|本期目录/Table of Contents|

[1]陈思雨,刘 慧*.环糊精在制药技术中的应用 [J].武汉工程大学学报,2026,48(02):140-148.[doi:10.19843/j.cnki.CN42-1779/TQ.202409012]
　CHEN Siyu,LIU Hui*.Application of cyclodextrins in pharmaceutical technology [J].Journal of Wuhan Institute of Technology,2026,48(02):140-148.[doi:10.19843/j.cnki.CN42-1779/TQ.202409012]
点击复制

环糊精在制药技术中的应用
(/HTML)

《武汉工程大学学报》[ISSN:1674-2869/CN:42-1779/TQ]

卷:
48
期数:
2026年02期
页码:
140-148
栏目:
现代大化工
出版日期:
2026-04-30

文章信息/Info

Title:
Application of cyclodextrins in pharmaceutical technology
文章编号:
1674 - 2869（2026）02 - 0133-0140- 09
作者:
陈思雨; 刘 慧*
武汉工程大学化工与制药学院，湖北 武汉 430205
Author(s):
CHEN Siyu;  LIU Hui*
School of Chemical Engineering and Pharmacy，Wuhan Institute of Technology， Wuhan 430205， China
关键词:
环糊精; 包合物; 溶解度; 稳定性; 主客体作用
Keywords:
cyclodextrin;  inclusion complex;  solubility;  stability;  host-guest interaction
分类号:
R944
DOI:
10.19843/j.cnki.CN42-1779/TQ.202409012
文献标志码:
A
摘要:
一些候选药物水溶性差导致生物利用度低，成为新药研发的障碍。本综述首先描述了环糊精从天然产物中纯化和分离的过程，由于其安全性高被广泛用于制药工业。其次介绍了环糊精内部疏水外部亲水的独特结构，可以通过主客体相互作用与难溶性药物形成包合物，在不改变分子结构的情况下改善药物的稳定性、溶解度和生物利用度。然后，针对药物的不同属性，讨论了环糊精包合物的制备方法、适用范围及其优缺点。最后总结了环糊精在制药领域方面的最新应用案例，及其药代动力学和毒理学数据。
Abstract:
Poor aqueous solubility of many drug candidates leads to low bioavailability, which is an obstacle to the development of new drugs. In this review, firstly, the purification and isolation of cyclodextrins from natural products were described. Due to their high safety, cyclodextrins are widely applied in the pharmaceutical industry. Secondly, the unique structure of cyclodextrins was described, which featured a hydrophobic interior and hydrophilic exterior. Inclusion complexes could be formed between cyclodextrins and insoluble guests through host-guest interactions, resulting in improved stability, solubility and bioavailability for the guests with unchanged molecular structures. In addition, various preparation methods were discussed according to the properties of drugs, highlighting their respective scopes, advantages and limitations. Lastly, the latest applications of cyclodextrins in the pharmaceutical field were summarized, along with their pharmacokinetic and toxicology data.

参考文献/References:

