Submitted Successfully!
To reward your contribution, here is a gift for you: A free trial for our video production service.
Thank you for your contribution! You can also upload a video entry or images related to this topic.
Version Summary Created by Modification Content Size Created at Operation
1
Clara Suprani Marques
 + 1633 word(s) 1633 2021-11-09 04:28:35 |
2 update layout
Rita Xu
 Meta information modification 1633 2021-11-18 02:34:10 |

Video Upload Options

We provide professional Video Production Services to translate complex research into visually appealing presentations. Would you like to try it?
No, upload directly Yes

Confirm

Are you sure to Delete?
Yes No
Cite
If you have any further questions, please contact Encyclopedia Editorial Office.
Marques, C. Natural and Modified Cyclodextrins as Packaging Additives. Encyclopedia. Available online: https://encyclopedia.pub/entry/16115 (accessed on 16 November 2024).
Marques C. Natural and Modified Cyclodextrins as Packaging Additives. Encyclopedia. Available at: https://encyclopedia.pub/entry/16115. Accessed November 16, 2024.
Marques, Clara. "Natural and Modified Cyclodextrins as Packaging Additives" Encyclopedia, https://encyclopedia.pub/entry/16115 (accessed November 16, 2024).
Marques, C. (2021, November 17). Natural and Modified Cyclodextrins as Packaging Additives. In Encyclopedia. https://encyclopedia.pub/entry/16115
Marques, Clara. "Natural and Modified Cyclodextrins as Packaging Additives." Encyclopedia. Web. 17 November, 2021.
Natural and Modified Cyclodextrins as Packaging Additives
Edit
This entry is adapted from the peer-reviewed paper 10.3390/polysaccharides2040050

Cyclodextrins (CDs) have been used by the pharmaceutical and food industries since the 1970s. Their cavities allow the accommodation of several hydrophobic molecules, leading to the formation of inclusion complexes (ICs) increasing the guest molecules’ stability, allowing their controlled release, enhancing their water solubility and biodisponibility.

polymers food packaging active packaging cyclodextrins

1. Introduction

Discovered in 1891 from starch degradation by the action of the microorganism Bacillus amylobacter, cyclodextrins (CDs) were patented for the first time almost sixty years later as an important agent for obtaining drug inclusion complexes (ICs) [1]. However, it was only in the 1970s, when toxicological studies ensured their innocuousness, that their use by the pharmaceutical industry in fact began, being used to this day in the elaboration of drugs, cosmetics, and hygiene products [2]. CDs have become an essential ingredient for these areas as they act as carriers of substances of interest, promote the controlled release of drugs, and increase the water solubility of poorly soluble compounds, enhancing their biodisponibility  [3][4][5].
Biotechnological advances that occurred between the 1970s and 1980s allowed the large-scale production of more purified CDs, increasing the interest in their use by sectors other than Pharmaceutical and Biomedical. In food-related areas, for example, their use was firstly authorized in the late 1970s, in Japan, in the production of spices, chocolates, teas, among other products. However, it was only in the early 2000s that the CDs entered the list of substances generally recognized as safe (GRAS) from the Food and Drug Administration (FDA), being recognized as a food additive [1][6]. Nowadays, enzymes involved in the formation of cyclodextrins from starch can be found in the market, as well as several types of cyclodextrins and their inclusion complexes for both pharmaceutics and food usage [7][8][9][10].
In addition to the aforementioned properties, CDs are also able to form complexes with a wide range of substances, from small molecules of low molecular weight to bigger compounds, depending on the type of CD used [11][12][13]. Besides, they can increase the stability of the guest molecules against external factors such as temperature, light, and oxygen [14][15]. Due to these, the CDs have come to be considered potential additives for packaging with active properties, especially when the active compound can be easily degraded or oxidized [16]. Since the production of packaging generally involves the use of high temperatures for polymers to melt, the use of several active compounds becomes unfeasible due to their thermal instability, an obstacle that can be overcome when performing the complexation of these substances with CDs.

