Hostname: page-component-586b7cd67f-rdxmf Total loading time: 0 Render date: 2024-11-23T21:48:18.212Z Has data issue: false hasContentIssue false
  • English
  • Français

In vivo antimalarial activity and pharmacokinetics of artelinic acid-choline derivative liposomes in rodents

Published online by Cambridge University Press:  26 September 2019

Shuai Duan Open the ORCID record for Shuai Duan [Opens in a new window] ,
Ruili Wang ,
Rongrong Wang ,
Jiaqi Tang ,
Xiaoyang Xiao ,
Ning Li ,
Wenju Guo ,
Qingshan Yang ,
Guolian Ren  and
Shuqiu Zhang Open the ORCID record for Shuqiu Zhang [Opens in a new window]
Shuai Duan
Affiliation:
School of Pharmacy, Shanxi Medical University, 56 Xinjian South Road, Taiyuan030001, Shanxi, China
Ruili Wang
Affiliation:
School of Pharmacy, Shanxi Medical University, 56 Xinjian South Road, Taiyuan030001, Shanxi, China
Rongrong Wang
Affiliation:
School of Pharmacy, Shanxi Medical University, 56 Xinjian South Road, Taiyuan030001, Shanxi, China
Jiaqi Tang
Affiliation:
School of Pharmacy, Shanxi Medical University, 56 Xinjian South Road, Taiyuan030001, Shanxi, China
Xiaoyang Xiao
Affiliation:
School of Pharmacy, Shanxi Medical University, 56 Xinjian South Road, Taiyuan030001, Shanxi, China
Ning Li
Affiliation:
School of Pharmacy, Shanxi Medical University, 56 Xinjian South Road, Taiyuan030001, Shanxi, China
Wenju Guo
Affiliation:
School of Pharmacy, Shanxi Medical University, 56 Xinjian South Road, Taiyuan030001, Shanxi, China
Qingshan Yang
Affiliation:
School of Pharmacy, Shanxi Medical University, 56 Xinjian South Road, Taiyuan030001, Shanxi, China
Guolian Ren*
Affiliation:
School of Pharmacy, Shanxi Medical University, 56 Xinjian South Road, Taiyuan030001, Shanxi, China
Shuqiu Zhang*
Affiliation:
School of Pharmacy, Shanxi Medical University, 56 Xinjian South Road, Taiyuan030001, Shanxi, China
*
Authors for correspondence: Shuqiu Zhang, E-mail: [email protected]; Guolian Ren, E-mail: [email protected]
Authors for correspondence: Shuqiu Zhang, E-mail: [email protected]; Guolian Ren, E-mail: [email protected]
Get access Rights & Permissions [Opens in a new window]

Abstract

It is urgent to develop new antimalarial drugs with good therapeutic effects to address the emergence of drug resistance. Here, the artelinic acid-choline derivative (AD) was synthesized by dehydration reaction and esterification reaction, aimed to avoid the emergence of drug resistance by synergistic effect of artemisinins and choline derivative, which could compete with choline for rate-limiting enzymes in the phosphatidylcholine (PC) biosynthetic pathway. AD was formulated into liposomes (ADLs) by the thin-film hydration method. Efficacy of ADLs was evaluated by Peters 4-day suppression test. The suppression percentage against Plasmodium yoelii BY265 (PyBY265) in ADLs group was higher than those of positive control groups (dihydroartemisinin liposomes, P < 0.05) and other control groups (P ⩽ 0.05) at the doses of 4.4, 8.8, 17.6 µmol (kg·d)−1, respectively. The negative conversion fraction, recrudescence fraction and survival fraction of ADLs group were superior to other control groups. Pharmacokinetics in rats after intravenous injection suggested that ADLs exhibited higher exposure levels (indexed by area under concentration-time curve) than that of AD solution, artelinic acid liposomes or artelinic acid solution (P < 0.01). Taken together, ADLs exhibited promising antimalarial efficacy and pharmacokinetic characteristics.

Keywords

Antimalariaartelinic acidcholine derivativepharmacokinetics
Type
Research Article
Information
Parasitology , Volume 147 , Issue 1 , January 2020 , pp. 58 - 64
Check for updates
Copyright
Copyright © Cambridge University Press 2019

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

Footnotes

*

Both authors had contributed equally to this work.

References

Cloete, TT, Breytenbach, JW, Kock, CD, Smith, PJ, Breytenbach, JC and N'da, DD (2012) Synthesis, antimalarial activity and cytotoxicity of 10-aminoethylether derivatives of artemisinin. Bioorganic & Medicinal Chemistry 20, 4701–4709.CrossRefGoogle ScholarPubMed
Contet, A, Pihan, E, Lavigne, M, Wengelnik, K, Maheshwari, S, Vial, H, Douguet, D and Cerdan, R (2015) Plasmodium falciparum CTP: phosphocholine cytidyltransferase possesses two functional catalytic domains and is inhibited by a CDP-choline analog selected from a virtual screening. FEBS Letters 589, 992–1000.CrossRefGoogle ScholarPubMed
Gibellini, F and Smith, TK (2010) The Kennedy pathway-De novo synthesis of phosphatidylethanolamine and phosphatidylcholine. IUBMB Life 62, 414–428.CrossRefGoogle ScholarPubMed
Gowrisankar, S, Sergeev, AG, Anbarasan, P, Spannenberg, A, Neumann, H and Beller, M (2011) Cheminform abstract: a general and efficient catalyst for palladium-catalyzed C–O coupling reactions of aryl halides with primary alcohols. Journal of the American Chemical Society 42, 11592–11598.Google Scholar
Itoe, MA, Sampaio, JL, Cabal, GG, Real, E, Zuzarte-Luis, V, March, S, Bhatia, SN, Frischknecht, F, Thiele, C, Shevchenko, A and Mota, MM (2014) Host cell phosphatidylcholine is a key mediator of malaria parasite survival during liver stage infection. Cell Host & Microbe 16, 778–786.CrossRefGoogle ScholarPubMed
Jia, XL, Li, YY, Sharma, A, Li, YL, Xie, GH, Wang, GY, Jiang, JH, Cheng, Y and Ding, XT (2017) Application of sequential factorial design and orthogonal array composite design (OACD) to study combination of 5 prostate cancer drugs. Computational Biology and Chemistry 67, 234–243.CrossRefGoogle ScholarPubMed
Jung, M, Lee, K, Kendrick, H, Robinson, BL and Croft, SL (2002) Synthesis, stability, and antimalarial activity of New hydrolytically stable and water-soluble (+)-deoxoartelinic acid. Journal of Medicinal Chemistry 45, 4940–4944.CrossRefGoogle ScholarPubMed
Mamoun, CB, Prigge, ST and Vial, H (2010) Targeting the lipid metabolic pathways for the treatment of malaria. Drug Development Research 71, 44–55.Google ScholarPubMed
Peyrottes, S, Caldarelli, S, Wein, S, