Encapsulation of Drug Molecules by Cucurbiturils: Effects on their Chemical Properties in Aqueous Solution

被引:137
作者
Macartney, Donal H. [1 ]
机构
[1] Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
acid-base properties; cucurbiturils; drug delivery; host-guest systems; supramolecular chemistry; HOST-GUEST COMPLEXES; INCLUSION COMPLEXES; PK(A) SHIFTS; SUPRAMOLECULAR ASSEMBLIES; FLUORESCENCE ENHANCEMENT; POLYMER NANOCAPSULES; BETA-CYCLODEXTRIN; LOCAL-ANESTHETICS; BASIC SOLUTION; BINDING;
D O I
10.1002/ijch.201100040
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The effects of the encapsulation of drugs and other molecules of biomedical interest by cucurbit[n]uril (n=5-8, 10) host molecules on the chemical properties of the drugs in aqueous solution are reviewed. The cucurbituril complexation of drug molecules has been shown to generally increase the guests' pK(a) values through preferential inclusion of the protonated species, modulate other equilibria involving the guest, improve the solubility in aqueous solution, reduce the toxicity and other side effects, as well as enhance the stability and targeted delivery of the drug molecule. These benefits have led to an increasing interest in the applications of cucurbit[n]urils in novel drug formulations.
引用
收藏
页码:600 / 615
页数:16
相关论文
共 213 条
[1]   Changes in the conformational structure, microscopic and macroscopic pKas of meloxicam on complexation with natural and modified cyclodextrins [J].
Abdoh, A. A. ;
El-Barghouthi, M. I. ;
Zughul, M. B. ;
Davies, J. E. ;
Badwan, A. A. .
PHARMAZIE, 2007, 62 (01) :55-59
[2]   pH Clock-Operated Mechanized Nanoparticles [J].
Angelos, Sarah ;
Khashab, Niveen M. ;
Yang, Ying-Wei ;
Trabolsi, Ali ;
Khatib, Hussam A. ;
Stoddart, J. Fraser ;
Zink, Jeffrey I. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (36) :12912-+
[3]   Supramolecular Cross-Linked Networks via Host-Guest Complexation with Cucurbit[8]uril [J].
Appel, Eric A. ;
Biedermann, Frank ;
Rauwald, Urs ;
Jones, Samuel T. ;
Zayed, Jameel M. ;
Scherman, Oren A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (40) :14251-14260
[4]  
Ariga K, 2009, EXPERT OPIN BIOL TH, V9, P307, DOI [10.1517/14712590802715772, 10.1517/14712590802715772 ]
[5]   Analysis of host-assisted guest protonation exemplified for p-sulfonatocalix[4]arene -: Towards enzyme-mimetic pKa shifts [J].
Bakirci, Hueseyin ;
Koner, Apurba L. ;
Schwarzlose, Thomas ;
Nau, Werner M. .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (18) :4799-4807
[6]   Cucurbituril binding of trans-[{PtCl(NH3)2}2(μ-NH2(CH2)8NH2)]2+ and the effect on the reaction with cysteine [J].
Bali, Mark S. ;
Buck, Damian P. ;
Coe, Andrew J. ;
Day, Anthony I. ;
Collins, J. Grant .
DALTON TRANSACTIONS, 2006, (45) :5337-5344
[7]  
Behrend R, 1905, LIEBIGS ANN CHEM, V339, P1
[8]  
BORN A, 2002, ANGEW CHEM, V114, P275
[9]  
Born A., 2002, ANGEW CHEM INT EDIT, V41, P265
[10]   Cyclodextrins as pharmaccutical solubilizers [J].
Brewster, Marcus E. ;
Loftsson, Thorsteinn .
ADVANCED DRUG DELIVERY REVIEWS, 2007, 59 (07) :645-666