Добавил:
kiopkiopkiop18@yandex.ru t.me/Prokururor I Вовсе не секретарь, но почту проверяю Опубликованный материал нарушает ваши авторские права? Сообщите нам.
Вуз: Предмет: Файл:
Ординатура / Хирургия / Библиотека им академика М.И. Перельмана / Книга_5362_Библиотеки_им_академика_М_И_Перельмана.pdf
Скачиваний:
0
Добавлен:
31.08.2026
Размер:
22 Мб
Скачать
Fullerene Based Materials for Drug Delivery 345
plasma pH. High drug loading, enhanced erythrocyte compatibility, better efficacy for SH-SY5Y neuroblastoma cells (in vitro), and suitable pharmacokinetic pattern recommended the conjugate to have significant merit for delivery of brain drug. Samanta and Das [93] employed DFT, based on M06-2X/6-31G(d) calculation, to assess the potential of some fullerene loaded chemotherapeutic drugs (temozolomide, carmustine, procarbazine, and lomustine) to cross the BBB. The chemical features of all the four studied drugs were found to be perturbed minimally by the C
moiety
60
and thus recommended as potent carrier for brain anticancer drug delivery to the target cells.

4.8 Ocular Drug Delivery

Ema et al. [150] demonstrated sensitizing including irritation effects of highly puri­fied C (Organization for Economic Co-operation and Development). Fullerenes concentra­tions when administered at the maximum allowable level, no abnormalities in the iris, corneal opacity, or chemosis was detected. However, conjunctival redness and blood vessel hyperemia observed at 1 h, vanished after 24 h of fullerene administra­tion. Fullerenes did not show any irritation or sensitization on the skin. The study, however, lacks toxicological studies of fullerene and its derivatives.
on eyes or skin of rabbits following the Guidelines 404 and 405 of OECD
60

5 Challenges and Future Perspectives

Research in nanotechnology particularly, with the pioneer nanoparticle fullerene, has enabled use of fullerenes and its functionalized derivatives for pharmaceutical applications including delivery of drug and biological substances including DNA, and several small molecules through the membrane of cell. However, the most of the studies are in the preliminary stage and there are lots of challenges to solve for efficacy of derivatized fullerene nanomaterials. Development of functionalized fullerene derivatives for targeted drug delivery requires a thorough and continued effort. The clinical impact of fullerene derivatives in drug delivery can be addressed from preclinical pharmacology as well as in vivo studies considering toxicity and pharmacokinetic aspects.
346 M. Sarkar and D. Santra

6 Concluding Remarks

Investigation on the water solubility and bioavailability of fullerene and function­alized fullerene are the key consideration for biomedical applications. Fullerene although is relatively nontoxic toxicity profile seems to change
s with its deriva­tizations. The characteristic smaller size, enhanced reactivity, high electronega­tivity, increased scope of ions encapsulation, etc. demonstrates newer dimensions in building drug delivery agents along with novel drug action. Fullerenes, in compar­ison to other different types of nanomaterials possess several advantages as a key component for drug delivery and in biomedicine. Fullerenes, even when derivatized, the sizes being regulated at nano level remain suitable for in vivo applications. More­over, any aggregation of fullerene derivatives in aqueous media occurs in reversible and fluxional manner assisting dynamic molecular interchanges. The high versa­tility of fullerenes due to the characteristic and specific surface functionalization, cage structure, and endohedral variability uplift fullerene derivatives as flexible but well-defined chemical scaffold. Still, with expanding modification of cage struc­tures, endohedral variability, exceptions to its structural rules as well as physical attributes (polarity, polarizability, electronegativity, etc.) fullerenes has enormous scope to contribute in biomedicine and targeted delivery of drug.

