Skip to main content
SpringerLink
Log in

Characterizations and bioactivities of abendazole sulfoxide-loaded thermo-sensitive hydrogel

  • Original Paper
  • Published:
Parasitology Research Aims and scope Submit manuscript

Abstract

Albendazole (ABZ), a widely used anthelmintic, attributes its primary metabolite—albendazole sulfoxide (ABZSO)—as an effective agent against helminthes. For a purpose of long-lasting releasing ABZSO in a special lesion, the present study successfully manufactured ABZSO-loaded thermo-sensitive hydrogel, which was proved by FTIR and 1H NMR, in the interim; in vitro and in vivo behaviors of the thermo-sensitive hydrogel containing ABZSO were studied too. The in vivo pharmacokinetics parameters indicated ABZSO-loaded hydrogel as a better choice for sustained release compared with simple ABZSO. Additionally, the effect of the prepared hydrogels against helminth was investigated by the lethality of Caenorhabditis elegans, the results indicated that the lethality of ABZSO-loaded hydrogel (1, 2, and 4 mg/ml, respectively) on C. elegans was higher than that of PLGA-PEG-PLGA group (P < 0.05). It suggested that the hydrogels loaded with albendazole sulfoxide could be considered highly effective against the nematode C. elegans.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  • Aksit D, Yalinkilinc HS, Sekkin S, Boyacioğlu M, Cirak VY, Ayaz E, Gokbulut C (2015) Comparative pharmacokinetics and bioavailability of albendazole sulfoxide in sheep and goats, and dose-dependent plasma disposition in goats. BMC Vet Res 11:124

    Article  PubMed  PubMed Central  Google Scholar 

  • Alexis F, Pridgen EM, Langer R, Farokhzad OC (2010) Nanoparticle technologies for cancer therapy. Handb Exp Pharmacol 197:55–86

    Article  CAS  Google Scholar 

  • Asthana J, Yadav D, Pant A, Yadav AK, Gupta MM, Pandey R (2016) Acacetin 7-O-α-l-rhamnopyranosyl (1-2) β-D-xylopyranoside elicits life-span extension and stress resistance in Caenorhabditis elegans. J Gerontol A Biol Sci Med Sci 71(9):1160–1168

    Article  PubMed  Google Scholar 

  • Cai X, Luan Y, Jiang Y, Song A, Shao W, Li Z, Zhao Z (2012) Huperzine A-phospholipid complex-loaded biodegradable thermosensitive polymer gel for controlled drug release. Int J Pharm 433(1–2):102–111

    Article  CAS  PubMed  Google Scholar 

  • Capece BP, Castells G, Pérez F, Arboix M, Cristòfol C (2000) Pharmacokinetic behaviour of albendazole sulphoxide enantiomers in male and female sheep. Vet Res Commun 24(5):339–348

    Article  CAS  PubMed  Google Scholar 

  • Capece BP, Virkel GL, Lanusse CE (2009) Enantiomeric behaviour of albendazole and fenbendazole sulfoxides in domestic animals: pharmacological implications. Vet J 181(3):241–250

    Article  CAS  PubMed  Google Scholar 

  • Castro SG, Sanchez Bruni SF, Urbizu LP, Confalonieri A, Ceballos L, Lanusse CE, Allemandi DA, Palma SD (2013) Enhanced dissolution and systemic availability of albendazole formulated as solid dispersions. Pharm Dev Technol 18(2):434–442

    Article  CAS  PubMed  Google Scholar 

  • Chen S, Pieper R, Webster DC, Singh J (2005) Triblock copolymers: synthesis, characterization, and delivery of a model protein. Int J Pharm 288(2):207–218

    Article  CAS  PubMed  Google Scholar 

  • Chen S, Singh J (2005) Controlled delivery of testosterone from smart polymer solution based systems: in vitro evaluation. Int J Pharm 295(1–2):183–190

    Article  CAS  PubMed  Google Scholar 

  • Chen S, Singh J (2008) Controlled release of growth hormone from thermosensitive triblock copolymer systems: In vitro and in vivo evaluation. Int J Pharm 352(1–2):58–65

    Article  CAS  PubMed  Google Scholar 

  • Cleland JL, Daugherty A, Mrsny R (2001) Emerging protein delivery methods. Curr Opin Biotechnol 12(2):212–219

    Article  CAS  PubMed  Google Scholar 

  • Cook GC (1990) Use of benzimidazole chemotherapy in human helminthiases: indications and efficacy. Parasitol Today 6(4):133–136

    Article  CAS  PubMed  Google Scholar 

  • Delatour P, Cure MC, Benoit E, Garnier F (1986) Netobimin (Totabin-SCH): preliminary investigations on metabolism and pharmacology. J Vet Pharmacol Ther 9(2):230–234

    Article  CAS  PubMed  Google Scholar 

  • Dengg M, van Meel JC (2004) Caenorhabditis elegans as model system for rapid toxicity assessment of pharmaceutical compounds. J Pharmacol Toxicol Methods 50(3):209–214

