Abstract
Cucurbituril-type (CB-type) molecules have played key roles in host-guest chemistry as well as supramolecular chemistry. Along with the development and synthetic expansion of CB-type molecules during the past two decades, their applications in a variety of research areas have been investigated. In particular, CB-type molecules have been found to modulate the chemical and biological properties of biomedically relevant molecules via host-guest complexations, including pKa shift, solubility/stability enhancement, therapeutic efficacy modulation, and toxicity reduction. This chapter summarizes these investigations and their implications in biomedical sciences.
References
Pedersen CJ (1967) Cyclic polyethers and their complexes with metal salts. J Am Chem Soc 89:2495–2496
Pedersen CJ (1967) Cyclic polyethers and their complexes with metal salts. J Am Chem Soc 89:7017–7036
Liu Z, Nalluri SKM, Stoddart JF (2017) Surveying macrocyclic chemistry: from flexible crown ethers to rigid cyclophanes. Chem Soc Rev 46:2459–2478
Liu S, Zavalij PY, Isaacs L (2005) Cucurbit[10]uril. J Am Chem Soc 127:16798–16799
Cheng X-J, Liang L-L, Chen K, Ji N-N, Xiao X, Zhang J-X, Zhang Y-Q, Xue S-F, Zhu Q-J, Ni X-L, Tao Z (2013) Twisted cucurbit[14]uril. Angew Chem Int Ed 52:7252–7255
Li Q, Qiu S-C, Zhang J, Chen K, Huang Y, Xiao X, Zhang Y, Li F, Zhang Y-Q, Xue S-F, Zhu Q-J, Tao Z, Lindoy LF, Wei G (2016) Twisted Cucurbit[n]urils. Org Lett 18:4020–4023
Barrow SJ, Kasera S, Rowland MJ, del Barrio J, Scherman OA (2015) Cucurbituril-based molecular recognition. Chem Rev 115:12320–12406
Kim S, Yun G, Khan S, Kim J, Murray J, Lee YM, Kim WJ, Lee G, Kim S, Shetty D, Kang JH, Kim JY, Park KM, Kim K (2017) Cucurbit[6]uril-based polymer nanocapsules as a non-covalent and modular bioimaging platform for multimodal in vivo imaging. Mater Horiz 4:450–455
Kuok KI, Li S, Wyman IW, Wang R (2017) Cucurbit[7]uril: an emerging candidate for pharmaceutical excipients. Ann N Y Acad Sci 1398:108–119
Yang X, Liu F, Zhao Z, Liang F, Zhang H, Liu S (2018) Cucurbit[10]uril-based chemistry. Chin Chem Lett 29:1560–1566
Ma D, Hettiarachchi G, Nguyen D, Zhang B, Wittenberg JB, Zavalij PY, Briken V, Isaacs L (2012) Acyclic cucurbit[n]uril molecular containers enhance the solubility and bioactivity of poorly soluble pharmaceuticals. Nat Chem 4:503
Hennig A, Bakirci H, Nau WM (2007) Label-free continuous enzyme assays with macrocycle-fluorescent dye complexes. Nat Methods 4:629
Biedermann F, Hathazi D, Nau WM (2015) Associative chemosensing by fluorescent macrocycle–dye complexes – a versatile enzyme assay platform beyond indicator displacement. Chem Commun 51:4977–4980
Yin H, Dumur F, Niu Y, Ayhan MM, Grauby O, Liu W, Wang C, Siri D, Rosas R, Tonetto A, Gigmes D, Wang R, Bardelang D, Ouari O (2017) Chameleonic dye adapts to various environments shining on macrocycles or peptide and polysaccharide aggregates. ACS Appl Mater Interfaces 9:33220–33228
Goehry C, Besora M, Maseras F (2015) Computational study on the mechanism of the acceleration of 1,3-dipolar cycloaddition inside cucurbit[6]uril. ACS Catal 5:2445–2451
Palma A, Artelsmair M, Wu G, Lu X, Barrow SJ, Uddin N, Rosta E, Masson E, Scherman OA (2017) Cucurbit[7]uril as a supramolecular artificial enzyme for Diels–Alder reactions. Angew Chem Int Ed 56:15688–15692
