Lipid–drug conjugates and associated carrier strategies for enhanced antiretroviral drug delivery

References

• Adhikari P, Pal P, Das KA, Ray S, Bhattacharjee A, Mazumder B. 2017. Nano lipid-drug conjugate: an integrated review. Int J Pharm. 529(1–2):629–641.
   PubMed Web of Science ®Google Scholar
• Agarwal HK, Chhikara BS, Bhavaraju S, Mandal D, Doncel GF, Parang K. 2013. Emtricitabine prodrugs with improved anti-hiv activity and cellular uptake. Mol Pharm. 10(2):467–476.
   PubMedGoogle Scholar
• Agarwal HK, Chhikara BS, Hanley MJ, Ye G, Doncel GF, Parang K. 2012. Synthesis and biological evaluation of fatty acyl ester derivatives of (−)-2′,3′-dideoxy-3′-thiacytidine. J Med Chem. 55(10):4861–4871.
   PubMed Web of Science ®Google Scholar
• Amly W, Karaman R. 2016. Overview on the recent drugs delivery approaches. J Pharmacol Drug Design. 2(1):1–29.
   Google Scholar
• Anderson RM, May RM, Boily MC, Garnett GP, Rowley JT, May RM. 1991. The spread of HIV-1 in Africa: sexual contact patterns and the predicted demographic impact of AIDS. Nature. 352(6336):581–589.
   PubMed Web of Science ®Google Scholar
• Arouri A, Mouritsen OG. 2011. Anticancer double lipid prodrugs: liposomal preparation and characterization. J Liposome Res. 21(4):296–305.
   PubMed Web of Science ®Google Scholar
• Bakhtiary Z, Barar J, Aghanejad A, Saei AA, Nemati E, Ezzati Nazhad Dolatabadi J, Omidi Y. 2017. Microparticles containing erlotinib-loaded solid lipid nanoparticles for treatment of non-small cell lung cancer. Drug Dev Ind Pharm. 43(8):1244–1253.
   PubMed Web of Science ®Google Scholar
• Banerjee S, Kundu A. 2018. Lipid-drug conjugates : a potential nanocarrier system for oral drug delivery applications. Daru. (26):65–75.
   PubMedGoogle Scholar
• Beloqui A, Solinís MÁ, des Rieux A, Préat V, Rodríguez-Gascón A. 2014. Dextran-protamine coated nanostructured lipid carriers as mucus-penetrating nanoparticles for lipophilic drugs. Int J Pharm. 468(1–2):105–111.
   PubMedGoogle Scholar
• Bender AR, von Briesen H, Kreuter J, Duncan IB, Rübsamen-Waigmann H. 1996. Efficiency of nanoparticles as a carrier system for antiviral agents in human immunodeficiency virus-infected human monocytes/macrophages in vitro. Antimicrob Agents Chemother. 40(6):1467–1471.
   PubMed Web of Science ®Google Scholar
• Carias AM, McCoombe S, McRaven M, Anderson M, Galloway N, Vandergrift N, Fought AJ, Lurain J, Duplantis M, Veazey RS, et al. 2013. Defining the interaction of HIV-1 with the mucosal barriers of the female reproductive tract. J Virol. 87(21):11388–11400.
   PubMed Web of Science ®Google Scholar
• Chattopadhyay N, Zastre J, Wong H-L, Wu XY, Bendayan R. 2008. Solid lipid nanoparticles enhance the delivery of the HIV protease inhibitor, atazanavir, by a human brain endothelial cell line. Pharm Res. 25(10):2262–2271.
   PubMed Web of Science ®Google Scholar
• Cheng L, Hostetler KY, Chaidhawangul S, Gardner MF, Beadle JR, Keefe KS, Bergeron-Lynn G, Severson GM, Soules KA, Mueller AJ, et al. 2000. Intravitreal toxicology and duration of efficacy of a novel antiviral lipid prodrug of ganciclovir in liposome formulation. Invest Ophthalmol Vis Sci. 41(6):1523–1532.
