Erlotinib complexation with randomly methylated β-cyclodextrin improves drug solubility, intestinal permeability, and therapeutic efficacy in non-small cell lung cancer

References

• Boulmedarat L, Bochot A, Lesieur S, Fattal E. 2005. Evaluation of buccal methyl-beta-cyclodextrin toxicity on human oral epithelial cell culture model. J Pharm Sci. 94(6):1300–1309.
   PubMed Web of Science ®Google Scholar
• Carneiro SB, Costa Duarte FI, Heimfarth L, Siqueira Quintans JS, Quintans-Junior LJ, Veiga Junior VFD, Neves de Lima AA. 2019. Cyclodextrin(-)drug inclusion complexes: in vivo and in vitro approaches. Int J Mol Sci. 20(3):642–664.
   Web of Science ®Google Scholar
• Chimento A, Casaburi I, Avena P, Trotta F, De Luca A, Rago V, Pezzi V, Sirianni R. 2018. Cholesterol and its metabolites in tumor growth: therapeutic potential of statins in cancer treatment. Front Endocrinol. 9:807.
   PubMed Web of Science ®Google Scholar
• Connors KA. 1997. The stability of cyclodextrin complexes in solution. Chem Rev. 97(5):1325–1358.
   PubMed Web of Science ®Google Scholar
• Devasari N, Dora CP, Singh C, Paidi SR, Kumar V, Sobhia ME, Suresh S. 2015. Inclusion complex of erlotinib with sulfobutyl ether-β-cyclodextrin: preparation, characterization, in silico, in vitro and in vivo evaluation . Carbohydr Polym. 134:547–556.
   PubMed Web of Science ®Google Scholar
• Dhoble S, Patravale V. 2019. Development of anti-angiogenic erlotinib liposomal formulation for pulmonary hypertension: a QbD approach. Drug Deliv Transl Res. 9(5):980–996.
   PubMed Web of Science ®Google Scholar
• Dora CP, Kushwah V, Katiyar SS, Kumar P, Pillay V, Suresh S, Jain S. 2017. Improved oral bioavailability and therapeutic efficacy of erlotinib through molecular complexation with phospholipid. Int J Pharm. 534(1–2):1–13.
   PubMedGoogle Scholar
• Dora CP, Trotta F, Kushwah V, Devasari N, Singh C, Suresh S, Jain S. 2016. Potential of erlotinib cyclodextrin nanosponge complex to enhance solubility, dissolution rate, in vitro cytotoxicity and oral bioavailability. Carbohydr Polym. 137:339–349.
   PubMed Web of Science ®Google Scholar
• Erdoğar N, Nemutlu E, İskit AB, Kara SC, Teksin ZŞ, Bilensoy E. 2020. Improved oral bioavailability of anticancer drug tamoxifen through complexation with water soluble cyclodextrins: in vitro and in vivo evaluation. J Incl Phenom Macrocycl Chem. 96(1–2):81–91.
   Web of Science ®Google Scholar
• Erdoğar N. 2021. Development of oral tablet formulation containing erlotinib: randomly methylated-β-cyclodextrin inclusion complex using direct compression method. TJPS.
   Google Scholar
• FDA. 2021. Dissolution methods. MD: FDA. [accessed 2021 May 11]. https://www.accessdata.fda.gov/scripts/cder/dissolution/dsp_SearchResults.cfm
   Google Scholar
• Fenyvesi E, Szeman J, Csabai K, Malanga M, Szente L. 2014. Methyl-beta-cyclodextrins: the role of number and types of substituents in solubilizing power. J Pharm Sci. 103(5):1443–1452.
   PubMed Web of Science ®Google Scholar
• Fenyvesi F, Kiss T, Fenyvesi E, Szente L, Veszelka S, Deli MA, Váradi J, Fehér P, Ujhelyi Z, Tósaki A, et al. 2011. Randomly methylated β-cyclodextrin derivatives enhance taxol permeability through human intestinal epithelial Caco-2 cell monolayer. J Pharm Sci. 100(11):4734–4744.
