271:
247:. First starch is liquified either by heat treatment or using α-amylase, then CGTase is added for the enzymatic conversion. CGTases produce mixtures of cyclodextrins, thus the product of the conversion results in a mixture of the three main types of cyclic molecules, in ratios that are strictly dependent on the enzyme used: each CGTase has its own characteristic α:β:γ synthesis ratio. Purification of the three types of cyclodextrins takes advantage of the different water solubility of the molecules: β-CD which is poorly water-soluble (18.5 g/L or 16.3 mM at 25 °C) can be easily retrieved through
337:
422:
researcher in this area, demonstrating that cyclodextrins formed stable aqueous complexes with many other chemicals. By the mid-1970s, each of the natural cyclodextrins had been structurally and chemically characterized and many more complexes had been studied. Since the 1970s, extensive work has been conducted by
Szejtli and others exploring encapsulation by cyclodextrins and their derivatives for industrial and pharmacologic applications. Among the processes used for complexation, the kneading process seems to be one of the best.
267:) form a complex with the desired cyclodextrin which subsequently precipitates. The complex formation drives the conversion of starch towards the synthesis of the precipitated cyclodextrin, thus enriching its content in the final mixture of products. Wacker Chemie AG uses dedicated enzymes, that can produce alpha-, beta- or gamma-cyclodextrin specifically. This is very valuable especially for the food industry, as only alpha- and gamma-cyclodextrin can be consumed without a daily intake limit.
328:) are capable of forming disulfide bonds with cysteine-rich subdomains of mucus glycoproteins. The gastrointestinal and ocular residence time of thiolated cyclodextrins is therefore substantially prolonged. Furthermore, thiolated cyclodextrins are actively taken up by target cells releasing their payload into the cytoplasma. The cellular uptake of various model drugs, for instance, was up to 20-fold improved by using thiolated α-cyclodextrin as carrier system.
414:
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122:
33:
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by the U.S. FDA. They have been applied for delivery of a variety of drugs, including hydrocortisone, prostaglandin, nitroglycerin, itraconazole, chloramphenicol. The cyclodextrin confers solubility and stability to these drugs. The inclusion compounds of cyclodextrins with hydrophobic molecules
421:
Cyclodextrins were called "cellulosine" when first described by A. Villiers in 1891. Soon after, F. Schardinger identified the three naturally occurring cyclodextrins: α, β, and γ, referred to as "Schardinger sugars". For 25 years, between 1911 and 1935, Hans
Pringsheim in Germany was the leading
146:
change of water solutions, leading to the loss of hydrogen or ionic bonds between the host and the guest molecules. Alternative means for the disruption of the complexes take advantage of heating or action of enzymes able to cleave α-1,4 linkages between glucose monomers. Cyclodextrins were also
314:
from cultured cells. The methylated form MβCD was found to be more efficient than β-cyclodextrin. The water-soluble MβCD is known to form soluble inclusion complexes with cholesterol, thereby enhancing its solubility in aqueous solution. MβCD is employed for the preparation of cholesterol-free
136:
Cyclodextrins are ingredients in more than 30 different approved medicines. With a hydrophobic interior and hydrophilic exterior, cyclodextrins form complexes with hydrophobic compounds. Alpha-, beta-, and gamma-cyclodextrin are all
1406:
Toydemir C, Hall S, Demirel E, Elmaci DN, Gol D, Vlaisavljevich E, et al. (December 2022). "Bioconjugated β-Cyclodextrin-Perfluorohexane
Nanocone Clusters as Functional Nanoparticles for Nanoparticle-Mediated Histotripsy".
222:
respectively. Because of this arrangement, the interior of the toroids is considerably less hydrophilic than the aqueous environment and thus able to host hydrophobic molecules. In contrast, the exterior is sufficiently
142:
are able to penetrate body tissues, these can be used to release biologically active compounds under specific conditions. In most cases the mechanism of controlled degradation of such complexes is based on
676:
Motoyama A, Suzuki A, Shirota O, Namba R (April 2002). "Direct determination of pindolol enantiomers in human serum by column-switching LC-MS/MS using a phenylcarbamate-beta-cyclodextrin chiral column".