6.1 Abbreviations

ALS Amyotrophic lateral sclerosis ASK1 Apoptosis signal-regulating kinase 1 Baa Bucky amino acid BBB Blood brain barriers CG MD Coarse-grained molecular dynamics CPO Chronic post-traumatic osteomyelitis CPP Cell penetrating peptides CNS Central nervous system cRGD Cyclic Arginylglycylaspartic acid DBU 1,8-Diazabicyclo [5.4.0] undec-7-ene DFT Density functional therapy DLPC Dilauroylphosphatidycholine DLS Dynamic light scattering DMA Dimethyl maleic acid DNA Deoxyribonucleic acid DOS Density of states DPPH 2,2-Diphenyl-1-picryhydrazyl radical dsDNA Double stranded DNA DTC
2+
60
N,N-dimethyl-2-(4-N,N,N-trimethylamino phenyl)fulleropyrrolidinium iodide
Fullerene Based Materials for Drug Delivery 347
DOXO Doxorubicin ESR Electron spin resonance EMF Endohedral metallofullerene EYFP Enhanced yellow fluorescent protein GC Glycol chitosan Gd Gadolinium GD-EMFs Gd-Endohedral metallofullerenes GFP Green Fluorescent Protein HEK 293 T Derivative of the parent HEK (Human Embryonic Kidney)
293 cell line HO• Hydroxyl radical HPLC High performance liquid chromatography HU Hydroxyurea IBP Ibuprofen JAK2 V617F Janus kinase 2 (JAK2) mutation (V617F) JNK C-Jun N-terminal kinase LLC Lewis lung carcinoma LNA Locked nucleic acid LPS Lipopolysaccharides MAPKs Mitogen-activated protein kinases MMF Monomethyl fumarate MRI Magnetic resonance imaging MRI-CA Magnetic resonance imaging contrast agents NMRD Nuclear magnetic relaxation dispersion NSC Neural stem cell NSCLC Non-small-cell lung carcinoma NU Nitrosourea
1
O
2
O
2
Singlet oxygen
Superoxide radical OECD Organization for Economic Co-operation and Development PCFD-Fl Polyanionic fullerene derivative with fluorescein PDT Photodynamic therapy PEG Poly(ethylene glycol) QSAR Quantitative structure–activity relationship RNA Ribonucleic acid ROS Reactive oxygen species siRNA Small interfering RNA TBAH Tetrabutylammonium hydroxide THF Tetrahydrofuran TLC Thin layer chromatography TNT Trimetallic nitride template TP Thiotepa TPFE Tetra(piperazino)fullerene epoxide TPN@F and TPS@F Thiotepa north head fullerene and Thiotepa south head
fullerene
348 M. Sarkar and D. Santra
UVA Ultraviolet A UVB Ultraviolet B VSV Vesicular stomatitis virus XPS X-ray photoelectron spectroscopy
Acknowledgements The authors sincerely acknowledge University of Kalyani, West Bengal, India, for providing infrastructural facilities. The financial assistance received under DST-FIST is duly acknowledged.
Conflict of Interest The authors declare that there is no conflict of interest in publishing this article.

References

1. Kadish KM, Ruoff RS (2000) Fullerenes: Chemistry, physics, and technology. Wiley
2. Krätschmer W, Lamb LD, Fostiropoulos K, Donald R (1990) Huffman, Solid C
: a new form
60
of carbon. Nature 347:354–358
3. Kroto HW, Heath JR, O’Brien SC, Curl RF, Smalley RE (1985) C
: B uckminsterfullerene.
60
Nature 318:162–163
4. Ajrin1 M, Akther A (2020) Review on Fullerene: A cutting edge trend in drug delivery. Int J Pharm Sci Rev Res 60(2):84–89
5. Xu Z, Liang Z, Ding F (2017) Isomerization of sp
2
-hybridized carbon nanomaterials: struc­tural transformation and topological defects of fullerene, carbon nanotube, and graphene. Wiley Interdiscip Rev Comput Mol Sci 7(2):1283
6. Hebard AF,Rosseinsky MJ, Haddon RC, Murphy DW,Glarum SH, Palstra TTM, Ramirez AP, Kortan AR (1991) Superconductivity at 18 K in potassium-doped C
. Nature 350:600–601
60
7. Kazemzadeh H, Mozafari M (2019) Fullerene-based delivery systems. Drug Discov Today 24(3):898–905
8. Taylor R, Walton DR (1993) The chemistry of fullerenes. Nature 363(6431):685–693
9. Bakry R, Vallant RM, Najam-ul-Haq M, Rainer M, Szabo Z, Huck CW, Bonn GK (2007) Medicinal applications of fullerenes. Int J Nanomedicine 4:639–649
10. Saunders M, Vazquez HAJ, Cross RJ, Mroczkowski S, Gross ML, Giblin DE, Poreda RJ (1994) Incorporation of helium, neon, argon, krypton, and xenon into fullerenes using high pressure. J Am Chem Soc 116(5):2193–2194
11. Fowler PW, Ceulemans A (1995) Electron deficiency of the fullerenes. J Phys Chem 99(2):508–510
12. Bhakta P, Barthunia B (2020) Fullerene and its applications: A review. J Indian Acad Oral M 32(2):159–163
