Multifunctional Cholesterol-modified Dendrimers for Targeted Drug Delivery to Cancer Cells Expressing Folate Receptors

Fan-Fan Fu; Ben-Qing Zhou; Zhi-Jun Ouyang; Yi-Lun Wu; Jing-Yi Zhu; Ming-Wu Shen; Jin-Dong Xia; Xiang-Yang Shi

doi:10.1007/s10118-019-2172-9

Your Location：

Home >

Browse articles >

Multifunctional Cholesterol-modified Dendrimers for Targeted Drug Delivery to Cancer Cells Expressing Folate Receptors

ARTICLE | Updated：2021-02-18

- Multifunctional Cholesterol-modified Dendrimers for Targeted Drug Delivery to Cancer Cells Expressing Folate Receptors
- Multifunctional Cholesterol-modified Dendrimers for Targeted Drug Delivery to Cancer Cells Expressing Folate Receptors
- Chinese Journal of Polymer Science 2019年37卷第2期页码：129-135
- Affiliations：
  
  a.Key Laboratory of Science & Technology of Eco-Textile, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China
  b.Department of Radiology, Shanghai Songjiang District Central Hospital, Shanghai 201600, China
- Author bio：
  
  mwshen@dhu.edu.cn (M.W.S.)
  xiajd_21@163.com (J.D.X.)
  xshi@dhu.edu.cn (X.Y.S.)
- Funds：
  
  This work was financially supported by the Fundamental Research Funds for the Central Universities (for M. Shen and X. Shi), the National Natural Science Foundation of China (Nos. 81761148028 and 21773026), and the Science and Technology Commission of Shanghai Municipality (Nos. 15520711400 and 17540712000).
- DOI：10.1007/s10118-019-2172-9
  中图分类号：
- 收稿：2018-07-29，
  
  修回：2018-9-14，
  
  录用：2018-9-18，
  
  网络首发：2018-10-22，
  
  纸质出版：2019-02
- Accepted：
Scan QR Code
Citation: Fu, F. F.; Zhou, B. Q.; Ouyang, Z. J.; Wu, Y. L.; Zhu, J. Y.; Shen, M. W.; Xia, J. D.; Shi, X. Y. Multifunctional cholesterol-modified dendrimers for targeted drug delivery to cancer cells expressing folate receptors. Chinese J. Polym. Sci. 2019, 37, 129–135

Fan-Fan Fu, Ben-Qing Zhou, Zhi-Jun Ouyang, et al. Multifunctional Cholesterol-modified Dendrimers for Targeted Drug Delivery to Cancer Cells Expressing Folate Receptors[J]. Chinese Journal of Polymer Science, 2019, 37(2): 129-135.
Citation: Fu, F. F.; Zhou, B. Q.; Ouyang, Z. J.; Wu, Y. L.; Zhu, J. Y.; Shen, M. W.; Xia, J. D.; Shi, X. Y. Multifunctional cholesterol-modified dendrimers for targeted drug delivery to cancer cells expressing folate receptors. Chinese J. Polym. Sci. 2019, 37, 129–135 DOI： 10.1007/s10118-019-2172-9.

Fan-Fan Fu, Ben-Qing Zhou, Zhi-Jun Ouyang, et al. Multifunctional Cholesterol-modified Dendrimers for Targeted Drug Delivery to Cancer Cells Expressing Folate Receptors[J]. Chinese Journal of Polymer Science, 2019, 37(2): 129-135. DOI： 10.1007/s10118-019-2172-9.

摘要

Abstract

We present here the development of cholesterol (Chol)-modified dendrimer system for targeted chemotherapy of folate (FA) receptor-expressing cancer cells. In our study

poly(amidoamine) (PAMAM) dendrimers of generation 5 (G5) were functionalized step-by-step with Chol

fluorescein isothiocyanate (FI)

and FA

via

a poly(ethylene glycol) (PEG) spacer (PEG-FA)

and then acetamide to shield their remaining surface amines. The synthesized G5.NHAc-Chol-FI-PEG-FA (for short

G5-CFPF) dendrimers were utilized to encapsulate 10-hydroxycamptothecin (HCP)

a hydrophobic anticancer drug. We find that each G5-CFPF dendrimer can encapsulate 13.8 HCP molecules. The complexes show a slower release profiles of HCP in a pH-dependent manner than the control complexes formed using the same dendrimers without Chol under the same conditions. Thanks to the targeting role played by FA

the complexes display a specific inhibition efficacy to FA receptor-expressing cervical cancer cells. The designed Chol-modified dendrimers may be adopted as a promising carrier for application in targeted cancer therapy.

