Supramolecular cyclodextrin complexes of biologically active nitrogen heterocycles
Abstract
The review is devoted to the rapidly developing field of modern supramolecular chemistry - cyclodextrin complexes of biologically active nitrogen heterocycles, such as piperidines, piperazines, morpholines and pyridines. Interest in cyclodextrin complexes is growing due to the search and construction of supramolecular assemblies for targeted drug delivery. The latter is achieved as a result of supramolecular self-assembly, based on the principles of molecular recognition, and is one of the areas of modern chemistry, leading to the creation of new materials with new properties.
This review fully demonstrates the ongoing scientific and practical interest in the problem of encapsulation with cyclodextrins, including nanoencapsulation. Encapsulation with cyclodextrins provides a wide range of advantages: obtaining solid dosage forms from liquid ones, stabilizing and protecting active substances from the adverse effects of external factors, increasing solubility, increasing bioavailability, reducing toxicity, prolonging action, etc.
The presented review includes recent advances in the field of supramolecular complexes of biologically active nitrogen heterocycles with cyclodextrins and concludes with a discussion and identification of future promising directions for research. The review presents the results of supramolecular self-assembly of biologically active azaheterocycles with cyclodextrins.
References
2 Jansook P, Ogawa N, Loftsson T (2018) Int J Pharm 535:272-284. Crossref
3 Muankaew C, Loftsson T (2018) Basic Clin Pharmacol Toxicol 122:46-55. Crossref
4 Dhiman P, Bhatia M (2020) J Incl Phenom Macrocycl Chem 98:171-186. Crossref
5 Arima H, Motoyama K, Higashi T (2017) Chem Pharm Bull 65:341-348. Crossref
6 Hu Q-D, Tang G-P, Chu PK (2014) Acc Chem Res 47:2017-2025. Crossref
7 Kim DH, Lee SE, Pyo YC, Tran P, Park JS (2020) J Pharm Investig 50:17-27. Crossref
8 He S, Zhou C, Zhang H, Zhou X (2013) J Incl Phenom Macrocycl Chem 76:333-344. Crossref
9 Marquez C, Hudgins RR, Nau WM (2004) J Am Chem Soc 126:5806-5816. Crossref
10 Luboradzki R, Lipowski J, Simonov YA, Fonari MS, Ganin EV, Yavolovskii AA (2001) J Incl Phenom Macrocycl Chem 40:59-65. Crossref
11 Natarajan Sathiyamoorth V, Suvitha A, Sahara R (2022) J Incl Phenom Macrocycl Chem 102:637-651. Crossref
12 Zhou XM, Wang Q, Sun M, Liu J-L, Jia A-Q, Zhang Q-F (2023) J Incl Phenom Macrocycl Chem 103:289-299. Crossref
13 Senushkina IA, Kurochkina GI, Grachev MK, Pugashova NM, Nifant’ev EE (2008) Russ. J Gen Chem 78:57-60. Crossref
14 Kurochkina GI, Kudryavtseva NA, Grachev MK, Lysenko SA, Vasyanina LK, Nifant’ev EE (2007) Russ J Gen Chem 77:442-449. Crossref
15 Grachev MK, Senyushkina IA, Kurochkina GI, Vasyanina IK, Nifant’ev EE (2006) Russ J Gen Chem 76:1679-1680. Crossref
16 Glazyrin AE, Grachev MK, Kurochkina GI, Nifant’ev EE (2004) Russ J Gen Chem 74:1922-1925. Crossref
17 Kurochkina GI, Trushkin IYu, Grachev MK, Nifant’ev EE (2004) 74:1620-1622. Crossref
18 Kurochkina GI, Grachev MK, Sutyagin AA, Nifant’ev EE (2003) Russ J Gen Chem 73:1945-1946. Crossref
19 Tang J, Tang W (2013) Modification of cyclodextrin In: Tang W, Ng S-C, Sun D (eds) Modified cyclodextrins for chiral separation. Springer, Berlin, Germany. Crossref
20 Wenz G, von der Bey E (1988) Inclusion properties of hydrophobic derivatives of cyclodextrins (CDs) In: Huber O, Szejtli J (eds) Proceedings of the Fourth International Symposium on Cyclodextrins. Advances in Inclusion Science. Springer, Dordrecht, Netherlands. Crossref
21 Basu HN, Vecchio AD (2001) J Am Oil Chem Soc 78:375-380. Crossref
22 Skalko BN, Pavelic Z, Becirevic LM (2000) Drug Dev Ind Pharm 26:1279-1284. Crossref
23 Sajeesh S, Sharma CP (2006) Int J Pharm 325:147-154. Crossref
24 Muhammed DS, Lefebvre RC, Razzouq N, Rosilio V, Gillet B, Couvreur P, Amiel C, Gref R (2007) J Colloid Interface Sci. 307:83-93. Crossref
25 Eguchi M, Da YZ, Ogawa Y, Okada T., Yumoto N., Kodaka M (2006) Int J Pharm 311:215-222. Crossref
