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For decades, macrocyclic compounds have been widely applied in various fields owing to essential physicochemical properties such as their rigid cyclic structures, geometric dimensions (diameter and height), hydrophobic cavity, and hydrophilic interface. This review is an attempt to summarize various research accomplishments involving macrocyclic compounds for drug and gene delivery in immune-modulating therapies: the structures and benefits of main host molecules, their mechanisms regulating the immune system from cell uptake to activation of dendritic cells and T helper lymphocytes, as well as their potential immunotherapy for different diseases. Macrocyclic compounds including cucurbiturils (CBs), calixarenes, pillararenes, cyclodextrins (CyDs), macrocyclic peptides and metallo-supramolecular compounds, have their own unique physicochemical properties and functional derivatizations that enable to improve the biocompatibility, responsiveness to stimuli, and effectiveness of immune-modulating therapy. Based on abundant clarifications of the biological immunity mechanisms, representative constructions of macrocyclic compounds for immune therapies have been conducted for the investigation of treatment of different diseases including cancer, atherosclerosis, Niemann-Pick type C1 disease (NPC1), diabetes, and inflammations. Although there are critical challenges that remain to be conquered, we believe the future of macrocyclic compounds in the immune-modulating therapy must be bright.

Bu çalışmada, trifenilamin birimleri içeren yeni makrosiklik bileşikler sentezlendi ve optik özellikleri incelendi. Hedeflenen bileşiklerin hazırlanması için 2,2'-dikarboksi-1,1'-bifenil (1) ve trifenilamin (7) bileşikleri çıkış maddeleri olarak kullanıldı. Bileşik 1'in aromatik halkalarının bromlanmasıyla 4,4'-dibromo-2,2'-dikarboksi-1,1'-bifenil (2) türevi hazırlandı. Bu bileşiğin karboksilik asit grupları metil alkol ile esterleştirildi. Daha sonra elde edilen ester türevi (3) indirgenerek 4,4'-dibromo-2,2'-bis(hidroksimetil)-1,1'-bifenil (4) bileşiği sentezlendi. Bileşik 4,tri(veya tetra)etilenglikolditosilat ile etkileştirilerek farklı halka boyutlarındaki makrosiklik taç eterler (5 ve 6) hazırlandı. Daha sonra, 5 ve 6 numaralı bileşiklerin 4-(difenilamino)-1-fenilboronik asit (9) ile çapraz kenetlenme reaksiyonu aracılığıylatrifenilamin birimleri içeren yeni makrosiklik bileşikler (10 ve 11) sentezlendi. Hazırlanan bileşiklerin yapıları 1H-NMR, 13C-NMR ve FT-IR spektroskopi yöntemleri kullanılarak aydınlatıldı. Çalışmanın sonraki aşamasında, sentezlenen yeni bileşiklerin optik özellikleri UV-Vis ve floresans spektroskopileri ile incelendi, In the present study, new macrocyclic compounds having triphenylamine units were synthesized and their optical properties were investigated. For the synthesis of target compounds, 2,2?-dicarboxy-1,1?-biphenyl (1) and triphenylamine (7) were used as starting materials. 4,4?-dibromo-2,2?-dikarboksi-1,1?-bifenil (2) were prepared by the bromination of aromatic rings of compound (1). Carboxyl groups of compound (2) were esterified with methyl alchohol. Then, 4,4'-dibromo-2,2'-bis(hidroksimetil)-1,1'-bifenil (4) were synthesized by the reduction of the obtained ester derivative (3). Macrocyclic crown ethers with different ring size were prepared from the reaction of compound (4) and tri(or tetra)ethyleneglycolditosylate. Afterwards, novel macrocylic compounds (10ve11)having triphenylamine units were synthesized from the cross-coupling reaction of compound 5 and 6 with 4-(diphenylamino)-1-phenylboronic acid (9). The structures of the obtained compounds were confirmed using 1H-NMR, 13C-NMR and FT-IR spectroscopy methods. In the next step of study, the optical properties of newly synthesized compounds were investigated by UV-Vis and fluorescence spectroscopy.