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Review
. 2024 Jan-Dec:23:15330338231225861.
doi: 10.1177/15330338231225861.

Research Progress on Structure-Activity Relationship of 1,8-Naphthalimide DNA Chimeras Against Tumor

Hai-Yang Zhang  1 , Li-Li Han  2 , Hong-Yi Wu  2 , Xiang-Xiang Xu  2 , Meng-Bin Yu  2 , Gao-Yun Chen  2 , Xiu-Li Qi  2
Affiliations
Review

Research Progress on Structure-Activity Relationship of 1,8-Naphthalimide DNA Chimeras Against Tumor

Hai-Yang Zhang et al. Technol Cancer Res Treat. 2024 Jan-Dec.

Abstract

The development of 1,8-naphthalimide derivatives as cell probes, DNA targeting agents, and anti-tumor drugs is one of the research hotspots in the field of medicine. Naphthalimide compounds are a kind of DNA embedder, which can change the topological structure of DNA by embedding in the middle of DNA base pairs, and then affect the recognition and action of topoisomerase on DNA. Aminofide and mitonafide are the first 2 drugs to undergo clinical trials. They have good DNA insertion ability, can embed DNA double-stranded structure, and induce topoisomerase II to cut part of pBR322DNA, but not yet entered the market due to their toxicity. In this paper, the design and structure-activity relationship of mononaphthalimide and bisaphthalimide compounds were studied, and the relationship between the structure of naphthalimide and anti-tumor activity was analyzed and discussed. It was found that a variety of structural modifications were significant in improving anti-tumor activity and reducing toxicity.

Keywords: 1; 8-naphthalimides; DNA intercalator; antitumor; structure-activity relationship.

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Conflict of interest statement

Declaration of Conflicting InterestsThe authors declared no potential conflicts of interest with respect to the research, authorship, and/or publication of this article.

Figures

Figure 1.
Figure 1.
Molecular structures of amonafide（compound 1） and mitonafide （compound 2).
Figure 2.
Figure 2.
Acetylation pathway of amonafide.
Figure 3.
Figure 3.
Amine substituted naphthalimide derivatives (compound 3(a-f) and compound 4).
Figure 4.
Figure 4.
The first bis-naphthalimide derivative (compound 5).
Figure 5.
Figure 5.
Molecular structure of bisnafide (compound 6) and irinafide (compound 7).
Figure 6.
Figure 6.
Molecular structure of 5 diamine bis-naphthalimide derivatives (compound 8-12).
Figure 7.
Figure 7.
Molecular structure of the bis-naphthalimide platinum (IV) complexes (compound 13-17).
Figure 8.
Figure 8.
Molecular structure of the naphthalimide cyclic amine conjugates (compound 18 and 19).
Figure 9.
Figure 9.
Molecular structure of the naphthalimide triamine conjugate (compound 20).
Figure 10.
Figure 10.
The first glycosylated naphthalimide derivative (compound 21).
Figure 11.
Figure 11.
Thioglycosyl naphthalimide derivatives (compound 22 and 23).
Figure 12.
Figure 12.
Benzimidazole substituted naphthalimide derivatives (compound 24 and 25).
Figure 13.
Figure 13.
Naphthalimide derivatives with fused thiazole rings (compound 26).
Figure 14.
Figure 14.
Naphthalimide benzothiazole derivatives (compound 27-29).
Figure 15.
Figure 15.
Flavonoid naphthalimide derivatives (compound 30).
See this image and copyright information in PMC

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