13. Prato M (1997) [60] Fullerene chemistry for materials science applications. J Mater Chem 7(7):1097–1109
14. Kadish KM, Ruoff RS (eds) Fullerenes: Chemistry, physics, and t echnology. John Wiley & Sons (2000)
15. Zhu S, Oberdörster E, Haasch M (2006) Toxicity of an engineered nanoparticle (fullerene, C
) in two aquatic species, Daphnia and fathead minnow. Mar Environ Res 62:S5–S9
60
16. Astefanei A, Núñez O, Galceran MT (2015) Characterisation and determination of fullerenes: A critical review. Anal Chim Acta 882:1–21
17. Henry TB, Menn FM, Fleming JT, Wilgus J, Compton RN, Sayler GS (2007) Attributing effects of aqueous C-60 nanoaggregates to tetrahydrofuran decomposition products in larval zebrafish by assessment of gene expression. Environ Health Persp 115(7):1059–1065
Fullerene Based Materials for Drug Delivery 349
18. Seda BC, Ke PC, Mount AS, Klaine SJ (2012) Toxicity of aqueous C
-gallic acid suspension
70
in Daphnia magna. Environ Toxicol Chem 31(1):215–220
19. Avdeev MV, Khokhryakov AA, Tropin TV, Andrievsky GV, Klochkov VK, Derevyanchenko LI, Rosta L, Garamus VM, Priezzhev VB, Korobov MV, Aksenov VL (2004) Structural features of molecular-colloidal solutions of C
fullerenes in water by small-angle neutron
60
scattering. Langmuir 20(11):4363–4368
20. Prylutskyy YI, Petrenko VI, Ivankov OI, Kyzyma OA, Bulavin LA, Litsis OO, Evstigneev MP, Cherepanov VV, Naumovets AG, Ritter U (2014) On the origin of C
fullerene solubility
60
in aqueous solution 30(14):3967–70
21. Goodarzi S, Ros TD, Conde J, Sefat F, Mozafari M (2017) Fullerene: Biomedical engineers get to revisit an old friend. Mater Today 20(8):460–480
22. Brettreich M, Hirsch A (1998) A highly water-soluble dendro[60]fullerene. Tetrahedron Lett 39(18):2731–2734
23. Biju V (2014) Chemical modifications and bioconjugate reactions of nanomaterials for sensing, imaging, drug delivery and therapy. Chem Soc Rev 43(3):744–764
24. Gul G, Ileri-Ercan N (2021) Fullerene translocation through peroxidized lipid membranes. RSC Adv 11(13):7575–7586
25. Hendrickson OD, Zherdev AV, Gmoshinskii IV, Dzantiev BB (2014) Fullerenes: in vivo studies of biodistribution, toxicity, and biological action. Nanotechnol Russ 9:601–617
26. Bolskar RD (2016) Fullerenes for Drug Delivery. In: Bhushan, B. (eds) Encyclopedia of Nanotechnology. Springer, Dordrecht 8:1267–1281
27. Lin HS, Matsuo Y (2018) Functionalization of [60] fullerene through fullerene cation intermediates. Chem Commun 54(80):11244–11259
28. Gaur M, Misra C, Yadav AB, Swaroop S, Maolmhuaidh FÓ, Bechelany M, Barhoum A (2021) Biomedical applications of carbon nanomaterials: fullerenes, quantum dots, nanotubes, nanofibers, and graphene. Materials 14(20):5978
29. Bobrowska DM, Plonska-Brzezinska ME (2020) Endohedral and Exohedral Single-Layered Fullerenes. In Synthesis and Applications of Nanocarbons (eds) J-C Arnault, D Eder 25–62
30. Haddon RC (1993) Chemistry of t he fullerenes: the manifestation of strain in a class of continuous aromatic molecules. Science 261(5128):1545–1550
31. Hirsch A, Brettreich M (2004) Fullerenes: Chemistry and reactions; WILEY-VCH Verlag GmbH and Co. KGaA, Weinheim
32. Maggini M, Scorrano G, Prato M (1993) Addition of azomethine ylides to C
: synthesis, char-
60
acterization, and functionalization of fullerene pyrrolidines. J Am Chem Soc 115(21):9798– 9799
33. Bingel C (1993) Cyclopropanierung von fullerenen. Chem Ber 126(8):1957–1959
34. Hirsch A, Grösser T, Skiebe A, Soi A (1993) Synthesis of isomerically pure organodihydro­fullerenes. Chem Ber 126(4):1061–1067
35. Fagan PJ, Krusic PJ, Evans DH, Lerke SA, Johnston E (1992) Synthesis, chemistry, and properties of a monoalkylated buckminsterfullerene derivative, t-BuC
anion. J Am Chem
60
Soc 114(24):9697–9699
36. Keshavarz-K M, Knight B, Srdanov G, Wudl F (1995) Cyanodihydrofullerenes and dicyan­odihydrofullerene: the first polar solid based on C60. J Am Chem Soc 117(45):11371–11372
37. Wudl F (1992) The chemical properties of buckminsterfullerene (C
) and the birth and
60
infancy of fulleroids. Acc Chem Res 25(3):157–161
38. Zhang X, Romero A, Foote CS (1993) Photochemical [2+ 2] cycloaddition of N, N­diethylpropynylamine to C
39. Zhang X, Foote CS (1994) Reaction of C
. J Am Chem Soc 115(23):11024–11025
60
