256:
232:. 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
322:
407:
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.
252:) 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.
313:) 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.
399:
192:
107:
22:
126:
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
406:
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
131:
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
299:
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
121:
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
1391:
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".
207:
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
127:
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
661:
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".
1188:
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".
98:
The largest well-characterized cyclodextrin contains 32 1,4-anhydroglucopyranoside units. Poorly-characterized mixtures, containing at least 150-membered cyclic oligosaccharides are also known.
160:. 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
1153:
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".
1299:
Khirallah J, Schmieley R, Demirel E, Rehman TU, Howell J, Durmaz YY, et al. (June 2019). "Nanoparticle-mediated histotripsy (NMH) using perfluorohexane 'nanocones'".
334:
825:"Enhancement of β-cyclodextrin Production and Fabrication of Edible Antimicrobial Films Incorporated with Clove Essential Oil/β-cyclodextrin Inclusion Complex"
587:
Becket G, Schep LJ, Tan MY (March 1999). "Improvement of the in vitro dissolution of praziquantel by complexation with alpha-, beta- and gamma-cyclodextrins".
300:
products: the bulky and hydrophobic cholesterol molecule is easily lodged inside cyclodextrin rings. MβCD is also employed in research to disrupt
240:
techniques. As an alternative a "complexing agent" can be added during the enzymatic conversion step: such agents (usually organic solvents like
276:
Interest in cyclodextrins is enhanced because their host–guest behavior can be manipulated by chemical modification of the hydroxyl groups. O-
1507:
1490:
307:
Due to the covalent attachment of thiol groups to cyclodextrins high mucoadhesive properties can be introduced as these thiolated oligomers (
538:
531:
524:
473:
292:
derivatives. The primary alcohols can be tosylated. The degree of derivatization is an adjustable, i.e. full methylation vs partial.
255:
864:
Stanier CA, O'Connell MJ, Clegg W, Anderson HL (2001). "Synthesis of fluorescent stilbene and tolan rotaxanes by Suzuki coupling".
236:
while the more soluble α- and γ-CDs (145 and 232 g/L respectively) are usually purified by means of expensive and time consuming
225:
1607:"2-Hydroxypropyl-beta-cyclodextrin (HPβCD) reduces age-related lipofuscin accumulation through a cholesterol-associated pathway"
382:, such as non-selectivity and the requirement for high pressure. This promising new method has potential applications in cell
321:
1231:
Harada A, Takashima Y, Nakahata M (July 2014). "Supramolecular polymeric materials via cyclodextrin-guest interactions".
203:. The cyclodextrins have toroidal shapes, with the larger and the smaller openings of the toroid exposing to the solvent
180:
141:
123:
419:(oral, rats) is on the order of grams per kilogram. Nevertheless, attempts to use β-Cyclodextrin for the prevention of
1803:
1508:"Evolution of the interaction of a new chemical entity, eflucimibe, with gamma-cyclodextrin during kneading process"
1057:"Thiolated α-cyclodextrin: The likely smallest drug carrier providing enhanced cellular uptake and endosomal escape"
916:"Extraction of cholesterol with methyl-beta-cyclodextrin perturbs formation of clathrin-coated endocytic vesicles"
378:, leading to the development of Nanoparticle-Mediated Histotripsy (NMH). NMH addresses limitations of traditional
212:
to impart cyclodextrins (or their complexes) water solubility. They are not soluble in typical organic solvents.
1798:
1783:
1446:
Crini G (26 July 2020). "Twenty years of dextrin research: a tribute to
Professor Hans Pringsheim (1876–1940)".
330:
1721:
Scantlebery AM, Ochodnicky P, Kors L, Rampanelli E, Butter LM, El
Boumashouli C, et al. (November 2019).
1664:"Hearing loss and hair cell death in mice given the cholesterol-chelating agent hydroxypropyl-β-cyclodextrin"
965:"Per-thiolated cyclodextrins: Nanosized drug carriers providing a prolonged gastrointestinal residence time"
1344:"Development of Acoustically Active Nanocones Using the Host-Guest Interaction as a New Histotripsy Agent"
352:
food colorants have been shown to intensify color, increase water solubility and improve light stability.
