Carbon-based materials for photodynamic therapy: A mini-review
Di Lu, Ran Tao, Zheng Wang()
School of Pharmaceutical Science & Technology, Tianjin Key Laboratory for Modern Drug Delivery & High Efficiency, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin University, Tianjin 300072, China
Carbon-based materials have been extensively applied in photodynamic therapy owing to the unique optical characteristics, good biocompatibility and tunable systematic toxicity. This mini-review mainly focuses on the recent application of carbon-based materials including graphene, carbon nanotube, fullerene, corannulene, carbon dot and mesoporous carbon nanoparticle. The carbon-based materials can perform not only as photosensitizers, but also effective carriers for photosensitizers in photodynamic therapy, and its combined treatment.
. [J]. Frontiers of Chemical Science and Engineering, 2019, 13(2): 310-323.
Di Lu, Ran Tao, Zheng Wang. Carbon-based materials for photodynamic therapy: A mini-review. Front. Chem. Sci. Eng., 2019, 13(2): 310-323.
T JDougherty, B WHenderson. Photodynamic therapy. Marcel Dekker, 1992, 1–15
2
T JDougherty, C JGomer, B WHenderson, GJori, D Kessel, MKorbelik, JMoan, Q Peng. Photodynamic therapy. Journal of the National Cancer Institute, 1998, 90(12): 889–905 https://doi.org/10.1093/jnci/90.12.889
pmid: 9637138
T CSilva, A F F Pereira, R A Exterkate, V S Bagnato, M A Buzalaf, M A Machado, J M Ten Cate, W Crielaard, D MDeng. Application of an active attachment model as a high-throughput demineralization biofilm model. Journal of Dentistry, 2012, 40(1): 41–47 https://doi.org/10.1016/j.jdent.2011.09.009
pmid: 21996336
5
J CKennedy, R H Pottier. Endogenous protoporphyrin IX, a clinically useful photosensitizer for photodynamic therapy. Journal of Photochemistry and Photobiology B: Biology, 1992, 14(4): 275–292 doi:10.1016/1011-1344(92)85108-7
pmid: 1403373
6
MSzygula, A Pietrusa, MAdamek, BWojciechowski, AKawczyk-Krupka, WCebula, WDuda, A Sieron. Combined treatment of urinary bladder cancer with the use of photodynamic therapy (PDT) and subsequent BCG-therapy: A pilot study. Photodiagnosis and Photodynamic Therapy, 2004, 1(3): 241–246 https://doi.org/10.1016/S1572-1000(04)00067-5
pmid: 25048338
7
MLyons, I Phang, SEljamel. The effects of PDT in primary malignant brain tumours could be improved by intraoperative radiotherapy. Photodiagnosis and Photodynamic Therapy, 2012, 9(1): 40–45 https://doi.org/10.1016/j.pdpdt.2011.12.001
pmid: 22369727
8
MDate, K Fukuchi, YNamiki, AOkumura, SMorita, HTakahashi, KOhura. Therapeutic effect of photodynamic therapy using PAD-S31 and diode laser on human liver cancer cells. Liver International, 2004, 24(2): 142–148 https://doi.org/10.1111/j.1478-3231.2004.00902.x
pmid: 15078479
9
A MAlgharib, A Sultan, JParekh, FVaz, C Hopper. Endoluminal tracheal stenting prior to head and neck PDT. Photodiagnosis and Photodynamic Therapy, 2014, 11(3): 444–446 https://doi.org/10.1016/j.pdpdt.2014.03.014
pmid: 24792454
FBerr, M Wiedmann, ATannapfel, UHalm, K R Kohlhaw, F Schmidt, CWittekind, JHauss, JMössner. Photodynamic therapy for advanced bile duct cancer: Evidence for improved palliation and extended survival. Hepatology, 2000, 31(2): 291–298 https://doi.org/10.1002/hep.510310205
pmid: 10655248
14
S GBown, A Z Rogowska, D E Whitelaw, W R Lees, L B Lovat, P Ripley, LJones, PWyld, A Gillams, A WHatfield. Photodynamic therapy for cancer of the pancreas. Gut, 2002, 50(4): 549–557 https://doi.org/10.1136/gut.50.4.549
pmid: 11889078
15
YQiang, X Zhang, JLi, ZHuang. Medical progress. Chinese Medical Journal, 2006, 119(10): 845–857
pmid: 16732988
16
