Combined Computational and Experimental Study of Inclusion Complexes of Lupinine and its 1,2,3-triazole Derivative with β-cyclodextrin

Zh.S. Nurmaganbetov; S.D. Fazylov; O.A. Nurkenov; A.Zh. Sarsenbekova; I.A. Pustolaikina; O.T. Seilkhanov; A.K. Sviderskiy; Ye.V. Minayeva

doi:10.18321/ectj1660

Authors

Zh.S. Nurmaganbetov Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, Alikhanov str., 1, Karaganda, Kazakhstan; Karaganda Medical University, Gogol str., 40, Karaganda, Kazakhstan
S.D. Fazylov Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, Alikhanov str., 1, Karaganda, Kazakhstan
O.A. Nurkenov Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, Alikhanov str., 1, Karaganda, Kazakhstan
A.Zh. Sarsenbekova Karaganda Buketov University, Universitetskaya str., 28, Karaganda, Kazakhstan
I.A. Pustolaikina Karaganda Buketov University, Universitetskaya str., 28, Karaganda, Kazakhstan
O.T. Seilkhanov Kokshetau University of the name of Sh. Ualikhanov, Abay St., 76, Kokshetau, Kazakhstan
A.K. Sviderskiy Department of Mining, Metallurgy and Natural Sciences, Zhezkazgan University named after O. Baikonurov, Alashakhan ave., 1b, Zhezkazgan, Kazakhstan
Ye.V. Minayeva Karaganda Buketov University, Universitetskaya str., 28, Karaganda, Kazakhstan

DOI:

https://doi.org/10.18321/ectj1660

Keywords:

Lupinine alkaloid, β-cyclodextrin, Quinolizidine derivatives, 1,2,3-triazoles, Inclusion complexes

Abstract

The study presents the results of obtaining clathrate inclusion complexes of the alkaloid lupinine (Lup) and its 1,2,3-triazole derivative (Lup-T) using the oligosaccharide β-cyclodextrin (β-CD). The structural features of the encapsulated forms of lupinine (Lup) and its derivatives were characterized by molecular modeling, IR spectroscopy, ¹H and ¹³C NMR, as well as two-dimensional 1H-1H (COSY) and ¹H-¹³C (HMBC, HSQC) NMR spectroscopy. A comparative thermal degradation study of lupinine, its triazole derivative, and their inclusion complexes with β-cyclodextrin was performed using differential thermogravimetry (DTG) and differential scanning calorimetry (DSC). The kinetic parameters of the thermal decomposition reactions of lupinine-based substrates at different heating rates, along with the values of apparent activation energy, were calculated using model-free isoconversional methods by Friedman and Ozawa-Flynn-Wall.

References

(1) J.P. Michael, Indolizidine and quinolizidine alkaloids, Nat. Prod. Rep. 19 (2002) 719–741. Crossref

(2) J.P. Michael, Simple indolizidine and quinolizidine alkaloids: in The Alkaloids: Chemistry and Biology, Academic Press, 2001, pp. 91–258. Crossref

(3) K.I. Takao, R. Munakata, K.I. Tadano, Recent Advances in Natural Product Synthesis by Using Intramolecular Diels−Alder Reactions, Chem. Rev. 105 (2005) 4779–4807. Crossref

(4) S.C.Q. Magalhães, F. Fernandes, A.R.J. Cabrita, et al., Alkaloids in the valorization of European Lupinus spp. seeds crop, Ind. Crops Prod. 95 (2017) 286–295. Crossref

(5) E.L. Konrath, C. Dos Santos Passos, L.C. Klein-Junior, A.T. Henriques, Alkaloids as a source of potential anticholinesterase inhibitors for the treatment of Alzheimer’s disease, J. Pharm. Pharmacol. 65 (2013) 1701–1725. Crossref

(6) R.T. Tlegenov, D.N. Dalimov, Kh.Kh. Khaitbaev, et al., Synthesis and anticholinesterase activites of a number of derivatives of the alkaloid lupinine, Chem. Nat. Compd. 26 (1990) 434–436. Crossref

