Mechanochemical Synthesis of Dendrimers as Nanocarriers: A Review

Abstract:

The process of mechanically activating chemical bonds usually involves applying external force. Since mechanical chemistry can be performed without solvents or with minimal amounts of solvent (catalytic quantities), it has become an imperative synthetic tool in multiple fields (e.g., physics, chemistry, and materials science) and is an attractive greener method for preparing diverse molecules. Catalysis, organic synthesis, solid-state medicinal preparation, metal complex synthesis, and many other chemistry fields have benefited from sustainable methods. The purpose of this paper is to shed light on the benefits of using mechanochemical methods to produce a pharmaceutical crystal that is composed of dendrimer nanocrystals. Consequently, we describe and examine the importance of mechanical procedures in forming dendrimers and pharmaceutical crystals in this review.

• Periodical: Advanced Materials Research (Volume 1175)
• Pages: 37-46
• DOI: https://doi.org/10.4028/p-a610b7
• Online since: February 2023
• Authors: Mohammad Alrbaihat*
• Keywords: Dendrimer, Drug Delivery, Mechanochemistry, Polymer, Solvent-Free

References

[1] M.A.A.-F. Ghada A.Al Bazedi, Aiman Eid Al-Rawajfeh, E.A. Mohammad R. Alrbaihat, Synthesis of nanomaterials by mechanochemistry, in Greener Synth. Nanomater. Compd., Elsevier Inc., Amsterdam, 2021: p.405–417.

DOI: 10.1016/b978-0-12-821938-6.00011-6

[2] J. Noh, G.I. Peterson, T.L. Choi, Mechanochemical Reactivity of Bottlebrush and Dendronized Polymers: Solid vs. the Solution States, Angew. Chemie - Int. Ed. 60 (2021) 18651–18659.

DOI: 10.1002/anie.202104447

[3] H. Nabipour, Y. Hu, Sustainable drug delivery systems through green nanotechnology, Elsevier Ltd., (2020).

[4] S.L. James, C.J. Adams, C. Bolm, D. Braga, P. Collier, T. Frišcic, F. Grepioni, K.D.M. Harris, G. Hyett, W. Jones, A. Krebs, J. Mack, L. Maini, A.G. Orpen, I.P. Parkin, W.C. Shearouse, J.W. Steed, D.C. Waddell, Playing with organic radicals as building blocks for functional molecular materials, Chem. Soc. Rev. 41 (2012) 413–447.

DOI: 10.1039/c1cs15171a

[5] M. Solares-Briones, G. Coyote-Dotor, J.C. Páez-Franco, M.R. Zermeño-Ortega, C.M. de la O. Contreras, D. Canseco-González, A. Avila-Sorrosa, D. Morales-Morales, J.M. Germán-Acacio, Mechanochemistry: A green approach in the preparation of pharmaceutical cocrystals, Pharmaceutics. 13 (2021) 1–49.

DOI: 10.3390/pharmaceutics13060790

[6] A. Beillard, T.-X. Métro, X. Bantreil, J. Martinez, F. Lamaty, Cu (0), O 2 and mechanical forces: A saving combination for efficient production of Cu–NHC complexes, Chem. Sci. 8 (2017) 1086–1089.

DOI: 10.1039/c6sc03182j

[7] M. Leonardi, M. Villacampa, J.C. Menéndez, Multicomponent mechanochemical synthesis, Chem. Sci. 9 (2018) 2042–(2064).

DOI: 10.1039/c7sc05370c

[8] T. Friščić, I. Halasz, V. Štrukil, M. Eckert-Maksić, R.E. Dinnebier, Clean and efficient synthesis using mechanochemistry: coordination polymers, metal-organic frameworks, and metallodrugs, Croat. Chem. Acta. 85 (2012) 367–378.

DOI: 10.5562/cca2014

[9] A.L. Garay, A. Pichon, S.L. James, Solvent-free synthesis of metal complexes, Chem. Soc. Rev. 36 (2007) 846–855.

DOI: 10.1039/b600363j

[10] A.A. Gečiauskaitė, F. García, Main group mechanochemistry, Beilstein J. Org. Chem. 13 (2017) 2068–(2077).