D JKereiakes, A MSzyniszewski, DWahr, H C Herrmann, D I Simon, C Rogers, PKramer, WShear, A CYeung, K AShunk, et al.. Phase I drug and light dose-escalation trial of motexafin lutetium and far red light activation (phototherapy) in subjects with coronary artery disease undergoing percutaneous coronary intervention and stent deployment: Procedural and long-term results. Circulation, 2003, 108(11): 1310–1315 https://doi.org/10.1161/01.CIR.0000087602.91755.19
pmid: 12939212
17
BPollock, D Turner, M RStringer, R ABojar, VGoulden, G IStables, W JCunliffe. Topical aminolaevulinic acid-photodynamic therapy for the treatment of acne vulgaris: A study of clinical efficacy and mechanism of action. British Journal of Dermatology, 2004, 151(3): 616–622 https://doi.org/10.1111/j.1365-2133.2004.06110.x
pmid: 15377348
18
D EDolmans, D Fukumura, R KJain. Photodynamic therapy for cancer. Nature Reviews: Cancer, 2003, 3(5): 380–387 https://doi.org/10.1038/nrc1071
pmid: 12724736
19
LDing. Phthalocyanine based photosensitizers for photodynamic therapy. Chinese Journal of Inorganic Chemistry, 2013, 29(8): 1591–1598
JCao, H An, XHuang, GFu, R Zhuang, LZhu, JXie, F Zhang. Monitoring of the tumor response to nano-graphene oxide-mediated photothermal/photodynamic therapy by diffusion-weighted and BOLD MRI. Nanoscale, 2016, 8(19): 10152–10159 https://doi.org/10.1039/C6NR02012G
pmid: 27121639
22
PRong, K Yang, ASrivastan, D OKiesewetter, XYue, F Wang, LNie, ABhirde, ZWang, Z Liu, et al.. Photosensitizer loaded nano-graphene for multimodality imaging guided tumor photodynamic therapy. Theranostics, 2014, 4(3): 229–239 https://doi.org/10.7150/thno.8070
pmid: 24505232
23
R OOgbodu, I Ndhundhuma, AKarsten, TNyokong. Photodynamic therapy effect of zinc monoamino phthalocyanine-folic acid conjugate adsorbed on single walled carbon nanotubes on melanoma cells. Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy, 2015, 137: 1120–1125 https://doi.org/10.1016/j.saa.2014.09.033
pmid: 25305603
24
R OOgbodu, E K Amuhaya, P Mashazi, TNyokong. Photophysical properties of zinc phthalocyanine-uridine single walled carbon nanotube--conjugates. Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy, 2015, 149: 231–239 https://doi.org/10.1016/j.saa.2015.04.040
pmid: 25965170
25
XWang, C X Yang, J T Chen, X P Yan. A dual-targeting upconversion nanoplatform for two-color fluorescence imaging-guided photodynamic therapy. Analytical Chemistry, 2014, 86(7): 3263–3267 https://doi.org/10.1021/ac500060c
pmid: 24621215
26
CYu, P Avci, TCanteenwala, L YChiang, B JChen, M RHamblin. Photodynamic therapy with hexa (sulfo-n-butyl) [60] fullerene against sarcoma in vitro and in vivo. Journal of Nanoscience and Nanotechnology, 2016, 16(1): 171–181 https://doi.org/10.1166/jnn.2016.10652
pmid: 27398442
27
B PJiang, L F Hu, X C Shen, S C Ji, Z Shi, C JLiu, LZhang, HLiang. One-step preparation of a water-soluble carbon nanohorn/phthalocyanine hybrid for dual-modality photothermal and photodynamic therapy. ACS Applied Materials & Interfaces, 2014, 6(20): 18008–18017 https://doi.org/10.1021/am504860c
pmid: 25248075
28
MZhang, T Murakami, KAjima, KTsuchida, A SSandanayaka, OIto, S Iijima, MYudasaka. Fabrication of ZnPc/protein nanohorns for double photodynamic and hyperthermic cancer phototherapy. Proceedings of the National Academy of Sciences of the United States of America, 2008, 105(39): 14773–14778 https://doi.org/10.1073/pnas.0801349105
pmid: 18815374
29
ABattigelli, M C Ménard, A Bianco. Carbon nanomaterials as new tools for immunotherapeutic applications. Journal of Materials Chemistry B: Materials for Biology and Medicine, 2014, 2(37): 6144–6156 https://doi.org/10.1039/C4TB00563E
30
QLi, L Hong, HLi, CLiu. Graphene oxide-fullerene C60 (GO-C60) hybrid for photodynamic and photothermal therapy triggered by near-infrared light. Biosensors & Bioelectronics, 2017, 89(Part 1): 477–482 https://doi.org/10.1016/j.bios.2016.03.072
pmid: 27055602
31
JShi, Y Liu, LWang, JGao, J Zhang, XYu, RMa, R Liu, ZZhang. A tumoral acidic pH-responsive drug delivery system based on a novel photosensitizer (fullerene) for in vitro and in vivo chemo-photodynamic therapy. Acta Biomaterialia, 2014, 10(3): 1280–1291 https://doi.org/10.1016/j.actbio.2013.10.037
pmid: 24211343
32
GHong, S Diao, A LAntaris, HDai. Carbon nanomaterials for biological imaging and nanomedicinal therapy. Chemical Reviews, 2015, 115(19): 10816–10906 https://doi.org/10.1021/acs.chemrev.5b00008
pmid: 25997028
33
GModugno, C Ménard-Moyon, MPrato, ABianco. Carbon nanomaterials combined with metal nanoparticles for theranostic applications. British Journal of Clinical Pharmacology, 2015, 172(4): 975–991 https://doi.org/10.1111/bph.12984
pmid: 25323135
34
DBitounis, H Ali-Boucetta, B HHong, D HMin, KKostarelos. Prospects and challenges of graphene in biomedical applications. Advanced Materials, 2013, 25(16): 2258–2268 https://doi.org/10.1002/adma.201203700
pmid: 23494834
35
KYang, L Feng, XShi, ZLiu. Nano-graphene in biomedicine: theranostic applications. Chemical Society Reviews, 2013, 42(2): 530–547 https://doi.org/10.1039/C2CS35342C
pmid: 23059655
36
SShi, K Yang, HHong, H FValdovinos, T RNayak, YZhang, C PTheuer, T EBarnhart, ZLiu, W Cai. Tumor vasculature targeting and imaging in living mice with reduced graphene oxide. Biomaterials, 2013, 34(12): 3002–3009 https://doi.org/10.1016/j.biomaterials.2013.01.047
pmid: 23374706
37
XShi, H Gong, YLi, CWang, L Cheng, ZLiu. Graphene-based magnetic plasmonic nanocomposite for dual bioimaging and photothermal therapy. Biomaterials, 2013, 34(20): 4786–4793 https://doi.org/10.1016/j.biomaterials.2013.03.023
pmid: 23557860
38
JQin, H Chen, HChang, YMa, Y Chen. Highly reusable and environmentally friendly solid fuel material based on three-dimensional graphene foam. Energy & Fuels, 2016, 30(11): 9876–9881 https://doi.org/10.1021/acs.energyfuels.6b01867
39
W SKuo, Y T Shao, K S Huang, T M Chou, C H Yang, P Chen, CChang, CHuang, CHsu, T Chou. Antimicrobial amino-functionalized nitrogen-doped graphene quantum dots for eliminating multidrug-resistant species in dual-modality photodynamic therapy and bioimaging under two-photon excitation. ACS Applied Materials & Interfaces, 2018, 10(17): 14438–14446 https://doi.org/10.1021/acsami.8b01429
pmid: 29620851
40
Z MMarkovic, B Z Ristic, K M Arsikin, D G Klisic, L M Harhaji-Trajkovic, B M Todorovic-Markovic, D P Kepic, T K Kravic-Stevovic, S P Jovanovic, M M Milenkovic, et al.. Graphene quantum dots as autophagy-inducing photodynamic agents. Biomaterials, 2012, 33(29): 7084–7092 https://doi.org/10.1016/j.biomaterials.2012.06.060
pmid: 22795854
41
JGe, M Lan, BZhou, WLiu, L Guo, HWang, QJia, G Niu, XHuang, HZhou, et al.. A graphene quantum dot photodynamic therapy agent with high singlet oxygen generation. Nature Communications, 2014, 5(1): 4596 https://doi.org/10.1038/ncomms5596
pmid: 25105845
42
YLiu, Y Xu, XGeng, YHuo, D Chen, KSun, GZhou, B Chen, KTao. Synergistic targeting and efficient photodynamic therapy based on graphene oxide quantum dot-upconversion nanocrystal hybrid nanoparticles. Small, 2018, 14(19): e1800293 https://doi.org/10.1002/smll.201800293
pmid: 29665272
43
D KChatterjee, L SFong, YZhang. Nanoparticles in photodynamic therapy: An emerging paradigm. Advanced Drug Delivery Reviews, 2008, 60(15): 1627–1637 https://doi.org/10.1016/j.addr.2008.08.003