(7) Z.S. Nurmaganbetov, O.A. Nurkenov, A.I. Khlebnikov, et al., Antiviral Activity of (1S,9aR)-1-[(1,2,3-Triazol-1-yl)methyl]octahydro-1H-quinolizines from the Alkaloid Lupinine, Molecules 29 (2024) 5742. Crossref

(8) K.M. Frik, L.G. Kamphuis, K.M. Siddique, et al., Front. Plant Sci. 31 (2017) 87. Crossref

(9) N.K. Gusarova, S.F. Malysheva, L.A. Oparina, et al., Synthesis of novel alkaloid derivatives from vinyl ether of lupinine and PH-addends, Arkivoc 7 (2009) 260–267. Crossref

(10) A.A. Abduvakhabov, R. Tlegenov, K.K. Khaitbaev, et al., Synthesis of lupinine esters and their interaction with cholinesterases, Chem. Nat. Compd. 26 (1990) 60–63. Crossref

(11) D. Su, X. Wang, C. Shao, et al., Total Synthesis of (+)-Epilupinine via An Intramolecular Nitrile Oxide-Alkene Cycloadditio, J. Org. Chem. 76 (2011) 188–194. Crossref

(12) V.E. Semenov, I.V. Zueva, M.A. Mukhamedyarov, et al., 6-Methyluracil Derivatives as Bifunctional Acetylcholinesterase Inhibitors for the Treatment of Alzheimer’s Disease, Chem. Med. Chem. 11 (2015) 1863–1874. Crossref

(13) M. Ahari, A. Perez, C. Menant, et al., A Direct Stereoselective Approach to trans-2,3-Disubstituted Piperidines: Application in the Synthesis of 2-Epi-CP-99,994 and (+)-Epilupinine, Org. Lett. 10 (2008) 2473–2476. Crossref

(14) A. Boido, I. Vazzana, F. Sparatore, et al., Preparation and pharmacological activity of some 1-lupinylbenzimidazoles and 1-lupinylbenzotriazoles, Farmaco 46 (1991) 775–788. PMID: 1772563.

(15) A. Sparatore, N. Basilico, S. Parapini, et al., 4-Aminoquinoline quinolizidinyl- and quinolizidinylalkyl-derivatives with antimalarial activity, Bioorg. Med. Chem. 13 (2005) 5338–5345. Crossref

(16) B. Tasso, F. Novelli, M. Tonelli, et al., Synthesis and Antiplasmodial Activity of Novel Chloroquine Analogues with Bulky Basic Side Chains, Chem. Med. Chem. 10 (2015) 1570–1583. Crossref

(17) N. Erdemoglu, S. Ozkan, F. Tosun, Alkaloid profile and antimicrobial activity of Lupinus angustifolius L. alkaloid extract, Phytochem. Rev. 6 (2007) 197–201. Crossref

(18) J.K. Przybylak, D. Ciesiołka, W. Wysocka, et al., Alkaloid profiles of Mexican wild lupin and an effect of alkaloid preparation from Lupinus exaltatus seeds on growth and yield of paprika (Capsicum annuum L.), Ind. Crops Prod. 21 (2005) 1–7. Crossref

(19) I.A. Schepetkin, Z.S. Nurmaganbetov, S.D. Fazylov, et al., Inhibition of Acetylcholinesterase by Novel Lupinine Derivatives, Molecules 28 (2023) 3357. Crossref

(20) C. Russoni, N. Vaiana, M. Casagranda, et al., Synthesis and comparison of antiplasmodial activity of (+), (−) and racemic 7-chloro-4-(N-lupinyl)aminoquinoline, Bioorg. Med. Chem. 20 (2012) 5980–5985. Crossref

(21) D.V. Katorov, G.F. Rudakov, I.N. Katorova, et al., Synthesis of 1,2,3-triazoles from heterocyclic α-nitro azides, Russ. Chem. Bull. 61 (2012) 2114–2123. Crossref