26 Maestrelli F, Fuentes GM, Mura P, Alonso MJ (2006) Eur J Pharm Biopharm 63:79-86. Crossref
27 Soares A, Francisca C, Rui de A, Francisco V (2007) Nanomedicine 2:183-202. Crossref
28 Duchene D, Ponchel G, Wouessidjewe D (1999) Adv Drug Del Rev 36:29–40. Crossref
29 Uekama K, Hirayama F, Irie T (1998) Chemical Reviews 98:2045-2076. Crossref
30 Muthukrishnan I, Sridharan V, Menéndez JC (2019) Chem Rev 119:5057-5191. Crossref
31 Janosik T, Rannug A, Rannug U, Wahlström N, Slätt J, Bergman J (2018) Chemistry and Properties of Indolocarbazoles. Chem Rev 118(18)9058-9128. Crossref
32 Kacprzak K, Skiera I, Piasecka M, Paryzek Z (2016) Chem Rev 116:5689-5743. Crossref
33 Buglioni L, Raymenants F, Slattery A, Zondag SDA, Noël T (2022) Chem Rev 122:2752-2906. Crossref
34 Kar S, Sanderson H., Roy K, Benfenati E, Leszczynski J (2022) Chem Rev 122:3637-3710. Crossref
35 Wu X-F, Neumann H, Beller M (2013) Chem Rev 113:1-35. Crossref
36 Godoi B, Schumacher RF, Zeni G (2011) Chem Rev 111:2937-2980. Crossref
37 Chizhik VI, Chernyshev YS, Donets AV, Frolo,v VV, Komolkin AV, Shelyapina MG (2014) Magnetic Resonance and its applications. Springer International Publishing, Switzerland. Crossref
38 Schneider H-J, Hacket F, Rudiger V, Ikeda H (1998) Chem Rev 98:1755-1785. Crossref
39 Kaldybekova GM, Kemel’bekov US, Abdildanova AA, Praliev KD, Volynkin VA, et al (2014) Pharm Chem J 48:196-200. Crossref
40 Sharapov KS, Volynkin VA, Panyushkin VT (2016) Russ Chem Bull 65:834-839. Crossref
41 Sharipov RA, Sharapov KS, Kemelbekov US, Volynkin VA, Yu VK, et al (2017) J Incl Phenom Macrocycl Chem 87:141-148. Crossref
42 Seilkhanov TM, Nazarenko LA, Poplavskii NN, Seilkhanov OT, Iskakova, TK, e al (2016) Russ J Gen Chem 86:110-115. Crossref
43 Kemelbekov US, Ramazanova KR, Kabdraissova AZ, Sabirov VK (2022) Chemical Data Collections 37:100811. Crossref
44 Ezawa T, Inoue Y, Murata I, Takao K, Sugita Y, Kanamoto I (2018) AAPS PharmSciTech 19:923-933. Crossref
45 Liu K, Liu H, Li Z, Li W, Li L (2020) J Incl Phenom Macrocycl Chem 96:233–243. Crossref
46 Zhumakova S, Ten A, Zharkynbek T, Yu V, Seilkhanov T, et al (2022) SN Applied Sciences 4:75. Crossref
47 Anshakova AV, Yermolenko YV, Konyukhov VY, Polshakov, VI, Maksimenko OO, Gelperina SE (2015) Russ J Phys Chem A 89:797-801. Crossref
48 Anshakova AV, Vinogradov EV, Sedush NG, Kurtikyan TS, Zhokhov SS, et al (2016) Russ J Phys Chem 90:983-989. Crossref
49 Seilkhanov TM, Nurkenov OA, Isaeva AZ, Nazarenko LA, Seilkhanov OT (2016) Chem Nat Compd 52:1066-1068. Crossref
50 Chen TC, Yu SC, Hsu CM, Tsai FJ, Tsai Y (2017) J Incl Phenom Macrocycl Chem 88:27-34. Crossref
51 Mic M, Pîrnău A, Floare CG, Miclăuș M, Kacso I, et al (2018) J Incl Phenom Macrocycl Chem 92:195-204. Crossref
52 Paczkowska M, Mizera M, Lewandowska K, Kozak M, Miklaszewski A, Cielecka-Piontek J (2018) J Incl Phenom Macrocycl Chem 91:149-159. Crossref
53 Imtiaz S, Muzaffar S, Ali SM (2021) J Inc Phenom Macrocycl Chem, 100:71-87. Crossref
54 Praphanwittaya P, Jansook P, Loftsson T (2020) J Incl Phenom Macrocycl Chem 98:57-67. Crossref
55 Jansook P, Praphanwittaya P, Sripetch S, Loftsson T (2020) J Incl Phenom Macrocycl Chem 97:195-203. Crossref
56 Seilkhanov TM, Nazarenko LA, Poplavskii NN, Seilkhanov OT, Iskakova TK, et al (2015) Russ J Gen Chem 85:1098-1102. Crossref
57 Bezamat JM, Yokaichiya F, Dias Franco MKK, Castro SK, de Paula E, Cabeça LF (2020) J Drug Deliv Sci Tec 55:101475. Crossref
58 Cifuentes T, Cayupi J, Celis-Barros C, Zapata-Torres G, Ballesteros R, et al (2016) Organic and Biomolecular Chemistry 14(41)9760-9767. Crossref
59 Heydari A, Iranmanesh M, Doostan F, Sheibani H (2015) Pharm Chem J 49:605-612. Crossref
60 Alonso ML, Sebastián E, Felices LS, Vitoria P, Alonso RM (2016) J Incl Phenom Macrocyc Chem 86:103-110. Crossref
61 Babenko SV, Tsentalovich YP, Kruppa AI (2017) J Incl Phenom Macrocycl Chem 89:117-125. Crossref
62 Stoicescu CS, Neacşu AD, Bădiceanu CD, Munteanuet G (2020) J Incl Phenom Macrocycl Chem 96:275-283. Crossref
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License (CC BY-NC-ND 4.0) that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.