pmid: 18930086
44
DChen, R Tao, KTao, BChen, S K Choi, Q Tian, YXu, GZhou, K Sun. Efficacy dependence of photodynamic therapy mediated by upconversion nanoparticles: Subcellular positioning and irradiation productivity. Small, 2017, 13(13): 1602053 https://doi.org/10.1002/smll.201602053
pmid: 28060457
45
DHu, J Zhang, GGao, ZSheng, HCui, L Cai. Indocyanine green-loaded polydopamine-reduced graphene oxide nanocomposites with amplifying photoacoustic and photothermal effects for cancer theranostics. Theranostics, 2016, 6(7): 1043–1052 https://doi.org/10.7150/thno.14566
pmid: 27217837
46
LZhou, L Zhou, SWei, XGe, J Zhou, HJiang, FLi, J Shen. Combination of chemotherapy and photodynamic therapy using graphene oxide as drug delivery system. Journal of Photochemistry and Photobiology B: Biology, 2014, 135(3): 7–16 https://doi.org/10.1016/j.jphotobiol.2014.04.010
pmid: 24792568
47
CMcCallion, J Burthem, KRees-Unwin, AGolovanov, APluen. Graphene in therapeutics delivery: Problems, solutions and future opportunities. European Journal of Pharmaceutics and Biopharmaceutics, 2016, 104: 235–250 https://doi.org/10.1016/j.ejpb.2016.04.015
pmid: 27113141
48
YCho, Y Choi. Graphene oxide-photosensitizer conjugate as a redox-responsive theranostic agent. Chemical Communications, 2012, 48(79): 9912–9914 https://doi.org/10.1039/c2cc35197h
pmid: 22932979
49
TAkbari, M Pourhajibagher, FHosseini, NChiniforush, EGholibegloo, MKhoobi, SShahabi, ABahador. The effect of indocyanine green loaded on a novel nano-graphene oxide for high performance of photodynamic therapy against Enterococcus faecalis. Photodiagnosis and Photodynamic Therapy, 2017, 20: 148–153 https://doi.org/10.1016/j.pdpdt.2017.08.017
pmid: 28867453
50
KYang, J Wan, SZhang, BTian, Y Zhang, ZLiu. The influence of surface chemistry and size of nanoscale graphene oxide on photothermal therapy of cancer using ultra-low laser power. Biomaterials, 2012, 33(7): 2206–2214 https://doi.org/10.1016/j.biomaterials.2011.11.064
pmid: 22169821
51
XMa, H Tao, KYang, LFeng, L Cheng, XShi, YLi, L Guo, ZLiu. A functionalized graphene oxide-iron oxide nanocomposite for magnetically targeted drug delivery, photothermal therapy, and magnetic resonance imaging. Nano Research, 2012, 5(3): 199–212 https://doi.org/10.1007/s12274-012-0200-y
52
BTian, C Wang, SZhang, LFeng, Z Liu. Photothermally enhanced photodynamic therapy delivered by nano-graphene oxide. ACS Nano, 2011, 5(9): 7000–7009 https://doi.org/10.1021/nn201560b
pmid: 21815655
53
ASahu, W I Choi, J H Lee, G Tae. Graphene oxide mediated delivery of methylene blue for combined photodynamic and photothermal therapy. Biomaterials, 2013, 34(26): 6239–6248 https://doi.org/10.1016/j.biomaterials.2013.04.066
pmid: 23706688
54
YWang, H Wang, DLiu, SSong, X Wang, HZhang. Graphene oxide covalently grafted upconversion nanoparticles for combined NIR mediated imaging and photothermal/photodynamic cancer therapy. Biomaterials, 2013, 34(31): 7715–7724 https://doi.org/10.1016/j.biomaterials.2013.06.045
pmid: 23859660
55
GGollavelli, Y C Ling. Magnetic and fluorescent graphene for dual modal imaging and single light induced photothermal and photodynamic therapy of cancer cells. Biomaterials, 2014, 35(15): 4499–4507 https://doi.org/10.1016/j.biomaterials.2014.02.011
pmid: 24602568
JPu, Y Mo, SWan, LWang. Fabrication of novel graphene-fullerene hybrid lubricating films based on self-assembly for MEMS applications. Chemical Communications, 2014, 50(4): 469–471 https://doi.org/10.1039/C3CC47486K
pmid: 24257346
58
