Development Of Novel Liposome-Encapsulated Combretastatin A4 Acylated Derivatives: Prodrug Approach For Improving Antitumor Efficacy

References

• Bray F, Ferlay J, Soerjomataram I, Siegel RL, Torre LA, Jemal A. Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J Clin. 2018;68(6):394–424. doi:10.3322/caac.2149230207593
   PubMed Web of Science ®Google Scholar
• Siegel RL, Miller KD, Jemal A. Cancer statistics, 2019. CA Cancer J Clin. 2019;69(1):7–34. doi:10.3322/caac.2155130620402
   PubMed Web of Science ®Google Scholar
• Wang Y, Cheetham AG, Angacian G, Su H, Xie L, Cui H. Peptide-drug conjugates as effective prodrug strategies for targeted delivery. Adv Drug Deliv Rev. 2017;110-111:112-126.
   Web of Science ®Google Scholar
• Fang JY, Al-Suwayeh SA. Nanoparticles as delivery carriers for anticancer prodrugs. Expert Opin Drug Deliv. 2012;9(6):657–669. doi:10.1517/17425247.2012.67992722507134
   PubMed Web of Science ®Google Scholar
• Vig BS, Huttunen KM, Laine K, Rautio J. Amino acids as promoieties in prodrug design and development. Adv Drug Deliv Rev. 2013;65(10):1370–1385. doi:10.1016/j.addr.2012.10.00123099277
   PubMed Web of Science ®Google Scholar
• Markovic M, Ben-Shabat S, Keinan S, Aponick A, Zimmermann EM, Dahan A. Lipidic prodrug approach for improved oral drug delivery and therapy. Med Res Rev. 2019;39(2):579–607.30320896
   PubMed Web of Science ®Google Scholar
• Bala V, Rao S, Boyd BJ, Prestidge CA. Prodrug and nanomedicine approaches for the delivery of the camptothecin analogue SN38. J Control Release. 2013;172(1):48–61. doi:10.1016/j.jconrel.2013.07.02223928356
   PubMed Web of Science ®Google Scholar
• Ulmschneider MB, Searson PC. Mathematical models of the steps involved in the systemic delivery of a chemotherapeutic to a solid tumor: from circulation to survival. J Control Release. 2015;212:78–84. doi:10.1016/j.jconrel.2015.06.02626103439
   PubMed Web of Science ®Google Scholar
• Hinna AH, Hupfeld S, Kuntsche J, Bauer-Brandl A, Brandl M. Mechanism and kinetics of the loss of poorly soluble drugs from liposomal carriers studied by a novel flow field-flow fractionation-based drug release-/transfer-assay. J Control Release. 2016;232:228–237. doi:10.1016/j.jconrel.2016.04.03127112112
   PubMedGoogle Scholar
• Tam YT, Shin DH, Chen KE, Kwon GS. Poly(ethylene glycol)-block-poly(d,l-lactic acid) micelles containing oligo(lactic acid)-paclitaxel prodrug: in vivo conversion and antitumor efficacy. J Control Release. 2019;298:186–193. doi:10.1016/j.jconrel.2019.02.01730790593
   PubMed Web of Science ®Google Scholar
• Böttger R, Knappe D, Hoffmann R. Readily adaptable release kinetics of prodrugs using protease-dependent reversible PEGylation. J Control Release. 2016;230:88–94. doi:10.1016/j.jconrel.2016.04.01027067364
   PubMed Web of Science ®Google Scholar
• Arosio D, Casagrande C. Advancement in integrin facilitated drug delivery. Adv Drug Deliv Rev. 2016;97:111–143. doi:10.1016/j.addr.2015.12.00126686830
   PubMed Web of Science ®Google Scholar
• Mura S, Bui DT, Couvreur P, Nicolas J. Lipid prodrug nanocarriers in cancer therapy. J Control Release. 2015;208:25–41. doi:10.1016/j.jconrel.2015.01.02125617724
   PubMed Web of Science ®Google Scholar
• Han F, Wang P, Zhang W, et al. CA-1H, a novel oxazole bearing analogue of combretastatin A-4, disrupts the tumor vasculatures and inhibits the tumor growth via inhibiting tubulin polymerization. Biomed Pharmacother. 2016;80:151–161. doi:10.1016/j.biopha.2016.03.01627133052
   PubMedGoogle Scholar
• Colliez F, Fruytier AC, Magat J, et al. Monitoring Combretastatin A4-induced tumor hypoxia and hemodynamic changes using endogenous MR contrast and DCE-MRI. Magn Reson Med. 2016;75(2):866–872. doi:10.1002/mrm.2564225765253
   PubMedGoogle Scholar