   PubMed Web of Science ®Google Scholar
• Chiappetta DA, Hocht C, Opezzo JAW, Sosnik A. 2013. Intranasal administration of antiretroviral-loaded micelles for anatomical targeting to the brain in HIV. Nanomedicine. 8(2):223–237.
   PubMed Web of Science ®Google Scholar
• Cholkar K, Trinh HM, Vadlapudi AD, Mitra AK. 2014. Synthesis and characterization of ganciclovir long chain lipid prodrugs. Adv Ophthalmol Vis Syst. 1(2):1–7.
   Google Scholar
• Chrastina A, Baron VT, Abedinpour P, Rondeau G, Welsh J, Borgström P. 2018. Plumbagin-loaded nanoemulsion drug delivery formulation and evaluation of antiproliferative effect on prostate cancer cells. Biomed Res Int. 2018:1–7.
   Google Scholar
• Clercq ED. 2018. The acyclic nucleoside phosphonates (ANPs): Antonín Holý’s legacy (2012–2018). J Infect. 1(2):11–13.
   Google Scholar
• Collier MA, Gallovic MD, Bachelder EM, Sykes CD, Kashuba A, Ainslie KM. 2016. Saquinavir loaded acetalated dextran microconfetti – a long acting protease inhibitor injectable. Pharm Res. 33(8):1998–2009.
   PubMed Web of Science ®Google Scholar
• Corsi F, Sorrentino L, Mazzucchelli S, Truffi M. 2016. Antiretroviral therapy through barriers: a prominent role for nanotechnology in HIV-1 eradication from sanctuaries. J Pharm Pharmacol. 4:328–339.
   Google Scholar
• Dalpiaz A, Contado C, Mari L, Perrone D, Pavan B, Paganetto G, Hanuskovà M, Vighi E, Leo E. 2014. Development and characterization of PLGA nanoparticles as delivery systems of a prodrug of zidovudine obtained by its conjugation with ursodeoxycholic acid. Drug Deliv. 21(3):221–232.
   PubMed Web of Science ®Google Scholar
• Date T, Paul K, Singh N, Jain S. 2019. Drug–lipid conjugates for enhanced oral drug delivery. AAPS J. 41(20):1–11.
   Google Scholar
• Dolatabadi JEN, Azami A, Mohammadi A, Hamishehkar H, Panahi-Azar V, Saadat YR, Saei AA. 2018. Formulation, characterization and cytotoxicity evaluation of ketotifen-loaded nanostructured lipid carriers. J Drug Deliv Sci Technol. 46:268–273.
   Web of Science ®Google Scholar
• Dolatabadi JEN, Hamishehkar H, Valizadeh H. 2014. Development of dry powder inhaler formulation loaded with alendronate solid lipid nanoparticles: solid-state characterization and aerosol dispersion performance. Drug Dev Ind Pharm. 41(9):1431–1437.
   Web of Science ®Google Scholar
• Dolatabadi JEN, Omidi Y. 2016. Solid lipid-based nanocarriers as efficient targeted drug and gene delivery systems. Trend Anal Chem. 77:100–108.
   Web of Science ®Google Scholar
• Edagwa B, Zhou T, McMillan J, Liu X-M, Gendelman H. 2014. Development of HIV reservoir targeted long acting nanoformulated antiretroviral therapies. Curr Med Chem. 21(36):4186–4198.
   PubMed Web of Science ®Google Scholar
• Fiandra L, Colombo M, Mazzuchelli S, Truffi M, Santini B, Allevi R, Nebuloni M, Capetti A, Rizzardini G, Prosperi D, et al. 2015. Nanoformulation of antiretroviral drugs enhances their penetration across the blood brain barrier in mice. Nanomedicine. 11:1387–1397.
