Low Molecular Weight Supramolecular Allobetuline-, Cyclohexanol-, or Undecanol-Appended 1,2,3-Triazole-Based Gelators: Synthesis and Molecular Dynamics Simulation Study

Victoria Lipson; Oleg Zhikol; Svetlana Shishkina; Alexander Semenenko; Karina Kulyk; Pavel Mateychenko; Vladimir Musatov; Alexander Mazepa; Vladimir Vakula; Alexander Borisov; Alexander Kyrychenko

doi:10.1055/s-0040-1720100

SynOpen, Inhaltsverzeichnis

CC BY 4.0 · SynOpen 2023; 07(04): 694-702
DOI: 10.1055/s-0040-1720100

paper

Low Molecular Weight Supramolecular Allobetuline-, Cyclohexanol-, or Undecanol-Appended 1,2,3-Triazole-Based Gelators: Synthesis and Molecular Dynamics Simulation Study

Victoria Lipson∗

^aState Scientiﬁc Institution, ‘Institute for Single Crystals’ of the National Academy of Sciences of Ukraine, 60, Nauky ave., Kharkiv 61001, Ukraine

^bSchool of Chemistry, V. N. Karazin Kharkiv National University, Kharkiv, Ukraine

^cState Institution ‘V. Ya. Danilevsky Institute for Endocrine Pathology Problems’, National Academy of Medical Sciences of Ukraine, Kharkiv, Ukraine

,

Oleg Zhikol

^aState Scientiﬁc Institution, ‘Institute for Single Crystals’ of the National Academy of Sciences of Ukraine, 60, Nauky ave., Kharkiv 61001, Ukraine

,

Svetlana Shishkina

^aState Scientiﬁc Institution, ‘Institute for Single Crystals’ of the National Academy of Sciences of Ukraine, 60, Nauky ave., Kharkiv 61001, Ukraine

^bSchool of Chemistry, V. N. Karazin Kharkiv National University, Kharkiv, Ukraine

,

Alexander Semenenko

^aState Scientiﬁc Institution, ‘Institute for Single Crystals’ of the National Academy of Sciences of Ukraine, 60, Nauky ave., Kharkiv 61001, Ukraine

,

Karina Kulyk

^aState Scientiﬁc Institution, ‘Institute for Single Crystals’ of the National Academy of Sciences of Ukraine, 60, Nauky ave., Kharkiv 61001, Ukraine

,

Pavel Mateychenko

^aState Scientiﬁc Institution, ‘Institute for Single Crystals’ of the National Academy of Sciences of Ukraine, 60, Nauky ave., Kharkiv 61001, Ukraine

,

Vladimir Musatov

^aState Scientiﬁc Institution, ‘Institute for Single Crystals’ of the National Academy of Sciences of Ukraine, 60, Nauky ave., Kharkiv 61001, Ukraine

,

Alexander Mazepa

^dA. V. Bogatsky Physico-Chemical Institute of the National Academy of Sciences of Ukraine, Odessa, Ukraine

,

Vladimir Vakula

^aState Scientiﬁc Institution, ‘Institute for Single Crystals’ of the National Academy of Sciences of Ukraine, 60, Nauky ave., Kharkiv 61001, Ukraine

^cState Institution ‘V. Ya. Danilevsky Institute for Endocrine Pathology Problems’, National Academy of Medical Sciences of Ukraine, Kharkiv, Ukraine

,

Alexander Borisov

^eENAMINE Ltd, Kyiv, Ukraine

,

Alexander Kyrychenko

^aState Scientiﬁc Institution, ‘Institute for Single Crystals’ of the National Academy of Sciences of Ukraine, 60, Nauky ave., Kharkiv 61001, Ukraine

^bSchool of Chemistry, V. N. Karazin Kharkiv National University, Kharkiv, Ukraine

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Abstract

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Abstract

Three novel isomeric supramolecular allobetuline-appended 1,2,3-triazole-based potential gelators and two model compounds with cyclohexanol or undecanol fragments in the structure instead of the triterpenoid platform were synthesized. Their ability to form gels in different solvents was studied experimentally and computationally by molecular dynamics simulations and quantum chemical calculations. We found that the gelling ability of such compounds is driven by the binding energy of intermolecular tail substituent interactions. The less significant factor is the molecule unfolding in a solvent, providing that the gelling substance is actually soluble. Preferred unfolded conformations were identified by classical molecular dynamics simulation and suggested the most prospective 1,2,3-triazole-based potential gelators.