with benzocyclobutenol: expeditious route to
60
fullerene adducts. J Org Chem 59(18):5235–5238
40. Muthu S, Maruthamuthu P, Ragunathan R, Rao PRV, Mathews CK (1994) Reaction of buck­minsterfullerene with 1, 3-diphenylnitrilimine: synthesis of pyrazoline derivativesof fullerene. Tetrahedron Lett 35(11):1763–1766
41. Meier MS, Poplawska M (1996) The addition of nitrile oxides to C60. Tetrahedron 52(14):5043–5052
350 M. Sarkar and D. Santra
42. Jagerovic N, Elguero J, Aubagnac JL (1996) Cycloaddition of tetracyanoethene oxide with [60] fullerene. J Chem Soc 6:499–499
43. Prato M, Suzuki T, Foroudian H, Li Q, Khemani K, Wudl F, Leonetti J, Little RD, White T (1993) [3+ 2] and [4+ 2] Cycloadditions of fullerene C
. J Am Chem Soc 115(4):1594–1595
60
44. Rašović I (2017) Water-soluble fullerenes for medical applications. Mater Sci Technol 33(7):777–794
45. Cardona C, Elliott B, Echegoyen L (2006) Unexpected chemical and electrochemical properties of M
N@ C80(M= Sc, Y, Er). J Am Chem Soc 128(19):6480–6485
3
46. Belik P, Guegel A, Kraus A, Walter M, Muellen K (1995) Diels-Alder adduct of C{sub 60} and 4-carboxy-o-quinodimethane: synthesis and chemical transformations. J Org Chem 60(11):3307–3310
47. García GT, Mattay J (1996) Exohedral functionalization of [60] fullerene by [4+ 2] cycload­ditions. Diels-Alder reactions of [60] fullerene with electron rich 2, 3-dioxysubstituted-1, 3-butadienes. Tetrahedron 52(15):5421–5426
48. Oliveras SO (2010) Theoretical studies of the exohedral reactivity of fullerene compounds. Doctoral dissertation, Universitat de Girona
49. Biglova YN, Mustafin AG (2019) Nucleophilic cyclopropanation of [60] fullerene by the addition–elimination mechanism. RSC Adv 9(39):22428–22498
50. Diederich F, Isaacs L, Philp D (1994) Syntheses, structures, and properties of methanofullerenes. Chem Soc Rev 23(4):243–255
51. Hirsch A (1995) Addition reactions of buckminsterfullerene (C
). Synthesis 1995(8):895–
60
913
52. Diederich F, T hilgen C (1996) Covalent fullerene chemistry. Science 271(5247):317–324
53. Chiang LY, Swirczewski JW, Hsu CS, Chowdhury SK, Cameron S, Creegan K (1992) Multi­hydroxy additions onto C
54. Li J, TakeuchiA, Ozawa M, Li X, Saigo K, Kitazawa K (1993) C
fullerene molecules. J Chem Soc, Chem Commun (24):1791–1793
60
fullerol formation catalysed
60
by quaternary ammonium hydroxides. J Chem Soc, Chem Commun (23):1784–1785
55. Arrais A, Diana E (2003) Highly water soluble C
derivatives: A new synthesis. Fuller
60
Nanotub Carbon Nanostructures 11(1):35–46
56. Kampe KD, Egger N, Vogel M (1993) Diamino and tetraamino derivatives of buckminster­fullerene C
. Angew Chem Int Ed Engl 32(8):1174–1176
60
57. Miller GP (2006) Reactions between aliphatic amines and [60] fullerene: a review. C R Chim 9(7–8):952–959
58. Chai Y, Guo T, Jin C, Haufler RE, Chibante LF, Fure J, Wang L, Alford JM, Smalley RE (1991) Fullerenes with metals inside. J Phys Chem 95(20):7564–7568
59. Cardona CM (2012) Functionalization of endohedral metallofullerenes. Curr Org Chem 16(9):1095–1108
60. López AM, Alonso AM, Prato M (2011) Materials chemistry of fullerene C
derivatives. J
60
Mater Chem 21(5):1305–1318
61. Krachmalnicoff A, Levitt MH, Whitby RJ (2014) An optimised scalable synthesis of H C
and a new synthesis of H2@C60. Chem Comm 50(86):13037–13040
60
2
O@
62. Takata M, Umeda B, Nishibori E, Sakata M, Saitot Y, Ohno M, Shinohara H (1995) Confir­mation by X-ray diffraction of the endohedral nature of the metallofullerene Y@ C
.Nature
82
377(6544):46–49
63. Haufler RE, Chai Y, Chibante LPF, Conceicao J, Jin C, Wang LS, Maruyama S, Smalley RE (1990) Carbon arc generation of C
. MRS Online Proceedings Library (OPL) 206:627
60
64. Smalley RE (1992) Self-assembly of the fullerenes. Acc Chem Res 25(3):98–105
65. Krätschmer W, Lamb L, Fostiropoulos K, Huffman D (1990) Solid C
: a new form of carbon.
60
Nature 347(6291):354–358
66. Thakral S, Thakral NK (2013) Potential Medical Applications of Fullerenes: An Overview. In Bio-Nanotechnology. In: Shahidi F, Bagchi D, Bagchi M, Moriyama H, Shahidi F (eds) 424–441
67. Pietzak B, Weidinger A, Dinse KP,Hirsch A (2002) Group V Endohedral Fullerenes: N@C N@C
,andP@C60. In Endofullerenes: A new family of carbon clusters (pp 13–65).