Scorsin L, Roehrs JA, Campedelli RR, Caramori GF, Ortolan AO, Parreira RLT, Fiedler HD, Acuña A, García-Río L, Nome F (2018) Cucurbituril-mediated catalytic hydrolysis: a kinetic and computational study with neutral and cationic Dioxolanes in CB7. ACS Catal 8:12067–12079
Gao C, Huang Q, Lan Q, Feng Y, Tang F, Hoi MPM, Zhang J, Lee SMY, Wang R (2018) A user-friendly herbicide derived from photo-responsive supramolecular vesicles. Nat Commun 9:2967
Appel EA, Biedermann F, Rauwald U, Jones ST, Zayed JM, Scherman OA (2010) Supramolecular cross-linked networks via host−guest complexation with cucurbit[8]uril. J Am Chem Soc 132:14251–14260
Tan CSY, Liu J, Groombridge AS, Barrow SJ, Dreiss CA, Scherman OA (2017) Controlling spatiotemporal mechanics of supramolecular hydrogel networks with highly branched cucurbit[8]uril Polyrotaxanes. Adv Funct Mater 28:1702994
Yin H, Wang R (2017) Applications of cucurbit[n]urils (n=7 or 8) in pharmaceutical sciences and complexation of biomolecules. Isr J Chem 58:188–198
Sun C, Zhang H, Li S, Zhang X, Cheng Q, Ding Y, Wang L-H, Wang R (2018) Polymeric nanomedicine with “Lego” surface allowing modular functionalization and drug encapsulation. ACS Appl Mater Interfaces 10:25090–25098
Wu D, Li Y, Yang J, Shen J, Zhou J, Hu Q, Yu G, Tang G, Chen X (2017) Supramolecular nanomedicine constructed from cucurbit[8]uril-based amphiphilic brush copolymer for Cancer therapy. ACS Appl Mater Interfaces 9:44392–44401
Hettiarachchi G, Nguyen D, Wu J, Lucas D, Ma D, Isaacs L, Briken V (2010) Toxicology and drug delivery by cucurbit[n]uril type molecular containers. PLoS One 5:e10514
Jin Jeon Y, Kim S-Y, Ho Ko Y, Sakamoto S, Yamaguchi K, Kim K (2005) Novel molecular drug carrier: encapsulation of oxaliplatin in cucurbit[7]uril and its effects on stability and reactivity of the drug. Org Biomol Chem 3:2122–2125
Uzunova VD, Cullinane C, Brix K, Nau WM, Day AI (2010) Toxicity of cucurbit[7]uril and cucurbit[8]uril: an exploratory in vitro and in vivo study. Org Biomol Chem 8:2037–2042
Oun R, Floriano RS, Isaacs L, Rowan EG, Wheate NJ (2014) The ex vivo neurotoxic, myotoxic and cardiotoxic activity of cucurbituril-based macrocyclic drug delivery vehicles. Toxicol Res 3:447–455
Chen H, Chan JYW, Yang X, Wyman IW, Bardelang D, Macartney DH, Lee SMY, Wang R (2015) Developmental and organ-specific toxicity of cucurbit[7]uril: in vivo study on zebrafish models. RSC Adv 5:30067–30074
Zhang X, Xu X, Li S, Wang L-H, Zhang J, Wang R (2018) A systematic evaluation of the biocompatibility of cucurbit[7]uril in mice. Sci Rep 8:8819
Zhao W-X, Wang C-Z, Chen L-X, Cong H, Xiao X, Zhang Y-Q, Xue S-F, Huang Y, Tao Z, Zhu Q-J (2015) A Hemimethyl-substituted cucurbit[7]uril derived from 3α-methyl-glycoluril. Org Lett 17:5072–5075
Yang X, Zhao W, Wang Z, Huang Y, Lee SMY, Tao Z, Wang R (2017) Toxicity of hemimethyl-substituted cucurbit[7]uril. Food Chem Toxicol 108:510–518
Macartney DH (2018) Cucurbit[n]uril host-guest complexes of acids, Photoacids, and super Photoacids. Isr J Chem 58:230–243
Ni S, Meetani MA, Al-Kaabi L, Ghosh I, Nau WM (2011) Effect of cucurbit[n]urils on tropicamide and potential application in ocular drug delivery. Supramol Chem 23:650–656
El-Sheshtawy HS, Chatterjee S, Assaf KI, Shinde MN, Nau WM, Mohanty J (2018) A supramolecular approach for enhanced antibacterial activity and extended shelf-life of fluoroquinolone drugs with cucurbit[7]uril. Sci Rep 8:13925
