| 363 | 0 | 241 |
| 下载次数 | 被引频次 | 阅读次数 |
柱芳烃特有的柱状结构和富电子空腔,使其具有独特的主客体络合能力,结构易于修饰的特性也使其在很多方面得到了广泛应用。为了提高肿瘤的治疗效果,主动靶向药物递送体系变得尤为重要。得益于柱芳烃优异的结构可变性,肿瘤靶向基团可以很容易地被引入到基于柱芳烃的药物递送体系中,以实现肿瘤部位的精准药物递送。文章总结了现阶段基于柱芳烃的主动靶向药物递送体系的设计策略:第一种策略是通过主客体络合引入靶向基团,将靶向基团通过非共价键的方式引入到药物递送体系,避免了复杂的有机合成;另一种更加直接的方法就是设计合成靶向基团修饰的柱芳烃,基于靶向基团修饰的柱芳烃的靶向药物递送体系靶向能力稳定性强,重现性大,但是这一方法往往需要成本较大的有机合成。
Abstract:Pillararenes feature columnar structures with electron-rich cavities, enabling distinctive host-guest comple-xation properties, while their structural adaptability supports diverse applications. In the context of improving cancer treatment outcomes, active targeted drug delivery systems(DDSs) are recognized as vital. The inherent structural flexibility and host-guest interactions of pillararenes facilitate the integration of tumor-targeting groups into pillararene-based DDSs, allowing precise drug delivery to tumor sites. This review delineates two design strategies for such systems. One approach employs host-guest complexation to incorporate targeting groups through noncovalent bonds,avoiding the need for intricate organic synthesis. Alternatively, pillararenes modified with targeting groups are synthesized directly, yielding DDSs with stable targeting capabilities and consistent reproducibility, albeit at the expense of increased time and cost due to complex organic synthesis processes.
[1]SIEGEL R L,MILLER K D,WAGLE N S,et al.Cancer statistics,2023[J].CA:A Cancer Journal for Clinicians,2023,73(1):17-48.
[2]OUYANG J,XIE A,ZHOU J,et al.Minimally invasive nanomedicine:nanotechnology in photo-/ultrasound-/radiation-/magnetism-mediated therapy and imaging[J].Chemical Society Reviews,2022,51(12):4996-5041.
[3]LU B,HUANG Y Y,ZHANG Z C,et al.Organic conjugated small molecules with donor-acceptor structures:design and application in the phototherapy of tumors[J].Materials Chemistry Frontiers,2022,6(20):2968-2993.
[4]LI H N,LUO Q,ZHANG H,et al.Nanomedicine embraces cancer radio-immunotherapy:mechanism,design,recent advances,and clinical translation[J].Chemical Society Reviews,2023,52(1):47-96.
[5]LU B,ZHANG Z C,JI Y,et al.Icing on the cake:combining a dual PEG-functionalized pillararene and an A-Da small molecule photosensitizer for multimodal phototherapy[J].Science China Chemistry,2022,65(6):1134-1141.
[6]LU B,QUAN H,ZHANG Z C,et al.End group nonplanarization enhances phototherapy efficacy of A-D-a fusedring photosensitizer for tumor phototherapy[J].Nano Letters,2023,23(7):2831-2838.
[7]FU X C,HUANG Y M,ZHAO H,et al.Near-infraredlight remote-controlled activation of cancer immunotherapy using photothermal conjugated polymer nanoparticles[J].Advanced Materials,2021,33(34):e2102570.
[8]ZHOU J,RAO L,YU G C,et al.Supramolecular cancer nanotheranostics[J].Chemical Society Reviews,2021,50(4):2839-2891.
[9]YU M M,CAO R,MA Z Y,et al.Development of"smart"drug delivery systems for chemo/PDT synergistic treatment[J].Journal of Materials Chemistry B,2023,11(7):1416-1433.
[10]CAI Y,ZHANG Z C,DING Y,et al.Recent development of pillar[n]arene-based amphiphiles[J].Chinese Chemical Letters,2021,32(4):1267-1279.
[11]DANHIER F,FERON O,PR魪AT V.To exploit the tumor microenvironment:passive and active tumor targeting of nanocarriers for anti-cancer drug delivery[J].Journal of Controlled Release,2010,148:135-146.
[12]DANHIER F.To exploit the tumor microenvironment:since the EPR effect fails in the clinic,what is the future of nanomedicine?[J].Journal of Controlled Release,2016,244:108-121.
[13]OGOSHI T,KANAI S,FUJINAMI S,et al.Para-bridged symmetrical pillar[5]arenes:their lewis acid catalyzed synthesis and host-guest property[J].Journal of the American Chemical Society,2008,130(15):5022-5023.
[14]TANG R W,YE Y P,ZHU S J,et al.Pillar[6]arenes:from preparation,host-guest property to self-assembly and applications[J].Chinese Chemical Letters,2023,34 (3):107734..