70
60
Dordrecht: Springer Netherlands
,
Fullerene Based Materials for Drug Delivery 351
68. Dresselhaus MS, Dresselhaus G, Eklund PC (1996) Science of fullerenes and carbon nanotubes. Academic Press
69. Akiyama K, Zhao Y, Sueki K, Haba H, Tsukada K, Asai M, Yaita T, Nagame Y, Kikuchi K, Katada M, Nakahara H (2003) Production and characterization of actinide metallofullerenes. J Radioanal Nucl Chem 255:155–158
70. Ohtsuki T, Ohno K (2005) Formation of Po@C
. Phys Rev B 72(15):153411
60
71. Shinohara H (2000) Endohedral metallofullerenes. Rep Prog Phys 63(6):843
72. Stevenson S, Rice G, Glass T, Harich K, Cromer F, Jordan MR, Craft J, Hadju E, Bible R, Olmstead MM, Maitra K (1999) Small-bandgap endohedral metallofullerenes in high yield and purity. Nature 401(6748):55–57
73. Dunsch L, Krause M, Noack J, Georgi P (2004) Endohedral nitride cluster fullerenes: Forma­tion and spectroscopic analysis of L
N@C2n(0≤ x≤ 3; N= 39, 40). J Phys Chem Solids
3-xMx
65(2–3):309–315
74. Li T, Dorn HC (2017) Biomedical applications of metal-encapsulated fullerene nanoparticles. Small 13(8):1603152
75. Tóth É, Bolskar RD, Borel A, González G, Helm L, Merbach AE, Sitharaman B, Wilson LJ (2005) Water-soluble gadofullerenes: toward high-relaxivity, pH-responsive MRI contrast agents. J Am Chem Soc 127(2):799–805
76. Laus S, Sitharaman B, TóthÉ, Bolskar RD, Helm L, Asokan S, WongMS, Wilson LJ, Merbach AE (2005) Destroying gadofullerene aggregates by salt addition in aqueous solution of Gd@ C
(OH)xand Gd@C60[C(COOH)2]10. J Am Chem Soc 127(26):9368–9369
60
77. Murphy SV, Hale A, Reid T, Olson J, Kidiyoor A, Tan J, Zhou Z, Jackson J, Atala A (2016) Use of trimetasphere metallofullerene MRI contrast agent for the non-invasive longitudinal tracking of stem cells in the lung. Methods 99:99–111
78. Fatouros PP, Corwin FD, Chen ZJ, Broaddus WC, Tatum JL, Kettenmann B, Ge Z, Gibson HW, Russ JL, Leonard AP, Duchamp JC (2006) In vitro and in vivo imaging studies of a new endohedral metallofullerene nanoparticle. Radiology 240(3):756–764
79. Zhang J, Ye Y,Chen Y, Pregot C, Li T, Balasubramaniam S, Hobart DB, Zhang Y, Wi S, Davis RM, Madsen LA (2014) Gd
N@C84(OH)x: a new egg-shaped metallofullerene magnetic
3
resonance imaging contrast agent. J Am Chem Soc 136(6):2630–2636
80. Li J, Wang T, Feng Y, Zhang Y, Zhen M, Shu C, Jiang L, Wang Y, Wang C (2016) A water­soluble gadolinium metallofullerenol: facile preparation, magnetic properties and magnetic resonance imaging application. Dalton Trans 45(21):8696–8699
81. Shakirova AA, Tomilin FN, Pomogaev VA, Vnukova NG, Churilov GN, Kudryasheva NS, Tchaikovskaya ON, Ovchinnikov SG, Avramov PV (2021) Synthesis, mass spectroscopy detection, and density functional theory investigations of the gd endohedral complexes of C
fullerenols. Computation 9(5):58
82
82. Zhao Z, Zhen M, Zhou C, Li L, Jia W, Liu S, Li X, Liao X, Wang C (2021) A gadofullerene based liver-specific MRI contrast agent for an early diagnosis of orthotopic hepatocellular carcinoma. J Mater Chem B 9(28):5722–5728
83. Xiao L, Li T, Ding M, Yang J, Rodríguez-Corrales J, LaConte SM, Nacey N, Weiss DB, Jin L, Dorn HC, Li X (2017) Detecting chronic post-traumatic osteomyelitis of mouse tibia via an IL-13Rα2 targeted metallofullerene magnetic resonance imaging probe. Bioconjugate Chem 28(2):649–658
84. Li T, Murphy S, Kiselev B, Bakshi KS, Zhang J, Eltahir A, Zhang Y, Chen Y, Zhu J, Davis RM, Madsen LA (2015) A new interleukin-13 amino-coated gadolinium metallo­fullerene nanoparticle for targeted MRI detection of glioblastoma tumor cells. J Am Chem Soc 137(24):7881–7888
85. Li J, Cui R, Chang Y, Guo X, Gu W, Huang H, Chen K, Lin G, Dong J, Xing G, Sun B (2016) Adaption of the structure of carbon nanohybrids towardhigh-relaxivity for a new MRI contrast agent. RSC Adv 6(63):58028–58033
86. Diener MD, Alford JM, Kennel SJ, Mirzadeh S (2007)
212
Pb@ C60and its water-soluble derivatives: Synthesis, stability, and suitability for radioimmunotherapy. J Am Chem Soc 129(16):5131–5138
352 M. Sarkar and D. Santra