   PubMed Web of Science ®Google Scholar
• Florescu DF, Keck MA. 2014. Development of CMX001 (Brincidofovir) for the treatment of serious diseases or conditions caused by dsDNA viruses. Expert Rev Anti-Infect Ther. 12(10):1171–1178.
   PubMed Web of Science ®Google Scholar
• Girard P-M, Pegram PS, Diquet B, Anderson R, Raffi F, Tubiana R, Sereni D, Boerner D. 2000. Phase II placebo-controlled trial of fozivudine tidoxil for HIV infection: pharmacokinetics, tolerability, and efficacy. J Acquir Immune Defic Syndr. 23(3):227–235.
   PubMed Web of Science ®Google Scholar
• Han S, Quach T, Hu L, Wahab A, Charman WN, Stella VJ, Trevaskis NL, Simpson JS, Porter CJH. 2014. Targeted delivery of a model immunomodulator to the lymphatic system: comparison of alkyl ester versus triglyceride mimetic lipid prodrug strategies. J Control Release. 177:1–10.
   PubMed Web of Science ®Google Scholar
• Hoang T, Date AA, Ortiza JO, Young TW, Bensouda S, Xiao P, Marzinke M, Rohan L, Fuchs EJ, Hendrix C, et al. 2018. Development of rectal enema as microbicide (DREAM): preclinical progressive selection of a tenofovir prodrug enema. Eur J Pharm Biopharm.138:23–29.
   PubMed Web of Science ®Google Scholar
• Hobson JJ, Edwards S, Slater RA, Martin P, Owen A, Rannard SP. 2018. Branched copolymer-stabilised nanoemulsions as new candidate oral drug delivery systems. RSC Adv. 8(23):12984–12991.
   PubMed Web of Science ®Google Scholar
• Hussain A, Usman M, Siddique M, Singh SK, Samad A, Beg S, Wais M. 2015. Lipid-drug conjugates for oral bioavailability enhancement. Nanomedicine. 5(2):87–95.
   Google Scholar
• Irby D, Du C, Li F. 2017. Lipid–drug conjugate for enhancing drug delivery. Mol Pharm. 14(5):1325–1338.
   PubMed Web of Science ®Google Scholar
• Jana S, Mandlekar S, Marathe P. 2010. Prodrug design to improve pharmacokinetic and drug delivery properties: challenges to the discovery scientists. Curr Med Chem. 17(32):3874–3908.
   PubMed Web of Science ®Google Scholar
• Jiao YY, Wang XQ, Lu WL, Yang ZJ, Zhang Q. 2013. A novel approach to improve the pharmacokinetic properties of 8-chloro-adenosine by the dual combination of lipophilic derivatisation and liposome formulation. Eur J Pharm Sci. 48(1–2):249–258.
   PubMed Web of Science ®Google Scholar
• Jin SX, Bi DZ, Wang J, Wang YZ, Hu HG, Deng YH. 2005. Pharmacokinetics and tissue distribution of zidovudine in rats following intravenous administration of zidovudine myristate loaded liposomes. Pharmazie. 60(11):840–843.
   PubMed Web of Science ®Google Scholar
• Kinman L, Brodie SJ, Tsai CC, Bui T, Larsen K, Schmidt A, Anderson D, Morton WR, Hu S-L, Ho RJY, et al. 2003. Lipid-drug association enhanced hiv-1 protease inhibitor indinavir localization in lymphoid tissues and viral load reduction: a proof of concept study in HIV-2287-infected macaques. J Acquir Immune Defic Syndr. 34(4):387–397.
   PubMed Web of Science ®Google Scholar
• Krovi SA, Gallovic MD, Keller AM, Bhat M, Tiet P, Chen N, Collier MA, Gurysh EG, Pino EN, Johnson MM, et al. 2018. Injectable long-acting human immunodeficiency virus antiretroviral prodrugs with improved pharmacokinetic profiles. Int J Pharm. 552(1–2):371–377.