关键词

Keywords

references

Xu, C.; Yang, D.; Mei, L.; Li, Q.; Zhu, H.; Wang, T . Targeting chemophotothermal therapy of hepatoma by gold nanorods/graphene oxide core/shell nanocomposites . ACS Appl. Mater. Interfaces , 2013 . 5 12911 - 12920 . DOI: 10.1021/am404714w http://doi.org/10.1021/am404714w .

Hu, Y.; Mignani, S.; Majoral, J. P.; Shen, M. W.; Shi, X. Y . Construction of iron oxide nanoparticle-based hybrid platforms for tumor imaging and therapy . Chem. Soc. Rev. , 2018 . 47 1874 - 1900 . DOI: 10.1039/C7CS00657H http://doi.org/10.1039/C7CS00657H .

Tang, F. Q.; Li, L. L.; Chen, D . Mesoporous silica nanoparticles: Synthesis, biocompatibility and drug delivery . Adv. Mater. , 2012 . 24 1504 - 1534 . DOI: 10.1002/adma.201104763 http://doi.org/10.1002/adma.201104763 .

Doane, T. L.; Burda, C . The unique role of nanoparticles in nanomedicine: Imaging, drug delivery and therapy . Chem. Soc. Rev. , 2012 . 41 2885 - 2911 . DOI: 10.1039/c2cs15260f http://doi.org/10.1039/c2cs15260f .

Fu, F. F.; Shang, L. R.; Zheng, F. Y.; Chen, Z. Y.; Wang, H.; Wang, J.; Gu, Z. Z.; Zhao, Y. J . Cells cultured on core-shell photonic crystal barcodes for drug screening . ACS Appl. Mater. Interfaces , 2016 . 8 13840 - 13848 . DOI: 10.1021/acsami.6b04966 http://doi.org/10.1021/acsami.6b04966 .

Raemdonck, K.; Braeckmans, K.; Demeester, J.; De Smedt, S. C . Merging the best of both worlds: Hybrid lipid-enveloped matrix nanocomposites in drug delivery . Chem. Soc. Rev. , 2014 . 43 444 - 472 . DOI: 10.1039/C3CS60299K http://doi.org/10.1039/C3CS60299K .

Malam, Y.; Loizidou, M.; Seifalian, A. M . Liposomes and nanoparticles: Nanosized vehicles for drug delivery in cancer . Trends Pharmacol. Sci. , 2009 . 30 592 - 599 . DOI: 10.1016/j.tips.2009.08.004 http://doi.org/10.1016/j.tips.2009.08.004 .

Fu, F. F.; Wu, Y. L.; Zhu, J. Y.; Wen, S. H.; Shen, M. W.; Shi, X. Y . Multifunctional lactobionic acid-modified dendrimers for targeted drug delivery to liver cancer cells: Investigating the role played by PEG spacer . ACS Appl. Mater. Interfaces , 2014 . 6 16416 - 16425 . DOI: 10.1021/am504849x http://doi.org/10.1021/am504849x .

Zhu, J. Y.; Fu, F. F.; Xiong, Z. J.; Shen, M. W.; Shi, X. Y . Dendrimer-entrapped gold nanoparticles modified with RGD peptide and alpha-tocopheryl succinate enable targeted theranostics of cancer cells . Colloids Surf. B , 2015 . 133 36 - 42 . DOI: 10.1016/j.colsurfb.2015.05.040 http://doi.org/10.1016/j.colsurfb.2015.05.040 .

Farokhzad, O. C.; Langer, R . Impact of nanotechnology on drug delivery . ACS Nano , 2009 . 3 16 - 20 . DOI: 10.1021/nn900002m http://doi.org/10.1021/nn900002m .

Hammond, P. T . Virtual issue on nanomaterials for drug delivery . ACS Nano , 2011 . 5 681 - 684 . DOI: 10.1021/nn2003508 http://doi.org/10.1021/nn2003508 .

