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Synthesis of New Picolylamine Bearing Calix[8]arene Derivatives as Antiproliferative Agents for Colorectal Carcinoma
Author(s) -
Oguz Mehmet,
Gul Alev,
Karakurt Serdar,
Yilmaz Mustafa
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202002881
Subject(s) - chemistry , calixarene , cytotoxicity , molecule , dna , macromolecule , stereochemistry , apoptosis , biochemistry , in vitro , organic chemistry
Calixarene macromolecules have been developed as essential candidate in pharmaceutical application as drug carrier. Possible functionalization with different small molecules at lower and upper rims uplifts biological activity in its structure. This work explain the application of lower rim‐functionalized 4‐picolylamine‐calix[8]arenes ( O‐1 b and O‐2 b ) in antiproliferative potentials of several human cancerous cells (DLD‐1, HT‐29, MDA‐231, and PC‐3) as well as healthy epithelium cell (PNT1 A). The death mechanism and DNA interaction of O‐1 b and O‐2 b were also investigated. Syntheses of 4‐picolylamine‐calix[8]arenes ( O‐1 b and O‐2 b ) confirmed with different spectroscopic techniques including 1 H NMR, 13 C NMR, elemental analysis and FTIR. Results demonstrated that O‐1 b and O‐2 b compounds dose‐dependently inhibited proliferation of DLD‐1, HT‐29, MDA‐231, and PC‐3 cells. The highest cytotoxicity was observed on colorectal carcinoma cells; DLD‐1 with an IC 50 value as 4.96 μM and 6.12 μM, respectively. These compounds were weak inhibitors on human healthy epithelium (PNT1 A) cells, while they significantly increased the apoptosis by interacting DNA molecule in a different manner. This is the first study to clarify the molecular mechanism of 4‐picolylamine derived calix[8]arene on human cancerous cells.