(22) N. Adki, N. Rana, R. Palthya, Synthesis and biological evaluation of pyrazol analogues linked with 1,2,3-triazol and 4-thiazolidinone as antimicrobial agents, Curr. Chem. Lett. 11 (2022) 139-146. Crossref

(23) M. Srinivas, A.S. Pathania, P. Mahajan, et al., Design and synthesis of 1,4-substituted 1H-1,2,3-triazolo-quinazolin-4(3H)-ones by Huisgen 1,3-dipolar cycloaddition with PI3Kγ isoform selective activity, Bioorg. Med. Chem. Lett. 28 (2018) 1005–1010. Crossref

(24) A.O. Finke, M.E. Mironov, A.B. Skorova, E.E. Shults, Copper-catalyzed 1,3-dipolar cycloaddition reaction of spirosolanederived azide for the preparation of modified solasodine alkaloid, Chem. Heterocycl. Compd. 54 (2018) 411–416. Crossref

(25) A. Sahu, Advance Synthetic Approaches to 1,2,3-triazole Derived Compounds: State of the Art 2004-2020, Curr. Organocatal. 8 (2021) 271-288. Crossref

(26) O.A. Nurkenov, Z.S. Nurmaganbetov, S.D. Fazylov, et al., Synthesis, structure and biological activity of (1S,9aR)-1H-1,2,3-triazol-1-yl)methyl)octahydro-1H-quinolizine derivatives of lupinine, Arch. Razi Inst. 77 (2022) 2307–2317. URL

(27) C.W. Tornoe, C. Christensen, M. Meldal, Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides, J. Org. Chem. 67 (2002) 3057–3064. Crossref

(28) P. Wu, V.V. Fokin, Catalytic Azide–Alkyne Cycloaddition: Reactivity and Applications, Aldrichimica Acta 40 (2007) 7–17. Crossref

(29) X. Creary, A. Anderson, C. Brophy, et al., Method for Assigning Structure of 1,2,3-Triazoles, J. Org. Chem. 77 (2012) 8756–8761. Crossref

(30) S.K. Upadhyay, G. Kumar, NMR and molecular modelling studies on the interaction of fluconazole with β-cyclodextrin, Chem. Cent. J. 3 (2009) 1–9. Crossref

(31) S.V. Kurkov, T. Loftsson, Cyclodextrins, Int. J. Pharm. 453 (2013) 167–180. Crossref

(32) M. Burkeev, S. Fazylov, R. Bakirova, et al., Thermal decomposition of β-cyclodextrin and its inclusion complex with vitamin E, Mendeleev Commun. 31 (2021) 76–78. Crossref

(33) R. Serra, J. Sempere, R. Nomen, A new method for the kinetic study of thermoanalytical data: The non-parametric kinetics method, Thermochim. Acta 316 (1998) 37–45. Crossref

(34) H.L. Friedman, Kinetics of thermal degradation of char-forming plastics from thermogravimetry. Application to a phenolic plastic, J. Polym. Sci. 6 (1964) 183–195. Crossref

(35) J.H. Flynn, L.A. Wall, A quick, direct method for the determination of activation energy from thermogravimetric data, Polym. Lett. 4 (1966) 323–328. Crossref

(36) R. Serra, R. Nomen, J. Sempere, The Non-Parametric Kinetics A New Method for the Kinetic Study of Thermoanalytical Data, J. Therm. Anal. Calorim. 52 (1998) 933–943. Crossref

(37) M.E. Wall, A. Rechtsteiner, L.M. Rocha, Singular Value Decomposition and Principal Component Analysis, A Pract. Approach Microarray Data Anal. 9 (2002) 91–109. Crossref

(38) J. Šesták, G. Berggren, Study of the kinetics of the mechanism of solid-state reactions at increasing temperatures, Thermochim. Acta 3 (1971) 1–12. Crossref

(39) X. Zhang, Applications of Kinetic Methods in Thermal Analysis: A Review, Engineered Science 14 (2021) 1–13. Crossref