PSong, L Liu, GHuang, YYu, Q Guo. Largely enhanced thermal and mechanical properties of polymer nanocomposites via incorporating C60@graphene nanocarbon hybrid. Nanotechnology, 2013, 24(50): 505706 https://doi.org/10.1088/0957-4484/24/50/505706
pmid: 24270978
YZhu, S Murali, WCai, XLi, J W Suk, J R Potts, R S Ruoff. Graphene and graphene oxide: Synthesis, properties, and applications. Advanced Materials, 2010, 22(35): 3906–3924 https://doi.org/10.1002/adma.201001068
pmid: 20706983
61
XSun, Z Liu, KWelsher, J TRobinson, AGoodwin, SZaric, HDai. Nano-graphene oxide for cellular imaging and drug delivery. Nano Research, 2008, 1(3): 203–212 https://doi.org/10.1007/s12274-008-8021-8
pmid: 20216934
62
AGulzar, J Xu, DYang, LXu, F He, SGai, PYang. Nano-graphene oxide-UCNP-Ce6 covalently constructed nanocomposites for NIR-mediated bioimaging and PTT/PDT combinatorial therapy. Dalton Transactions, 2018, 47(11): 3931–3939 https://doi.org/10.1039/C7DT04141A
pmid: 29459928
63
M RFalvo, G J Clary, R M Taylor II, V Chi, F PBrooks Jr, SWashburn, RSuperfine. Bending and buckling of carbon nanotubes under large strain. Nature, 1997, 389(6651): 582–584 https://doi.org/10.1038/39282
pmid: 9335495
64
M RFalvo, R M Taylor II, A Helser, VChi, F PBrooks Jr, SWashburn, RSuperfine. Nanometre-scale rolling and sliding of carbon nanotubes. Nature, 1999, 397(6716): 236–238 https://doi.org/10.1038/16662
pmid: 9930698
65
M N A W MYazid, N A CSidik, RMamat, GNajafi. A review of the impact of preparation on stability of carbon nanotube nanofluids. International Communications in Heat and Mass Transfer, 2016, 78: 253–263 https://doi.org/10.1016/j.icheatmasstransfer.2016.09.021
66
B QWei, R Vajtai, YJung, JWard, R Zhang, GRamanath, P MAjayan. Microfabrication technology: Organized assembly of carbon nanotubes. Nature, 2002, 416(6880): 495–496 https://doi.org/10.1038/416495a
pmid: 11932732
67
NGandra, P L Chiu, W Li, Y RAnderson, SMitra, HHe, R Gao. Photosensitized singlet oxygen production upon two-photon excitation of single-walled carbon nanotubes and their functionalized analogs. Journal of Physical Chemistry C: Nanomaterials and Interfaces, 2009, 113(13): 5182–8185 https://doi.org/10.1021/jp809268q
pmid: 20046942
68
TMurakami, H Nakatsuji, MInada, YMatoba, TUmeyama, MTsujimoto, SIsoda, MHashida, HImahori. Photodynamic and photothermal effects of semiconducting and metallic-enriched single-walled carbon nanotubes. Journal of the American Chemical Society, 2012, 134(43): 17862–17865 https://doi.org/10.1021/ja3079972
pmid: 23083004
69
LWang, J Shi, RLiu, YLiu, J Zhang, XYu, JGao, C Zhang, ZZhang. Photodynamic effect of functionalized single-walled carbon nanotubes: A potential sensitizer for photodynamic therapy. Nanoscale, 2014, 6(9): 4642–4651 https://doi.org/10.1039/C3NR06835H
pmid: 24647856
70
HAli-Boucetta, K Kostarelos. Carbon nanotubes in medicine & biology—therapy and diagnostics. Advanced Drug Delivery Reviews, 2013, 65(15): 1897–1898 https://doi.org/10.1016/j.addr.2013.11.002
pmid: 24220279
71
A JAndersen, J T Robinson, H Dai, A CHunter, T LAndresen, S MMoghimi. Single-walled carbon nanotube surface control of complement recognition and activation. ACS Nano, 2013, 7(2): 1108–1119 https://doi.org/10.1021/nn3055175
pmid: 23301860
72
XMa, L H Zhang, L R Wang, X Xue, J HSun, YWu, G Zou, XWu, P CWang, W GWamer, et al.. Single-walled carbon nanotubes alter cytochrome c electron transfer and modulate mitochondrial function. ACS Nano, 2012, 6(12): 10486–10496 https://doi.org/10.1021/nn302457v
pmid: 23171082
73
AStaicu, A Smarandache, APascu, M LPascu. Photophysics of covalently functionalized single wall carbon nanotubes with verteporfin. Applied Surface Science, 2017, 417: 170–174 https://doi.org/10.1016/j.apsusc.2017.03.031