1006:"Thiolated Hydroxypropyl-β-cyclodextrin: A Potential Multifunctional Excipient for Ocular Drug Delivery"
345:. Illustrative, α-cyclodextrin form second-sphere coordination complex with tetrabromoaurate anion (-).
1793:
1734:
1675:
1618:
1308:
1197:
1109:
199:
Typical cyclodextrins are constituted by 6-8 glucopyranoside units. These subunits are linked by 1,4
1055:
Kaplan Ö, Truszkowska M, Kali G, Knoll P, Blanco
Massani M, Braun DE, et al. (September 2023).
204:
887:
Brady B, Lynam N, O'Sullivan T, Ahern C, Darcy R (2000). "6A-O-p-Toluenesulfonyl-β-Cyclodextrin".
489:
Gu A, Wheate N (2021). "Macrocycles as drug-enhancing excipients in pharmaceutical formulations".
164:, which claims that the β-cyclodextrins "trap" odor-causing compounds, thereby reducing the odor.
1538:
1463:
846:
805:
506:
379:
375:
176:
1342:
Rehman TU, Khirallah J, Demirel E, Howell J, Vlaisavljevich E, Yuksel Durmaz Y (February 2019).
415:
Cyclodextrins are of wide interest in part because they appear nontoxic in animal studies. The
1760:
1723:"β-Cyclodextrin counteracts obesity in Western diet-fed mice but elicits a nephrotoxic effect"
1703:
1644:
1587:
1530:
1486:
1409:
1373:
1324:
1248:
1213:
1170:
1135:
1078:
1037:
986:
945:
797:
762:
679:
643:
604:
569:
469:
110:
91:
85:
79:
780:
Biwer A, Antranikian G, Heinzle E (September 2002). "Enzymatic production of cyclodextrins".
1750:
1742:
1693:
1683:
1634:
1626:
1577:
1569:
1522:
1455:
1401:
1363:
1355:
1316:
1279:
1240:
1205:
1162:
1125:
1117:
1068:
1027:
1017:
976:
935:
927:
896:
869:
836:
789:
754:
671:
635:
596:
561:
498:
461:
387:
45:
33:
1098:"Selective isolation of gold facilitated by second-sphere coordination with α-cyclodextrin"
179:
when mixed with water, or can also be taken in a pill. The approval of powdered alcohol by
1788:
431:
encounter an obstacle in the form of damage to the auditory nerve and nephrotoxic effect.
420:
367:
285:
233:
200:
1004:
Grassiri B, Knoll P, Fabiano A, Piras AM, Zambito Y, Bernkop-Schnürch A (February 2022).
1738:
1679:
1622:
1312:
1201:
1113:
63:
Cyclodextrins are composed of 5 or more α-D-glucopyranoside units linked 1->4, as in
1755:
1722:
1698:
1663:
1639:
1606:
1582:
1557:
1427:
Villiers A. "Sur la transformation de la fécule en dextrine par le ferment butyrique".
1368:
1343:
1130:
1097:
1032:
1005:
697:
325:
Synthesis of acoustically active nanoparticles for 'Nanoparticle
Mediated Histotripsy'.
237:
168:
745:
Szejtli J (July 1998). "Introduction and
General Overview of Cyclodextrin Chemistry".
675:
600:
1777:
1467:
940:
915:
850:
624:"Cyclodextrin-mediated enhancement of riboflavin solubility and corneal permeability"
510:
289:
57:
1556:
Zimmer S, Grebe A, Bakke SS, Bode N, Halvorsen B, Ulas T, et al. (April 2016).
1542:
809:
398:
371:
191:
1662:
Crumling MA, Liu L, Thomas PV, Benson J, Kanicki A, Kabara L, et al. (2012).
1073:
1056:
981:
964:
914:
Rodal SK, Skretting G, Garred O, Vilhardt F, van Deurs B, Sandvig K (April 1999).
1688:
1573:
1284:
1267:
60:, and chemical industries, as well as agriculture and environmental engineering.
301:
296:
281:
277:
209:
1746:
1630:
1558:"Cyclodextrin promotes atherosclerosis regression via macrophage reprogramming"
1526:
1459:
1405:
1320:
721:
623:
552:
Uekama K, Hirayama F, Irie T (July 1998). "Cyclodextrin Drug
Carrier Systems".
502:
1506:
Gil A, Chamayou A, Leverd E, Bougaret J, Baron M, Couarraze G (October 2004).