2. Natural and Modified Cyclodextrins

2.1. Structure, General Characteristic and Properties of Interest

CDs are cyclic molecules composed of glucose subunits linked through α-1,4-glycosidic bonds. Their classification is made according to the number of glucopyranoses units, being α-CD (6 units), β-CD (7 units), and γ-CD (8 units) the three native or “parent” CDs [17]. CDs containing 9 or more glucose units in their structure are also described in the literature and have been conventionally named large ring CDs [18]. The cyclic conformation and molecular arrangement of the hydroxyl groups give the CDs a toroidal shape, similar to a hollow cone, with an external face of polar nature due to the presence of hydroxyl groups, and a non-polar cavity, in which hydrophobic compounds can be accommodated [2].
One of the main characteristics of CDs of importance for application in food-related areas is their water solubility. Native CDs have a certain solubility in water, γ-CD being the most soluble of the three (249 mg·mL−1) and β-CD the least soluble (18.5 mg·mL−1) [19]. Such functionality allows, by forming ICs with nonpolar compounds, that the solubility of the guest molecule when compared to the pristine substance to be increased, consequently enhancing its bioavailability in the medium. In general, the formation of inclusion complexes with CDs also allows the controlled release of the compound of interest and protects unstable substances from external factors as well as from undesirable interactions that may occur in the environment, being an interesting alternative for the food packaging industry [14][19][20]. The main properties of the native CDs, as well as their commercial names, are briefly described in Table 1.
Table 1. Main properties of α-, β-, and γ-cyclodextrins.
Property α-Cyclodextrin β-Cyclodextrin γ-Cyclodextrin
Commercial name on the Market Cavamax® W6 [8], Trappsol® Native Alpha [10] Cavamax® W7 [8], Kleptose® [9], Trappsol® Native Beta [10] Cavamax® W8 [8], Trappsol® Native Gamma [10]
Functions on Markets products Solubilizer, stabilizer, delivery of drugs [8][10] Solubilizer, stabilizer, delivery of drugs and taste-masking agent [9][10] Solubilizer, stabilizer, stabilization enhancer, delivery of drugs [8][10]
Number of glucose subunits 6 7 8
Molar mass (g·mol−1) 972 1135 1297
External size (nm) 1.4–1.5 [19] 1.5–1.6 [19] 1.7–1.8 [19]
Internal diameter (nm) 0.47–0.52 [21] 0.60–0.80 [21] 0.75–1.00 [21]
Water solubility at 25 °C(mg·mL−1) 145 [21] 18.5 [21] 232 [21]
Solubility in organic solvents Insoluble in chloroform, isopropanol, acetone, ethanol, glycerin, methanol, and ethyl ether. Soluble in propylene glycol (10 mg·mL−1), dimethyl sulfoxide (20 mg·mL−1), and dimethylformamide (540 mg·mL−1) [21] Insoluble in chloroform, isopropanol, acetone, ethanol, methanol, and ethyl ether. Soluble in dimethyl sulfoxide (350 mg·mL−1), ethylene glycol (210 mg·mL−1), dimethylformamide (320 mg·mL−1), and glycerin (43 mg·mL−1) [21] Insoluble in chloroform and ethyl ether. Soluble (>1 mg·mL−1) in isopropanol, acetone, ethanol, and methanol [21]