87. Shultz MD, Duchamp JC, Wilson JD, Shu CY,Ge J, Zhang J, Gibson HW, Fillmore HL, Hirsch JI, Dorn HC, Fatouros PP (2010) Encapsulation of a radiolabeled cluster inside a fullerene cage, 177Lux Lu(3–x)N@C80: An interleukin-13-conjugated radiolabeled metallofullerene platform. J Am Chem Soc 132(14):4980–4981
88. Mwakisege JG, Schweitzer G, Mirzadeh S (2020) Synthesis and stability of actinium-225 endohedral fullerenes,
225
Ac@C60. ACS Omega 5(42):27016–27025
89. Beuerle F, Lebovitz R, Hirsch A (2008) Antioxidant properties of water-soluble fullerene derivatives. In: Cataldo F,Da Ros T (eds) Medicinal Chemistry and Pharmacological Potential of Fullerenes and Carbon Nanotubes, pp. 51–78. Springer, Berlin
90. Zhu J, Ji Z, Wang J, Sun R, Zhang X, Gao Y,Sun H, Liu Y, Wang Z, Li A, Ma J, Wang T, Jia G, Gu Y (2008) Tumor-inhibitory effect and immunomodulatory activity of fullerol C60(OH)x. Small 4:1168–1175
91. Mroz P, Tegos GP, Gali H, Wharton T, Sarna T, Hamblin MR (2008) Fullerenes as photo­sensitizers in photodynamic therapy. In: Cataldo F, Da Ros T (eds) Medicinal Chemistry and Pharmacological Potential of Fullerenes and Carbon Nanotubes. Springer, Berlin, pp 79–106
92. Friedman SH, DeCamp DL, Sijbesma RP, Srdanov G, Wudl F, Kenyon GL (1993) Inhibi­tion of the HIV-1 protease by fullerene derivatives: model building studies and experimental verification. J Am Chem Soc 115(15):6506–6509
93. Samanta PN, Das KK. Noncovalent interaction assisted fullerene for the transportation of some brain anticancer drugs: a theoretical study.
94. Neal R, Samanta PN, Leszczynski J (2022) First-principles modeling of complexation of anticancer antibiotics with fullerene (C
) nanocage: Probing non-covalent interactions by
60
vibrational and electronic spectroscopy. J Mol Struct 1255:132449
95. Yamada M, Kurihara Y, Koizumi M, Tsuji K, Maeda Y, Suzuki M (2022) Understanding the nature and strength of noncovalent face-to-face arene–fullerene interactions. Angew Chem 134(43):e202212279
96. Zakharian TY, Seryshev A, Sitharaman B, Gilbert BE, Knight V, Wilson LJ (2005) A fullerenepaclitaxel chemotherapeutic: synthesis, characterization, and study of biological activity in tissue culture. J Am Chem Soc 127(36):12508–12509
97. Zacchigna M, Klumpp C, Prato M, Bianco A (2009) In vitro behavior of multifunctionalized fullerene-warfarin conjugates. J Nanosci Nanotechnol 9(10):6210–6221
98. Rybkin AY, Belik AY, Kraevaya OA, Khakina EA, Zhilenkov AV, Goryachev NS, Volyniuk D, Grazulevicius JV, Troshin PA, Kotelnikov AI (2019) Covalently linked water-soluble fullerene–fluorescein dyads as highly efficient photosensitizers: Synthesis, photophysical properties and photochemical action. Dyes Pigm 160:457–466
99. Clancy KFA,Hardy JG (2017) Gene delivery with organic electronic biomaterials. Curr Pharm Des 23(24):3614–3625
100. Nakamura E, Isobe H, Tomita N, Sawamura M, Jinno S, Okayama H (2000) Functionalized fullerene as an artificial vector for transfection. Angew. Chemie. 112(23):4424–4427
101. Wang J, Xie L, Wang T, Wu F, Meng J, Liu J, Xu H (2017) Visible light-switched cytosol release of siRNA by amphiphilic fullerene derivative to enhance RNAi efficacy in vitro and in vivo. Acta Biomater 59:158–169
102. Isobe H, Tomita N, Jinno S, Okayama H, Nakamura E (2001) Synthesis and transfection capability of multi-functionalized fullerene polyamine. Chem Lett 30(12):1214–1215
103. Isobe H, Nakanishi W, Tomita N, Jinno S, Okayama H, Nakamura E (2006) Gene delivery by aminofullerenes: structural requirements for efficient transfection. Chem Asian J 1(1–2):167– 175
104. Isobe H, Nakanishi W, Tomita N, Jinno S, Okayama H, Nakamura E (2006) Nonviral gene delivery by tetraamino fullerene. Mol Pharmaceutics 3(2):124–134
105. Xu JR, Xie Y, Li JW, Liu R, Chen M, Ren YX, Luo Q, Duan JL, Bao CJ, Liu YX, Li PS (2022) Development of fullerene nanospherical miRNA and application in overcoming resistant breast cancer. Mater. Today Chem 26:101019
106. Uritu CM, Varganici CD, Ursu L, Coroaba A, Nicolescu A, Dascalu AI, Peptanariu D, Stan D, Constantinescu CA, Simion V, Calin M (2015) Hybrid fullerene conjugates as vectors for DNA cell-delivery. J Mater Chem B 3(12):2433–2446