74
BAveline, T Hasan, R WRedmond, BAveline, THasan, R WRedmond. Photophysical and photosensitizing properties of benzoporphyrin derivative monoacid ring A (BPD-MA). Photochemistry and Photobiology, 1994, 59(3): 328–335 https://doi.org/10.1111/j.1751-1097.1994.tb05042.x
pmid: 8016212
75
USah, K Sharma, NChaudhri, MSankar, PGopinath. Antimicrobial photodynamic therapy: Single-walled carbon nanotube (SWCNT)-Porphyrin conjugate for visible light mediated inactivation of Staphylococcus aureus. Colloids and Surfaces B: Biointerfaces, 2018, 162: 108–117 https://doi.org/10.1016/j.colsurfb.2017.11.046
pmid: 29190461
76
S MBachilo, M S Strano, C Kittrell, R HHauge, R ESmalley, R BWeisman. Structure-assigned optical spectra of single-walled carbon nanotubes. Science, 2002, 298(5602): 2361–2366 https://doi.org/10.1126/science.1078727
pmid: 12459549
77
MZhang, J Wang, WWang, JZhang, NZhou. Magnetofluorescent photothermal micelles packaged with GdN@CQDs as photothermal and chemical dual-modal therapeutic agents. Chemical Engineering Journal, 2017, 330: 442–452 https://doi.org/10.1016/j.cej.2017.07.138
CLiang, S Diao, CWang, HGong, T Liu, GHong, XShi, H Dai, ZLiu. Tumor metastasis inhibition by imaging-guided photothermal therapy with single-walled carbon nanotubes. Advanced Materials, 2014, 26(32): 5646–5652 https://doi.org/10.1002/adma.201401825
pmid: 24924258
80
BZhang, H Wang, SShen, XShe, W Shi, JChen, QZhang, YHu, Z Pang, XJiang. Fibrin-targeting peptide CREKA-conjugated multi-walled carbon nanotubes for self-amplified photothermal therapy of tumor. Biomaterials, 2016, 79: 46–55 https://doi.org/10.1016/j.biomaterials.2015.11.061
pmid: 26695116
81
V SMurali, C Mikoryak, RWang, R KDraper. Abstract 5374: Effect of carbon nanotube amount and subcellular location on the near infrared (NIR) photothermal ablation of cells. Cancer Research, 2014, 74(19): 5374–5374 https://doi.org/10.1158/1538-7445.AM2014-5374
82
YHashida, H Tanaka, SZhou, SKawakami, FYamashita, TMurakami, TUmeyama, HImahori, MHashida. Photothermal ablation of tumor cells using a single-walled carbon nanotube-peptide composite. Journal of Controlled Release, 2014, 173(1): 59–66 https://doi.org/10.1016/j.jconrel.2013.10.039
pmid: 24211651
83
IMarangon, C Ménard-Moyon, A K ASilva, ABianco, NLuciani, FGazeau. Synergic mechanisms of photothermal and photodynamic therapies mediated by photosensitizer/carbon nanotube complexes. Carbon, 2016, 97(6): 110–123 https://doi.org/10.1016/j.carbon.2015.08.023
84
LXie, G Wang, HZhou, FZhang, ZGuo, C Liu, XZhang, LZhu. Functional long circulating single walled carbon nanotubes for fluorescent/photoacoustic imaging-guided enhanced phototherapy. Biomaterials, 2016, 103: 219–228 https://doi.org/10.1016/j.biomaterials.2016.06.058
pmid: 27392290
85
MZhang, W Wang, YCui, XChu, B Sun, NZhou, JShen. Magnetofluorescent Fe3O4/carbon quantum dots coated single-walled carbon nanotubes as dual-modal targeted imaging and chemo/photodynamic/photothermal triple-modal therapeutic agents. Chemical Engineering Journal, 2018, 338: 526–538 https://doi.org/10.1016/j.cej.2018.01.081
86
H WKroto, J R Heath, S C O’Brien, R F Curl, R E Smalley. C60: Buckminsterfullerene. Nature, 1985, 318(6042): 162–163 https://doi.org/10.1038/318162a0
87
WKrätschmer, L D Lamb, K Fostiropoulos, D RHuffman. Solid C60: A new form of carbon. Nature, 1990, 347(6291): 354–358 https://doi.org/10.1038/347354a0
88
R JWilson, G Meijer, D SBethune, R DJohnson, DChambliss, M Sde Vries, H EHunziker, H RWendt. Imaging C60 clusters on a surface using a scanning tunnelling microscope. Nature, 1990, 348(6302): 621–622 https://doi.org/10.1038/348621a0