DOI: 10.3762/bjoc.13.204

[11] D. Tan, F. García, Main group mechanochemistry: from curiosity to established protocols, Chem. Soc. Rev. 48 (2019) 2274–2292.

DOI: 10.1039/c7cs00813a

[12] C. Mottillo, T. Friščić, Advances in solid-state transformations of coordination bonds: From the ball mill to the aging chamber, Molecules. 22 (2017) 144.

DOI: 10.3390/molecules22010144

[13] T. Stolar, K. Užarević, Mechanochemistry: an efficient and versatile toolbox for synthesis, transformation, and functionalization of porous metal-organic frameworks, CrystEngComm. 22 (2020) 4511–4525.

DOI: 10.1039/d0ce00091d

[14] D. Chen, J. Zhao, P. Zhang, S. Dai, Mechanochemical synthesis of metal-organic frameworks, Polyhedron. 162 (2019) 59–64.

DOI: 10.1016/j.poly.2019.01.024

[15] P.A. May, J.S. Moore, Polymer mechanochemistry: techniques to generate molecular force via elongational flows, Chem. Soc. Rev. 42 (2013) 7497–7506.

DOI: 10.1039/c2cs35463b

[16] S. Akbulatov, R. Boulatov, Experimental polymer mechanochemistry and its interpretational frameworks, ChemPhysChem. 18 (2017) 1422–1450.

DOI: 10.1002/cphc.201601354

[17] N. Willis-Fox, E. Rognin, T.A. Aljohani, R. Daly, Polymer mechanochemistry: manufacturing is now a force to be reckoned with, Chem. 4 (2018) 2499–2537.

DOI: 10.1016/j.chempr.2018.08.001

[18] S.-E. Zhu, F. Li, G.-W. Wang, Mechanochemistry of fullerenes and related materials, Chem. Soc. Rev. 42 (2013) 7535–7570.

[19] T. Friscic, W. Jones, Recent advances in understanding the mechanism of cocrystal formation via grinding, Cryst. Growth Des. 9 (2009) 1621–1637.

DOI: 10.1021/cg800764n

[20] D. Braga, L. Maini, F. Grepioni, Mechanochemical preparation of co-crystals, Chem. Soc. Rev. 42 (2013) 7638–7648.

DOI: 10.1039/c3cs60014a

[21] D. Tan, L. Loots, T. Friščić, Towards medicinal mechanochemistry: evolution of milling from pharmaceutical solid form screening to the synthesis of active pharmaceutical ingredients (APIs), Chem. Commun. 52 (2016) 7760–7781.

DOI: 10.1039/c6cc02015a

[22] E. AlShamaileh, A.E. Al-Rawajfeh, M. Alrbaihat, Mechanochemical Synthesis of Slow-release Fertilizers: A Review, Open Agric. J. 12 (2018) 11–19.

DOI: 10.2174/1874331501812010011

[23] P. Baláž, Applied Mechanochemistry, Mechanochemistry Nanosci. Miner. Eng. (2008)297–405.

[24] R. Borges, V. Prevot, C. Forano, F. Wypych, Design and Kinetic Study of Sustainable Potential Slow-Release Fertilizer Obtained by Mechanochemical Activation of Clay Minerals and Potassium Monohydrogen Phosphate, Ind. Eng. Chem. Res. 56 (2017) 708–716.

DOI: 10.1021/acs.iecr.6b04378

[25] A. Mikhak, A. Sohrabi, M.Z. Kassaee, M. Feizian, Synthetic nanozeolite/nanohydroxyapatite as a phosphorus fertilizer for German chamomile (Matricariachamomilla L.), Ind. Crops Prod. 95 (2017) 444–452.

DOI: 10.1016/j.indcrop.2016.10.054

[26] M.R. Alrbaihat, A.E. Al-rawajfeh, E. Alshamaileh, A mechanochemical preparation , properties and kinetic study of kaolin – N , P fertilizers for agricultural applications **, 2021 (2021) 265–271.

DOI: 10.1515/jmbm-2021-0028

[27] M. Alrbaihat, A Review of Size Reduction techniques Using Mechanochemistry Approach, Egypt. J. Chem. 65 (2021) 551–558.

[28] L. Takacs, Mechanochemistry and the Other Branches of Chemistry : Similarities and Di erences, 121 (2012).