2.2. α-CD

α-CDs are constituted of 6 subunits of d-glucopyranoses, being obtained enzymatically from starch and its derivatives, and, among the native CDs, they are the ones with the smallest internal diameter, ranging from 0.47 to 0.52 nm [22]. As functional properties, these molecules have moderate solubility in water (almost eight times greater than that presented by β-CDs, but less than γ-CDs), relative thermal stability, stability under extreme conditions of pH (alkaline and acidic solutions), and slightly pronounced sensory characteristics (imperceptible taste and odor) [23]. The molecule was granted GRAS status by the FDA in 2004 (GRN 000155), and in 2016, the agency waived the requirement for pre-marketing approval, provided it meets the maximum level of 3% (w/w) in processed foods and 1.05% in beverages [24].
Among the applications of α-CDs in the Food Industry, it is worth mentioning their role as an emulsifier agent, as a functional ingredient, and as a carrier and stabilizing agent for different molecules, such as hormones and flavorings [25][26][27]. Furthermore, its ability to act as a host for smaller bioactive components opens doors for its use in the development of active packaging. Besides, when we talk about sustainable packaging, the water solubility of α-CDs can be an advantage since several biopolymers investigated are dispersible in water [28][29][30][31]. In addition, the chemical structure of α-CDs makes their hydrolysis impossible by human saliva, as well as pancreatic amylases. Therefore, this characteristic gives a probiotic character to these substances and a possible application as dietary fibers [32].

2.3. β-CD

Among the three native types of CDs, β-CD is the most used and studied due its low cost when compared to the other two CDs, its good complexation efficiency, and the size of its cavity, which, in practice, allows a good accommodation of a large amount of molecules [14][19][33][34][35][36][37][38][39][40]. About 90% of the CDs produced and consumed are β-CDs [41]. In addition, the internal diameter of the β-CD’s cavity makes it popular in the pharmaceutical industry since it is suitable for the inclusion of several substances with a molar mass between 200–800 g·mol−1 [22]. However, the β-CD low water solubility is a disadvantage and the reason why CD derivatives were developed with various substituents (methyl, carboxymethyl, hydroxypropyl, sulfobutyl, among others) [42]. Hydroxypropyl-β-CD and randomly methylated β-CD, for example, have water solubility greater than 600 mg·mL−1, a much more considerable value than the solubility of the native β-CD [2].

2.4. γ-CD

The last native CD to be discovered (1935), γ-CD consists of 8 subunits of glucopyranose, with a larger internal diameter among the three native molecules [22][43]. Due to its high solubility in water, γ-CD can be used as a solubilizing agent by carrying highly hydrophobic molecules [44][45]. Considering the pharmaceutical industry, several inclusion complexes γ-CD-based containing bioactive molecules tend to form aggregated structures in aqueous solutions, indicating potential activity as a drug-containing vehicle [44][46]. Other applications include the production of cosmetics (e.g., increased stability and solubility of components) [47]; chemical industry (e.g., separation of isomers, functional groups, homologous and enantiomers) [48]; textile industry (e.g., restoration of colors, good completion of cotton-based materials) [49]; and agriculture (e.g., immobilization of fragrances and repellents, reduction of the risk of contact with chemicals, increased effect of pesticides) [50].

2.5. Large Ring CDs

CDs composed of more than 8 units of glucopyranoses are known as large rings CDs and were first described in 1948. Compared to the other CDs, fewer studies have been conducted on this broad group of molecules [1]. In fact, some CDs can have more than 100 glucose units, which can be obtained through the use of specific enzymes or very specific conditions of temperature and incubation time [51]. The difficulties associated with their purification and very low yield are barriers to their use on a larger scale [52]. More recently, however, some works have been described in the literature seeking alternatives for the production and purification of large ring CDs, also aiming for their application by the chemical, pharmaceutical, and food industries [52].

2.6. Modified CDs

Although it has been discussed in the literature that the complexation with CDs can increase the guest compound solubility in water, the native CDs present limited solubilization in the solvent. β-CD, for example, the most affordable and the most suitable for the inclusion of substances due to its cavity volume, is also the least soluble of the three natives CDs, which is a disadvantage. In this regard, synthetic derivatives were developed from the substitution of hydroxyl groups in the structure of the original CD, conferring different properties and improving the molecule solubility in water, consequently, opening a wider range of applications [2][4][42][53].
The CDs’ derivatives can be classified into three groups: anionic, cationic, and non-ionic, depending on the inserted group [54]. As an example of anionic derivatives, we can cite the sulfobutylether-β-CD and the per(6-carboxylate)-CD, which have potential in pharmaceutical research for controlled released and advanced targeted delivery of drugs [55]. 2-Hydroxypropyl-β-CD (HP-β-CD) is an example of a non-ionic structure largely studied both in pharmaceutical and food-related areas, and permethylated propylenediamine-β-CD is one of the synthesized cationic derivatives [54][56][57].