Key words

allobetuline - cyclohexanol - undecanol - supramolecular 1,2,3-triazole-based gelators - click reaction - molecular dynamics simulation - low-molecular-weight organogelator

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References
1 Pérez-Ruiz R, Díaz Díaz D. Soft Matter 2015; 11: 5180
2 Lim HC, Min SH, Lee E, Jang J, Kim SH, Hong J.-I. ACS Appl. Mater. Interfaces 2015; 7: 11069
3 Steed JW. Chem. Commun. 2011; 47: 1379
4 Ibrahim MM, Hafez SA, Mahdy MM. Asian J. Pharm. Sci. 2013; 8: 48
5 Meng Y, Yang Y. Electrochem. Commun. 2007; 9: 1428
6 Chen S, Tong XQ, He HW, Ma M, Shi YQ, Wang X. ACS Appl. Mater. Interfaces 2017; 9: 11924
7 Zhikol OA, Shishkina SV, Lipson VV, Semenenko AN, Mazepa AV, Borisov AV, Mateychenko PV. New J. Chem. 2019; 43: 13112
8 Ghosh K, Panja A, Panja S. New J. Chem. 2016; 40: 3476
9 Bag BG, Dinda SK, Dey PP, Mallia VA, Weiss RG. Langmuir 2009; 25: 8663
10 Ramírez-López P, de la Torre MC, Asenjo M, Ramírez-Castellanos J, González-Calbet JM, Rodríguez-Gimeno A, Ramírez de Arellano C, Sierra MA. Chem. Commun. 2011; 47: 10281
11 Gao A, Li Y, Lv H, Liu D, Zhao N, Ding Q, Cao X. New J. Chem. 2017; 41: 7924
12 Lu J, Hu J, Song Y, Ju Y. Org. Lett. 2011; 13: 2011
13 Panja A, Ghosh S, Ghosh K. New J. Chem. 2019; 43: 10270
14 Takahashi A, Sakai M, Kato T. Polym. J. 1980; 12: 335
15 Tan HM, Moet A, Hiltner A, Baer E. Macromolecules 1983; 16: 28
16 McCullagh M, Prytkova T, Tonzani S, Winter ND, Schatz GC. J. Phys. Chem. B 2008; 112: 10388
17 Frederix PW. J. M, Scott GG, Abul-Haija YM, Kalafatovic D, Pappas CG, Javid N, Hunt NT, Ulijn RV, Tuttle T. Nat. Chem. 2015; 7: 30
18 Lee O.-S, Cho V, Schatz GC. Nano Lett. 2012; 12: 4907
19 Velichko YS, Stupp SI, de la Cruz MO. J. Phys. Chem. B 2008; 112: 2326
20 Tsuzuki S, Honda K, Uchimaru T, Mikami M. J. Phys. Chem. A 2004; 108: 10311
21 Jalkanen J.-P, Pakkanen TA, Rowley RL. J. Chem. Phys. 2004; 120: 1705
22 Kim KS, Karthikeyan S, Singh NJ. J. Chem. Theory Comput. 2011; 7: 3471
23 Krasutsky PA, Carlson RM, Karim R. US 2002128210, 2002
24 Bi J, Zeng X, Tian D, Li H. Org. Lett. 2016; 18: 1092
25 Bodor N, El-Koussi AA, Kano M, Khalifa MM. J. Med. Chem. 1988; 31: 1651
26 Venuti MC, Alvarez R, Bruno JJ, Strosberg AM, Gu L, Chiang HS, Massey IJ, Chu N, Fried JH. J. Med. Chem. 1988; 31: 2145
27 Dega-Szafran Z, Dulewicz E, Brycki B. ARKIVOC 2007; (vi): 90
28 Kahn K, Bruice TC. J. Comput. Chem. 2002; 23: 977
29 Berendsen HJ. C, van der Spoel D, van Drunen R. Comput. Phys. Commun. 1995; 91: 43
30 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision B01. Gaussian, Inc; Wallingford CT: 2009
31 Humphrey W, Dalke A, Schulten K. J. Mol. Graphics 1996; 14: 33

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