    Article  CAS  PubMed  Google Scholar 

  • Dvoroznáková E, Hrcková G, Borosková Z, Velebný S, Dubinský P (2004) Effect of treatment with free and liposomized albendazole on selected immunological parameters and cyst growth in mice infected with Echinococcus multilocularis. Parasitol Int 53(4):315–325

    Article  PubMed  Google Scholar 

  • Eckardt K, Kaltenhäuser J, Kilb C, Seiler A, Stahlmann R (2012) Relative potency of albendazole and its sulfoxide metabolite in two in vitro tests for developmental toxicity: the rat whole embryo culture and the mouse embryonic stem cell test. Reprod Toxicol 34(3):378–384

    Article  CAS  PubMed  Google Scholar 

  • Eeckman F, Moës AJ, Amighi K (2004) Poly (N-isopropylacrylamide) copolymers for constant temperature controlled drug delivery. Int J Pharm 273(1–2):109–119

    Article  CAS  PubMed  Google Scholar 

  • Formentini EA, Mestorino N, Errecalde JO (2005) Pharmacokinetics of ricobendazole after its intravenous, intraruminal and subcutaneous administration in sheep. Vet Res Commun 29(7):595–608

    Article  CAS  PubMed  Google Scholar 

  • Formentini EA, Mestorino ON, Mariño EL, Errecalde JO (2001) Pharmacokinetics of ricobendazole in calves. J Vet Pharmacol Ther 24(3):199–202

    Article  CAS  PubMed  Google Scholar 

  • Gao Y, Ren F, Ding B, Sun N, Liu X, Ding X, Gao S (2011) A thermo-sensitive PLGA-PEG-PLGA hydrogel for sustained release of docetaxel. J Drug Target 19(7):516–527

    Article  CAS  PubMed  Google Scholar 

  • García A, Leonardi D, Vasconi MD, Hinrichsen LI, Lamas MC (2014) Characterization of albendazole-randomly methylated-β-cyclodextrin inclusion complex and in vivo evaluation of its antihelmitic activity in a murine model of Trichinellosis. PLoS One 9(11):e113296

    Article  PubMed  PubMed Central  Google Scholar 

  • Ghahremankhani AA, Dorkoosh F, Dinarvand R (2008) PLGA-PEG-PLGA tri-block copolymers as in situ gel-forming peptide delivery system: effect of formulation properties on peptide release. Pharm Dev Technol 13(1):49–55

    Article  CAS  PubMed  Google Scholar 

  • Hao L, Buttner EA (2014) Methods for studying the mechanisms of action of antipsychotic drugs in Caenorhabditis elegans. J Vis Exp 84:e50864

    Google Scholar 

  • Hemphill A, Stadelmann B, Rufener R, Spiliotis M, Boubaker G, Müller J, Müller N, Gorgas D, Gottstein B (2014) Treatment of echinococcosis: albendazole and mebendazole—what else? Parasite 21:70

    Article  PubMed  PubMed Central  Google Scholar 

  • Jung H, Medina L, García L, Fuentes I, Moreno-Esparza R (1998) Absorption studies of albendazole and some physicochemical properties of the drug and its metabolite albendazole sulphoxide. J Pharm Pharmacol 50(1):43–48

    Article  CAS  PubMed  Google Scholar 

  • Kenyon CJ (2010) The genetics of ageing. Nature 464(7288):504–512

    Article  CAS  PubMed  Google Scholar 

  • Khodaverdi E, Tekie FS, Mohajeri SA, Ganji F, Zohuri G, Hadizadeh F (2012) Preparation and investigation of sustained drug delivery systems using an injectable, thermosensitive, in situ forming hydrogel composed of PLGA-PEG-PLGA. AAPS PharmSciTech 13(2):590–600

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Lanusse CE, Virkel GL, Sanchez SF, Alvarez LI, Lifschitz AL, Imperiale F, Monfrinotti A (1998) Ricobendazole kinetics and availability following subcutaneous administration of a novel injectable formulation to calves. Res Vet Sci 65(1):5–10

    Article  CAS  PubMed  Google Scholar 

  • Lavasanifar A, Samuel J, Kwon GS (2001) Micelles self-assembled from poly(ethylene oxide)-block-poly(N-hexyl stearate L-aspartamide) by a solvent evaporation method: effect on the solubilization and haemolytic activity of amphotericin B. J Control Release 77(1–2):155–160

    Article  CAS  PubMed  Google Scholar 

  • Marriner SE, Bogan JA (1980) Pharmacokinetics of albendazole in sheep. Am J Vet Res 41(7):1126–1129

    CAS  PubMed  Google Scholar 

  • Molina I, Li S, Martinez MB, Vert M (2001) Protein release from physically crosslinked hydrogels of the PLA/PEO/PLA triblock copolymer-type. Biomaterials 22(4):363–369