89
GJia, H Wang, LYan, XWang, R Pei, TYan, YZhao, X Guo. Cytotoxicity of carbon nanomaterials: Single-wall nanotube, multi-wall nanotube, and fullerene. Environmental Science & Technology, 2005, 39(5): 1378–1383 https://doi.org/10.1021/es048729l
pmid: 15787380
90
XCai, J Hao, XZhang, BYu, J Ren, CLuo, QLi, Q Huang, XShi, WLi, J Liu. The polyhydroxylated fullerene derivative C60(OH)24 protects mice from ionizing-radiation-induced immune and mitochondrial dysfunction. Toxicology and Applied Pharmacology, 2010, 243(1): 27–34 https://doi.org/10.1016/j.taap.2009.11.009
pmid: 19914272
91
ZLi, L L Pan, F L Zhang, Z Wang, Y YShen, Z ZZhang. Preparation and characterization of fullerene (C60) amino acid nanoparticles for liver cancer cell treatment. Journal of Nanoscience and Nanotechnology, 2014, 14(6): 4513–4518 https://doi.org/10.1166/jnn.2014.8242
pmid: 24738422
92
EOtake, S Sakuma, KTorii, AMaeda, HOhi, S Yano, AMorita. Effect and mechanism of a new photodynamic therapy with glycoconjugated fullerene. Photochemistry and Photobiology, 2010, 86(6): 1356–1363 https://doi.org/10.1111/j.1751-1097.2010.00790.x
pmid: 20796243
93
J WArbogast, A P Darmanyan, C S Foote, F N Diederich, R L Whetten, Y Rubin, M MAlvarez, S JAnz. Photophysical properties of sixty atom carbon molecule (C60). Journal of Physical Chemistry, 2002, 95(1): 11–12 https://doi.org/10.1021/j100154a006
94
YSaitoh, A Miyanishi, HMizuno, SKato, H Aoshima, KKokubo, NMiwa. Super-highly hydroxylated fullerene derivative protects human keratinocytes from UV-induced cell injuries together with the decreases in intracellular ROS generation and DNA damages. Journal of Photochemistry and Photobiology B: Biology, 2011, 102(1): 69–76 https://doi.org/10.1016/j.jphotobiol.2010.09.006
pmid: 20943412
95
YIwamoto, Y Yamakoshi. A highly water-soluble C60-NVP copolymer: A potential material for photodynamic therapy. Chemical Communications, 2006, 46(46): 4805–4807 https://doi.org/10.1039/B614305A
pmid: 17345735
96
RAsada, F Liao, YSaitoh, NMiwa. Photodynamic anti-cancer effects of fullerene [C60]-PEG complex on fibrosarcomas preferentially over normal fibroblasts in terms of fullerene uptake and cytotoxicity. Molecular and Cellular Biochemistry, 2014, 390(1–2): 175–184 https://doi.org/10.1007/s11010-014-1968-8
pmid: 24496749
97
ZLi, F L Zhang, L L Pan, X L Zhu, Z Z Zhang. Preparation and characterization of injectable Mitoxantrone poly (lactic acid)/fullerene implants for in vivo chemo-photodynamic therapy. Journal of Photochemistry and Photobiology B: Biology, 2015, 149: 51–57 https://doi.org/10.1016/j.jphotobiol.2015.05.018
pmid: 26046749
98
JShi, B Wang, LWang, TLu, Y Fu, HZhang, ZZhang. Fullerene (C60)-based tumor-targeting nanoparticles with “off-on” state for enhanced treatment of cancer. Journal of Controlled Release, 2016, 235: 245–258 https://doi.org/10.1016/j.jconrel.2016.06.010
pmid: 27276066
99
HWang, P Agarwal, SZhao, JYu, X Lu, XHe. Combined cancer therapy with hyaluronan-decorated fullerene-silica multifunctional nanoparticles to target cancer stem-like cells. Biomaterials, 2016, 97: 62–73 https://doi.org/10.1016/j.biomaterials.2016.04.030
pmid: 27162075
100
QHu, W Sun, YLu, H NBomba, YYe, T Jiang, A JIsaacson, ZGu. Tumor microenvironment-mediated construction and deconstruction of extracellular drug-delivery depots. Nano Letters, 2016, 16(2): 1118–1126 https://doi.org/10.1021/acs.nanolett.5b04343
pmid: 26785163
101
W EBarth, R G Lawton. Dibenzo [ghi,mno] fluoranthene. Journal of the American Chemical Society, 1966, 88(2): 380–381 https://doi.org/10.1021/ja00954a049