[29] B. Nasiri-tabrizi, S. Baradaran, E. Zalnezhad, W.J. Basirun, Applications of electron microscopy in mechanochemistry, (2014) 791–802.

[30] A.M. Klibanov, G.P. Samokhin, K. Martinek, I. V Berezin, Enzymatic mechanochemistry: a new approach to studying the mechanism of enzyme action, Biochim. Biophys. Acta (BBA)-Enzymology. 438 (1976) 1–12.

DOI: 10.1016/0005-2744(76)90218-7

[31] C.E. Diesendruck, G.I. Peterson, H.J. Kulik, J.A. Kaitz, B.D. Mar, P.A. May, S.R. White, T.J. Martínez, A.J. Boydston, J.S. Moore, Mechanically triggered heterolytic unzipping of a low-ceiling-temperature polymer, Nat. Chem. 6 (2014) 623–628.

DOI: 10.1038/nchem.1938

[32] J.M. Lenhardt, M.T. Ong, R. Choe, C.R. Evenhuis, T.J. Martinez, S.L. Craig, Trapping a diradical transition state by mechanochemical polymer extension, Science (80-. ). 329 (2010) 1057–1060.

DOI: 10.1126/science.1193412

[33] A.G. Tennyson, K.M. Wiggins, C.W. Bielawski, Mechanical activation of catalysts for C− C bond forming and anionic polymerization reactions from a single macromolecular reagent, J. Am. Chem. Soc. 132 (2010) 16631–16636.

DOI: 10.1021/ja107620y

[34] A. Piermattei, S. Karthikeyan, R.P. Sijbesma, Activating catalysts with mechanical force, Nat. Chem. 1 (2009) 133–137.

DOI: 10.1038/nchem.167

[35] Y. Li, A. Nese, N. V Lebedeva, T. Davis, K. Matyjaszewski, S.S. Sheiko, Molecular tensile machines: intrinsic acceleration of disulfide reduction by dithiothreitol, J. Am. Chem. Soc. 133 (2011) 17479–17484.

DOI: 10.1021/ja207491r

[36] R.J. Camp, M. Liles, J. Beale, N. Saeidi, B.P. Flynn, E. Moore, S.K. Murthy, J.W. Ruberti, Molecular mechanochemistry: low force switch slows enzymatic cleavage of human type I collagen monomer, J. Am. Chem. Soc. 133 (2011) 4073–4078.

DOI: 10.1021/ja110098b

[37] A.P. Wiita, S.R.K. Ainavarapu, H.H. Huang, J.M. Fernandez, Force-dependent chemical kinetics of disulfide bond reduction observed with single-molecule techniques, Proc. Natl. Acad. Sci. 103 (2006) 7222–7227.

DOI: 10.1073/pnas.0511035103

[38] K. Visscher, M.J. Schnitzer, S.M. Block, Single kinesin molecules studied with a molecular force clamp, Nature. 400 (1999) 184–189.

DOI: 10.1038/22146

[39] Y.I. Golovin, S.L. Gribanovskii, N.L. Klyachko, A. V Kabanov, Nanomechanical control of the activity of enzymes immobilized on single-domain magnetic nanoparticles, Tech. Phys. 59 (2014) 932–935.

DOI: 10.1134/s1063784214060085

[40] K.M. Wiggins, J.N. Brantley, C.W. Bielawski, Polymer mechanochemistry: force enabled transformations, (2012).

[41] D. Bensimon, Force: a new structural control parameter?, Structure. 4 (1996) 885–889.

DOI: 10.1016/s0969-2126(96)00095-0

[42] A. Santos, F. Veiga, A. Figueiras, Dendrimers as pharmaceutical excipients: Synthesis, properties, toxicity and biomedical applications, (2020).

DOI: 10.3390/ma13010065

[43] R.A. Cross, A. McAinsh, Prime movers: the mechanochemistry of mitotic kinesins, Nat. Rev. Mol. Cell Biol. 15 (2014) 257–271.

DOI: 10.1038/nrm3768

[44] K.S. Bloom, Beyond the code: the mechanical properties of DNA as they relate to mitosis, Chromosoma. 117 (2008) 103–110.