[ 1 ] AMIDON G L, LENNERN?S H, SHAH V P, et al. A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability [J]. Pharmaceutical Research, 1995, 12(3): 413-420.
[ 2 ] TAKAGI T, RAMACHANDRAN C, BERMEJO M, et al. A provisional biopharmaceutical classification of the top 200 oral drug products in the United States, Great Britain, Spain, and Japan [J]. Molecular Pharmaceutics, 2006, 3(6): 631-643.
[ 3 ] KALEPU S, NEKKANTI V. Insoluble drug delivery strategies: review of recent advances and business prospects [J]. Acta Pharmaceutica Sinica B, 2015, 5(5): 442-453.
[ 4 ] VONCINA B, VIVOD V, CHEN W T. Surface modification of PET fibers with the use of β-cyclodextrin [J]. Journal of Applied Polymer Science, 2009, 113(6): 3891-3895.
[ 5 ] KURKOV S V, LOFTSSON T. Cyclodextrins [J]. International Journal of Pharmaceutics, 2013, 453(1): 167-180.
[ 6 ] SZEJTLI J. Medicinal applications of cyclodextrins [J]. Medicinal Research Reviews, 1994, 14(3): 353-386.
[ 7 ] VILLIERS A. Sur la fermentation de la fécule par l’action du ferment butyrique[J]. Comptes Rendus De L Academie Bulgare Des Sciences, 1891, 112: 536-538.
[ 8 ] SCHARDINGER F. über thermophile Bakterien aus verschiedenen Speisen und Milch: sowie über einige Umsetzungsprodukte derselben in kohlenhy-drathaltigen N?hrl?sungen, darunter krystallisierte Polysaccharide (Dextrine) aus St?rke [J]. Zeitschrift Für Untersuchung der Nahrungs- und Genu?mittel, 1903, 6(19): 865-880.
[ 9 ] CRAMER F. Einschlussverbindungen[M]. Berlin, Heidelberg: Springer, 1954 .
[10] LOFTSSON T, DUCHêNE D. Cyclodextrins and their pharmaceutical applications [J]. International Journal of Pharmaceutics, 2007, 329(1/2): 1-11.
[11] UEKAMA K, HIRAYAMA F, ARIMA H. Recent aspect of cyclodextrin-based drug delivery system [J]. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2006, 56(1): 3-8.
[12] STRICKLEY R G. Solubilizing excipients in oral and injectable formulations [J]. Pharmaceutical Research, 2004, 21(2): 201-230.
[13] MARQUES H M C. A review on cyclodextrin encapsulation of essential oils and volatiles [J]. Flavour and Fragrance Journal,2010,25(5):313-326.
[14] ZHANG L Z, ZHOU J P, ZHANG L N. Structure and properties of β-cyclodextrin/cellulose hydrogels prepared in NaOH/urea aqueous solution [J]. Carbohydrate Polymers, 2013, 94(1): 386-393.
[15] DEMIREL M, YURTDA? G, GEN? L. Inclusion complexes of ketoconazole with beta-cyclodextrin: physicochemical characterization and in vitro dissolution behaviour of its vaginal suppositories [J]. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2011, 70(3): 437-445.
[16] PATEL R, PUROHIT N. Physico-chemical charac-terization and in vitro dissolution assessment of clonazepam-cyclodextrins inclusion compounds [J]. AAPS PharmSciTech, 2009, 10(4): 1301-1312.
[17] ?EZANKA M. Synthesis of substituted cyclodextrins [J]. Environmental Chemistry Letters, 2019, 17(1): 49-63.
[18] DE ARAUJO D R, TSUNEDA S S, CEREDA C M S, et al. Development and pharmacological evaluation of ropivacaine-2-hydroxypropyl-β-cyclodextrin inclusion complex [J]. European Journal of Pharmaceutical Sciences, 2008, 33(1): 60-71.
[19] YUAN C, JIN Z Y, XU X M, et al. Preparation and stability of the inclusion complex of astaxanthin with hydroxypropyl-β-cyclodextrin [J]. Food Chemistry, 2008, 109(2): 264-268.
[20] DING Y L, ZHANG Z Y, DING C, et al. The use of cyclodextrin inclusion complexes to increase the solubility and pharmacokinetic profile of albendazole [J]. Molecules, 2023, 28(21): 7295.
[21] EINAFSHAR E, JAVID H, AMIRI H, et al. Curcumin loaded β-cyclodextrin-magnetic graphene oxide nanoparticles decorated with folic acid receptors as a new theranostic agent to improve prostate cancer treatment [J]. Carbohydrate Polymers, 2024, 340: 122328.