102
LZoppi, L Martin-Samos, K KBaldridge. Effect of molecular packing on corannulene-based materials electroluminescence. Journal of the American Chemical Society, 2011, 133(35): 14002–14009 https://doi.org/10.1021/ja2040688
pmid: 21793582
103
S NSpisak, A V Zabula, A S Filatov, A Y Rogachev, M A Petrukhina. Selective endo and exo binding of alkali metals to corannulene. Angewandte Chemie, 2011, 50(35): 8090–8094 https://doi.org/10.1002/anie.201103028
pmid: 21748832
104
K KBaldridge, J SSiegel. Corannulene-based fullerene fragments C20H10-C50H10: When does a buckybowl become a buckytube? Theoretical Chemistry Accounts, 1997, 97(1–4): 67–71 https://doi.org/10.1007/s002140050238
105
F JLovas, R J McMahon, J U Grabow, M Schnell, JMack, L TScott, R LKuczkowski. Interstellar chemistry: A strategy for detecting polycyclic aromatic hydrocarbons in space. Journal of the American Chemical Society, 2005, 127(12): 4345–4349 https://doi.org/10.1021/ja0426239
pmid: 15783216
106
SLiu, D Lu, XWang, DDing, D Kong, ZWang, YZhao. Topology dictates function: Controlled ROS production and mitochondria accumulation via curved carbon materials. Journal of Materials Chemistry B: Materials for Biology and Medicine, 2017, 5(25): 4918–4925 https://doi.org/10.1039/C7TB00954B
107
LZhang, X Dong, DLu, SLiu, D Ding, DKong, AFan, Z Wang, YZhao. Controlled ROS production by corannulene: The vehicle makes a difference. Biomaterials Science, 2017, 5(7): 1236–1240 https://doi.org/10.1039/C7BM00221A
pmid: 28589978
108
J HLiu, L Cao, G ELeCroy, PWang, M J Meziani, Y Dong, YLiu, P GLuo, Y PSun. Carbon quantum dots for fluorescecne labelling of cells. ACS Applied Materials & Interfaces, 2015, 7(34): 19439–19445 https://doi.org/10.1021/acsami.5b05665
pmid: 26262834
109
PHuang, J Lin, XWang, ZWang, C Zhang, MHe, KWang, F Chen, ZLi, GShen, et al.. Light-triggered theranostics based on photosensitizer-conjugated carbon dots for simultaneous enhanced-fluorescence imaging and photodynamic therapy. Advanced Materials, 2012, 24(37): 5104–5110 https://doi.org/10.1002/adma.201200650
pmid: 22718562
110
D WZheng, B Li, C XLi, J XFan, QLei, C Li, ZXu, X ZZhang. Carbon-dot-decorated carbon nitride nanoparticles for enhanced photodynamic therapy against hypoxic tumor via water splitting. ACS Nano, 2016, 10(9): 8715–8722 https://doi.org/10.1021/acsnano.6b04156
pmid: 27532320
111
YFang, Y Lv, FGong, ZWu, X Li, HZhu, LZhou, C Yao, FZhang, GZheng, et al.. Interface tension-induced synthesis of monodispersed mesoporous carbon hemispheres. Journal of the American Chemical Society, 2015, 137(8): 2808–2811 https://doi.org/10.1021/jacs.5b01522
pmid: 25680067
112
G JXu, S J Liu, H Niu, W PLv, R AWu. Functionalized mesoporous carbon nanoparticles for targeted chemo-photothermal therapy of cancer cells under near-infrared irradiation. RSC Advances, 2014, 4(64): 33986–33997 https://doi.org/10.1039/C4RA03993A
113
LZhou, K Dong, Z WChen, J SRen, X GQu. Near-infrared absorbing mesoporous carbon nanoparticle as an intelligent drug carrier for dual-triggered synergistic cancer therapy. Carbon, 2015, 82: 479–488 https://doi.org/10.1016/j.carbon.2014.10.091
D HShin, Y T Tam, G S Kwon. Polymeric micelle nanocarriers in cancer research. Frontiers of Chemical Science and Engineering, 2016, 10(3): 348–359 https://doi.org/10.1007/s11705-016-1582-2
118
PZhang, J Ye, ELiu, LSun, J Zhang, SLee, JGong, H He, V CYang. Aptamer-coded DNA nanoparticles for targeted doxorubicin delivery using pH-sensitive spacer. Frontiers of Chemical Science and Engineering, 2017, 11(4): 529–536 https://doi.org/10.1007/s11705-017-1645-z