793:
424:
356:
349:
264:
37:
1359:
900:
465:
157:
106:
1764:
1707:
1648:
1591:
1534:
1413:
1377:
1328:
1252:
1217:
1174:
1139:
1082:
1041:
990:
949:
841:
801:
766:
683:
647:
608:
573:
75:
monomers ranging from six to eight units in a ring, creating a cone shape:
21:
1022:
931:
383:
360:
342:
338:
260:
183:
in 2014 was met with wide-spread bans and backlash in the United States.
963:
Kali G, Haddadzadegan S, Laffleur F, Bernkop-Schnürch A (January 2023).
1121:
428:
309:
249:
245:
241:
229:
172:
161:
72:
64:
41:
1244:
1209:
1166:
1096:
Liu Z, Frasconi M, Lei J, Brown ZJ, Zhu Z, Cao D, et al. (2013).
758:
639:
565:
873:
221:
68:
53:
49:
824:
359:
derivatives have been used to make self-healing materials, such as
1266:
Wang Y, Sun Y, Avestro AJ, McGonigal PR, Zhang H (November 2021).
397:
320:
254:
190:
105:
20:
416:
145:
541:. U.S Food and Drug Administration. GRAS Notice No. GRN 000046.
534:. U.S Food and Drug Administration. GRAS Notice No. GRN 000074.
527:. U.S Food and Drug Administration. GRAS Notice No. GRN 000155.
1485:. Vol. 1. Dordrecht; Boston: Kluwer Academic Publishers.
366:
Using the host-guest interaction between β-Cyclodextrin and
295:
Both β-cyclodextrin and methyl-β-cyclodextrin (MβCD) remove
25:
Chemical structure of the three main types of cyclodextrins.
128:
622:
Morrison PW, Connon CJ, Khutoryanskiy VV (February 2013).
1268:"Supramolecular repair of hydration lubrication surfaces"
1448:
Journal of Inclusion Phenomena and Macrocyclic Chemistry
491:
Journal of Inclusion Phenomena and Macrocyclic Chemistry
1454:(1–2). Springer Science and Business Media LLC: 11–27.
374:
were created. These nanoparticles were combined with
220:
Cyclodextrins are prepared by enzymatic treatment of
56:
conversion. They are used in food, pharmaceutical,
195:γ-CD toroid structure showing spatial arrangement.
664:Journal of Pharmaceutical and Biomedical Analysis
335:mechanically interlocked molecular architectures
132:shown to enhance mucosal penetration of drugs.
458:Ullmann's Encyclopedia of Industrial Chemistry
702:National Alcohol Beverage Control Association
71:). Typical cyclodextrins contain a number of
8:
355:Complexes formed between β-cyclodextrin and
1605:Gaspar J, Mathieu J, Alvarez P (May 2017).
1515:European Journal of Pharmaceutical Sciences
1010:International Journal of Molecular Sciences
1155:Journal of Agricultural and Food Chemistry
1754:
1697:
1687:
1638:
1581:
1367:
1283:
1129:
1072:
1031:
1021:
980:
939:
840:
451:
449:
447:
445:
443:
304:by removing cholesterol from membranes.
439:
167:Cyclodextrins are also used to produce
829:Microbiology and Biotechnology Letters
782:Applied Microbiology and Biotechnology
589:International Journal of Pharmaceutics
402:Space filling model of β-cyclodextrin.
348:β-Cyclodextrin complexes with certain
205:secondary and primary hydroxyl groups
16:Polysaccharide with six glucose units
7:
698:"Powdered Alcohol: An Encapsulation"
140:β-cyclodextrins are used to produce
1190:The Journal of Physical Chemistry A
456:Wimmer T (2012). "Cyclodextrins".
333:, cyclodextrins are precursors to
228:(CGTase) is employed along with α-
48:. Cyclodextrins are produced from
14:
386:for various purposes, including
226:cyclodextrin glycosyltransferase
1301:Physics in Medicine and Biology
1562:Science Translational Medicine
1:
1233:Accounts of Chemical Research
1074:10.1016/j.carbpol.2023.121070
982:10.1016/j.carbpol.2022.120275
920:Molecular Biology of the Cell
676:10.1016/S0731-7085(01)00631-8
601:10.1016/S0378-5173(98)00382-2
1689:10.1371/journal.pone.0053280
1574:10.1126/scitranslmed.aad6100
1285:10.1016/j.chempr.2021.11.001
124:generally recognized as safe
363:and low-friction surfaces.
