present in these systems and that the unusual behavior of protons in 1H-NMR spectra is caused by temperature-driven changes in the carbonyl group geometry
Summary
1,8-Naphthalimide derivatives are a very important class of compounds. Their photophysical properties are useful in many applications as organic light-emitting diodes, [1] fluorescent dyes for solar energy collectors, [2] laser active media, [3] potential photosensitive biologically active units, [4]. In order to use any active substance as a drug, the recognition of all possible interactions with target molecules is essential Neglecting this can lead to tragic results as in case of thalidomide. Some years ago Barrett et al [35] and Howell et al [36] observed an unusual temperature behavior of the aromatic protons of phthalimide derivatives in 1H-NMR. Caused by n-π interactions of the n-electrons of substituents with the π-electrons of aromatic rings together with the molecular dynamics of these phthalimide systems. They calculated some thermodynamic parameters of these interactions. In our paper we have very proven precisely, without any doubts, that no n-π interactions are present in these systems and that the unusual behavior of protons in 1H-NMR spectra is caused by temperature-driven changes in the carbonyl group geometry
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