Wang, Y.; Deng, Y.; Luo, H.; Zhu, A.; Ke, H.; Yang, H.; Chen, H . Light-responsive nanoparticles for highly efficient cytoplasmic delivery of anticancer agents . ACS nano , 2017 . 11 12134 - 12144 . DOI: 10.1021/acsnano.7b05214 http://doi.org/10.1021/acsnano.7b05214 .

Luo, H.; Wang, Q.; Deng, Y.; Yang, T.; Ke, H.; Yang, H.; He, H.; Guo, Z.; Yu, D.; Wu, H . Mutually synergistic nanoparticles for effective thermo‐molecularly targeted therapy . Adv. Funct. Mater. , 2017 . 27 1702834 DOI: 10.1002/adfm.v27.39 http://doi.org/10.1002/adfm.v27.39 .

De Koker, S.; Hoogenboom, R.; De Geest, B. G . Polymeric multilayer capsules for drug delivery . Chem. Soc. Rev. , 2012 . 41 2867 - 2884 . DOI: 10.1039/c2cs15296g http://doi.org/10.1039/c2cs15296g .

Jang, W. D.; Yim, D.; Hwang, I. H . Photofunctional hollow nanocapsules for biomedical applications . J. Mater. Chem. B , 2014 . 2 2202 - 2211 . .

Prakash, S.; Malhotra, M.; Shao, W.; Tomaro-Duchesneau, C.; Abbasi, S . Polymeric nanohybrids and functionalized carbon nanotubes as drug delivery carriers for cancer therapy . Adv. Drug Deliver. Rev. , 2011 . 63 1340 - 1351 . DOI: 10.1016/j.addr.2011.06.013 http://doi.org/10.1016/j.addr.2011.06.013 .

Wen, S. H.; Liu, H.; Cai, H. D.; Shen, M. W.; Shi, X. Y . Targeted and pH-responsive delivery of doxorubicin to cancer cells using multifunctional dendrimer-modified multi-walled carbon nanotubes . Adv. Healthcare Mater. , 2013 . 2 1267 - 1276 . DOI: 10.1002/adhm.v2.9 http://doi.org/10.1002/adhm.v2.9 .

Wu, Y. L.; Guo, R.; Wen, S. H.; Shen, M. W.; Zhu, M. F.; Wang, J. H.; Shi, X. Y . Folic acid-modified laponite nanodisks for targeted anticancer drug delivery . J. Mater. Chem. B , 2014 . 2 7410 - 7418 . .

Diaz, A.; Saxena, V.; Gonzalez, J.; David, A.; Casanas, B.; Carpenter, C.; Batteas, J. D.; Colon, J. L.; Clearfield, A.; Hussain, M. D . Zirconium phosphate nano-platelets: A novel platform for drug delivery in cancer therapy . Chem. Commun. , 2012 . 48 1754 - 1756 . DOI: 10.1039/c2cc16218k http://doi.org/10.1039/c2cc16218k .

Wang, S. G.; Wu, Y. L.; Guo, R.; Huang, Y. P.; Wen, S. H.; Shen, M. W.; Wang, J. H.; Shi, X. Y . Laponite nanodisks as an efficient platform for doxorubicin delivery to cancer cells . Langmuir , 2013 . 29 5030 - 5036 . DOI: 10.1021/la4001363 http://doi.org/10.1021/la4001363 .

Cheng, J.; Teply, B. A.; Sherifi, I.; Sung, J.; Luther, G.; Gu, F. X.; Levy-Nissenbaum, E.; Radovic-Moreno, A. F.; Langer, R.; Farokhzad, O. C . Formulation of functionalized PLGA-PEG nanoparticles for in vivo targeted drug delivery . Biomaterials , 2007 . 28 869 - 876 . DOI: 10.1016/j.biomaterials.2006.09.047 http://doi.org/10.1016/j.biomaterials.2006.09.047 .

Zhou, B. Q.; Zhao, L. Z.; Shen, M. W.; Zhao, J. H.; Shi, X. Y . A multifunctional polyethylenimine-based nanoplatform for targeted anticancer drug delivery to tumors in vivo . J. Mater. Chem. B , 2017 . 5 1542 - 1550 . DOI: 10.1039/C6TB02620F http://doi.org/10.1039/C6TB02620F .