Koner AL, Ghosh I, Ni S, Nau WM (2011) Supramolecular encapsulation of benzimidazole-derived drugs by cucurbit[7]uril. Can J Chem 89:139–147
Ni S, Ajeb SM, Sham A, AbuQamar SF (2014) Enhancement of in vitro fungicidal activity of fuberidazole to Botrytis cinerea by cucurbiturils. J Incl Phenom Macrocycl Chem 79:301–309
Barooah N, Mohanty J, Pal H, Bhasikuttan AC (2012) Stimulus-responsive supramolecular pKa tuning of cucurbit[7]uril encapsulated Coumarin 6 dye. J Phys Chem B 116:3683–3689
Barooah N, Sundararajan M, Mohanty J, Bhasikuttan AC (2014) Synergistic effect of intramolecular charge transfer toward supramolecular pKa shift in cucurbit[7]uril encapsulated Coumarin dyes. J Phys Chem B 118:7136–7146
Gavvala K, Koninti RK, Sengupta A, Hazra P (2014) Cucurbit[7]uril assisted ultraviolet to visible fluorescence switch of a heart medicine. Phys Chem Chem Phys 16:2823–2826
Basílio N, Laia CAT, Pina F (2015) Excited-state proton transfer in confined medium. 4-Methyl-7-hydroxyflavylium and β-Naphthol incorporated in cucurbit[7]uril. J Phys Chem B 119:2749–2757
Mallick S, Pal K, Chandra F, Koner AL (2016) Investigation of the effect of cucurbit[7]uril complexation on the photophysical and acid-base properties of the antimalarial drug quinine. Phys Chem Chem Phys 18:30520–30529
Boraste Deepak R, Chakraborty G, Ray Alok K, Shankarling Ganapati S, Pal H (2017) pH-responsive interaction of Fluorogenic antimalarial drug quinine with macrocyclic host cucurbit[7]uril: modulations in Photophysical and Acid-Base properties. Chem Sel 2:5128–5142
Wang R, Macartney DH (2008) Cucurbit[7]uril host–guest complexes of the histamine H2-receptor antagonist ranitidine. Org Biomol Chem 6:1955–1960
Li S, Yin H, Martinz G, Wyman IW, Bardelang D, Macartney DH, Wang R (2016) Supramolecular encapsulation of benzocaine and its metabolite Para-aminobenzoic acid by cucurbit[7]uril. New J Chem 40:3484–3490
Li S, Wyman IW, Wang C, Wang Y, Macartney DH, Wang R (2016) Inhibition of C(2)-H activity on alkylated imidazolium Monocations and Dications upon inclusion by cucurbit[7]uril. J Org Chem 81:9494–9498
Yin H, Chen L, Yang B, Bardelang D, Wang C, Lee SMY, Wang R (2017) Fluorescence enhancement and pKa shift of a rho kinase inhibitor by a synthetic receptor. Org Biomol Chem 15:4336–4343
Yin H, Wang R, Wan J, Zheng Y, Ouyang D, Wang R (2016) Molecular encapsulation of histamine H2-receptor antagonists by cucurbit[7]Uril: an experimental and computational study. Molecules 21:1178
Shaikh M, Mohanty J, Singh PK, Nau WM, Pal H (2008) Complexation of acridine orange by cucurbit[7]uril and β-cyclodextrin: photophysical effects and pKa shifts. Photochem Photobiol Sci 7:408–414
Khurana R, Barooah N, Bhasikuttan AC, Mohanty J (2017) Modulation in the acidity constant of acridine dye with cucurbiturils: stimuli-responsive pKa tuning and dye relocation into live cells. Org Biomol Chem 15:8448–8457
Huang Y, Hu Q-H, Song G-X, Tao Z, Xue S-F, Zhu Q-J, Q-d Z, Wei G (2014) Cucurbit[7,8]urils binding to gefitinib and the effect of complex formation on the solubility and dissolution rate of the drug. RSC Adv 4:3348–3354
Huang Y, Song G, Tang Q, Wang J, Tao Z, Xue S, Zhang J (2014) Encapsulation of Cytarabine in cucurbit [7] uril and its effects on stability of the drug. Chem J Chinese U 35:1224–1228