References

  1. Nadia Morin-Crini; Sophie Fourmentin; Éva Fenyvesi; Eric Lichtfouse; Giangiacomo Torri; Marc Fourmentin; Grégorio Crini; 130 years of cyclodextrin discovery for health, food, agriculture, and the industry: a review. Environmental Chemistry Letters 2021, 19, 2581-2617, 10.1007/s10311-020-01156-w.
  2. Phatsawee Jansook; Noriko Ogawa; Thorsteinn Loftsson; Cyclodextrins: structure, physicochemical properties and pharmaceutical applications. International Journal of Pharmaceutics 2017, 535, 272-284, 10.1016/j.ijpharm.2017.11.018.
  3. Yahui He; Shaomei Zeng; A. M. Abd El-Aty; Ahmet Hacımüftüoğlu; Woldemariam Kalekristos Yohannes; Majid Khan; Yongxin She; Development of Water-Compatible Molecularly Imprinted Polymers Based on Functionalized β-Cyclodextrin for Controlled Release of Atropine. Polymers 2020, 12, 130, 10.3390/polym12010130.
  4. Nguyen Ngoc Sao Mai; Riko Nakai; Yayoi Kawano; Takehisa Hanawa; Enhancing the Solubility of Curcumin Using a Solid Dispersion System with Hydroxypropyl-β-Cyclodextrin Prepared by Grinding, Freeze-Drying, and Common Solvent Evaporation Methods. Pharmacy 2020, 8, 203, 10.3390/pharmacy8040203.
  5. Alessandro Torchio; Claudio Cassino; Mario Lavella; Andrea Gallina; Alice Stefani; Monica Boffito; Gianluca Ciardelli; Injectable supramolecular hydrogels based on custom-made poly(ether urethane)s and α-cyclodextrins as efficient delivery vehicles of curcumin. Materials Science and Engineering: C 2021, 127, 112194, 10.1016/j.msec.2021.112194.
  6. Hitoshi Hashimoto; Present Status of Industrial Application of Cyclodextrins in Japan. Journal of Inclusion Phenomena and Macrocyclic Chemistry 2001, 44, 57-62, 10.1023/a:1023036406829.
  7. Novozymes Home Page . Novozymes Home Page. Retrieved 2021-11-17
  8. Wacker Chemie AG Home Page . Wacker Chemie AG Home Page. Retrieved 2021-11-17
  9. Roquette Frères Home Page . Roquette Frères Home Page. Retrieved 2021-11-17
  10. Cyclo Therapeutics, Inc Home Page . Cyclo Therapeutics, Inc Home Page. Retrieved 2021-11-17
  11. Violeta Yeguas; Muhannad Altarsha; Gérald Monard; Ramón López; Manuel F. Ruiz-López; Peptide Binding to β-Cyclodextrins: Structure, Dynamics, Energetics, and Electronic Effects. The Journal of Physical Chemistry A 2011, 115, 11810-11817, 10.1021/jp2053037.
  12. Clara Suprani Marques; Marali Vilela Dias; Nilda De Fátima Ferreira Soares; Soraia Vilela Borges; Isadora Rebouças Nolasco de Oliveira; Ana Clarissa Dos Santos Pires; Eber Antônio Alves Medeiros; Eduardo Alves; Ultrastructural and antimicrobial impacts of allyl isothiocyanate incorporated in cellulose, β‐cyclodextrin, and carbon nanotubes nanocomposites. Journal of Vinyl and Additive Technology 2021, 27, 795-805, 10.1002/vnl.21850.
  13. Doni Dermawan; Nasrul Wathoni; Muchtaridi Muchtaridi; Host-Guest Interactions of α−Mangostin with (α,β,γ)−Cyclodextrins: Semi-Empirical Quantum Mechanical Methods of PM6 and PM7. Journal of Young Pharmacists 2018, 11, 31-35, 10.5530/jyp.2019.11.7.