DOI: 10.1007/s00412-007-0138-0

[45] A.M. Gordon, E. Homsher, M. Regnier, Regulation of contraction in striated muscle, Physiol. Rev. 80 (2000) 853–924.

DOI: 10.1152/physrev.2000.80.2.853

[46] P. Baláž, Mechanochemistry in Minerals Engineering, Mechanochemistry Nanosci. Miner. Eng. (2008) 257–296.

DOI: 10.1007/978-3-540-74855-7_5

[47] V. V. Boldyrev, Topochemistry of thermal decompositions of solids, Thermochim. Acta. 100 (1986) 315–338.

DOI: 10.1016/0040-6031(86)87063-0

[48] Y. Chen, M. Bibole, R. Le Hazif, G. Martin, Ball-milling-induced amorphization in NixZry compounds: A parametric study, Phys. Rev. B. 48 (1993) 14–21.

[49] V. Klika, F. Maršík, Coupling effect between mechanical loading and chemical reactions, J. Phys. Chem. B. 113 (2009) 14689–14697.

DOI: 10.1021/jp903054y

[50] D.L. Zhang, Processing of advanced materials using high-energy mechanical milling, Prog. Mater. Sci. 49 (2004) 537–560.

[51] D. Hasa, W. Jones, Screening for new pharmaceutical solid forms using mechanochemistry: A practical guide, Adv. Drug Deliv. Rev. 117 (2017) 147–161.

DOI: 10.1016/j.addr.2017.05.001

[52] D. Tan, L. Loots, T. Friščić, Towards medicinal mechanochemistry: Evolution of milling from pharmaceutical solid form screening to the synthesis of active pharmaceutical ingredients (APIs), Chem. Commun. 52 (2016) 7760–7781.

DOI: 10.1039/c6cc02015a

[53] D. Douroumis, S.A. Ross, A. Nokhodchi, Advanced methodologies for cocrystal synthesis, Adv. Drug Deliv. Rev. 117 (2017) 178–195.

DOI: 10.1016/j.addr.2017.07.008

[54] R.B. Chavan, B. Yadav, A. Lodagekar, N.R. Shastri, Multicomponent Solid Forms: A New Boost to Pharmaceuticals, in: Multifunct. Nanocarriers Contemp. Healthc. Appl., IGI Global, 2018: p.273–300.

DOI: 10.4018/978-1-5225-4781-5.ch010

[55] S. Datta, D.J.W. Grant, Crystal structures of drugs: Advances in determination, prediction and engineering, Nat. Rev. Drug Discov. 3 (2004) 42–57.

DOI: 10.1038/nrd1280

[56] X. Zhao, Y. Wei, Z. Wang, B. Zhang, F. Chen, P. Zhang, Mechanochemistry in Thermomechanical Processing of Foods : Kinetic Aspects, 76 (2011).

DOI: 10.1111/j.1750-3841.2011.02301.x

[57] A.I. Aleksandrov, V.G. Shevchenko, A.N. Tarasenkov, N.M. Surin, G. V. Cherkaev, I.Y. Metlenkova, E.A. Svidchenko, V.G. Krasovsky, A.A. Dubinsky, E.N. Degtyarev, Mechanochemical synthesis and structure of a nanocluster {organosilicon dendrimer - Copper dimer}, J. Organomet. Chem. 950 (2021) 121976.

DOI: 10.1016/j.jorganchem.2021.121976

[58] R. Mohammadinejad, G.A. Mansoori, Large-scale production/biosynthesis of biogenic nanoparticles, (2020).

[59] M.A. Ghanem, A. Basu, R. Behrou, N. Boechler, A.J. Boydston, S.L. Craig, Y. Lin, B.E. Lynde, A. Nelson, H. Shen, D.W. Storti, The role of polymer mechanochemistry in responsive materials and additive manufacturing, Nat. Rev. Mater. 6 (2021) 84–98.

DOI: 10.1038/s41578-020-00249-w

[60] J. Li, C. Nagamani, J.S. Moore, Polymer mechanochemistry: from destructive to productive, Acc. Chem. Res. 48 (2015) 2181–2190.

DOI: 10.1021/acs.accounts.5b00184

[61] J.F. Patrick, M.J. Robb, N.R. Sottos, J.S. Moore, S.R. White, Polymers with autonomous life-cycle control, Nature. 540 (2016) 363–370.