1820:
1747:10.1038/s41598-019-53890-z
1631:10.1038/s41598-017-02387-8
1527:10.1016/j.ejps.2004.06.002
1460:10.1007/s10847-020-01013-x
1406:10.1021/acs.biomac.2c01110
503:10.1007/s10847-021-01055-9
794:10.1007/s00253-002-1057-x
284:are typical conversions.
175:. The powder produces an
44:subunits joined by α-1,4
1360:10.1021/acsomega.8b02922
1321:10.1088/1361-6560/ab207e
901:10.15227/orgsyn.077.0220
823:Farahat M (2020-03-28).
466:10.1002/14356007.e08_e02
331:supramolecular chemistry
1483:Cyclodextrin Technology
866:Chemical Communications
628:Molecular Pharmaceutics
263:with an α-cyclodextrin
259:Crystal structure of a
32:are a family of cyclic
1429:Compt. Rend. Acad. Sci
842:10.4014/mbl.1909.09016
403:
370:, acoustically active
326:
268:
196:
113:
92:γ (gamma)-cyclodextrin
80:α (alpha)-cyclodextrin
26:
1102:Nature Communications
1061:Carbohydrate Polymers
969:Carbohydrate Polymers
401:
324:
258:
194:
109:
86:β (beta)-cyclodextrin
24:
1023:10.3390/ijms23052612
932:10.1091/mbc.10.4.961
539:"Gamma-cyclodextrin"
525:"Alpha-cyclodextrin"
94:: 8 glucose subunits
88:: 7 glucose subunits
82:: 6 glucose subunits
1739:2019NatSR...917633S
1680:2012PLoSO...753280C
1623:2017NatSR...7.2197G
1313:2019PMB....64l5018K
1202:2011JPCA..115.8511D
1114:2013NatCo...4.1855L
532:"Beta-cyclodextrin"
156:Cyclodextrins bind
1804:E-number additives
1727:Scientific Reports
1611:Scientific Reports
1481:Szejtli J (1988).
1122:10.1038/ncomms2891
722:"Powdered Alcohol"
404:
327:
269:
197:
177:alcoholic beverage
114:
36:, consisting of a
27:
1492:978-90-277-2314-7
1400:(12): 5297–5311.
1394:Biomacromolecules
1245:10.1021/ar500109h
1210:10.1021/jp2028142
1196:(30): 8511–8519.
1167:10.1021/jf104223k
889:Organic Syntheses
759:10.1021/cr970022c
640:10.1021/mp3005963
566:10.1021/CR970025P
427:accumulation and
290:hydroxypropylated
171:by encapsulating
1811:
1799:Chelating agents
1784:Oligosaccharides
1769:
1768:
1758:
1718:
1712:
1711:
1701:
1691:
1659:
1653:
1652:
1642:
1602:
1596:
1595:
1585:
1568:(333): 333ra50.
1553:
1547:
1546:
1512:
1503:
1497:
1496:
1478:
1472:
1471:
1443:
1437:
1436:
1424:
1418:
1417:
1388:
1382:
1381:
1371:
1354:(2): 4176–4184.
1339:
1333:
1332:
1296:
1290:
1289:
1287:
1263:
1257:
1256:
1239:(7): 2128–2140.
1228:
1222:
1221:
1185:
1179:
1178:
1161:(7): 3348–3357.
1150:
1144:
1143:
1133:
1093:
1087:
1086:
1076:
1052:
1046:
1045:
1035:
1025:
1001:
995:
994:
984:
960:
954:
953:
943:
911:
905:
904:
884:
878:
877:
874:10.1039/b010015n
861:
855:
854:
844:
820:
814:
813:
777:
771:
770:
753:(5): 1743–1754.
747:Chemical Reviews
742:
736:
735:
733:
732:
718:
712:
711:
709:
708:
694:
688:
687:
658:
652:
651:
619:
613:
612:
584:
578:
577:
560:(5): 2045–2076.