  14. Raquel Piletti; Micheli Zanetti; Guilherme Jung; Josiane Maria Muneron de Mello; Francieli Dalcanton; Cíntia Soares; Humberto Riella; Márcio Antônio Fiori; Microencapsulation of garlic oil by β‑cyclodextrin as a thermal protection method for antibacterial action. Materials Science and Engineering: C 2018, 94, 139-149, 10.1016/j.msec.2018.09.037.
  15. Sunil Kumar; Pooja; Francesco Trotta; Rekha Rao; Encapsulation of Babchi Oil in Cyclodextrin-Based Nanosponges: Physicochemical Characterization, Photodegradation, and In Vitro Cytotoxicity Studies. Pharmaceutics 2018, 10, 169, 10.3390/pharmaceutics10040169.
  16. Lajos Szente; Éva Fenyvesi; Cyclodextrin-Enabled Polymer Composites for Packaging. Molecules 2018, 23, 1556, 10.3390/molecules23071556.
  17. Thorsteinn Loftsson; Marcus E. Brewster; Cyclodextrins as Functional Excipients: Methods to Enhance Complexation Efficiency. Journal of Pharmaceutical Sciences 2012, 101, 3019-3032, 10.1002/jps.23077.
  18. Christian Sonnendecker; Susanne Melzer; Wolfgang Zimmermann; Engineered cyclodextrin glucanotransferases from Bacillus sp. G-825-6 produce large-ring cyclodextrins with high specificity. MicrobiologyOpen 2018, 8, e00757, 10.1002/mbo3.757.
  19. Helena Ma Cabral Marques; A review on cyclodextrin encapsulation of essential oils and volatiles. Flavour and Fragrance Journal 2010, 25, 313-326, 10.1002/ffj.2019.
  20. Miriana Kfoury; Lizette Auezova; Steven Ruellan; Hélène Greige-Gerges; Sophie Fourmentin; Complexation of estragole as pure compound and as main component of basil and tarragon essential oils with cyclodextrins. Carbohydrate Polymers 2015, 118, 156-164, 10.1016/j.carbpol.2014.10.073.
  21. Janisse Crestani De Miranda; Tércio Elyan Azevedo Martins; Francisco Veiga; Humberto Gomes Ferraz; Cyclodextrins and ternary complexes: technology to improve solubility of poorly soluble drugs. Brazilian Journal of Pharmaceutical Sciences 2011, 47, 665-681, 10.1590/s1984-82502011000400003.
  22. Lachowicz, M; Andrzej Stańczak; Michał Kołodziejczyk; Characteristic of Cyclodextrins: Their Role and Use in the Pharmaceutical Technology. Current Drug Targets 2020, 21, 1495-1510, 10.2174/1389450121666200615150039.
  23. Buckley, J.D.; Coates, A.M.; Ranald, P., Howe, C. Fiber ingredients: Food applications and health benefits; Cho, S.S.; Samuel, P., Eds.; CRC Press: Florida, 2009; pp. 9-18.
  24. U.S. Food and Drug Administration Home Page . U.S. Food and Drug Administration Home Page. Retrieved 2021-11-17
  25. Kati Väkeväinen; Noora Rinkinen; Roosa-Maria Willman; Jenni Lappi; Kaisa Raninen; Anna Kårlund; Santtu Mikkonen; Carme Plumed-Ferrer; Marjukka Kolehmainen; Potential of Probiotic Frozen Blackcurrant Products: Consumer Preference, Physicochemical Characterization, and Cell Viability. Foods 2021, 10, 792, 10.3390/foods10040792.
  26. Jenifer M.M. Henck; Camila V. Bis-Souza; Marise A.R. Pollonio; Jose M. Lorenzo; Andrea Carla Da Silva Barretto; Alpha-cyclodextrin as a new functional ingredient in low-fat chicken frankfurter. British Poultry Science 2019, 60, 716-723, 10.1080/00071668.2019.1664726.