   PubMed Web of Science ®Google Scholar
• Fitzmaurice C, Abate D, Abbasi N, Abbastabar H, Abd-Allah F, Abdel-Rahman O, Abdelalim A, Abdoli A, Abdollahpour I, Abdulle ASM, et al. 2019. Global, regional, and national cancer incidence, mortality, years of life lost, years lived with disability, and disability-adjusted life-years for 29 cancer groups, 1990 to 2017: a systematic analysis for the global burden of disease study. JAMA Oncol. 5(12):1749–1768.
   PubMed Web of Science ®Google Scholar
• Gidwani B, Vyas A. 2015. A comprehensive review on cyclodextrin-based carriers for delivery of chemotherapeutic cytotoxic anticancer drugs. Biomed Res Int. 2015:198268.
   PubMed Web of Science ®Google Scholar
• Gupta J, Safdari HA, Hoque M. 2021. Nanoparticle mediated cancer immunotherapy. Semin Cancer Biol. 69:307–324.
   PubMed Web of Science ®Google Scholar
• Hidalgo M, Siu LL, Nemunaitis J, Rizzo J, Hammond LA, Takimoto C, Eckhardt SG, Tolcher A, Britten CD, Denis L, et al. 2001. Phase I and pharmacologic study of OSI-774, an epidermal growth factor receptor tyrosine kinase inhibitor, in patients with advanced solid malignancies. J Clin Oncol. 19(13):3267–3279.
   PubMed Web of Science ®Google Scholar
• Higuchi T, Connors KA. 1965. Phase solubility techniques. Adv Anal Chem Instrum. 4:117–212.
   Google Scholar
• Jadhav P, Petkar B, Pore Y, Kulkarni A, Burade K. 2013. Physicochemical and molecular modeling studies of cefixime-L-arginine-cyclodextrin ternary inclusion compounds. Carbohydr Polym. 98(2):1317–1325.
   PubMed Web of Science ®Google Scholar
• Jain AK, Thanki K, Jain S. 2013. Co-encapsulation of tamoxifen and quercetin in polymeric nanoparticles: implications on oral bioavailability, antitumor efficacy, and drug-induced toxicity. Mol Pharm. 10(9):3459–3474.
   PubMed Web of Science ®Google Scholar
• Kim ST, Lee J, Kim JH, Won YW, Sun JM, Yun J, Park YH, Ahn JS, Park K, Ahn MJ. 2010. Comparison of gefitinib versus erlotinib in patients with nonsmall cell lung cancer who failed previous chemotherapy. Cancer. 116(12):3025–3033.
   PubMed Web of Science ®Google Scholar
• Kopecka J, Trouillas P, Gasparovic AC, Gazzano E, Assaraf YG, Riganti C. 2020. Phospholipids and cholesterol: Inducers of cancer multidrug resistance and therapeutic targets. Drug Resist Updat. 49:100670.
   PubMed Web of Science ®Google Scholar
• Loftsson T, Jarho P, Masson M, Jarvinen T. 2005. Cyclodextrins in drug delivery. Expert Opin Drug Deliv. 2(2):335–351.
   PubMedGoogle Scholar
• Maestrelli F, Cecchi M, Cirri M, Capasso G, Mennini N, Mura P. 2009. Comparative study of oxaprozin complexation with natural and chemically-modified cyclodextrins in solution and in the solid state. J Incl Phenom Macrocycl Chem. 63(1–2):17–25.
   Web of Science ®Google Scholar
• Maestrelli F, Mura P, Cirri M, Mennini N, Ghelardini C, Di Cesare Mannelli L. 2017. Development and characterization of fast dissolving tablets of oxaprozin based on hybrid systems of the drug with cyclodextrins and nanoclays. Int J Pharm. 531(2):640–649.