   PubMedGoogle Scholar
• Krugner-Higby L, Goff D, Edwards T, Iyer N, Neufeld JAY, Kute T, Morris-Natschke S, Ishaq K, Piantadosi C, Kucera LS, et al. 1995. Membrane-interactive phospholipids inhibit HIV type 1-induced cell fusion and surface gpl60/gpl20 binding to monoclonal antibody. AIDS Res Hum Retrovir. 11(6):705–712.
   PubMed Web of Science ®Google Scholar
• Kucera LS, Morris‐Natschke SL, Ishaq KS, Hes J, Iyer N, Furman PA, Fleming RA. 2004. Synthesis and evaluation of a novel synthetic phosphocholine lipid-AZT conjugate that double-targets wild-type and drug resistant variants of HIV. Nucleosides Nucleotides Nucleic Acids. 23(1–2):385–399.
   PubMed Web of Science ®Google Scholar
• Lanier ER, Ptak RG, Lampert BM, Keilholz L, Hartman T, Buckheit RW, Mankowski MK, Osterling MC, Almond MR, Painter GR, et al. 2010. Development of hexadecyloxypropyl tenofovir (CMX157) for treatment of infection caused by wild-type and nucleoside/nucleotide-resistant HIV. Antimicrob Agents Chemother. 54(7):2901–2909.
   PubMed Web of Science ®Google Scholar
• Lee J. H, Yeo Y. 2015. Controlled drug release from pharmaceutical nanocarriers. Chem Eng Sci. 125:75–84.
   PubMed Web of Science ®Google Scholar
• Li F, Snow-Davis C, Du C, Bondarev ML, Saulsbury MD, Heyliger SO. 2016. Preparation and characterization of lipophilic doxorubicin pro-drug micelles. J Vis Exp. 114:1–8.
   Google Scholar
• Li J, Wang X, Zhang T, Wang C, Huang Z, Luo X, Deng Y. 2014. A review on phospholipids and their main applications in drug delivery systems. Asian J Pharm Sci. 10:81–98.
   Web of Science ®Google Scholar
• Lundberg BB, Risovic V, Ramaswamy M, Wasan KM. 2003. A lipophilic paclitaxel derivative incorporated in a lipid emulsion for parenteral administration. J Control Release. 86(1):93–100.
   PubMed Web of Science ®Google Scholar
• Mahajan HS, Mahajan MS, Nerkar PP, Agrawal A. 2014. Nanoemulsion-based intranasal drug delivery system of saquinavir mesylate for brain targeting. Drug Deliv. 21(2):148–154.
   PubMed Web of Science ®Google Scholar
• Manyarara TE, Khoza S, Dube A, Maponga CC. 2018. Formulation and characterization of a paediatric nanoemulsion dosage form with modified oral drug delivery system for improved dissolution rate of nevirapine. MRS Adv. 3:2203–2219.
   Web of Science ®Google Scholar
• Markovic M, Ben‐Shabat S, Keinan S, Aponick A, Zimmermann EM, Dahan A. 2019. Lipidic prodrug approach for improved oral drug delivery and therapy. Med Res Rev. 39(2):579–607.
   PubMed Web of Science ®Google Scholar
• Morison L, Weiss HA, Buvé A, Caraël M, Abega S-C, Kaona F, Kanhonou L, Chege J, Hayes RJ. 2001. Commercial sex and the spread of HIV in four cities in sub-Saharan Africa. AIDS. 15(4):S61–S69.
   PubMedGoogle Scholar
• Nayak D, Boxi A, Ashe S, Thathapudi NC, Nayak B. 2017. Stavudine loaded gelatin liposomes for HIV therapy: preparation, characterization and in vitro cytotoxic evaluation. Mater Sci Eng C. 73:406–416.
   PubMed Web of Science ®Google Scholar
• Nemati E, Mokhtarzadeh A, Panahi-Azar V. 2019. Ethambutol-loaded solid lipid nanoparticles as dry powder inhalable formulation for tuberculosis therapy. AAPS J. 20(120):1–9.