  27. Marco Bazzano; Claudia Barolo; Roberto Buscaino; Giulia D’Agostino; Ada Ferri; Marco Sangermano; Roberto Pisano; Controlled Atmosphere in Food Packaging Using Ethylene−α-Cyclodextrin Inclusion Complexes Dispersed in Photocured Acrylic Films. Industrial & Engineering Chemistry Research 2016, 55, 579-585, 10.1021/acs.iecr.5b03980.
  28. Hermawan Dwi Ariyanto; Makoto Chiba; Keisuke Oguma; Miho Tatsuki; Hidefumi Yoshii; Release behavior of 1‐methylcylopropene coated paper‐based shellac solution in response to stepwise humidity changes to develop novel functional packaging for fruit. Packaging Technology and Science 2019, 32, 523-533, 10.1002/pts.2468.
  29. Fatma Kayaci; Tamer Uyar; Encapsulation of vanillin/cyclodextrin inclusion complex in electrospun polyvinyl alcohol (PVA) nanowebs: Prolonged shelf-life and high temperature stability of vanillin. Food Chemistry 2012, 133, 641-649, 10.1016/j.foodchem.2012.01.040.
  30. Fatma Kayaci; Yelda Ertas; Tamer Uyar; Enhanced Thermal Stability of Eugenol by Cyclodextrin Inclusion Complex Encapsulated in Electrospun Polymeric Nanofibers. Journal of Agricultural and Food Chemistry 2013, 61, 8156-8165, 10.1021/jf402923c.
  31. Cristian Samperio; Renee Boyer; William N. Eigel; Kevin W. Holland; Julie S. McKinney; Sean F. O’Keefe; Richard Smith; Joseph E. Marcy; Enhancement of Plant Essential Oils' Aqueous Solubility and Stability Using Alpha and Beta Cyclodextrin. Journal of Agricultural and Food Chemistry 2010, 58, 12950-12956, 10.1021/jf103275a.
  32. Câmara, A.K.F.I.; Paglarini, C.S.; Vidal, V.A.S.; Santos, M.; Pollonio, M.A.R. Advances in Food and Nutrition Research; da Cruz, A.G.; Prudencio, E.S.; Esmerino, E.A.; da Silva, M.C, Eds.; Academic Press: Cambridge, MA, USA, 2020; pp. 223–265.
  33. Jiefeng Pan; Fangmi Ai; Ping Shao; Hangjun Chen; Haiyan Gao; Development of polyvinyl alcohol/β-cyclodextrin antimicrobial nanofibers for fresh mushroom packaging. Food Chemistry 2019, 300, 125249, 10.1016/j.foodchem.2019.125249.
  34. Haiying Cui; Yiwei Wang; Changzhu Li; Xiaochen Chen; Lin Lin; Antibacterial efficacy of Satureja montana L. essential oil encapsulated in methyl-β-cyclodextrin/soy soluble polysaccharide hydrogel and its assessment as meat preservative. LWT 2021, 152, 112427, 10.1016/j.lwt.2021.112427.
  35. Yiyuan Zou; Chao Yuan; Bo Cui; Jialin Wang; Bin Yu; Li Guo; Die Dong; Mechanical and antimicrobial properties of high amylose corn starch/konjac glucomannan composite film enhanced by cinnamaldehyde/β-cyclodextrin complex. Industrial Crops and Products 2021, 170, 113781, 10.1016/j.indcrop.2021.113781.
  36. Yiyuan Zou; Chao Yuan; Bo Cui; Haojie Sha; Pengfei Liu; Lu Lu; Zhengzong Wu; High-Amylose Corn Starch/Konjac Glucomannan Composite Film: Reinforced by Incorporating β-Cyclodextrin. Journal of Agricultural and Food Chemistry 2021, 69, 2493-2500, 10.1021/acs.jafc.0c06648.
  37. Zhijie Chen; Lin Zong; Chenwei Chen; Jing Xie; Development and characterization of PVA-Starch active films incorporated with β-cyclodextrin inclusion complex embedding lemongrass (Cymbopogon citratus) oil. Food Packaging and Shelf Life 2020, 26, 100565, 10.1016/j.fpsl.2020.100565.