554:Chemical Reviews
549:
543:
542:
535:
528:
521:
515:
514:
486:
480:
479:
453:
388:cancer treatment
201:glycosidic bonds
142:stationary phase
46:glycosidic bonds
34:oligosaccharides
1819:
1818:
1814:
1813:
1812:
1810:
1809:
1808:
1774:
1773:
1772:
1720:
1719:
1715:
1661:
1660:
1656:
1604:
1603:
1599:
1555:
1554:
1550:
1510:
1505:
1504:
1500:
1493:
1480:
1479:
1475:
1445:
1444:
1440:
1426:
1425:
1421:
1390:
1389:
1385:
1341:
1340:
1336:
1298:
1297:
1293:
1265:
1264:
1260:
1230:
1229:
1225:
1187:
1186:
1182:
1152:
1151:
1147:
1095:
1094:
1090:
1054:
1053:
1049:
1003:
1002:
998:
962:
961:
957:
913:
912:
908:
886:
885:
881:
863:
862:
858:
822:
821:
817:
779:
778:
774:
744:
743:
739:
730:
728:
720:
719:
715:
706:
704:
696:
695:
691:
660:
659:
655:
621:
620:
616:
586:
585:
581:
551:
550:
546:
537:
530:
523:
522:
518:
488:
487:
483:
476:
455:
454:
441:
437:
421:atherosclerosis
413:
396:
368:Perfluorohexane
319:
286:Propylene oxide
274:
234:crystallization
218:
189:
154:
138:
119:
104:
67:(a fragment of
17:
12:
11:
5:
1817:
1815:
1807:
1806:
1801:
1796:
1791:
1786:
1776:
1775:
1771:
1770:
1713:
1674:(12): e53280.
1654:
1597:
1548:
1521:(2): 123–129.
1498:
1491:
1473:
1438:
1419:
1383:
1334:
1307:(12): 125018.
1291:
1278:(2): 480–493.
1258:
1223:
1180:
1145:
1088:
1047:
996:
955:
926:(4): 961–974.
906:
879:
868:(5): 493–494.
856:
815:
788:(6): 609–617.
772:
737:
713:
689:
653:
634:(2): 756–762.
614:
579:
544:
516:
497:(1–2): 55–69.
481:
475:978-3527306732
474:
438:
436:
433:
423:, age-related
412:
409:
395:
392:
318:
315:
273:
270:
238:chromatography
217:
214:
188:
185:
169:alcohol powder
153:
150:
137:
136:Chromatography
134:
118:
115:
111:β-Cyclodextrin
103:
100:
96:
95:
89:
83:
15:
13:
10:
9:
6:
4:
3:
2:
1816:
1805:
1802:
1800:
1797:
1795:
1792:
1790:
1787:
1785:
1782:
1781:
1779:
1766:
1762:
1757:
1752:
1748:
1744:
1740:
1736:
1732:
1728:
1724:
1717:
1714:
1709:
1705:
1700:
1695:
1690:
1685:
1681:
1677:
1673:
1669:
1665:
1658:
1655:
1650:
1646:
1641:
1636:
1632:
1628:
1624:
1620:
1616:
1612:
1608:
1601:
1598:
1593:
1589:
1584:
1579:
1575:
1571:
1567:
1563:
1559:
1552:
1549:
1544:
1540:
1536:
1532:
1528:
1524:
1520:
1516:
1509:
1502:
1499:
1494:
1488:
1484:
1477:
1474:
1469:
1465:
1461:
1457:
1453:
1449:
1442:
1439:
1434:
1430:
1423:
1420:
1415:
1411:
1407:
1403:
1399:
1395:
1387:
1384:
1379:
1375:
1370:
1365:
1361:
1357:
1353:
1349:
1345:
1338:
1335:
1330:
1326:
1322:
1318:
1314:
1310:
1306:
1302:
1295:
1292:
1286:
1281:
1277:
1273:
1269:
1262:
1259:
1254:
1250:
1246:
1242:
1238:
1234:
1227:
1224:
1219:
1215:
1211:
1207:
1203:
1199:
1195:
1191:
1184:
1181:
1176:
1172:
1168:
1164:
1160:
1156:
1149:
1146:
1141:
1137:
1132:
1127:
1123:
1119:
1115:
1111:
1107:
1103:
1099:
1092:
1089:
1084:
1080:
1075:
1070:
1066:
1062:
1058:
1051:
1048:
1043:
1039:
1034:
1029:
1024:
1019:
1015:
1011:
1007:
1000:
997:
992:
988:
983:
978:
974:
970:
966:
959:
956:
951:
947:
942:
937:
933:
929:
925:
921:
917:
910:
907:
902:
898:
894:
890:
883:
880:
875:
871:
867:
860:
857:
852:
848:
843:
838:
834:
830:
826:
819:
816:
811:
807:
803:
799:
795:
791:
787:
783:
776:
773:
768:
764:
760:
756:
752:
748:
741:
738:
727:
723:
717:
714:
703:
699:
693:
690:
685:
681:
677:
673:
670:(1): 97–106.