   PubMedGoogle Scholar
• Mahammad S, Parmryd I. 2015. Cholesterol depletion using methyl-β-cyclodextrin. In: Owen D, editor. Methods in membrane lipids methods in molecular biology (methods and protocols). New York (NY): Humana Press; p. 91–102.
   Google Scholar
• Malli S, Bories C, Ponchel G, Loiseau PM, Bouchemal K. 2018. Phase solubility studies and anti-Trichomonas vaginalis activity evaluations of metronidazole and methylated β-cyclodextrin complexes: comparison of CRYSMEB and RAMEB. Exp Parasitol. 189:72–75.
   PubMed Web of Science ®Google Scholar
• Nikolic IL, Savic IM, Popsavin MM, Rakic SJ, Mihajilov-Krstev TM, Ristic IS, Eric SP, Savić-Gajic IM. 2018. Preparation, characterization and antimicrobial activity of inclusion complex of biochanin A with (2-hydroxypropyl)-β-cyclodextrin. J Pharm Pharmacol. 70(11):1485–1493.
   PubMed Web of Science ®Google Scholar
• Piel G, Piette M, Barillaro V, Castagne D, Evrard B, Delattre L. 2007. Study of the relationship between lipid binding properties of cyclodextrins and their effect on the integrity of liposomes. Int J Pharm. 338(1–2):35–42.
   PubMedGoogle Scholar
• Rebuzzi SE, Alfieri R, La Monica S, Minari R, Petronini PG, Tiseo M. 2020. Combination of EGFR-TKIs and chemotherapy in advanced EGFR mutated NSCLC: review of the literature and future perspectives. Crit Rev Oncol Hematol. 146:102820.
   PubMed Web of Science ®Google Scholar
• Reti-Nagy K, Malanga M, Fenyvesi E, Szente L, Vamosi G, Varadi J, Bacskay I, Feher P, Ujhelyi Z, Roka E, et al. 2015. Endocytosis of fluorescent cyclodextrins by intestinal Caco-2 cells and its role in paclitaxel drug delivery. Int J Pharm. 496(2):509–517.
   PubMedGoogle Scholar
• Reul R, Renette T, Bege N, Kissel T. 2011. Nanoparticles for paclitaxel delivery: a comparative study of different types of dendritic polyesters and their degradation behavior. Int J Pharm. 407(1–2):190–196.
   PubMedGoogle Scholar
• Rouf MA, Vural I, Bilensoy E, Hincal AA, Demir Erol D. 2011. Rapamycin-cyclodextrin complexation: improved solubility and dissolution rate. J Incl Phenom Macrocycl Chem. 70(1–2):167–175.
   Web of Science ®Google Scholar
• Salem LB, Bosquillon C, Dailey LA, Delattre L, Martin GP, Evrard B, Forbes B. 2009. Sparing methylation of beta-cyclodextrin mitigates cytotoxicity and permeability induction in respiratory epithelial cell layers in vitro. J Control Release. 136(2):110–116.
   PubMed Web of Science ®Google Scholar
• Sangpheak W, Kicuntod J, Schuster R, Rungrotmongkol T, Wolschann P, Kungwan N, Viernstein H, Mueller M, Pongsawasdi P. 2015. Physical properties and biological activities of hesperetin and naringenin in complex with methylated β-cyclodextrin. Beilstein J Org Chem. 11:2763–2773.
   PubMed Web of Science ®Google Scholar
• Savic IM, Jocic E, Nikolic VD, Popsavin MM, Rakic SJ, Savic-Gajic IM. 2019. The effect of complexation with cyclodextrins on the antioxidant and antimicrobial activity of ellagic acid. Pharm Dev Technol. 24(4):410–418.