[22] YARDY A, ENTZ K, BENNETT D, et al. Incorporation of loratadine-cyclodextrin complexes in oral thin films for rapid drug delivery [J]. Journal of Pharmaceutical Sciences, 2024, 113(5): 1220-1227.
[23] 方世通, 祝宏, 金学平, 等. 乙酰水杨酸-异烟肼的包合工艺优化与抗菌活性测试[J]. 武汉工程大学学报, 2022, 44(1): 36-41.
[24] LIU N, XIAO J, ZANG L H, et al. Preparation of trans-crocetin with high solubility, stability, and oral bioavailability by incorporation into three types of cyclodextrins [J]. Pharmaceutics, 2023, 15(12): 2790.
[25] PARK C, ZUO J Y, GIL M C, et al. Investigation of cannabinoid acid/cyclodextrin inclusion complex for improving physicochemical and biological performance [J]. Pharmaceutics, 2023, 15(11): 2533.
[26] NAEEM A, YU C Q, ZANG Z Z, et al. Synthesis and evaluation of rutin-hydroxypropyl β-cyclodextrin inclusion complexes embedded in xanthan gum-based (HPMC-g-AMPS) hydrogels for oral controlled drug delivery [J]. Antioxidants, 2023, 12(3): 552.
[27] VERZA B S, van den BEUCKEN J J J P, BRANDT J V, et al. A long-term controlled drug-delivery with anionic beta cyclodextrin complex in layer-by-layer coating for percutaneous implants devices [J]. Carbohydrate Polymers, 2021, 257: 117604.
[28] YASMIN T, MAHMOOD A, FAROOQ M, et al. Development and evaluation of a pH-responsive Mimosa pudica seed mucilage/β- cyclodextrin-co-poly(methacrylate) hydrogel for controlled drug delivery: in vitro and in vivo assessment [J]. International Journal of Biological Macromolecules, 2024, 268: 131832.
[29] GUO Z, WU F, SINGH V, et al. Host-guest kinetic interactions between HP-β-cyclodextrin and drugs for prediction of bitter taste masking [J]. Journal of Pharmaceutical and Biomedical Analysis, 2017, 140: 232-238.
[30] CHALLA R, AHUJA A, ALI J, et al. Cyclodextrins in drug delivery: an updated review [J]. AAPS PharmSciTech, 2005, 6(2): 43.
[31] MOKHTAR M S, SULIMAN F O, ELBASHIR A A. Experimental and molecular modeling investigations of inclusion complexes of imazapyr with 2-hydroxypropyl(β/γ) cyclodextrin [J]. Journal of Molecular Liquids, 2018, 262: 504-513.
[32] RUDRANGI S R S, BHOMIA R, TRIVEDI V, et al. Influence of the preparation method on the physicochemical properties of indomethacin and methyl-β-cyclodextrin complexes [J]. International Journal of Pharmaceutics, 2015, 479(2): 381-390.
[33] GIGLIO V, VIALE M, BERTONE V, et al. Cyclodextrin polymers as nanocarriers for sorafenib [J]. Investigational New Drugs, 2018, 36(3): 370-379.
[34] PASSOS J J, DE SOUSA F B, MUNDIM I M, et al. Double continuous injection preparation method of cyclodextrin inclusion compounds by spray drying [J]. Chemical Engineering Journal, 2013, 228: 345-351.
[35] CHAROENCHAITRAKOOL M, DEHGHANI F, FOSTER N R. Utilization of supercritical carbon dioxide for complex formation of ibuprofen and methyl-β-cyclodextrin [J]. International Journal of Pharmaceutics, 2002, 239(1/2): 103-112.
[36] ABBASZADEGAN S, AL-MARZOUQI A H, SALEM A A, et al. Physicochemical characteriza-tions of safranal-β-cyclodextrin inclusion complexes prepared by supercritical carbon dioxide and conventional methods [J]. Journal of Inclusion Phenomena and Macrocyclic Chemistry,2015,83(3): 215-226.
[37] 孙宇君, 吕中. 季铵盐类聚合物增强纳米抗菌材料性能的研究进展[J]. 武汉工程大学学报,2021,43(1): 12-20.
[38] DAS S, JOSEPH M T, SARKAR D. Hydrogen bonding interpolymer complex formation and study of its host-guest interaction with cyclodextrin and its application as an active delivery vehicle [J]. Langmuir, 2013, 29(6): 1818-1830.
[39] GRA?A SUáREZ L, VERBOOM W, HUSKENS J. Cyclodextrin-based supramolecular nanoparticles stabilized by balancing attractive host-guest and repulsive electrostatic interactions [J]. Chemical Communications, 2014, 50(55): 7280-7282.
[40] NAMGUNG R, LEE Y M, KIM J, et al. Poly-cyclodextrin and poly-paclitaxel nano-assembly for anticancer therapy [J]. Nature Communications, 2014, 5: 3702.