• Daswani VP, Ayesa U, Venegas B, Chong. PL. Concentration-induced J-aggregate formation causes a biphasic change in the release of trans-combretastatin A4 disodium phosphate from archaeosomes and the subsequent cytotoxicity on mammary cancer cells. Mol Pharm. 2015;12(10):3724–3734. doi:10.1021/acs.molpharmaceut.5b0050026355665
   PubMedGoogle Scholar
• Su M, Huang J, Liu S, et al. The anti-angiogenic effect and novel mechanisms of action of Combretastatin A-4. Sci Rep. 2016;6:28139. doi:10.1038/srep2813927338725
   PubMedGoogle Scholar
• Liu H, Wang J. Loading IR820 using multifunctional dendrimers with enhanced stability and specificity. Pharmaceutics. 2018;10(3):77. doi:10.3390/pharmaceutics10030077
   PubMed Web of Science ®Google Scholar
• Mahal K, Biersack B, Caysa H, Schobert R, Mueller. T. Combretastatin A-4 derived imidazoles show cytotoxic, antivascular, and antimetastatic effects based on cytoskeletal reorganisation. Invest New Drugs. 2015;33(3):541–554. doi:10.1007/s10637-015-0215-925678082
   PubMedGoogle Scholar
• Venegas B, Zhu W, Haloupek NB, et al. Cholesterol superlattice modulates CA4P release from liposomes and CA4P cytotoxicity on mammary cancer cells. Biophys J. 2012;102(9):2086–2094. doi:10.1016/j.bpj.2012.03.06322824272
   PubMedGoogle Scholar
• Zheng S, Zhong Q, Mottamal M, et al. Design, synthesis, and biological evaluation of novel pyridine-bridged analogues of combretastatin-A4 as anticancer agents. J Med Chem. 2014;57(8):3369–3381. doi:10.1021/jm500002k24669888
   PubMed Web of Science ®Google Scholar
• Li G, Song YZ, Huang ZJ, Chen K, Chen DW, Deng YH. Novel, nano-sized, liposome-encapsulated polyamidoamine dendrimer derivatives facilitate tumour targeting by overcoming the polyethylene glycol dilemma and integrin saturation obstacle. J Drug Target. 2017;25(8):734–746. doi:10.1080/1061186X.2017.132486028452577
   PubMed Web of Science ®Google Scholar
• Xu Q, Qi H, Sun M, et al. Synthesis and biological evaluation of 3-Alkyl-1,5-Diaryl-1H-Pyrazoles as rigid analogues of Combretastatin A-4 with potent antiproliferative activity. PLoS One. 2015;10(6):e0128710. doi:10.1371/journal.pone.012871026061410
   PubMedGoogle Scholar
• Lorscheider M, Tsapis N, Simón-Vázquez R, et al. Nanoscale lipophilic prodrugs of dexamethasone with enhanced pharmacokinetics. Mol Pharm. 2019;16(7):2999–3010. doi:10.1021/acs.molpharmaceut.9b0023731117740
   PubMedGoogle Scholar
• Allen TM, Cullis PR. Liposomal drug delivery systems: from concept to clinical applications. Adv Drug Deliv Rev. 2013;65(1):36–48. doi:10.1016/j.addr.2012.09.03723036225
   PubMed Web of Science ®Google Scholar
• Zhang C, An T, Wang D, et al. Stepwise pH-responsive nanoparticles containing charge-reversible pullulan-based shells and poly(β-amino ester)/poly(lactic-co-glycolic acid) cores as carriers of anticancer drugs for combination therapy on hepatocellular carcinoma. J Control Release. 2016;226:193–204. doi:10.1016/j.jconrel.2016.02.03026896737
   PubMed Web of Science ®Google Scholar
• Hu L, Luo X, Zhou S, et al. Neutrophil-mediated delivery of dexamethasone palmitate-loaded liposomes decorated with a sialic acid conjugate for rheumatoid arthritis treatment. Pharm Res. 2019;36(7):97. doi:10.1007/s11095-019-2609-431076925
   PubMed Web of Science ®Google Scholar
• N’Guessan A, Fattal E, Chapron D, Gueutin C, Koffi A, Tsapis N. Dexamethasone palmitate large porous particles: a controlled release formulation for lung delivery of corticosteroids. Eur J Pharm Sci. 2018;113:185–192. doi:10.1016/j.ejps.2017.09.01328890202
   PubMedGoogle Scholar
• Gaekens T, Guillaume M, Borghys H, et al. Lipophilic nalmefene prodrugs to achieve a one-month sustained release. J Control Release. 2016;232:196–202. doi:10.1016/j.jconrel.2016.04.02927107723
   PubMedGoogle Scholar
• Terakawa MS, Lin Y, Kinoshita M, et al. Impact of membrane curvature on amyloid aggregation. Biochim Biophys Acta Biomembr. 2018;1860:1741–1764. doi:10.1016/j.bbamem.2018.04.012
   PubMed Web of Science ®Google Scholar