1203:
de
Oliveira VE, Almeida EW, Castro HV, Edwards HG, Dos Santos HF, de Oliveira LF (August 2011). "Carotenoids and β-cyclodextrin inclusion complexes: Raman spectroscopy and theoretical investigation".
113:
The largest well-characterized cyclodextrin contains 32 1,4-anhydroglucopyranoside units. Poorly-characterized mixtures, containing at least 150-membered cyclic oligosaccharides are also known.
175:. Such devices are capable of releasing fragrances when heated, such as by ironing, body heat, or a dryer. A common application is a typical 'dryer sheet'. They are also the main ingredient in
1168:
Marcolino VA, Zanin GM, Durrant LR, Benassi M, Matioli G (April 2011). "Interaction of curcumin and bixin with β-cyclodextrin: complexation methods, stability, and applications in food".
1314:
Khirallah J, Schmieley R, Demirel E, Rehman TU, Howell J, Durmaz YY, et al. (June 2019). "Nanoparticle-mediated histotripsy (NMH) using perfluorohexane 'nanocones'".
349:
840:"Enhancement of β-cyclodextrin Production and Fabrication of Edible Antimicrobial Films Incorporated with Clove Essential Oil/β-cyclodextrin Inclusion Complex"
602:
Becket G, Schep LJ, Tan MY (March 1999). "Improvement of the in vitro dissolution of praziquantel by complexation with alpha-, beta- and gamma-cyclodextrins".
315:
products: the bulky and hydrophobic cholesterol molecule is easily lodged inside cyclodextrin rings. MβCD is also employed in research to disrupt
255:
techniques. As an alternative a "complexing agent" can be added during the enzymatic conversion step: such agents (usually organic solvents like
291:
Interest in cyclodextrins is enhanced because their host–guest behavior can be manipulated by chemical modification of the hydroxyl groups. O-
1522:
1505:
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Due to the covalent attachment of thiol groups to cyclodextrins high mucoadhesive properties can be introduced as these thiolated oligomers (
553:
546:
539:
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307:
derivatives. The primary alcohols can be tosylated. The degree of derivatization is an adjustable, i.e. full methylation vs partial.
270:
879:
Stanier CA, O'Connell MJ, Clegg W, Anderson HL (2001). "Synthesis of fluorescent stilbene and tolan rotaxanes by Suzuki coupling".
251:
while the more soluble α- and γ-CDs (145 and 232 g/L respectively) are usually purified by means of expensive and time consuming
240:
1622:"2-Hydroxypropyl-beta-cyclodextrin (HPβCD) reduces age-related lipofuscin accumulation through a cholesterol-associated pathway"
397:, such as non-selectivity and the requirement for high pressure. This promising new method has potential applications in cell
336:
1246:
Harada A, Takashima Y, Nakahata M (July 2014). "Supramolecular polymeric materials via cyclodextrin-guest interactions".
218:. The cyclodextrins have toroidal shapes, with the larger and the smaller openings of the toroid exposing to the solvent
195:
156:
138:
434:(oral, rats) is on the order of grams per kilogram. Nevertheless, attempts to use β-Cyclodextrin for the prevention of
1818:
1523:"Evolution of the interaction of a new chemical entity, eflucimibe, with gamma-cyclodextrin during kneading process"
1072:"Thiolated α-cyclodextrin: The likely smallest drug carrier providing enhanced cellular uptake and endosomal escape"
931:"Extraction of cholesterol with methyl-beta-cyclodextrin perturbs formation of clathrin-coated endocytic vesicles"
393:, leading to the development of Nanoparticle-Mediated Histotripsy (NMH). NMH addresses limitations of traditional
227:
to impart cyclodextrins (or their complexes) water solubility. They are not soluble in typical organic solvents.
1813:
1798:
1461:
Crini G (26 July 2020). "Twenty years of dextrin research: a tribute to
Professor Hans Pringsheim (1876–1940)".
345:
1736:
Scantlebery AM, Ochodnicky P, Kors L, Rampanelli E, Butter LM, El
Boumashouli C, et al. (November 2019).