  38. Clara Suprani Marques; Suzana Gonçalves Carvalho; Larissa Diirr Bertoli; Janaína Cecília Oliveira Villanova; Patrícia Fontes Pinheiro; Délia Chaves Moreira dos Santos; Maria Irene Yoshida; Jair Carlos Checon de Freitas; Daniel Fernandes Cipriano; Patricia Bernardes; et al. β-Cyclodextrin inclusion complexes with essential oils: Obtention, characterization, antimicrobial activity and potential application for food preservative sachets. Food Research International 2019, 119, 499-509, 10.1016/j.foodres.2019.01.016.
  39. Haijun Chen; Li Li; Yichao Ma; Timothy P. Mcdonald; Yifen Wang; Development of active packaging film containing bioactive components encapsulated in β-cyclodextrin and its application. Food Hydrocolloids 2018, 90, 360-366, 10.1016/j.foodhyd.2018.12.043.
  40. Marali Vilela Dias; Miriane Maria Sousa; Bruna Rage Baldone Lara; Viviane Machado de Azevedo; Nilda De Fátima Ferreira Soares; Soraia Vilela Borges; Fabiana Queiroz; Thermal and morphological properties and kinetics of diffusion of antimicrobial films on food and a simulant. Food Packaging and Shelf Life 2018, 16, 15-22, 10.1016/j.fpsl.2018.01.007.
  41. Bojana Voncina; Vera Vivod; Wen-Tung Chen; Surface modification of PET fibers with the use of β-cyclodextrin. Journal of Applied Polymer Science 2009, 113, 3891-3895, 10.1002/app.30400.
  42. Lajos Szente; Highly soluble cyclodextrin derivatives: chemistry, properties, and trends in development. Advanced Drug Delivery Reviews 1999, 36, 17-28, 10.1016/s0169-409x(98)00092-1.
  43. Karl Freudenberg; Richard Jacobi; Über Schardingers Dextrine aus Stärke. European Journal of Organic Chemistry 1934, 518, 102-108, 10.1002/jlac.19355180107.
  44. Phennapha Saokham; Thorsteinn Loftsson; γ-Cyclodextrin. International Journal of Pharmaceutics 2016, 516, 278-292, 10.1016/j.ijpharm.2016.10.062.
  45. Pitsiree Praphanwittaya; Phennapha Saokham; Phatsawee Jansook; Thorsteinn Loftsson; Aqueous solubility of kinase inhibitors: I the effect of hydrophilic polymers on their γ-cyclodextrin solubilization. Journal of Drug Delivery Science and Technology 2019, 55, 101462, 10.1016/j.jddst.2019.101462.
  46. Phatsawee Jansook; Wiwat Pichayakorn; Chutimon Muankaew; Thorsteinn Loftsson; Cyclodextrin–poloxamer aggregates as nanocarriers in eye drop formulations: dexamethasone and amphotericin B. Drug Development and Industrial Pharmacy 2016, 42, 1446-1454, 10.3109/03639045.2016.1141932.
  47. Maria Bastianini; Michele Sisani; Annarita Petracci; Ascorbyl Tetraisopalmitate Inclusion into Υ-Cyclodextrin and Mesoporous SBA-15: Preparation, Characterization and In Vitro Release Study. Cosmetics 2017, 4, 21, 10.3390/cosmetics4030021.
  48. Le Chen; Dan-Dan Zhu; Guo-Jian Ji; Sheng Yuan; Jun-Feng Qian; Ming-Yang He; Qun Chen; Zhi-Hui Zhang; Efficient adsorption separation of xylene isomers using a facilely fabricated cyclodextrin-based metal-organic framework. Journal of Chemical Technology & Biotechnology 2018, 93, 2898-2905, 10.1002/jctb.5644.
  49. P. Savarino; G. Viscardi; P. Quagliotto; E. Montoneri; E. Barni; Reactivity and effects of cyclodextrins in textile dyeing. Dyes and Pigments 1999, 42, 143-147, 10.1016/s0143-7208(99)00004-2.