Zhao Y, Buck DP, Morris DL, Pourgholami MH, Day AI, Collins JG (2008) Solubilisation and cytotoxicity of albendazole encapsulated in cucurbit[n]uril. Org Biomol Chem 6:4509–4515
Ma W-J, Chen J-M, Jiang L, Yao J, Lu T-B (2013) The delivery of triamterene by cucurbit[7]uril: synthesis, structures and pharmacokinetics study. Mol Pharm 10:4698–4705
Huang Y, Xue S-F, Tao Z, Zhu Q-J, Zhang H, Lin J-X, Yu D-H (2008) Solubility enhancement of kinetin through host–guest interactions with cucurbiturils. J Incl Phenom Macrocycl Chem 61:171–177
Dong N, Dong M, Zhao A, Zhu Q, Tao Z, Zhao Y (2010) Preparation and characterization of inclusion complexes of antitumor camptothecin with cucurbit[n = 7, 8]urils. Sci China Chem 53:2304
Liu Q, Tang Q, Xi Y-Y, Huang Y, Xiao X, Tao Z, Xue S-F, Zhu Q-J, Zhang J-X, Wei G (2015) Host–guest interactions of thiabendazole with normal and modified cucurbituril: 1H NMR, phase solubility and antifungal activity studies. Supramol Chem 27:386–392
Xu Z, Lian X, Li M, Zhang X, Wang Y, Tao Z, Zhang Q (2017) Effects of inclusion of chrysin in cucurbit[8]uril on its stability, solubility and antioxidant potential. Chem Res Chin Univ 33:736–741
Li M, Lian X, Xu Z, Xing X, Zhang J, Li R, Tao Z, Zhang Q (2017) Influence of interaction with cucurbit [7] uril on solubility, stability and antioxidant activity of 2'-Hydroxychalcone. Chem J Chinese U 38:442–447
Li S, Chan JY-W, Li Y, Bardelang D, Zheng J, Yew WW, Chan DP-C, Lee SMY, Wang R (2016) Complexation of clofazimine by macrocyclic cucurbit[7]uril reduced its cardiotoxicity without affecting the antimycobacterial efficacy. Org Biomol Chem 14:7563–7569
Yang X, Huang Q, Bardelang D, Wang C, Lee SMY, Wang R (2017) Supramolecular alleviation of cardiotoxicity of a small-molecule kinase inhibitor. Org Biomol Chem 15:8046–8053
Kuok KI, In Ng PC, Ji X, Wang C, Yew WW, Chan DPC, Zheng J, Lee SMY, Wang R (2018) Supramolecular strategy for reducing the cardiotoxicity of bedaquiline without compromising its antimycobacterial efficacy. Food Chem Toxicol 119:425–429
Ni S, Koner AL, Nau WM (2008) Activation and stabilization of drugs by supramolecular pKa shifts: drug-delivery applications tailored for Cucurbiturils. Angew Chem Int Ed 47:5398–5401
Appel EA, Rowland MJ, Loh XJ, Heywood RM, Watts C, Scherman OA (2012) Enhanced stability and activity of temozolomide in primary glioblastoma multiforme cells with cucurbit[n]uril. Chem Commun 48:9843–9845
Webber MJ, Appel EA, Vinciguerra B, Cortinas AB, Thapa LS, Jhunjhunwala S, Isaacs L, Langer R, Anderson DG (2016) Supramolecular PEGylation of biopharmaceuticals. Proc Natl Acad Sci USA 113:14189
Li S, Miao X, Wyman IW, Li Y, Zheng Y, Wang Y, Macartney DH, Wang R (2015) High-affinity host–guest complex of cucurbit[7]uril with a bis(thiazolium) salt. RSC Adv 5:56110–56115
Li S, Yin H, Wyman IW, Zhang Q, Macartney DH, Wang R (2016) Encapsulation of vitamin B1 and its phosphate derivatives by cucurbit[7]uril: tunability of the binding site and affinity by the presence of phosphate groups. J Org Chem 81:1300–1303
Li S, Ding Y-F, Yin H, Wang C, Bardelang D, Wang L-H, Wang R (2016) Encapsulation of AGE-breaker Alagebrium by cucurbit[7]uril improved the stability of both its carbonyl α-hydrogen and Thiazolium C2-hydrogen. Chem Asian J 11:3126–3133