DOI: 10.1038/nature21002

[62] B.H. Bowser, S.L. Craig, Empowering mechanochemistry with multi-mechanophore polymer architectures, Polym. Chem. 9 (2018) 3583–3593.

DOI: 10.1039/c8py00720a

[63] J. Wang, T.B. Kouznetsova, Z. Niu, M.T. Ong, H.M. Klukovich, A.L. Rheingold, T.J. Martinez, S.L. Craig, Inducing and quantifying forbidden reactivity with single-molecule polymer mechanochemistry, Nat. Chem. 7 (2015) 323–327.

DOI: 10.1038/nchem.2185

[64] K. Wei, Z. Gao, H. Liu, X. Wu, F. Wang, H. Xu, Mechanical activation of platinum–acetylide complex for olefin hydrosilylation, ACS Macro Lett. 6 (2017) 1146–1150.

DOI: 10.1021/acsmacrolett.7b00487

[65] Z. Wang, Z. Ma, Y. Wang, Z. Xu, Y. Luo, Y. Wei, X. Jia, A novel mechanochromic and photochromic polymer film: when rhodamine joins polyurethane, Adv. Mater. 27 (2015) 6469–6474.

DOI: 10.1002/adma.201503424

[66] G.A. Filonenko, J.A.M. Lugger, C. Liu, E.P.A. van Heeswijk, M.M.R.M. Hendrix, M. Weber, C. Müller, E.J.M. Hensen, R.P. Sijbesma, E.A. Pidko, Tracking local mechanical impact in heterogeneous polymers with direct optical imaging, Angew. Chemie Int. Ed. 57 (2018) 16385–16390.

DOI: 10.1002/anie.201809108

[67] Y. Sagara, M. Karman, E. Verde-Sesto, K. Matsuo, Y. Kim, N. Tamaoki, C. Weder, Rotaxanes as mechanochromic fluorescent force transducers in polymers, J. Am. Chem. Soc. 140 (2018) 1584–1587.

DOI: 10.1021/jacs.7b12405

[68] H. Sakai, T. Sumi, D. Aoki, R. Goseki, H. Otsuka, Thermally stable radical-type mechanochromic polymers based on difluorenylsuccinonitrile, ACS Macro Lett. 7 (2018) 1359–1363.

DOI: 10.1021/acsmacrolett.8b00755

[69] H. Zhang, F. Gao, X. Cao, Y. Li, Y. Xu, W. Weng, R. Boulatov, Mechanochromism and mechanical‐force‐triggered cross‐linking from a single reactive moiety incorporated into polymer chains, Angew. Chemie. 128 (2016) 3092–3096.

DOI: 10.1002/ange.201510171

[70] M.B. Gordon, S. Wang, G.A. Knappe, N.J. Wagner, T.H. Epps, C.J. Kloxin, Force-induced cleavage of a labile bond for enhanced mechanochemical crosslinking, Polym. Chem. 8 (2017) 6485–6489.

DOI: 10.1039/c7py01431g

[71] T. Matsuda, R. Kawakami, R. Namba, T. Nakajima, J.P. Gong, Mechanoresponsive self-growing hydrogels inspired by muscle training, Science (80-. ). 363 (2019) 504–508.

DOI: 10.1126/science.aau9533

[72] T. Watabe, D. Aoki, H. Otsuka, Enhancement of Mechanophore Activation in Mechanochromic Dendrimers by Functionalization of Their Surface, Macromolecules. 54 (2021) 1725–1731.

DOI: 10.1021/acs.macromol.0c02497

[73] A. Parat, D. Felder-Flesch, General introduction on dendrimers, classical versus accelerated syntheses and characterizations, in: Dendrimers in Nanomedicine, Jenny Stanford Publishing, 2016: p.1–22.

DOI: 10.1201/9781315364513-2

[74] I.M. Klein, C.C. Husic, D.P. Kovács, N.J. Choquette, M.J. Robb, Validation of the CoGEF Method as a Predictive Tool for Polymer Mechanochemistry, J. Am. Chem. Soc. 142 (2020) 16364–16381.