  50. Ke Huang; Dan Zhang; Jing-Jing Ren; Rui Dong; Hua Wu; Screening of the Repellent Activity of 12 Essential Oils Against Adult German Cockroach (Dictyoptera: Blattellidae): Preparation of a Sustained Release Repellent Agent of Binary Oil-γ-CD and its Repellency in a Small Container. Journal of Economic Entomology 2020, 113, 2171-2178, 10.1093/jee/toaa162.
  51. Tao Feng; Haining Zhuang; Ye Ran; The Application of Cyclodextrin Glycosyltransferase in Biological Science. Journal of Bioequivalence & Bioavailability 2010, 03, 202–206, 10.4172/jbb.1000086.
  52. Khaleel I. Assaf; Detlef Gabel; Wolfgang Zimmermann; Werner M. Nau; High-affinity host–guest chemistry of large-ring cyclodextrins. Organic & Biomolecular Chemistry 2016, 14, 7702-7706, 10.1039/c6ob01161f.
  53. Tingxuan Yan; Mengru Ji; Yuxi Sun; Jie Zhao; Huiwen Zhang; Zhixiang Wang; Preparation and characterization of baicalein/hydroxypropyl-β-cyclodextrin inclusion complex for enhancement of solubility, antioxidant activity and antibacterial activity using supercritical antisolvent technology. Journal of Inclusion Phenomena and Macrocyclic Chemistry 2019, 96, 285-295, 10.1007/s10847-019-00970-2.
  54. Pablo F. Garrido; Martín Calvelo; Alexandre Blanco-González; Uxía Veleiro; Fabián Suárez; Daniel Conde; Alfonso Cabezón; Ángel Piñeiro; Rebeca Garcia-Fandino; The Lord of the NanoRings: Cyclodextrins and the battle against SARS-CoV-2. International Journal of Pharmaceutics 2020, 588, 119689-119689, 10.1016/j.ijpharm.2020.119689.
  55. Irene M. Mavridis; Konstantina Yannakopoulou; Anionic cyclodextrins as versatile hosts for pharmaceutical nanotechnology: Synthesis, drug delivery, enantioselectivity, contrast agents for MRI. International Journal of Pharmaceutics 2015, 492, 275-290, 10.1016/j.ijpharm.2015.06.004.
  56. Aun Raza; Huifang Sun; Shumaila Bano; Yingying Zhao; Xiuquan Xu; Jian Tang; Preparation, characterization, and in vitro anti-inflammatory evaluation of novel water soluble kamebakaurin/hydroxypropyl-β-cyclodextrin inclusion complex. Journal of Molecular Structure 2017, 1130, 319-326, 10.1016/j.molstruc.2016.10.059.
  57. Achillia Lakka; Stavros Lalas; Dimitris P. Makris; Hydroxypropyl-β-Cyclodextrin as a Green Co-Solvent in the Aqueous Extraction of Polyphenols from Waste Orange Peels. Beverages 2020, 6, 50, 10.3390/beverages6030050.
More
© Text is available under the terms and conditions of the Creative Commons Attribution (CC BY) license; additional terms may apply. By using this site, you agree to the Terms and Conditions and Privacy Policy.
Upload a video for this entry
Information
Subjects: Polymer Science; Materials Science, Coatings & Films
Contributor MDPI registered users' name will be linked to their SciProfiles pages. To register with us, please refer to https://encyclopedia.pub/register :
Clara Marques
View Times: 703
Revisions: 2 times (View History)
Update Date: 18 Nov 2021
Table of Contents
    1000/1000
    Hot Most Recent
    ScholarVision Creations
    Feedback