Miao X, Li Y, Wyman I, Lee SMY, Macartney DH, Zheng Y, Wang R (2015) Enhanced in vitro and in vivo uptake of a hydrophobic model drug coumarin-6 in the presence of cucurbit[7]uril. Med Chem Commun 6:1370–1374
Plumb JA, Venugopal B, Oun R, Gomez-Roman N, Kawazoe Y, Venkataramanan NS, Wheate NJ (2012) Cucurbit[7]uril encapsulated cisplatin overcomes cisplatin resistance via a pharmacokinetic effect. Metallomics 4:561–567
Gomez-Roman N, McGregor F, Wheate NJ, Plumb JA (2015) Cucurbit [7] uril encapsulated cisplatin overcomes resistance to cisplatin induced by Rab25 overexpression in an intraperitoneal ovarian cancer model. J Ovarian Res 8:62
Hettiarachchi G, Samanta SK, Falcinelli S, Zhang B, Moncelet D, Isaacs L, Briken V (2016) Acyclic cucurbit[n]uril-type molecular container enables systemic delivery of effective doses of Albendazole for treatment of SK-OV-3 xenograft tumors. Mol Pharm 13:809–818
Chen Y, Huang Z, Xu J-F, Sun Z, Zhang X (2016) Cytotoxicity regulated by host–guest interactions: a supramolecular strategy to realize controlled disguise and exposure. ACS Appl Mater Interfaces 8:22780–22784
Chen Y, Huang Z, Zhao H, Xu J-F, Sun Z, Zhang X (2017) Supramolecular chemotherapy: cooperative enhancement of antitumor activity by combining controlled release of Oxaliplatin and consuming of Spermine by cucurbit[7]uril. ACS Appl Mater Interfaces 9:8602–8608
Chen H, Chen Y, Wu H, Xu J-F, Sun Z, Zhang X (2018) Supramolecular polymeric chemotherapy based on cucurbit[7]uril-PEG copolymer. Biomaterials 178:697–705
Yin H, Rosas R, Gigmes D, Ouari O, Wang R, Kermagoret A, Bardelang D (2018) Metal actuated ring translocation switches in water. Org Lett 20:3187–3191
Cheng Q, Yin H, Rosas R, Gigmes D, Ouari O, Wang R, Kermagoret A, Bardelang D (2018) A pH-driven ring translocation switch against cancer cells. Chem Commun 54:13825–13828
Bai H, Yuan H, Nie C, Wang B, Lv F, Liu L, Wang S (2015) A supramolecular antibiotic switch for antibacterial regulation. Angew Chem Int Ed 54:13208–13213
Chen L, Bai H, Xu J-F, Wang S, Zhang X (2017) Supramolecular porphyrin photosensitizers: controllable disguise and Photoinduced activation of antibacterial behavior. ACS Appl Mater Interfaces 9:13950–13957
Yang Y, He P, Wang Y, Bai H, Wang S, Xu J-F, Zhang X (2017) Supramolecular radical anions triggered by bacteria in situ for selective photothermal therapy. Angew Chem Int Ed 56:16239–16242
Li S, Jiang N, Zhao W, Ding Y-F, Zheng Y, Wang L-H, Zheng J, Wang R (2017) An eco-friendly in situ activatable antibiotic via cucurbit[8]uril-mediated supramolecular crosslinking of branched polyethylenimine. Chem Commun 53:5870–5873
Chen H, Chan JYW, Li S, Liu JJ, Wyman IW, Lee SMY, Macartney DH, Wang R (2015) In vivo reversal of general anesthesia by cucurbit[7]uril with zebrafish models. RSC Adv 5:63745–63752
Li S, Chen H, Yang X, Bardelang D, Wyman IW, Wan J, Lee SMY, Wang R (2015) Supramolecular inhibition of neurodegeneration by a synthetic receptor. ACS Med Chem Lett 6:1174–1178
Huang Q, Kuok KI, Zhang X, Yue L, Lee SMY, Zhang J, Wang R (2018) Inhibition of drug-induced seizure development in both zebrafish and mouse models by a synthetic nanoreceptor. Nanoscale 10:10333–10336
