Medical Applications of Macrocyclic Polyamines

Abstract

Macrocyclic polyamines comprise a special group of heterocycles that bind different guests. Over the past decade, medical interest has focused on macrocyclic polyamines owning to their chemical and biological properties. The discovery and development of the bicyclam AMD3100 highlighted the clinical potential of such compounds in AIDS, cancer and stem-cell mobilization. Many macrocyclic polyamines and their transition metal complexes had the cytotoxic activities to tumors through binding DNA, cleaving DNA, crosslinking DNA, or depleting the endogenous ATP levels of the tumor cells. Furthermore, macrocyclic polyamines also could be labeled with metal ionic radii and have applications in cancer radioimmunotherapy and in vivo magnetic resonance imaging (MRI). The current rational design, and medical applications of macrocyclic polyamines will be reviewed in this manuscript.

Cell proliferation effects of calix[4]arene derivatives

“…In particular, an inverse correlation between ∆T m and IC50 values emerges: calix-NH 2 is a moderate G-quadruplex stabilizer but is a potent active agent in cancer cells (MCF-7, LNCaP and U87) comparing with their homologues on the basis of its pharmacological profile. 23 Also, based on our co-localization studies, calix-NH 2 did not localize nucleus and therefore is not a telomerase inhibitor. We cannot discard the possibility that the observed cellular effects may not be mediated through the Gquadruplexes examined here but derived from quite distinct mechanisms, such as, cellular ATP and interfering with enzymes involved in the polyamine biosynthetic pathway; or it may be that other DNA or RNA quadruplexes, which we have not evaluated, could be involved since it is well established that calixarenes derivatives are able to interact with a multitude of biochemical targets and exert cytotoxic activity through several mechanisms.…”

Pachychalines A–C: Novel 3‐Alkylpyridinium Salts from the Marine Sponge Pachychalina sp.

“…Even if polyamines have found large applications in medicinal chemistry, they are seldom found in marine organisms. [11] Squalamine isolated from the dogfish shark, Squalus acanthias, is a famous example of an aminosterol with a spermine used in anticancer therapy. [12] To the best of our knowl-edge, pachychaline B (2) is the third occurrence of a norspermidine moiety in marine natural products after the motuporamines [13] and the penaramides.…”

[12]aneN3-based BODIPY as a selective and sensitive off–on sensor for the sequential recognition of Cu2+ ions and ADP

“…The chemistry of macrocyclic polyamines has been received much attention due to their widespread applications in coordination chemistry, medicinal chemistry, biochemistry, and material chemistry [1][2][3][4]. Because of their protonation property at physiological conditions, macrocyclic polyamines often act as positive-charged units in constructing DNA condensation agents and non-viral gene vectors [5][6][7][8].…”