[15]LU B,ZHANG Z C,QI M Y,et al.All-in-one functional supramolecular nanoparticles based on pillar[5]arene for controlled generation,storage and release of singlet oxygen[J].Frontiers of Chemical Science and Engineering,2023,17(3):307-313.
[16]姚勇,陈娇,王陈威.基于柱芳烃的3D超分子聚合物网络的构筑及应用[J].南通大学学报(自然科学版),2019,18(4):8-15.YAO Y,CHEN J,WANG C W.Construction and application of 3D supramolecular polymers based on Pillar[n]-arenes[J].Journal of Nantong University (Natural Science Edition),2019,18(4):8-15.(in Chinese)
[17]LI Z,YANG Y W.Functional materials with pillarene struts[J].Accounts of Materials Research,2021,2 (4):292-305.
[18]YANG Q L,XU W W,CHENG M,et al.Controlled release of drug molecules by pillararene-modified nanosystems[J].Chemical Communications,2022,58 (20):3255-3269.
[19]SONG N,LOU X Y,MA L J,et al.Supramolecular nanotheranostics based on pillarenes[J].Theranostics,2019,9(11):3075-3093.
[20]郭旭,蔡燕,陈婷婷,等.浅谈癌胚抗原及其检测方法[J].南通大学学报(自然科学版),2023,22(1):26-33.GUO X,CAI Y,CHEN T T,et al.Carcinoembryonic antigen and its detection methods[J].Journal of Nantong University (Natural Science Edition),2023,22 (1):26-33.(in Chinese)
[21]WANG C,LI H,DONG J,et al.Pillararene-based supramolecular vesicles for stimuli-responsive drug delivery[J].Chemistry (Weinheim an Der Bergstrasse,Germany),2022,28(71):e202202050.
[22]SHI B B,JIE K C,ZHOU Y J,et al.Nanoparticles with near-infrared emission enhanced by pillararene-based molecular recognition in water[J].Journal of the American Chemical Society,2016,138(1):80-83.
[23]YAO Q F,LüB Z,JI C D,et al.Supramolecular hostguest system as ratiometric Fe3+ion sensor based on watersoluble pillar[5]arene[J].ACS Applied Materials&Interfaces,2017,9(41):36320-36326.
[24]LIBERMAN E A,TOPALY V P,TSOFINA L M,et al.Mechanism of coupling of oxidative phosphorylation and the membrane potential of mitochondria[J].Nature,1969,222(5198):1076-1078.
[25]ZIELONKA J,JOSEPH J,SIKORA A,et al.Mitochondria-targeted triphenylphosphonium-based compounds:syntheses,mechanisms of action,and therapeutic and diagnostic applications[J].Chemical Reviews,2017,117(15):10043-10120.
[26]GUO X L,YANG N D,JI W H,et al.Mito-bomb:targeting mitochondria for cancer therapy[J].Advanced Materials,2021,33(43):2007778.
[27]YU G C,WU D,LI Y,et al.A pillar[5]arene-based[2]rotaxane lights up mitochondria[J].Chemical Science,2016,7(5):3017-3024.
[28]GUO H,YAN X,LU B,et al.Pillar[5]arene-based supramolecular assemblies with two-step sequential fluorescence enhancement for mitochondria-targeted cell imaging[J].Journal of Materials Chemistry C,2020,8 (44):15622-15625.
[29]CEN M P,DING Y,WANG J,et al.Cationic water-soluble pillar[5]arene-modified Cu2-xSe nanoparticles:supramolecular trap for ATP and application in targeted photothermal therapy in the NIR-II window[J].ACS Macro Letters,2020,9(11):1558-1562.
[30]TOFFOLI G,CERNIGOI C,RUSSO A,et al.Overexpression of folate binding protein in ovarian cancers[J].International Journal of Cancer,1997,74(2):193-198.
[31]ELNAKAT H,RATNAM M.Distribution,functionality and gene regulation of folate receptor isoforms:implications in targeted therapy[J].Advanced Drug Delivery Reviews,2004,56(8):1067-1084.
[32]WU M X,YAN H J,GAO J,et al.Multifunctional supramolecular materials constructed from Polypyrrole@Ui O-66 nanohybrids and pillararene nanovalves for targeted chemophotothermal therapy[J].ACS Applied Materials&Interfaces,2018,10(40):34655-34663.
[33]LAN S,LIU Y M,SHI K J,et al.Acetal-functionalized pillar[5]arene:a p H-responsive and versatile nanomaterial for the delivery of chemotherapeutic agents[J].ACS Applied Bio Materials,2020,3(4):2325-2333.
[34]WANG J,WANG D,CEN M P,et al.GOx-assisted synthesis of pillar[5]arene based supramolecular polymeric nanoparticles for targeted/synergistic chemo-chemodynamic cancer therapy[J].Journal of Nanobiotechnology,2022,20(1):33.
