Macrocycle-Based Supramolecular Drug Delivery Systems: A Concise Review

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2024 Aug 29

PMID 39202907

Authors

Yanrui Yang

Pengcheng Li

Haibo Feng

Rui Zeng

Shanshan Li

Qixiong Zhang

Affiliations

Soon will be listed here.

Abstract

Efficient delivery of therapeutic agents to the lesion site or specific cells is an important way to achieve "toxicity reduction and efficacy enhancement". Macrocycles have always provided many novel ideas for drug or gene loading and delivery processes. Specifically, macrocycles represented by crown ethers, cyclodextrins, cucurbit[n]urils, calix[n]arenes, and pillar[n]arenes have unique properties, which are different cavity structures, good biocompatibility, and good stability. Benefited from these diverse properties, a variety of supramolecular drug delivery systems can be designed and constructed to effectively improve the physical and chemical properties of guest molecules as needed. This review provides an outlook on the current application status and main limitations of macrocycles in supramolecular drug delivery systems.

References

Ha W, Yu J, Song X, Chen J, Shi Y . Tunable temperature-responsive supramolecular hydrogels formed by prodrugs as a codelivery system. ACS Appl Mater Interfaces. 2014; 6(13):10623-30. DOI: 10.1021/am5022864. View

Lu X, Isaacs L . Synthesis and Recognition Properties of Enantiomerically Pure Acyclic Cucurbit[n]uril-Type Molecular Containers. Org Lett. 2015; 17(16):4038-41. DOI: 10.1021/acs.orglett.5b01948. View

Ma W, Chen J, Jiang L, Yao J, Lu T . The delivery of triamterene by cucurbit[7]uril: synthesis, structures and pharmacokinetics study. Mol Pharm. 2013; 10(12):4698-705. DOI: 10.1021/mp400529m. View

Zhao L, Tang B, Tang P, Sun Q, Suo Z, Zhang M . Chitosan/Sulfobutylether-β-Cyclodextrin Nanoparticles for Ibrutinib Delivery: A Potential Nanoformulation of Novel Kinase Inhibitor. J Pharm Sci. 2019; 109(2):1136-1144. DOI: 10.1016/j.xphs.2019.10.007. View

Rahmani A, Rahimi F, Iranshahi M, Kahroba H, Zarebkohan A, Talebi M . Co-delivery of doxorubicin and conferone by novel pH-responsive β-cyclodextrin grafted micelles triggers apoptosis of metastatic human breast cancer cells. Sci Rep. 2021; 11(1):21425. PMC: 8563731. DOI: 10.1038/s41598-021-00954-8. View

Nascimento Vieira A, Franz-Montan M, Cabeca L, de Paula E . Anaesthetic benefits of a ternary drug delivery system (Ropivacaine-in-Cyclodextrin-in-Liposomes): in-vitro and in-vivo evaluation. J Pharm Pharmacol. 2019; 72(3):396-408. DOI: 10.1111/jphp.13211. View

Wu D, Wang J, Du X, Cao Y, Ping K, Liu D . Cucurbit[8]uril-based supramolecular theranostics. J Nanobiotechnology. 2024; 22(1):235. PMC: 11084038. DOI: 10.1186/s12951-024-02349-z. View

Hao Q, Chen Y, Huang Z, Xu J, Sun Z, Zhang X . Supramolecular Chemotherapy: Carboxylated Pillar[6]arene for Decreasing Cytotoxicity of Oxaliplatin to Normal Cells and Improving Its Anticancer Bioactivity Against Colorectal Cancer. ACS Appl Mater Interfaces. 2018; 10(6):5365-5372. DOI: 10.1021/acsami.7b19784. View

You X, Ju X, He F, Wang Y, Liu Z, Wang W . Polymersomes with Rapid K-Triggered Drug-Release Behaviors. ACS Appl Mater Interfaces. 2017; 9(22):19258-19268. DOI: 10.1021/acsami.7b05701. View

10.

Gharib R, Greige-Gerges H, Fourmentin S, Charcosset C, Auezova L . Liposomes incorporating cyclodextrin-drug inclusion complexes: Current state of knowledge. Carbohydr Polym. 2015; 129:175-86. DOI: 10.1016/j.carbpol.2015.04.048. View

11.

Kumar R, Kaur K, Uppal S, Mehta S . Ultrasound processed nanoemulsion: A comparative approach between resveratrol and resveratrol cyclodextrin inclusion complex to study its binding interactions, antioxidant activity and UV light stability. Ultrason Sonochem. 2017; 37:478-489. DOI: 10.1016/j.ultsonch.2017.02.004. View

12.

Kass L, Nguyen J . Nanocarrier-hydrogel composite delivery systems for precision drug release. Wiley Interdiscip Rev Nanomed Nanobiotechnol. 2021; 14(2):e1756. PMC: 9811486. DOI: 10.1002/wnan.1756. View

13.

Muraoka Y, Watanabe H, Kometani M, Hasegawa T . Effect of androgens on phalloidin-induced liver toxicity in mice. Toxicol Lett. 1988; 40(3):203-8. DOI: 10.1016/0378-4274(88)90042-2. View

14.

Barooah N, Mohanty J, Bhasikuttan A . Cucurbituril-Based Supramolecular Assemblies: Prospective on Drug Delivery, Sensing, Separation, and Catalytic Applications. Langmuir. 2022; 38(20):6249-6264. DOI: 10.1021/acs.langmuir.2c00556. View

15.

Xia J, Wang J, Zhao Q, Lu B, Yao Y . Dual-Responsive Drug-Delivery System Based on PEG-Functionalized Pillararenes Containing Disulfide and Amido Bonds for Cancer Theranostics. Chembiochem. 2023; 24(21):e202300513. DOI: 10.1002/cbic.202300513. View

16.

Zhang P, Liu X, Hu W, Bai Y, Zhang L . Preparation and evaluation of naringenin-loaded sulfobutylether-β-cyclodextrin/chitosan nanoparticles for ocular drug delivery. Carbohydr Polym. 2016; 149:224-30. DOI: 10.1016/j.carbpol.2016.04.115. View

17.

Liu Y, Liu C, Wang Z, Zhou W, Wang H, Zhang Y . Supramolecular organic frameworks improve the safety of clinically used porphyrin photodynamic agents and maintain their antitumor efficacy. Biomaterials. 2022; 284:121467. DOI: 10.1016/j.biomaterials.2022.121467. View

18.

Dudhipala N, Ettireddy S, Youssef A, Puchchakayala G . Development and Pharmacokinetic and Pharmacodynamic Evaluation of an Oral Innovative Cyclodextrin Complexed Lipid Nanoparticles of Irbesartan Formulation for Enhanced Bioavailability. Nanotheranostics. 2023; 7(1):117-127. PMC: 9760361. DOI: 10.7150/ntno.78102. View

19.

Wang X, An P, Gu Z, Luo Y, Luo J . Mitochondrial Metal Ion Transport in Cell Metabolism and Disease. Int J Mol Sci. 2021; 22(14). PMC: 8305404. DOI: 10.3390/ijms22147525. View

20.

Cirri M, Maestrelli F, Mura P, Ghelardini C, Di Cesare Mannelli L . Combined Approach of Cyclodextrin Complexationand Nanostructured Lipid Carriers for the Development of a Pediatric Liquid Oral Dosage Form of Hydrochlorothiazide. Pharmaceutics. 2018; 10(4). PMC: 6321408. DOI: 10.3390/pharmaceutics10040287. View