   Google Scholar
• Neupane YR, Sabir MD, Ahmad N, Ali M, Kohli K. 2013. Lipid drug conjugate nanoparticle as a novel lipid nanocarrier for the oral delivery of decitabine: ex vivo gut permeation studies. Nanotechnology. 24(41):415102–415113.
   PubMed Web of Science ®Google Scholar
• Painter W, Robertson A, Trost LC, Godkin S, Lampert B, Painter G. 2012. First pharmacokinetic and safety study in humans of the novel lipid antiviral conjugate CMX001, a broad-spectrum oral drug active against double-stranded DNA viruses. Antimicrob Agents Chemother. 56(5):2726–2734.
   PubMed Web of Science ®Google Scholar
• Periyasamy PC, Leijten JCH, Dijkstra PJ, Karperien M, Post JN. 2012. Nanomaterials for the local and targeted delivery of osteoarthritis drugs. J Nanomater. 2012:1–13.
   Google Scholar
• Poudel AJ, He F, Huang L, Xiao L, Yang G. 2018. Supramolecular hydrogels based on poly (ethylene glycol)-poly (lactic acid) block copolymer micelles and α-cyclodextrin for potential injectable drug delivery system. Carbohydr Polym. 194:69–79.
   PubMed Web of Science ®Google Scholar
• Prajapati VK, Awasthi K, Gautam S, Yadav TP, Rai M, Srivastava ON, Sundar S. 2011. Targeted killing of Leishmania donovani in vivo and in vitro with amphotericin β attached to functionalized carbon nanotubes. J Antimicrob Chemother. 66(4):874–879.
   PubMed Web of Science ®Google Scholar
• Rafati AA, Afraz A. 2014. Amperometric sensing of anti-HIV drug zidovudine on Ag nanofilm-multiwalled carbon nanotubes modified glassy carbon electrode. Mater Sci Eng C. 39:105–112.
   PubMedGoogle Scholar
• Rajabi M, Mousa AS. 2016. Lipid nanoparticles and their application in nanomedicine. Curr Pharm Biotechnol. 17(8):662–672.
   PubMed Web of Science ®Google Scholar
• Ramana LN, Sethuraman S, Ranga U, Krishnan UM. 2010. Development of a liposomal nanodelivery system for nevirapine. J Biomed Sci. 17(1):57–59.
   PubMedGoogle Scholar
• Ramana LN, Sharma S, Sethuraman S, Ranga U, Krishnan UM. 2015. Stealth anti-CD4 conjugated immunoliposomes with dual antiretroviral drugs- Modern trojan horses to combat HIV. Eur J Pharm Biopharm. 89:300–311.
   PubMed Web of Science ®Google Scholar
• Rautio J, Kärkkäinen J, Sloan KB. 2017. Prodrugs – recent approvals and a glimpse of the pipeline. Eur J Pharm Sci. 109:146–161.
   PubMed Web of Science ®Google Scholar
• Ray AS, Fordyce MW, Hitchcock MJM. 2016. Tenofovir alafenamide: a novel prodrug of tenofovir for the treatment of human immunodeficiency virus. Antiviral Res. 125:63–70.
   PubMed Web of Science ®Google Scholar
• Reddy S, Rudhrabatla P, Sudhakar B. 2018. Ritonavir loaded surface modified stealth solid lipid nanoparticles: full factorial design and pharmacokinetic studies. Int J Pharm Sci Res. 10(1):77–89.
   Google Scholar
• Sarma A, Das MK. 2019. Formulation by design (FbD) approach to develop tenofovir disoproxil fumarate loaded nanostructured lipid carriers (NLCs) for the aptness of nose to brain delivery. J Drug Deliv Ther. 9(2):148–159.
   Google Scholar
• Shao W, Paul A, Zhao B, Lee C, Rodes L, Prakash S. 2013. Carbon nanotube lipid drug approach for targeted delivery of a chemotherapy drug in a human breast cancer xenograft animal model. Biomaterials. 34(38):10109–10119.