Guo, R.; Yao, Y.; Cheng, G. C.; Wang, S. H.; Li, Y.; Shen, M. W.; Zhang, Y. H.; Baker, J. R.; Wang, J. H.; Shi, X. Y . Synthesis of glycoconjugated poly(amindoamine) dendrimers for targeting human liver cancer cells . RSC Adv. , 2012 . 2 99 - 102 . DOI: 10.1039/C1RA00320H http://doi.org/10.1039/C1RA00320H .

Liu, H.; Wang, H.; Xu, Y. H.; Guo, R.; Wen, S. H.; Huang, Y. P.; Liu, W. N.; Shen, M. W.; Zhao, J. L.; Zhang, G. X.; Shi, X. Y . Lactobionic acid-modified dendrimer-entrapped gold nanoparticles for targeted computed tomography imaging of human hepatocellular carcinoma . ACS Appl. Mater. Interfaces , 2014 . 6 6944 - 6953 . DOI: 10.1021/am500761x http://doi.org/10.1021/am500761x .

Zhu, J. Y.; Zheng, L. F.; Wen, S. H.; Tang, Y. Q.; Shen, M. W.; Zhang, G. X.; Shi, X. Y . Targeted cancer theranostics using alpha-tocopheryl succinate-conjugated multifunctional dendrimer-entrapped gold nanoparticles . Biomaterials , 2014 . 35 7635 - 7646 . DOI: 10.1016/j.biomaterials.2014.05.046 http://doi.org/10.1016/j.biomaterials.2014.05.046 .

Zheng, Y.; Fu, F. F.; Zhang, M. G.; Shen, M. W.; Zhu, M. F.; Shi, X. Y . Multifunctional dendrimers modified with alpha-tocopheryl succinate for targeted cancer therapy . Medchemcomm , 2014 . 5 879 - 885 . DOI: 10.1039/C3MD00324H http://doi.org/10.1039/C3MD00324H .

Shukla, R.; Thomas, T. P.; Desai, A. M.; Kotlyar, A.; Park, S. J.; Baker, J. R . HER2 specific delivery of methotrexate by dendrimer conjugated anti-HER2 mAb . Nanotechnology , 2008 . 19 295102 DOI: 10.1088/0957-4484/19/29/295102 http://doi.org/10.1088/0957-4484/19/29/295102 .

Dung, T. H.; Kim, J. S.; Juliano, R. L.; Yoo, H . Preparation and evaluation of cholesteryl PAMAM dendrimers as nano delivery agents for antisense oligonucleotides . Colloids Surf. A , 2008 . 313 273 - 277 . .

Dhanikula, R. S.; Argaw, A.; Bouchard, J. F.; Hildgen, P . Methotrexate loaded polyether-copolyester dendrimers for the treatment of gliomas: Enhanced efficacy and intratumoral transport capability . Mol. Pharmaceutics , 2008 . 5 105 - 116 . DOI: 10.1021/mp700086j http://doi.org/10.1021/mp700086j .

Shi, X. Y.; Lee, I.; Chen, X. S.; Shen, M. W.; Xiao, S. L.; Zhu, M. F.; Baker, J. R.; Wang, S. H . Influence of dendrimer surface charge on the bioactivity of 2-methoxyestradiol complexed with dendrimers . Soft Matter , 2010 . 6 2539 - 2545 . DOI: 10.1039/b925274f http://doi.org/10.1039/b925274f .

Morgan, M. T.; Nakanishi, Y.; Kroll, D. J.; Griset, A. P.; Carnahan, M. A.; Wathier, M.; Oberlies, N. H.; Manikumar, G.; Wani, M. C.; Grinstaff, M. W . Dendrimer-encapsulated camptothecins: Increased solubility, cellular uptake, and cellular retention affords enhanced anticancer activity in vitro . Cancer Res. , 2006 . 66 11913 - 11921 . DOI: 10.1158/0008-5472.CAN-06-2066 http://doi.org/10.1158/0008-5472.CAN-06-2066 .

Mignani, S.; Rodrigues, J.; Tomas, H.; Zablocka, M.; Shi, X.; Caminade, A. M.; Majoral, J. P . Dendrimers in combination with natural products and analogues as anti-cancer agents . Chem. Soc. Rev. , 2018 . 47 514 - 532 . DOI: 10.1039/C7CS00550D http://doi.org/10.1039/C7CS00550D .