   PubMed Web of Science ®Google Scholar
• Savic IM, Savic-Gajic IM, Nikolic VD, Nikolic LB, Radovanovic BC, Milenkovic-Andjelkovic A. 2016. Enhencemnet of solubility and photostability of rutin by complexation with β-cyclodextrin and (2-hydroxypropyl)-β-cyclodextrin. J Incl Phenom Macrocycl Chem. 86(1–2):33–43.
   Web of Science ®Google Scholar
• Savic-Gajic I, Savic IM, Nikolic VD, Nikolic LB, Popsavin MM, Kapor AJ. 2016. Study of the solubility, photostability and structure of inclusion complexes of carvedilol with β-cyclodextrin and (2-hydroxypropyl)-β-cyclodextrin. J Incl Phenom Macrocycl Chem. 86(1–2):7–17.
   Web of Science ®Google Scholar
• Scheffler M, Di Gion P, Doroshyenko O, Wolf J, Fuhr U. 2011. Clinical pharmacokinetics of tyrosine kinase inhibitors: focus on 4-anilinoquinazolines. Clin Pharmacokinet. 50(6):371–403.
   PubMed Web of Science ®Google Scholar
• Solassol I, Pinguet F, Quantin X. 2019. FDA- and EMA-approved tyrosine kinase inhibitors in advanced EGFR-mutated non-small cell lung cancer: safety, tolerability, plasma concentration monitoring, and management. Biomolecules. 9(11):668.
   PubMed Web of Science ®Google Scholar
• Tan AR, Yang X, Hewitt SM, Berman A, Lepper ER, Sparreboom A, Parr AL, Figg WD, Chow C, Steinberg SM, et al. 2004. Evaluation of biologic end points and pharmacokinetics in patients with metastatic breast cancer after treatment with erlotinib, an epidermal growth factor receptor tyrosine kinase inhibitor. J Clin Oncol. 22(15):3080–3090.
   PubMed Web of Science ®Google Scholar
• Trapani G, Latrofa A, Franco M, Pantaleo MR, Sanna E, Massa F, Tuveri F, Liso G. 2000. Complexation of zolpidem with 2-hydroxypropyl-beta-, methyl-beta-, and 2-hydroxypropyl-gamma-cyclodextrin: effect on aqueous solubility, dissolution rate, and ataxic activity in rat. J Pharm Sci. 89(11):1443–1451.
   PubMed Web of Science ®Google Scholar
• Vaidya B, Parvathaneni V, Kulkarni NS, Shukla SK, Damon JK, Sarode A, Kanabar D, Garcia JV, Mitragotri S, Muth A, et al. 2019. Cyclodextrin modified erlotinib loaded PLGA nanoparticles for improved therapeutic efficacy against non-small cell lung cancer. Int J Biol Macromol. 122:338–347.
   PubMed Web of Science ®Google Scholar
• Varan G, Akkın S, Demirtürk N, Benito JM, Bilensoy E. 2021. Erlotinib entrapped in cholesterol-depleting cyclodextrin nanoparticles shows improved antitumoral efficacy in 3D spheroid tumors of the lung and the liver. J Drug Target. 29(4):439–453.
   PubMed Web of Science ®Google Scholar
• Wang H, Cui Y, Fu Q, Deng B, Li G, Yang J, Wu T, Xie Y. 2015. A phospholipid complex to improve the oral bioavailability of flavonoids. Drug Dev Ind Pharm. 41(10):1693–1703.
   PubMed Web of Science ®Google Scholar
• Yavuz B, Bilensoy E, Vural I, Sumnu M. 2010. Alternative oral exemestane formulation: improved dissolution and permeation. Int J Pharm. 398(1–2):137–145.
   PubMedGoogle Scholar
• Zhang AP, Liu WP, Wang LM, Wen YZ. 2005. Characterization of inclusion complexation between fenoxaprop-p-ethyl and cyclodextrin. J Agric Food Chem. 53(18):7193–7197.
   PubMed Web of Science ®Google Scholar