   PubMed Web of Science ®Google Scholar
• Sharma P, Dube B, Sawant K. 2012. Synthesis of cytarabine lipid drug conjugate for treatment of meningeal leukemia: development, characterization and in vitro cell line studies. J Biomed Nanotechnol. 8(6):928–937.
   PubMed Web of Science ®Google Scholar
• Sharma A, Kushawaha SK, Anghore D, Pandit V. 2015. HIV/AIDS overview – recent advancement made by WHO. IJPTP. 1(6):1582–1590.
   Google Scholar
• Singh D, McMillan J, Hilaire J, Gautam N, Palandri D, Alnouti Y, Gendelman HE, Edagwa B. 2016. Development and characterization of a long-acting nanoformulated abacavir prodrug. Nanomedicine. 11(15):1913–1927.
   PubMed Web of Science ®Google Scholar
• Singh G, Pai RS. 2014. Pharmacokinetics and in vivo biodistribution of optimized PLGA nanoparticulate drug delivery system for controlled release of emtricitabine. Drug Deliv. 21(8):627–635.
   PubMed Web of Science ®Google Scholar
• Sinikrot H, Smerat T, Najjar A, Karaman R. 2017. Advanced prodrug strategies in nucleoside and non-nucleoside antiviral agents: a review of the recent five years. Molecules. 22:1–18.
   Web of Science ®Google Scholar
• Spinks CB, Zidan AS, Khan AM, Habib MJ, Faustino PJ. 2017. Pharmaceutical characterization of novel tenofovir liposomal formulations for enhanced oral drug delivery: in vitro pharmaceutics and Caco-2 permeability investigations. Clin Pharmacol. 9:29–38.
   PubMed Web of Science ®Google Scholar
• Takasawa K, Terasaki T, Suzuki H, Sugiyama Y. 1997. In vivo evidence for carrier-mediated efflux transport of 39-azido-39-deoxythymidine and 29,39-dideoxyinosine across the blood-brain barrier via a probenecid-sensitive transport system. J Pharmacol Exp Ther. 281(1):369–375.
   PubMed Web of Science ®Google Scholar
• Tsotinis A, Calogeropoulou T, Koufaki M, Souli C, Balzarini J, De Clercq E, Makriyannis A. 1996. Synthesis and antiretroviral evaluation of new alkoxy and aryloxy phosphate derivatives of 3’-azido-3’-deoxythymidine. J Med Chem. 39(17):3418–3422.
   PubMed Web of Science ®Google Scholar
• Wang Y, Fan W, Dai X, Katragadda U, Mckinley D, Teng Q, Tan C. 2014. Enhanced tumor delivery of gemcitabine via PEG-DSPE/TPGS mixed micelles. Mol Pharm. 11(4):1140–1150.
   PubMedGoogle Scholar
• Xu X, Khan MA, Burgess DJ. 2012. A two-stage reverse dialysis in vitro dissolution testing method for passive targeted liposomes. Int J Pharm. 426(1–2):211–218.
   PubMed Web of Science ®Google Scholar
• Ye F, Guo H, Zhang H, He X. 2010. Polymeric micelle-templated synthesis of hydroxyapatite hollow nanoparticles for a drug delivery system. Acta Biomater. 6(6):2212–2218.
   PubMed Web of Science ®Google Scholar
• Zaro JL. 2015. Lipid-based drug carriers for prodrugs to enhance drug delivery. AAPS J. 17(1):83–92.
   PubMed Web of Science ®Google Scholar
• Zhang Z, Yang X, Zhang Y, Zeng B, Wang S, Zhu T, Roden RB, Chen Y, Yang R. 2006. Delivery of telomerase reverse transcriptase small interfering RNA in complex with positively charged single-walled carbon nanotubes suppresses tumor growth. Clin Cancer Res. 12(16):4933–4939.
   PubMed Web of Science ®Google Scholar