Zhao, Y.; Peng, J.; Li, J.; Huang, L.; Yang, J.; Huang, K.; Li, H.; Jiang, N.; Zheng, S.; Zhang, X . Tumor-targeted and clearable human protein-based MRI nanoprobes . Nano Lett. , 2017 . 17 4096 - 4100 . DOI: 10.1021/acs.nanolett.7b00828 http://doi.org/10.1021/acs.nanolett.7b00828 .

Zhao, L.; Wu, X.; Wang, X.; Duan, C.; Wang, H.; Punjabi, A.; Zhao, Y.; Zhang, Y.; Xu, Z.; Gao, H . Development of excipient-free freeze-dryable unimolecular hyperstar polymers for efficient siRNA silencing . ACS Macro Lett. , 2017 . 6 700 - 704 . DOI: 10.1021/acsmacrolett.7b00242 http://doi.org/10.1021/acsmacrolett.7b00242 .

Li, Z.; Zhang, Y.; Huang, L.; Yang, Y.; Zhao, Y.; El-Banna, G.; Han, G . Nanoscale " fluorescent stone”: Luminescent calcium fluoride nanoparticles as theranostic platforms . Theranostics , 2016 . 6 2380 DOI: 10.7150/thno.15914 http://doi.org/10.7150/thno.15914 .

Mercado-Lubo, R.; Zhang, Y.; Zhao, L.; Rossi, K.; Wu, X.; Zou, Y.; Castillo, A.; Leonard, J.; Bortell, R.; Greiner, D. L . A Salmonella nanoparticle mimic overcomes multidrug resistance in tumours . Nat. Commun. , 2016 . 7 12225 DOI: 10.1038/ncomms12225 http://doi.org/10.1038/ncomms12225 .

Peng, C.; Qin, J. B.; Zhou, B. Q.; Chen, Q.; Shen, M. W.; Zhu, M. F.; Lu, X.W.; Shi, X. Y . Targeted tumor CT imaging using folic acid-modified PEGylated dendrimer-entrapped gold nanoparticles . Polym. Chem. , 2013 . 4 4412 - 4424 . DOI: 10.1039/c3py00521f http://doi.org/10.1039/c3py00521f .

Liu, H.; Wang, H.; Xu, Y. H.; Shen, M. W.; Zhao, J. L.; Zhang, G. X.; Shi, X. Y . Synthesis of PEGylated low generation dendrimer-entrapped gold nanoparticles for CT imaging applications . Nanoscale , 2014 . 6 4521 - 4526 . DOI: 10.1039/C3NR06694K http://doi.org/10.1039/C3NR06694K .

Zhang, Y. Q.; Sun, Y. H.; Xu, X. P.; Zhang, X. Z.; Zhu, H.; Huang, L. L.; Qi, Y. J.; Shen, Y. M . Synthesis, biodistribution, and microsingle photon emission computed tomography (SPECT) imaging study of technetium-99m labeled PEGylated dendrimer poly(amidoamine) (PAMAM)-folic acid conjugates . J. Med. Chem. , 2010 . 53 3262 - 3272 . DOI: 10.1021/jm901910j http://doi.org/10.1021/jm901910j .

Maxfield, F. R.; Tabas, I . Role of cholesterol and lipid organization in disease . Nature , 2005 . 438 612 - 621 . DOI: 10.1038/nature04399 http://doi.org/10.1038/nature04399 .

Chen, Q. F.; Pan, Z. Z.; Zhao, M.; Wang, Q.; Qiao, C.; Miao, L. Y.; Ding, X. S . High cholesterol in lipid rafts reduces the sensitivity to EGFR-TKI therapy in non-small cell lung cancer . J. Cell. Physiol. , 2018 . 233 6722 - 6732 . DOI: 10.1002/jcp.v233.9 http://doi.org/10.1002/jcp.v233.9 .

Nelson, E. R . The significance of cholesterol and its metabolite, 27-hydroxycholesterol in breast cancer . Mol. Cell. Endocrinol. , 2018 . 466 73 - 80 . DOI: 10.1016/j.mce.2017.09.021 http://doi.org/10.1016/j.mce.2017.09.021 .