Huang Q, Li S, Yin H, Wang C, Lee SMY, Wang R (2018) Alleviating the hepatotoxicity of trazodone via supramolecular encapsulation. Food Chem Toxicol 112:421–426
Yang X, Li S, Wang Z, Lee SMY, Wang L-H, Wang R (2017) Constraining the teratogenicity of pesticide pollution by a synthetic nanoreceptor. Chem Asian J 13:41–45
Ma D, Zhang B, Hoffmann U, Sundrup MG, Eikermann M, Isaacs L (2012) Acyclic cucurbit[n]uril-type molecular containers bind neuromuscular blocking agents in vitro and reverse neuromuscular block in vivo. Angew Chem Int Ed 51:11358–11362
Hoffmann U, Grosse-Sundrup M, Eikermann-Haerter K, Zaremba S, Ayata C, Zhang B, Ma D, Isaacs L, Eikermann M (2013) CalabadionA new agent to reverse the effects of Benzylisoquinoline and steroidal neuromuscular-blocking agents. Anesthesiology 119:317–325
Yang X, Wang Z, Niu Y, Chen X, Lee SMY, Wang R (2016) Influence of supramolecular encapsulation of camptothecin by cucurbit[7]uril: reduced toxicity and preserved anti-cancer activity. Med Chem Commun 7:1392–1397
Li S, Yang X, Niu Y, Andrew GL, Bardelang D, Chen X, Wang R (2017) Alleviation of hepatotoxicity of Arecoline (Areca alkaloid) by a synthetic receptor. Chem Sel 2:2219–2223
Li W, Yin H, Bardelang D, Xiao J, Zheng Y, Wang R (2017) Supramolecular formulation of nitidine chloride can alleviate its hepatotoxicity and improve its anticancer activity. Food Chem Toxicol 109:923–929
Konda SK, Maliki R, McGrath S, Parker BS, Robinson T, Spurling A, Cheong A, Lock P, Pigram PJ, Phillips DR, Wallace L, Day AI, Collins JG, Cutts SM (2017) Encapsulation of mitoxantrone within cucurbit[8]uril decreases toxicity and enhances survival in a mouse model of Cancer. ACS Med Chem Lett 8:538–542
Yin H, Huang Q, Zhao W, Bardelang D, Siri D, Chen X, Lee SMY, Wang R (2018) Supramolecular encapsulation and bioactivity modulation of a Halonium ion by cucurbit[n]uril (n = 7, 8). J Org Chem 83:4882–4887
Huang Q, Li S, Ding Y-F, Yin H, Wang L-H, Wang R (2018) Macrocycle-wrapped polyethylenimine for gene delivery with reduced cytotoxicity. Biomater Sci 6:1031–1039
Huang Q, Cheng Q, Zhang X, Yin H, Wang L-H, Wang R (2018) Alleviation of polycation-induced blood coagulation by the formation of polypseudorotaxanes with macrocyclic cucurbit[7]uril. ACS Appl Bio Mater 1:544–548
Acknowledgments
This work was supported by National Science Foundation of China (21871301), Macau Science and Technology Development Fund (FDCT 030/2017/A1 and FDCT 0121/2018/A3) and the Research Committee at the University of Macau (MYRG2016-00008-ICMS-QRCM, MYRG2016-00165-ICMS-QRCM and MYRG2017-00010-ICMS).
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2019 Springer Nature Singapore Pte Ltd.
About this entry
Cite this entry
Yin, H., Wang, Z., Wang, R. (2019). Modulation of Chemical and Biological Properties of Biomedically Relevant Guest Molecules by Cucurbituril-Type Hosts. In: Liu, Y., Chen, Y., Zhang, HY. (eds) Handbook of Macrocyclic Supramolecular Assembly . Springer, Singapore. https://doi.org/10.1007/978-981-13-1744-6_28-1
Download citation
DOI: https://doi.org/10.1007/978-981-13-1744-6_28-1
Received:
Accepted:
Published:
Publisher Name: Springer, Singapore
Print ISBN: 978-981-13-1744-6
Online ISBN: 978-981-13-1744-6
eBook Packages: Springer Reference Chemistry and Mat. ScienceReference Module Physical and Materials ScienceReference Module Chemistry, Materials and Physics