[35]STOCKERT R J,MORELL A G,SCHEINBERG I H.Mammalian hepatic lectin[J].Science,1974,186 (4161):365-366.
[36]LUNDQUIST J J,TOONE E J.The cluster glycoside effect[J].Chemical Reviews,2002,102(2):555-578.
[37]MA P A,LIU S,HUANG Y B,et al.Lactose mediated liver-targeting effect observed by ex vivo imaging technology[J].Biomaterials,2010,31(9):2646-2654.
[38]YANG K,CHANG Y C,WEN J,et al.Supramolecular vesicles based on complex of trp-modified pillar[5]arene and galactose derivative for synergistic and targeted drug delivery[J].Chemistry of Materials,2016,28 (7):1990-1993.
[39]WANG Y,WEN Y F,QU Y,et al.Pillar[5]arene based glyco-targeting nitric oxide nanogenerator for hyperthermia-induced triple-mode cancer therapy[J].Journal of Colloid and Interface Science,2022,615:386-394.
[40]LI Q L,SUN Y,REN L,et al.Supramolecular nanosystem based on pillararene-capped Cu S nanoparticles for targeted chemo-photothermal therapy[J].ACS Applied Materials&Interfaces,2018,10(35):29314-29324.
[41]WANG Y,JIN M,CHEN Z L,et al.Tumor microenvironment responsive supramolecular glyco-nanovesicles based on diselenium-bridged pillar[5]arene dimer for targeted chemotherapy[J].Chemical Communications,2020,56(73):10642-10645.
[42]YU G C,YU W,SHAO L,et al.Fabrication of a targeted drug delivery system from a pillar[5]arene-based supramolecular diblock copolymeric amphiphile for effective cancer therapy[J].Advanced Functional Materials,2016,26(48):8999-9008.
[43]YU G C,MA Y J,HAN C Y,et al.A sugar-functionalized amphiphilic pillar[5]arene:synthesis,self-assembly in water,and application in bacterial cell agglutination[J].Journal of the American Chemical Society,2013,135(28):10310-10313.
[44]WU X W,ZHANG Y,LU Y C,et al.Synergistic and targeted drug delivery based on nano-Ce O2capped with galactose functionalized pillar[5]arene via host-guest interactions[J].Journal of Materials Chemistry B,2017,5(19):3483-3487.
[45]SHANG K,WANG Y,LU Y C,et al.Dual-targeted supramolecular vesicles based on the complex of galactose capped pillar[5]arene and triphenylphosphonium derivative for drug delivery[J].Israel Journal of Chemistry,2018,58(11):1241-1245.
[46]PENG H B,XIE B B,YANG X H,et al.Pillar[5]arenebased,dual p H and enzyme responsive supramolecular vesicles for targeted antibiotic delivery against intracellular MRSA[J].Chemical Communications,2020,56 (58):8115-8118.
[47]WEI P,CZAPLEWSKA J A,WANG L M,et al.Straightforward access to glycosylated,acid sensitive nanogels by host-guest interactions with sugar-modified pillar[5]arenes[J].ACS Macro Letters,2020,9(4):540-545.
[48]PENG H B,XIE B B,CEN X F,et al.Glutathione-responsive multifunctional nanoparticles based on mannosemodified pillar[5]arene for targeted antibiotic delivery against intracellular methicillin-resistant S.aureus[J].Materials Chemistry Frontiers,2022,6(3):360-367.
[49]CHAO S,HUANG P,SHEN Z Y,et al.A mannosefunctionalized pillar[5]arene-based supramolecular fluorescent probe for real-time monitoring of gemcitabine delivery to cancer cells[J].Organic Chemistry Frontiers,2023,10(14):3491-3497.
[50]LI J X,LV X M,LI J H,et al.A supramolecular nearinfrared nanophotosensitizer from host-guest complex of lactose-capped pillar[5]arene with aza-BODIPY derivative for tumor eradication[J].Organic Chemistry Frontiers,2023,10(8):1927-1935.
[51]GUO S W,HUANG Q X,WEI J W,et al.Efficient intracellular delivery of native proteins facilitated by preorganized guanidiniums on pillar[5]arene skeleton[J].Nano Today,2022,43:101396.
[52]CHAO S,SHEN Z Y,LI B W,et al.An L-argininefunctionalized pillar[5]arene-based supramolecular photosensitizer for synergistically enhanced cancer therapeutic effectiveness[J].Chemical Communications,2023,59(23):3455-3458.
基本信息:
DOI:10.12194/j.ntu.20231113001
中图分类号:TQ460.1
引用信息:
[1]全慧,卢冰.基于柱芳烃的主动靶向药物递送体系的设计策略[J].南通大学学报(自然科学版),2025,24(01):85-94.DOI:10.12194/j.ntu.20231113001.
基金信息:
国家自然科学基金青年科学基金项目(32301184)
2024-02-02
2024-02-02
2024-02-02