1679:"Hearing loss and hair cell death in mice given the cholesterol-chelating agent hydroxypropyl-β-cyclodextrin"
980:"Per-thiolated cyclodextrins: Nanosized drug carriers providing a prolonged gastrointestinal residence time"
1359:"Development of Acoustically Active Nanocones Using the Host-Guest Interaction as a New Histotripsy Agent"
367:
food colorants have been shown to intensify color, increase water solubility and improve light stability.
1021:"Thiolated Hydroxypropyl-β-cyclodextrin: A Potential Multifunctional Excipient for Ocular Drug Delivery"
360:. Illustrative, α-cyclodextrin form second-sphere coordination complex with tetrabromoaurate anion (-).
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Typical cyclodextrins are constituted by 6-8 glucopyranoside units. These subunits are linked by 1,4
1070:
Kaplan Ö, Truszkowska M, Kali G, Knoll P, Blanco
Massani M, Braun DE, et al. (September 2023).
219:
902:
Brady B, Lynam N, O'Sullivan T, Ahern C, Darcy R (2000). "6A-O-p-Toluenesulfonyl-β-Cyclodextrin".
504:
Gu A, Wheate N (2021). "Macrocycles as drug-enhancing excipients in pharmaceutical formulations".
179:, which claims that the β-cyclodextrins "trap" odor-causing compounds, thereby reducing the odor.
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Rehman TU, Khirallah J, Demirel E, Howell J, Vlaisavljevich E, Yuksel Durmaz Y (February 2019).
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Cyclodextrins are of wide interest in part because they appear nontoxic in animal studies. The
1775:
1738:"β-Cyclodextrin counteracts obesity in Western diet-fed mice but elicits a nephrotoxic effect"
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Biwer A, Antranikian G, Heinzle E (September 2002). "Enzymatic production of cyclodextrins".
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1113:"Selective isolation of gold facilitated by second-sphere coordination with α-cyclodextrin"
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when mixed with water, or can also be taken in a pill. The approval of powdered alcohol by
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encounter an obstacle in the form of damage to the auditory nerve and nephrotoxic effect.
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Grassiri B, Knoll P, Fabiano A, Piras AM, Zambito Y, Bernkop-Schnürch A (February 2022).
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Villiers A. "Sur la transformation de la fécule en dextrine par le ferment butyrique".
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Synthesis of acoustically active nanoparticles for 'Nanoparticle
Mediated Histotripsy'.
252:
183:
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Szejtli J (July 1998). "Introduction and
General Overview of Cyclodextrin Chemistry".
690:
615:
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1482:
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865:
639:"Cyclodextrin-mediated enhancement of riboflavin solubility and corneal permeability"
525:
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Zimmer S, Grebe A, Bakke SS, Bode N, Halvorsen B, Ulas T, et al. (April 2016).
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Crumling MA, Liu L, Thomas PV, Benson J, Kanicki A, Kabara L, et al. (2012).
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Rodal SK, Skretting G, Garred O, Vilhardt F, van Deurs B, Sandvig K (April 1999).
17:
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71:, and chemical industries, as well as agriculture and environmental engineering.
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1573:"Cyclodextrin promotes atherosclerosis regression via macrophage reprogramming"
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1335:
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638:
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Uekama K, Hirayama F, Irie T (July 1998). "Cyclodextrin Drug
Carrier Systems".
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Gil A, Chamayou A, Leverd E, Bougaret J, Baron M, Couarraze G (October 2004).
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monomers ranging from six to eight units in a ring, creating a cone shape:
32:
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in 2014 was met with wide-spread bans and backlash in the United States.
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Kali G, Haddadzadegan S, Laffleur F, Bernkop-Schnürch A (January 2023).
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Liu Z, Frasconi M, Lei J, Brown ZJ, Zhu Z, Cao D, et al. (2013).
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derivatives have been used to make self-healing materials, such as
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Wang Y, Sun Y, Avestro AJ, McGonigal PR, Zhang H (November 2021).
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556:. U.S Food and Drug Administration. GRAS Notice No. GRN 000046.
549:. U.S Food and Drug Administration. GRAS Notice No. GRN 000074.
542:. U.S Food and Drug Administration. GRAS Notice No. GRN 000155.
