In the realm of supramolecular chemistry, the synthesis and exploration of innovative macrocycles play a pivotal role in advancing materials suitable for applications in drug delivery, catalysis, sensing, and various other fields. 1 Cycloparaphenylenes (CPPs) represent a unique class of π-conjugated macrocycles, distinguished by their strained structure and size-dependent chemical and photophysical properties . These intriguing molecules have attracted considerable attention from researchers in the fields of chemistry and materials science. Recent studies have highlighted the fascinating properties of topologically unique multi-macrocycles, which exhibit behavior distinct from that of monocyclic structures (Figure ). For instance, Du et al. reported CPP-based bismacrocycles that exhibit dual-emission behavior, characterized by tunable aggregation-induced emission and enhanced chiroptical properties. Similarly, Yam and Jiang have independently synthesized rigid and heterotopic bismacrocycles combining CPP and pillar [5]arene, showcasing remarkable luminescent and host-guest recognition properties (Figure ). Crown ethers as an intriguing class of macrocycles with flexible skeleton, renowned for their ability to selectively bind metal cations through coordination interactions and adeptly fabricate mechanically interlocked molecules (MIMs) via hydrogen bonding. This synergy of properties offers exciting opportunities for innovative molecular designs. For example, we recently have reported the synthesis of a rare hetero [3]catenane using a ring-in-ring assembly strategy, incorporating unaltered [12]CPP, 24-crown-8 and a dibenzylammonium macrocycle (Figure ). To further explore the potential of the hydrids of CPPs and crown ethers. Herein, we present the synthesis of hybrid bis-and trimacrocycles combining CPPs and crown ethers. We then investigated their supramolecular properties. Additionally, we conducted cell imaging and in vitro antitumor activity studies to evaluate their potential for biological applications.