Li, L. H.; Guo, K.; Lu, J.; Venkatraman, S. S.; Luo, D.; Ng, K. C.; Ling, E. A.; Moochhala, S.; Yang, Y. Y . Biologically active core/shell nanoparticles self-assembled from cholesterol-terminated PEG-TAT for drug delivery across the blood-brain barrier . Biomaterials , 2008 . 29 1509 - 1517 . DOI: 10.1016/j.biomaterials.2007.11.014 http://doi.org/10.1016/j.biomaterials.2007.11.014 .

Tsai, Y. C.; Vijayaraghavan, P.; Chiang, W. H.; Chen, H. H.; Liu, T. I.; Shen, M. Y.; Omoto, A.; Kamimura, M.; Soga, K.; Chiu, H. C . Targeted delivery of functionalized upconversion nanoparticles for externally triggered photothermal/photodynamic therapies of brain glioblastoma . Theranostics , 2018 . 8 1435 - 1448 . DOI: 10.7150/thno.22482 http://doi.org/10.7150/thno.22482 .

Zhou, B. Q.; Xiong, Z. G.; Wang, P.; Peng, C.; Shen, M. W.; Mignani, S.; Majoral, J. P.; Shi, X. Y . Targeted tumor dual mode CT/MR imaging using multifunctional polyethylenimine-entrapped gold nanoparticles loaded with gadolinium . Drug Deliver. , 2018 . 25 178 - 186 . DOI: 10.1080/10717544.2017.1422299 http://doi.org/10.1080/10717544.2017.1422299 .

Wang, Y.; Cao, X.; Guo, R.; Shen, M.; Zhang, M.; Zhu, M.; Shi, X . Targeted delivery of doxorubicin into cancer cells using a folic acid-dendrimer conjugate . Polym. Chem. , 2011 . 2 1754 - 1760 . DOI: 10.1039/c1py00179e http://doi.org/10.1039/c1py00179e .

Wang, Y.; Guo, R.; Cao, X. Y.; Shen, M. W.; Shi, X. Y . Encapsulation of 2-methoxyestradiol within multifunctional poly(amidoamine) dendrimers for targeted cancer therapy . Biomaterials , 2011 . 32 3322 - 3329 . DOI: 10.1016/j.biomaterials.2010.12.060 http://doi.org/10.1016/j.biomaterials.2010.12.060 .

Luo, Y.; Zhao, L. Z.; Li, X.; Yang, J.; Guo, L. L.; Zhang, G. X.; Shen, M. W.; Zhao, J. H.; Shi, X. Y . The design of a multifunctional dendrimer-based nanoplatform for targeted dual mode SPECT/MR imaging of tumors . J. Mater. Chem. B , 2016 . 4 7220 - 7225 . DOI: 10.1039/C6TB02190E http://doi.org/10.1039/C6TB02190E .

Yang, J.; Luo, Y.; Xu, Y. H.; Li, J. C.; Zhang, Z. X.; Wang, H.; Shen, M. W.; Shi, X. Y.; Zhang, G. X . Conjugation of iron oxide nanoparticles with RGD-modified dendrimers for targeted tumor MR imaging . ACS Appl. Mater. Interfaces , 2015 . 7 5420 - 5428 . DOI: 10.1021/am508983n http://doi.org/10.1021/am508983n .

Morgan, M. T.; Carnahan, M. A.; Immoos, C. E.; Ribeiro, A. A.; Finkelstein, S.; Lee, S. J.; Grinstaff, M. W . Dendritic molecular capsules for hydrophobic compounds . J. Am. Chem. Soc. , 2003 . 125 15485 - 15489 . DOI: 10.1021/ja0347383 http://doi.org/10.1021/ja0347383 .

浏览量

295

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

Cisplatin-loaded Polymer/Magnetite Composite Nanoparticles as Multifunctional Therapeutic Nanomedicine

CONTRIBUTION OF CHOLESTEROL MOIETIES ATTACHED ON MPEG-b-PCL-b-PLL TO THE CELL UPTAKE, ENDOSOMAL ESCAPE AND GENE KNOCKDOWN OF THE MICELLEPLEXES OF siRNA

VISIBLE AND NEAR-INFRARED CHIROPTICAL GELS CONTAINING ELECTROCHROMIC ANTHRAQUINONE IMIDE GROUPS

2026-9 Contents

Advances in Polymer-based Circularly Polarized Luminescent Materials