1500:. Vol. 1. Dordrecht; Boston: Kluwer Academic Publishers.
381:
Using the host-guest interaction between β-Cyclodextrin and
310:
Both β-cyclodextrin and methyl-β-cyclodextrin (MβCD) remove
36:
Chemical structure of the three main types of cyclodextrins.
143:
637:
Morrison PW, Connon CJ, Khutoryanskiy VV (February 2013).
1283:"Supramolecular repair of hydration lubrication surfaces"
1463:
Journal of Inclusion Phenomena and Macrocyclic Chemistry
506:
Journal of Inclusion Phenomena and Macrocyclic Chemistry
1469:(1–2). Springer Science and Business Media LLC: 11–27.
389:
were created. These nanoparticles were combined with
235:
Cyclodextrins are prepared by enzymatic treatment of
67:
conversion. They are used in food, pharmaceutical,
210:γ-CD toroid structure showing spatial arrangement.
679:Journal of Pharmaceutical and Biomedical Analysis
74:Cyclodextrins are composed of 5 or more α-D-gluco
350:mechanically interlocked molecular architectures
147:shown to enhance mucosal penetration of drugs.
473:Ullmann's Encyclopedia of Industrial Chemistry
717:National Alcohol Beverage Control Association
86:). Typical cyclodextrins contain a number of
8:
370:Complexes formed between β-cyclodextrin and
1620:Gaspar J, Mathieu J, Alvarez P (May 2017).
1530:European Journal of Pharmaceutical Sciences
1025:International Journal of Molecular Sciences
1170:Journal of Agricultural and Food Chemistry
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319:by removing cholesterol from membranes.
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182:Cyclodextrins are also used to produce
844:Microbiology and Biotechnology Letters
797:Applied Microbiology and Biotechnology
604:International Journal of Pharmaceutics
417:Space filling model of β-cyclodextrin.
363:β-Cyclodextrin complexes with certain
220:secondary and primary hydroxyl groups
27:Polysaccharide with six glucose units
7:
713:"Powdered Alcohol: An Encapsulation"
155:β-cyclodextrins are used to produce
1205:The Journal of Physical Chemistry A
471:Wimmer T (2012). "Cyclodextrins".
348:, cyclodextrins are precursors to
243:(CGTase) is employed along with α-
59:. Cyclodextrins are produced from
25:
401:for various purposes, including
241:cyclodextrin glycosyltransferase
1316:Physics in Medicine and Biology
1577:Science Translational Medicine
1:
1248:Accounts of Chemical Research
1089:10.1016/j.carbpol.2023.121070
997:10.1016/j.carbpol.2022.120275
935:Molecular Biology of the Cell
691:10.1016/S0731-7085(01)00631-8
616:10.1016/S0378-5173(98)00382-2
1704:10.1371/journal.pone.0053280
1589:10.1126/scitranslmed.aad6100
1300:10.1016/j.chempr.2021.11.001
139:generally recognized as safe
78:units linked 1->4, as in
378:and low-friction surfaces.
1835:
1762:10.1038/s41598-019-53890-z
1646:10.1038/s41598-017-02387-8
1542:10.1016/j.ejps.2004.06.002
1475:10.1007/s10847-020-01013-x
1421:10.1021/acs.biomac.2c01110
518:10.1007/s10847-021-01055-9
809:10.1007/s00253-002-1057-x
299:are typical conversions.
190:. The powder produces an
55:subunits joined by α-1,4
1375:10.1021/acsomega.8b02922
1336:10.1088/1361-6560/ab207e
916:10.15227/orgsyn.077.0220
838:Farahat M (2020-03-28).
