Drug Delivery with a Calixpyrrole–trans-Pt(II) Complex

Abstract

A meso-p-nitroaniline-calix[4]pyrrole derivative trans-coordinated to a Pt(II) center was synthesized and its structure solved by X-ray analysis. Adenosine monophosphate (AMP) was used as a model compound to evaluate the potential for the assisted delivery of the metal to the DNA nucleobases via the phosphate anion-binding properties of the calix[4]pyrrole unit. An NMR investigation of the kinetics of AMP complexation in the absence of an H-bonding competing solvent (dry CD(3)CN) was consistent with this hypothesis, but we could not detect the interaction of the calix[4]pyrrole with phosphate in the presence of water. However, in vitro tests of the new trans-calixpyrrole-Pt(II) complex on different cancer cell lines indicate a cytotoxic activity that is unquestionably derived from the coexistence of both the trans-Pt(II) fragment and the calix[4]pyrrole unit.

Host–Guest Chemistry of a Bis‐Calix[4]pyrrole Derivative Containing a trans/cis‐Switchable Azobenzene Unit with Several Aliphatic Bis‐Carboxylates

“…As part of our work aimed at investigating the potential use of calixpyrroles in drug‐delivery systems,6 we considered not only binding of a given guest to be a key factor, but also the possibility to trigger its efficient release. We recently reported the ability of several bis‐and tris‐calix[4]pyrrole receptors, in which the macrocyclic units are connected by aromatic amide linkers, to bind several bis‐carboxylates 7.…”

Recent Advancements in Calix[4]pyrrole‐Based Anion‐Receptor Chemistry

“…[24] In follow-up studies, a few calix [4]pyrrole derivatives, including strapped calix [4]pyrroles and electron-deficient two-wall calix [4]pyrroles, were shown to be promising candidates for the transmembrane transport of ions. [122,123] Kohnke et al, for the first time, employed meso-p-aminophenyl calix [4]pyrrole-Pt II conjugate trans-83 as a drugdelivery system for the transport of Pt II to adenosine monophosphate (AMP)(in DNA, Figure 28). [122,123] Kohnke et al, for the first time, employed meso-p-aminophenyl calix [4]pyrrole-Pt II conjugate trans-83 as a drugdelivery system for the transport of Pt II to adenosine monophosphate (AMP)(in DNA, Figure 28).…”

“…[25,27,29,70] Recently, the transmembrane transport of ion pairs by calix [4]pyrroles was reviewed by Sessler et al [10] Thus, we will focus on two new findings: one, meso-p-aminophenyl calix [4]pyrrole-Pt II conjugates as drug-delivery systems; two, pyridine diamide strapped calix [4]pyrroles that can induce apoptosis by assisting chloride-anion transport in liposomal model membranes and in mammalian cells. [122] Specifically, the phosphate anion recognition properties of calix [4]pyrrole play a key role in the transfer process. [122] Specifically, the phosphate anion recognition properties of calix [4]pyrrole play a key role in the transfer process.…”

A degradable triple temperature‐, pH‐, and redox‐responsive drug system for cancer chemotherapy

“…Traditional chemotherapy with devoid selectivity usually causes systemic toxicity . In order to overcome this obstacle, plenty of stimuli‐responsive drug delivery system have been developed to achieve the goal of precise treatment, good biocompatibility, and effective drug utilization .…”

“…Traditional chemotherapy with devoid selectivity usually causes systemic toxicity. 1,2 In order to overcome this obstacle, plenty of stimuli-responsive drug delivery system have been developed to achieve the goal of precise treatment, good biocompatibility, and effective drug utilization. 1,3,4 Cancer tissue possess some characteristic heterogeneous traits, 5,6 such as decreased extracellular pH and much higher intracellular GSH concentration than normal cells and tissues.…”