[41] 何祖政, 谢冰倩, 刘慧. 基于大环化合物的刺激响应组装体的研究进展[J]. 武汉工程大学学报, 2020, 42(6): 597-603.
[42] XIAO W, CHEN W H, ZHANG J, et al. Design of a photoswitchable hollow microcapsular drug delivery system by using a supramolecular drug-loading approach [J]. The Journal of Physical Chemistry B, 2011, 115(46): 13796-13802.
[43] WANG Y, LIU Y Y, LIANG J H, et al. A cyclodextrin-core star copolymer with Y-shaped ABC miktoarms and its unimolecular micelles [J]. RSC Advances, 2017, 7(19): 11691-11700.
[44] VICO R V, VOSKUHL J, RAVOO B J. Multivalent interaction of cyclodextrin vesicles, carbohydrate guests, and lectins: a kinetic investigation [J]. Langmuir, 2011, 27(4): 1391-1397.
[45] JIN H B, LIU Y, ZHENG Y L, et al. Cytomimetic large-scale vesicle aggregation and fusion based on host-guest interaction [J]. Langmuir, 2012, 28(4): 2066-2072.
[46] POURJAVADI A, ADELI M, YAZDI M. Fully supramolecular vesicles as anticancer drug delivery systems [J]. New Journal of Chemistry, 2013, 37(2): 295-298.
[47] YANG B, DONG X, LEI Q, et al. Host-guest interaction-based self-engineering of nano-sized vesicles for co-delivery of genes and anticancer drugs [J]. ACS Applied Materials & Interfaces, 2015, 7(39): 22084-22094.
[48] SWAMINATHAN S, PASTERO L, SERPE L, et al. Cyclodextrin-based nanosponges encapsulating camptothecin: physicochemical characterization, stability and cytotoxicity [J]. European Journal of Pharmaceutics and Biopharmaceutics, 2010, 74(2): 193-201.
[49] TROTTA F, ZANETTI M, CAVALLI R. Cyclodextrin-based nanosponges as drug carriers [J]. Beilstein Journal of Organic Chemistry, 2012, 8: 2091-2099.
[50] ANSARI K A, TORNE S J, VAVIA P R, et al. Paclitaxel loaded nanosponges: in-vitro characterization and cytotoxicity study on MCF-7 cell line culture [J]. Current Drug Delivery, 2011, 8(2): 194-202.
[51] LUMHOLDT L R, HOLM R, J?RGENSEN E B, et al. In vitro investigations of α-amylase mediated hydrolysis of cyclodextrins in the presence of ibuprofen, flurbiprofen, or benzo [a] pyrene [J]. Carbohydrate Research, 2012, 362: 56-61.
[52] SAOKHAM P, LOFTSSON T. γ-cyclodextrin [J]. International Journal of Pharmaceutics, 2017, 516(1/2): 278-292.
[53] STELLA V J, HE Q R. Cyclodextrins [J]. Toxicologic Pathology, 2008, 36(1): 30-42.
[54] van OMMEN B, de BIE A T H J, B?R A. Disposition of 14C-alpha-cyclodextrin in germ-free and conventional rats [J]. Regulatory Toxicology and Pharmacology, 2004, 39(Suppl 1): 57-66.
[55] HAFNER V, CZOCK D, BURHENNE J, et al. Pharmacokinetics of sulfobutylether-beta-cyclodextrin and voriconazole in patients with end-stage renal failure during treatment with two hemodialysis systems and hemodiafiltration [J]. Antimicrobial Agents and Chemotherapy, 2010, 54(6): 2596-2602.
[56] KLEIJN H J, ZOLLINGER D P, VAN DEN HEUVEL M W, et al. Population pharmacokinetic-pharmacodynamic analysis for sugammadex-mediated reversal of rocuronium-induced neuromuscular blockade [J]. British Journal of Clinical Pharmacology, 2011, 72(3): 415-433.
[57] KURKOV S V, UKHATSKAYA E V, LOFTSSON T. Drug/cyclodextrin: beyond inclusion complexation [J]. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2011, 69(3): 297-301.
[58] LOFTSSON T. Excipient pharmacokinetics and profiling [J]. International Journal of Pharmaceutics, 2015, 480(1/2): 48-54.

相似文献/References:

[1]方世通,祝　宏,金学平,等.乙酰水杨酸-异烟肼的包合工艺优化与抗菌活性测试[J].武汉工程大学学报,2022,44(01):36.[doi:10.19843/j.cnki.CN42-1779/TQ. 202011017]
　FANG Shitong,ZHU Hong,JIN Xueping,et al.Optimization of Inclusion Process of Acetylsalicylic Acid-Isoniazid and Test of Antibacterial Activity[J].Journal of Wuhan Institute of Technology,2022,44(02):36.[doi:10.19843/j.cnki.CN42-1779/TQ. 202011017]

备注/Memo

备注/Memo:
收稿日期：2024-09-13
基金项目：武汉工程大学研究生教育创新基金（CX2023032）
作者简介：陈思雨，硕士研究生。Email：2813177270@qq.com
*通信作者：刘 慧，博士，副教授。Email：huiliu@wit.edu.cn
更新日期/Last Update: 2026-05-07