481:10.1002/14356007.e08_e02
346:supramolecular chemistry
1498:Cyclodextrin Technology
881:Chemical Communications
643:Molecular Pharmaceutics
278:with an α-cyclodextrin
274:Crystal structure of a
43:are a family of cyclic
1444:Compt. Rend. Acad. Sci
857:10.4014/mbl.1909.09016
418:
385:, acoustically active
341:
283:
211:
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107:γ (gamma)-cyclodextrin
95:α (alpha)-cyclodextrin
37:
1117:Nature Communications
1076:Carbohydrate Polymers
984:Carbohydrate Polymers
416:
339:
273:
209:
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101:β (beta)-cyclodextrin
35:
1038:10.3390/ijms23052612
947:10.1091/mbc.10.4.961
554:"Gamma-cyclodextrin"
540:"Alpha-cyclodextrin"
109:: 8 glucose subunits
103:: 7 glucose subunits
97:: 6 glucose subunits
1754:2019NatSR...917633S
1695:2012PLoSO...753280C
1638:2017NatSR...7.2197G
1328:2019PMB....64l5018K
1217:2011JPCA..115.8511D
1129:2013NatCo...4.1855L
547:"Beta-cyclodextrin"
171:Cyclodextrins bind
1819:E-number additives
1742:Scientific Reports
1626:Scientific Reports
1496:Szejtli J (1988).
1137:10.1038/ncomms2891
737:"Powdered Alcohol"
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192:alcoholic beverage
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47:, consisting of a
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18:Beta-cyclodextrins
1507:978-90-277-2314-7
1415:(12): 5297–5311.
1409:Biomacromolecules
1260:10.1021/ar500109h
1225:10.1021/jp2028142
1211:(30): 8511–8519.
1182:10.1021/jf104223k
904:Organic Syntheses
774:10.1021/cr970022c
655:10.1021/mp3005963
581:10.1021/CR970025P
442:accumulation and
305:hydroxypropylated
186:by encapsulating
16:(Redirected from
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216:glycosidic bonds
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1809:Macrocycles
1632:(1): 2197.
1031:(5): 2612.
741:Alcohol.org
395:histotripsy
391:histotripsy
317:lipid rafts
312:cholesterol
297:acetylation
293:Methylation
287:Derivatives
239:. Commonly
225:hydrophilic
49:macrocyclic
1793:Categories
1082:: 121070.
990:: 120275.
746:2024-01-22
722:2024-01-22
450:References
440:lipofuscin
372:adamantane
365:carotenoid
352:, such as
280:macrocycle
173:fragrances
159:media for
76:pyranoside
1483:220774604
1363:ACS Omega
866:216203179
526:233139034
376:hydrogels
358:catenanes
354:rotaxanes
231:Synthesis
202:Structure
65:enzymatic
1780:31776357
1723:23285273
1683:PLOS ONE
1664:28526856
1607:27053774
1558:31860374
1550:15451000
1450:: 536–8.
1429:36418020
1393:31459627
1344:31071701
1268:24911321
1233:21728366
1190:21381747
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1098:37321712
1057:35269753
1006:36372469
965:10198050
825:12163906
817:12226716
782:11848947
699:11861113
663:23294178
624:10053203
589:11848959
399:ablation
332:Research
325:thiomers
276:rotaxane
51:ring of
1771:6881402
1750:Bibcode
1714:3532434
1691:Bibcode
1655:5438378
1634:Bibcode
1598:4878149
1384:6649115
1324:Bibcode
1213:Bibcode
1146:3674257
1125:Bibcode
1048:8910138
910:: 220.
444:obesity
409:History
265:ethanol
261:acetone
257:toluene
245:amylase
196:the FDA
188:ethanol
177:Febreze
88:glucose
80:amylose
53:glucose
1804:Starch
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303:gives
237:starch
84:starch
61:starch
1554:S2CID
1526:(PDF)
1479:S2CID
956:25220
862:S2CID
821:S2CID
522:S2CID
167:Other
1776:PMID
1719:PMID
1660:PMID
1603:PMID
1546:PMID
1502:ISBN
1448:1891
1425:PMID
1389:PMID
1340:PMID
1287:Chem
1264:PMID
1229:PMID
1186:PMID
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1094:PMID
1053:PMID
1002:PMID
961:PMID
813:PMID
778:PMID
695:PMID
659:PMID
620:PMID
585:PMID
485:ISBN
432:LD50
356:and
295:and
161:HPLC
1766:PMC
1758:doi
1709:PMC
1699:doi
1650:PMC
1642:doi
1593:PMC
1585:doi
1538:doi
1471:doi
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770:doi
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