DOI: 10.1021/jacs.0c06868

[75] M. Sayedul Islam, M. Wahab Khan, Synthesis of Dendrimer Assisted Co-Pd Bimetallic Nanoparticles and Catalytic Activity for Suzuki–Miyaura Coupling Reactions, Am. J. Nanosci. 5 (2019) 1.

DOI: 10.11648/j.ajn.20190501.11

[76] P. Arshad, P. Dineshkumar, K. Naga Jyothi, M. Karthik, G. Saravanan, Dendrimers as a Novel Carrier in Anti-HIV Therapy, J. Drug Deliv. Ther. 9 (2019) 195–200.

DOI: 10.22270/jddt.v9i5-s.3650

[77] T. Watabe, K. Ishizuki, D. Aoki, H. Otsuka, Mechanochromic dendrimers: The relationship between primary structure and mechanochromic properties in the bulk, Chem. Commun. 55 (2019) 6831–6834.

DOI: 10.1039/c9cc03011e

[78] E. Abbasi, S.F. Aval, A. Akbarzadeh, M. Milani, H.T. Nasrabadi, S.W. Joo, Y. Hanifehpour, K. Nejati-Koshki, R. Pashaei-Asl, Dendrimers: Synthesis, applications, and properties, Nanoscale Res. Lett. 9 (2014) 1–10.

DOI: 10.1186/1556-276x-9-247

[79] A.S. Chauhan, Dendrimers for Drug Delivery, Molecules. 23 (2018).

[80] A. Chauhan, S. Svenson, L. Reyna, D. Tomalia, Solubility enhancement propensity of PAMAM nanoconstructs, Mater. Matters Nanomater. 2 (2007) 24–26.

[81] H. Kulhari, D. Pooja, M.K. Singh, A.S. Chauhan, Optimization of carboxylate-terminated poly (amidoamine) dendrimer-mediated cisplatin formulation, Drug Dev. Ind. Pharm. 41 (2015) 232–238.

DOI: 10.3109/03639045.2013.858735

[82] F. García-Álvarez, M. Martínez-García, Click reaction in the synthesis of dendrimer drug-delivery systems, Curr. Med. Chem. (2022).

DOI: 10.2174/0929867328666211027124724

[83] D.A. Davis, A. Hamilton, J. Yang, L.D. Cremar, D. Van Gough, S.L. Potisek, M.T. Ong, P. V Braun, T.J. Martínez, S.R. White, Force-induced activation of covalent bonds in mechanoresponsive polymeric materials, Nature. 459 (2009) 68–72.

DOI: 10.1038/nature07970

[84] K. Imato, A. Irie, T. Kosuge, T. Ohishi, M. Nishihara, A. Takahara, H. Otsuka, Mechanophores with a reversible radical system and freezing‐induced mechanochemistry in polymer solutions and gels, Angew. Chemie. 127 (2015) 6266–6270.

DOI: 10.1002/ange.201412413

[85] M.E. McFadden, M.J. Robb, Force-dependent multicolor mechanochromism from a single mechanophore, J. Am. Chem. Soc. 141 (2019) 11388–11392.

DOI: 10.1021/jacs.9b05280

[86] C.E. Diesendruck, B.D. Steinberg, N. Sugai, M.N. Silberstein, N.R. Sottos, S.R. White, P. V Braun, J.S. Moore, Proton-coupled mechanochemical transduction: a mechanogenerated acid, J. Am. Chem. Soc. 134 (2012) 12446–12449.

DOI: 10.1021/ja305645x

[87] X. Hu, T. Zeng, C.C. Husic, M.J. Robb, Mechanically triggered small molecule release from a masked furfuryl carbonate, J. Am. Chem. Soc. 141 (2019) 15018–15023.

DOI: 10.1021/jacs.9b08663

[88] Z. Chen, J.A.M. Mercer, X. Zhu, J.A.H. Romaniuk, R. Pfattner, L. Cegelski, T.J. Martinez, N.Z. Burns, Y. Xia, Mechanochemical unzipping of insulating polyladderene to semiconducting polyacetylene, Science (80-. ). 357 (2017) 475–479.

DOI: 10.1126/science.aan2797

[89] P. Michael, W.H. Binder, A mechanochemically triggered click, catalyst, Angew. Chemie. 127 (2015) 14124–14128.

DOI: 10.1002/ange.201505678