669:
665:
657:
654:
649:
645:
641:
637:
633:
629:
625:
618:
615:
610:
606:
602:
598:
594:
590:
583:
580:
575:
571:
567:
563:
559:
555:
548:
545:
540:
533:
526:
520:
517:
512:
508:
504:
500:
496:
492:
485:
482:
477:
471:
467:
463:
460:. Wiley-VCH.
459:
452:
450:
448:
446:
444:
440:
434:
432:
430:
426:
422:
418:
410:
408:
400:
393:
391:
389:
385:
381:
377:
373:
372:nanoparticles
369:
364:
362:
358:
353:
351:
346:
344:
340:
336:
332:
323:
316:
314:
312:
311:
305:
303:
298:
293:
291:
287:
283:
279:
271:
266:
262:
257:
253:
251:
247:
243:
239:
235:
231:
227:
223:
215:
213:
211:
206:
202:
193:
186:
184:
182:
178:
174:
170:
165:
163:
159:
151:
149:
148:separations.
147:
143:
135:
133:
130:
125:
117:Drug delivery
116:
112:
108:
101:
99:
93:
90:
87:
84:
81:
78:
77:
76:
74:
70:
66:
61:
59:
58:drug delivery
55:
51:
47:
43:
39:
35:
31:
30:Cyclodextrins
23:
19:
1733:(1): 17633.
1730:
1726:
1716:
1671:
1667:
1657:
1614:
1610:
1600:
1565:
1561:
1551:
1518:
1514:
1501:
1482:
1476:
1451:
1447:
1441:
1432:
1428:
1422:
1397:
1393:
1386:
1351:
1347:
1337:
1304:
1300:
1294:
1275:
1271:
1261:
1236:
1232:
1226:
1193:
1189:
1183:
1158:
1154:
1148:
1105:
1101:
1091:
1064:
1060:
1050:
1013:
1009:
999:
972:
968:
958:
923:
919:
909:
892:
888:
882:
865:
859:
835:(1): 12–23.
832:
828:
818:
785:
781:
775:
750:
746:
740:
729:. Retrieved
725:
716:
705:. Retrieved
701:
692:
667:
663:
656:
631:
627:
617:
595:(1): 65–71.
592:
588:
582:
557:
553:
547:
519:
494:
490:
484:
457:
414:
405:
365:
354:
347:
328:
308:
306:
294:
275:
219:
198:
166:
155:
139:
120:
102:Applications
97:
62:
29:
28:
18:
1794:Macrocycles
1617:(1): 2197.
1016:(5): 2612.
726:Alcohol.org
380:histotripsy
376:histotripsy
302:lipid rafts
297:cholesterol
282:acetylation
278:Methylation
272:Derivatives
224:. Commonly
210:hydrophilic
38:macrocyclic
1778:Categories
1067:: 121070.
975:: 120275.
731:2024-01-22
707:2024-01-22
435:References
425:lipofuscin
357:adamantane
350:carotenoid
337:, such as
265:macrocycle
158:fragrances
144:media for
1468:220774604
1348:ACS Omega
851:216203179
511:233139034
361:hydrogels
343:catenanes
339:rotaxanes
216:Synthesis
187:Structure
54:enzymatic
1765:31776357
1708:23285273
1668:PLOS ONE
1649:28526856
1592:27053774
1543:31860374
1535:15451000
1435:: 536–8.
1414:36418020
1378:31459627
1329:31071701
1253:24911321
1218:21728366
1175:21381747
1140:23673640
1108:: 1855.