Fullerene Based Materials for Drug Delivery 353
107. Sitharaman B, Zakharian TY,Saraf A, Misra P,Ashcroft J, Pan S, Pham QP,MikosAG, Wilson LJ, Engler DA (2008) Water-soluble fullerene (C
) derivatives as nonviral gene-delivery
60
vectors. Mol pharmaceutics 5(4):567–578
108. Yang J, Wang K, Driver J, Yang J, Barron AR (2007) The use of fullerene substituted pheny­lalanine amino acid as a passport for peptides through cell membranes. Org Biomol Chem 5(2):260–266
109. Tanzi L, Terreni M, Zhang Y (2022) Synthesis and biological application of glyco-and peptide derivatives of fullerene C
. Eur J Med Chem 230:114104
60
110. Barron AR (2016) [60] Fullerene-peptides: bio-nano conjugates with structural and chemical diversity. J Enzyme Inhib Med Chem 31(sup1):164–176
111. Montellano A, Ros TD, Bianco A, Prato M (2011) Fullerene C
as a multifunctional system
60
for drug and gene delivery. Nanoscale 3(10):4035–4041
112. Rondags A, Yuen WY, Jonkman MF, Horváth B (2017) Fullerene C
with cytoprotective
60
and cytotoxic potential: prospects as a novel treatment agent in Dermatology. Exp Dermatol 26(3):220–224
113. Zhou Z, Lenk R, Dellinger A, MacFarland D, Kumar K, Wilson SR, Kepley CL (2009) Fullerene nanomaterials potentiate hair growth. Nanomed: Nanotechnol Biol Med 5(2):202– 207
114. Chirico F, Fumelli C, Marconi A, Tinari A, Straface E, Malorni W, Pellicciari R, Pincelli C (2007) Carboxyfullerenes localize within mitochondria and prevent the UVB-induced intrinsic apoptotic pathway. Exp Dermatol 16(5):429–436
115. Kato S, Aoshima H, Saitoh Y, Miwa N (2011) Fullerene-C60 incorporated in liposome exerts persistent hydroxyl radical-scavenging activity and cytoprotection in UVA/B-irradiated keratinocytes. J Nanosci Nanotechnol 11(5):3814–3823
116. Abdullaeva Z (2017) Nanomaterials in health care and cosmetics. In Nanomaterials in Daily Life. Springer
117. Gupta R, Rai B (2017) Molecular dynamics simulation study of translocation of fullerene C 60 through skin bilayer: effect of concentration on barrier properties Nanoscale 9(12):4114–4127
118. Martins M, Azoia NG, Melle-Franco M, Ribeiro A, Cavaco-Paulo A (2017) Permeation of skin with (C
) fullerene dispersions. Eng Life Sci 17(7):732–738
60
119. Hadad A, Azevedo DL, Caetano EW, Freire VN, Mendonca GL, Neto PL, Albuquerque EL, Margis R, Gottfried C (2011) Two-level adsorption of ibuprofen on C
fullerene for trans-
60
dermal delivery: classical molecular dynamics and density functional theory computations. J Phys Chem C 115(50):24501–24511
120. Issa Z, Hamblin MR (2015) Photodynamic therapy of infectious disease mediated by function­alized fullerenes. In: Nanotechnology in Diagnosis, Treatment and Prophylaxis of Infectious Diseases (pp 69–86). Academic Press
121. Hirayama J, Abe H, Kamo N, Shinbo T, Ohnishi-Yamada Y, Kurosawa S, Ikebuchi K, Sekiguchi S (1999) Photoinactivation of vesicular stomatitis virus with fullerene conjugated with methoxy polyethylene glycol amine. Biol Pharm Bull 22(10):1106–1109
122. Tegos GP, Demidova TN, Arcila-Lopez D, Lee H, Wharton T, Gali H, Hamblin MR (2005) Cationic fullerenes are effective and selective antimicrobial photosensitizers. Chem Biol 12(10):1127–1135
123. Mroz P, Tegos GP, Gali H, Wharton T, Sarna T, Hamblin MR (2007) Photodynamic therapy with fullerenes. Photochem Photobiol Sci 6(11):1139–1149
124. Spesia MB, Milanesio ME, Durantini EN (2008) Synthesis, properties and photodynamic inactivation of Escherichia coli by novel cationic fullerene C
derivatives. Eur J Med Chem
60
43(4):853–861
125. Calzavara-Pinton PG, Venturini M, Sala R (2005) A comprehensive overview of photody­namic therapy in the treatment of superficial fungal infections of the skin. J Photochem Photobiol B, Biol 78(1):1–6
126. Milanesio ME, Spesia MB, Cormick MP, Durantini EN (2013) Mechanistic studies on the photodynamic effect induced by a dicationic fullerene C60 derivative on Escherichia coli and Candida albicans cells. PhotodiagnosisPhotodyn. Ther. 10(3):320–327
354 M. Sarkar and D. Santra
127. Sherr CJ (1996) Cancer cell cycles. Science 274(5293):1672–1677