    Article  CAS  PubMed  Google Scholar 

  • Naseri M, Akbarzadeh A, Spotin A, Akbari NA, Mahami-Oskouei M, Ahmadpour E (2016) Scolicidal and apoptotic activities of albendazole sulfoxide and albendazole sulfoxide-loaded PLGA-PEG as a novel nanopolymeric particle against Echinococcus granulosus protoscoleces. Parasitol Res

  • Opperman CH, Chang S (1991) Effects of aldicarb and fenamiphos on acetycholinesterase and motility of caenorhabditis elegans. J Nematol 23(1):20–7

  • Palomares-Alonso F, González CR, Bernad-Bernad MJ, Montiel MD, Hernández GP, González-Hernández I, Castro-Torres N, Estrada EP, Jung-Cook H (2010) Two novel ternaryal bendazole-cyclodextrin-polymer systems: dissolution, bioavailability and efficacy against Taenia crassiceps cysts. Acta Trop 113(1):56–60

    Article  CAS  PubMed  Google Scholar 

  • Pratoomsoot C, Tanioka H, Hori K, Kawasaki S, Kinoshita S, Tighe PJ, Dua H, Shakesheff KM, Rose FR (2008) A thermoreversible hydrogel as a biosynthetic bandage for corneal wound repair. Biomaterials 29(3):272–281

    Article  CAS  PubMed  Google Scholar 

  • Qiao M, Chen D, Ma X, Liu Y (2005) Injectable biodegradable temperature-responsive PLGA-PEG-PLGA copolymers: synthesis and effect of copolymer composition on the drug release from the copolymer-based hydrogels. Int J Pharm 294(1–2):103–112

    Article  CAS  PubMed  Google Scholar 

  • Saraner N, Özkan GY, Güney B, Alkan E, Burul-Bozkurt N, Sağlam O, Fikirdeşici E, Yıldırım M (2016) Determination of albendazole sulfoxide in human plasma by using liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 1022:1–5

    Article  CAS  PubMed  Google Scholar 

  • Schouest K, Zitova A, Spillane C, Papkovsky D (2009) Toxicological assessment of chemicals using Caenorhabditis elegans and optical oxygen respirometry. Environ Toxicol Chem 28(4):791–799

    Article  CAS  PubMed  Google Scholar 

  • Shuhua X, Jiqing Y, Mingjie W, Pieying J, Fanghua G, Junjie C, Wei J, Hotez P (2002) Augmented bioavailability and cysticidal activity of albendazole reformulated in soybean emulsion in mice infected with Echinococcus granulosus or Echinococcus multilocularis. Acta Trop 82(1):77–84

    Article  PubMed  Google Scholar 

  • Wang H, Wick RL, Xing B (2009) Toxicity of nanoparticulate and bulk ZnO, Al2O3 and TiO2 to the nematode Caenorhabditis elegans. Environ Pollut 157(4):1171–1177

    Article  CAS  PubMed  Google Scholar 

  • Yan Q, Xiao LQ, Tan L, Sun W, Wu T, Chen LW, Mei Y, Shi B (2015) Controlled release of simvastatin-loaded thermo-sensitive PLGA-PEG-PLGA hydrogel for bone tissue regeneration: in vitro and in vivo characteristics. J Biomed Mater Res A 103(11):3580–3589

    Article  CAS  PubMed  Google Scholar 

  • Zentner GM, Rathi R, Shih C, McRea JC, Seo MH, Oh H, Rhee BG, Mestecky J, Moldoveanu Z, Morgan M, Weitman S (2001) Biodegradable block copolymers for delivery of proteins and water-insoluble drugs. J Control Release 72(1–3):203–15

Download references

Acknowledgements

We would like to acknowledge Ms. Huai-Ling Wang at South China University of Technology for kindly providing the N2 wild-type C. elegans. This study was partly supported by the grant of the National Natural Science Foundation of China (grant numbers 30972567 and 30371258).

Author information

Authors and Affiliations

  1. Department of Pathogenic Biology, Chongqing Medical University, Chongqing, 400016, People’s Republic of China

    Yi Feng, Fen Wang, Xue-Wei Zhang & Bin Ye

  2. Batch 2013, Clinical Medicine, College of Overseas Student, Chongqing Medical University, Chongqing, 400016, People’s Republic of China

    Harshit Bhutani

  3. Research Center for Molecule Medicine and Tumor, Chongqing Medical University, Chongqing, 400016, People’s Republic of China

    Bin Ye

Authors
  1. Yi Feng
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Fen Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xue-Wei Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Harshit Bhutani
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Bin Ye
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Bin Ye.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Feng, Y., Wang, F., Zhang, XW. et al. Characterizations and bioactivities of abendazole sulfoxide-loaded thermo-sensitive hydrogel. Parasitol Res 116, 921–928 (2017). https://doi.org/10.1007/s00436-016-5365-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00436-016-5365-y

Keywords

Search

Navigation