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. 2023 Oct 25;13(1):18241.
doi: 10.1038/s41598-023-45455-y.

Synthesis of potent MDA-MB 231 breast cancer drug molecules from single step

Senthilnathan Govindaraj  1 , Kilivelu Ganesan  2 , Mahendiran Dharmasivam  3 , Lakshmisundaram Raman  4 , Mohammed Mujahid Alam  5 , Mohammed Amanullah  6
Affiliations

Synthesis of potent MDA-MB 231 breast cancer drug molecules from single step

Senthilnathan Govindaraj et al. Sci Rep. .

Abstract

We have prepared novel potent breast cancer drug molecules from non-toxic and inexpensive method. Column chromatography is not necessary for purification of target molecules. The value of overall atom economy, environmental factor, environmental catalyst and product mass intensity gives additional merits for this synthetic method. Synthesized flexible dimeric imidazolium bromides showed less toxicity and gives excellent anticancer response against normal mammary epithelial cells. Novel dimeric pyridinium bromides showed excellent anticancer response against tested cancer cell lines. In cell cycle, novel flexible dimeric pyridinium bromides showed significant arrest in the G2/M phase by nearly three folds, when compared with control drug. We have studied the targeting epidermal growth factor receptor for all the synthesized flexible amino substituted and methyl substituted dimeric pyridinium bromides.

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Conflict of interest statement

The authors declare no competing interests.

Figures

Figure 1
Figure 1
Synthesis of flexible substituted dimeric pyridinium bromides.
Figure 2
Figure 2
Chemical reaction used for atom economy calculation.
Figure 3
Figure 3
Chemical reaction used for environmental factor calculation.
Figure 4
Figure 4
Chemical reaction used for product mass intensity calculation.
Figure 5
Figure 5
IC50 values comparison between available literature and our target molecules.
Figure 6
Figure 6
AO/EB assay of MDA-MB-231 cells after 24 h: (A) Control; (B) 1; (C) 2; (D) 3; (E) 4.
Figure 7
Figure 7
Hoechst 33258 assay of MDA-MB-231 cells after 24 h: (A) Control; (B) 1; (C) 2; (D) 3; (E) 4.
Figure 8
Figure 8
Cell cycle progression of MDA-MB-231 cells for 24 h: (A) Control; (B) 1; (C) 2; (D) Cell population.
Figure 9
Figure 9
The assessment of apoptosis in MDA-MB-231 cells via the annexin V-FITC and propidium iodide assay at 48 h. The figure presents four separate conditions: (A) Control, (B) Positive control 5-fluorouracil, (C) Compound 1, (D) Compound 2. The figure show four distinct cell states within these conditions: necrotic cells (Q1), late apoptotic cells (Q2), viable cells (Q3), and early apoptotic cells (Q4). This method uses the protocol previously published in another study.
Figure 10
Figure 10
Drug likeness parameters of dimeric pyridinium bromides 1–4 assessed using Swiss ADME. LIPO lipophilicity, POLAR polarity, FLEX flexibility, INSATU insaturation or saturation asper the fraction of carbons in sp3 hybridization, INSOLU solubility.
Figure 11
Figure 11
The best docking poses and interactions of compounds (1–4, a–b) with EGFR.
See this image and copyright information in PMC

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