• Zhang W, Song Y, Eldi P, et al. Targeting prostate cancer cells with hybrid elastin-like polypeptide/liposome nanoparticles. Int J Nanomedicine. 2018;13:293–305. doi:10.2147/IJN.S15248529391790
   PubMed Web of Science ®Google Scholar
• Mishra D, Garg M, Dubey V, Jain S, Jain NK. Elastic liposomes mediated transdermal delivery of an anti-hypertensive agent: propranolol hydrochloride. J Pharm Sci. 2007;96(1):145–155. doi:10.1002/jps.2073716960826
   PubMed Web of Science ®Google Scholar
• Gu Y, Tang X, Yang M, Yang D, Liu J. Transdermal drug delivery of triptolide-loaded nanostructured lipid carriers: preparation, pharmacokinetic, and evaluation for rheumatoid arthritis. Int J Pharm. 2019;554:235–244. doi:10.1016/j.ijpharm.2018.11.02430423415
   PubMed Web of Science ®Google Scholar
• Su T, Long Y, Deng C, et al. Construction of a two-in-one liposomal system (TWOLips) for tumor-targeted combination therapy. Int J Pharm. 2014;476:241–252. doi:10.1016/j.ijpharm.2014.09.05525300591
   PubMedGoogle Scholar
• Monteiro LOF, Fernandes RS, Castro L, et al. Paclitaxel-loaded folate-coated pH-sensitive liposomes enhance cellular uptake and antitumor activity. Mol Pharm. 2019;16:3477–3488. doi:10.1021/acs.molpharmaceut.9b0032931257891
   PubMed Web of Science ®Google Scholar
• Lakkadwala S, Dos Santos Rodrigues B, Sun C, Singh J. Dual functionalized liposomes for efficient co-delivery of anti-cancer chemotherapeutics for the treatment of glioblastoma. J Control Release. 2019;307:247–260. doi:10.1016/j.jconrel.2019.06.03331252036
   PubMed Web of Science ®Google Scholar
• Ravar F, Saadat E, Gholami M, et al. Hyaluronic acid-coated liposomes for targeted delivery of paclitaxel, in-vitro characterization and in-vivo evaluation. J Control Release. 2016;229:10–22. doi:10.1016/j.jconrel.2016.03.01226968799
   PubMed Web of Science ®Google Scholar
• Yuba E, Kanda Y, Yoshizaki Y, et al. pH-sensitive polymer-liposome-based antigen delivery systems potentiated with interferon-γ gene lipoplex for efficient cancer immunotherapy. Biomaterials. 2015;67:214–224. doi:10.1016/j.biomaterials.2015.07.03126222284
   PubMed Web of Science ®Google Scholar
• Yang Q. Liu S., Gu Y., et al. Development of sulconazole-loaded nanoemulsions for enhancement of transdermal permeation and antifungal activity. Int J Nanomedicine. 2019;14:3955–3966. doi:10.2147/IJN.S20665731239665
   PubMed Web of Science ®Google Scholar
• Gaspar DP, Serra C, Lino PR, et al. Microencapsulated SLN: an innovative strategy for pulmonary protein delivery. Int J Pharm. 2017;516(1–2):231–246. doi:10.1016/j.ijpharm.2016.11.03727864069
   PubMedGoogle Scholar
• Liu M, Du H, Khan AR, Ji J, Yu A, Zhai G. Redox/enzyme sensitive chondroitin sulfate-based self-assembled nanoparticles loading docetaxel for the inhibition of metastasis and growth of melanoma. Carbohydr Polym. 2018;184:82–93. doi:10.1016/j.carbpol.2017.12.04729352946
   PubMed Web of Science ®Google Scholar
• Liu M, Khan AR, Ji J, Lin G, Zhao X, Zhai G. Crosslinked self-assembled nanoparticles for chemo-sonodynamic combination therapy favoring antitumor, antimetastasis management and immune responses. J Control Release. 2018;290:150–164. doi:10.1016/j.jconrel.2018.10.00730308258
   PubMed Web of Science ®Google Scholar
• Nagaiah G, Remick SC. Combretastatin A4 phosphate: a novel vascular disrupting agent. Future Oncol. 2010;6(8):1219–1228. doi:10.2217/fon.10.9020799867
   PubMedGoogle Scholar
• China Food And Drug Administration [homepage on the Internet]. Available from: http://app1.sfda.gov.cn/datasearch/face3/base.jsp?tableId=36&tableName=TABLE36&title=%BD%F8%BF%DA%D2%A9%C6%B7&bcId=124356651564146415214424405468 Accessed 1031, 2019.
   Google Scholar
• China Food And Drug Administration [homepage on the Internet]. Available from: http://app1.sfda.gov.cn/datasearch/face3/base.jsp?tableId=25&tableName=TABLE25&title=%B9%FA%B2%FA%D2%A9%C6%B7&bcId=124356560303886909015737447882 Accessed 1031, 2019.
   Google Scholar