1083:37321712
1042:35269753
991:36372469
950:10198050
810:12163906
802:12226716
767:11848947
684:11861113
648:23294178
609:10053203
574:11848959
384:ablation
317:Research
310:thiomers
261:rotaxane
40:ring of
1756:6881402
1735:Bibcode
1699:3532434
1676:Bibcode
1640:5438378
1619:Bibcode
1583:4878149
1369:6649115
1309:Bibcode
1198:Bibcode
1131:3674257
1110:Bibcode
1033:8910138
895:: 220.
429:obesity
394:History
250:ethanol
246:acetone
242:toluene
230:amylase
181:the FDA
173:ethanol
162:Febreze
73:glucose
65:amylose
42:glucose
1789:Starch
1763:
1753:
1706:
1696:
1647:
1637:
1590:
1580:
1541:
1533:
1489:
1466:
1412:
1376:
1366:
1327:
1251:
1216:
1173:
1138:
1128:
1081:
1040:
1030:
989:
948:
938:
849:
808:
800:
765:
682:
646:
607:
572:
509:
472:
411:Safety
288:gives
222:starch
69:starch
50:starch
1539:S2CID
1511:(PDF)
1464:S2CID
941:25220
847:S2CID
806:S2CID
507:S2CID
152:Other
1761:PMID
1704:PMID
1645:PMID
1588:PMID
1531:PMID
1487:ISBN
1433:1891
1410:PMID
1374:PMID
1325:PMID
1272:Chem
1249:PMID
1214:PMID
1171:PMID
1136:PMID
1079:PMID
1038:PMID
987:PMID
946:PMID
798:PMID
763:PMID
680:PMID
644:PMID
605:PMID
570:PMID
470:ISBN
417:LD50
341:and
280:and
146:HPLC
1751:PMC
1743:doi
1694:PMC
1684:doi
1635:PMC
1627:doi
1578:PMC
1570:doi
1523:doi
1456:doi
1402:doi
1364:PMC
1356:doi
1317:doi
1280:doi
1241:doi
1206:doi
1194:115
1163:doi
1126:PMC
1118:doi
1069:doi
1065:316
1028:PMC
1018:doi
977:doi
973:300
936:PMC
928:doi
897:doi
870:doi
837:doi
790:doi
755:doi
672:doi
636:doi
597:doi
593:179
562:doi
499:doi
495:100
462:doi
329:In
248:or
52:by
1780::
1759:.
1749:.
1741:.
1729:.
1725:.
1702:.
1692:.
1682:.
1670:.
1666:.
1643:.
1633:.
1625:.
1613:.
1609:.
1586:.
1576:.
1564:.
1560:.
1537:.
1529:.
1519:23
1517:.
1513:.
1462:.
1452:98
1450:.
1431:.
1408:.
1398:23
1396:.
1372:.
1362:.
1350:.
1346:.
1323:.
1315:.
1305:64
1303:.
1274:.
1270:.
1247:.
1237:47
1235:.
1212:.
1204:.
1192:.
1169:.
1159:59
1157:.
1134:.
1124:.
1116:.
1104:.
1100:.
1077:.
1063:.
1059:.
1036:.
1026:.
1014:23
1012:.
1008:.
985:.
971:.
967:.
944:.
934:.
924:10
922:.
918:.
893:77
891:.
845:.
833:48
831:.
827:.
804:.
796:.
786:59
784:.
761:.
751:98
749:.
724:.
700:.
678:.
668:28
666:.
642:.
632:10
630:.
626:.
603:.
591:.
568:.
558:98
556:.
536:;
529:;
505:.
493:.
468:.
442:^
390:.
244:,
129:pH
1767:.
1745::
1737::
1731:9
1710:.
1686::
1678::
1672:7
1651:.
1629::
1621::
1615:7
1594:.
1572::
1566:8
1545:.
1525::
1495:.
1470:.
1458::
1416:.
1404::
1380:.
1358::
1352:4
1331:.
1319::
1311::
1288:.
1282::
1276:8
1255:.
1243::
1220:.
1208::
1200::
1177:.
1165::
1142:.
1120::
1112::
1106:4
1085:.
1071::
1044:.
1020::
993:.
979::
952:.
930::
903:.
899::
876:.
872::
853:.
839::
812:.
792::
769:.
757::
734:.
710:.
686:.
674::
650:.
638::
611:.
599::
576:.
564::
513:.
501::
478:.
464::
267:.
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