128. Sun M, Kiourti A, Wang H, Zhao S, Zhao G, Lu X, Volakis JL, He X (2016) Enhanced microwavehyperthermia of cancer cells with fullerene. Mol Pharmaceutics 13(7):2184–2192
129. Wu G, Gao XJ, Jang J, Gao X (2016) Fullerenes and their derivatives as inhibitors of tumor necrosis factor-α with highly promoted affinities. J Mol Model 22:1–7
130. Nishizawa C, Hashimoto N, Yokoo S, Funakoshi-Tago M, Kasahara T, Takahashi K, Naka­mura S, Mashino T (2009) Pyrrolidinium-type fullerene derivative-induced apoptosis by the generation of reactive oxygen species in HL-60 cells. Free Radic Res 43(12):1240–1247
131. Funakoshi-Tago M, Tsukada M, Watanabe T, Mameda Y, Tago K, Ohe T, Nakamura S, Mashino T, Kasahara T (2014) Effect of chemical modification on the ability of pyrro­lidinium fullerene to induce apoptosis of cells transformed by JAK2 V617F mutant. Int Immunopharmacol 20(1):258–263
132. Castro E, Garcia AH, Zavala G, Echegoyen L (2017) Fullerenes in biology and medicine. J Mater Chem B 5(32):6523–6535
133. Yin JJ, Lao F, Meng J, Fu PP, Zhao Y, Xing G, Gao X, Sun B, Wang PC, Chen C, Liang XJ (2008) Inhibition of tumor growth by endohedral metallofullerenol nanoparticles optimized as reactive oxygen species scavenger. Mol Pharmacol 74(4):1132–1140
134. Yin JJ, Lao F, Fu PP, Wamer WG, Zhao Y, Wang PC, Qiu Y, Sun B, Xing G, Dong J, Liang XJ (2009) The scavenging of reactive oxygen species and the potential for cell protection by functionalized fullerene materials. Biomaterials 30(4):611–621
135. Tokuyama H, Yamago S, Nakamura E, Shiraki T, Sugiura Y (1993) Photoinduced biochemical activity of fullerene carboxylic acid. J Am Chem Soc 115(17):7918–7919
136. Burlaka AP, Sidorik YP, Prylutska SV, Маtyshevska OP, Golub OA, Prylutskyy YI, Scharff P (2004) Catalytic system of the reactive oxygen species on the C
fullerene basis. Exp Oncol
60
26(4):326–327
137. Rancan F, Rosan S, Boehm F, Cantrell A, Brellreich M, Schoenberger H, Hirsch A, Moussa F (2002) Cytotoxicity and photocytotoxicity of a dendritic C acid C
tris-adduct on Jurkat cells. J Photochem Photobiol B, Biol 67(3):157–162
60
mono-adduct and a malonic
60
138. Li W, Zhao T (2021) Hydroxyurea anticancer drug adsorption on the pristine and doped C fullerene as potential carriers for drug delivery. J Mol Liq 340:117226
139. Vuong BX, Hajali N, Asadi A, Baqer AA, Hachim SK, Canli G (2022) Drug delivery assess­ment of an iron-doped fullerene cage towards thiotepa anticancer drug. Inorg Chem Commun 141:109558
140. Zhang L, Ye YL, Li XH, Chen JH, Sun WM (2021) On the potential of all-boron fullerene B
as a carrier for anti-cancer drug nitrosourea. J Mol Liq 342:117533
40
141. Esrafili MD, Khan AA (2022) Alkali metal decorated C 60 fullerenes as promising materials for delivery of the 5-fluorouracil anticancer drug: a DFT approach. RSC Adv 12(7):3948–3956
142. YounYS, Kwag DS, Lee ES (2017) Multifunctional nano-sized fullerenes for advanced tumor therapy. J Pharm Investig 47:1–10
143. Huang HJ, Chetyrkina M, Wong CW, Kraevaya OA, Zhilenkov AV, Voronov II, Wang PH, Troshin PA, Hsu SH (2021) Identification of potential descriptors of water-soluble fullerene derivatives responsible for antitumor effects on lung cancer cells via QSAR analysis. Comput Struct Biotechnol J 19:812–825
144. Grebinyk A, Prylutska S, Grebinyk S, Evstigneev M, Krysiuk I, Skaterna T, Horak I, Sun Y, Drobot L, Matyshevska O, Prylutskyy Y (2021) Antitumor efficiency of the natural alkaloid berberine complexed with C60 fullerene in Lewis lung carcinoma in vitro and in vivo. Cancer Nanotechnol. 12(1):1–18
145. Minami K, Okamoto K, Doi K, Harano K, Noiri E, Nakamura E (2014) SiRNA delivery targeting to the lung via agglutination-induced accumulation and clearance of cationic tetraamino fullerene. Sci Rep 4(1):4916
146. Zhao L, Li H, Tan L (2017) A novel fullerene-based drug delivery system delivering doxorubicin for potential lung cancer therapy. J Nanosci Nanotechnol 17(8):5147–5154
147. Piotrovskiy LB, Litasova EV, Dumpis MA, Nikolaev DN, Yakovleva EE, Dravolina OA, Bespalov AYu (2016) Enhanced brain penetration of hexamethonium in complexes with derivatives of fullerene C
. Dokl Biochem Biophys 468:173–175
60
70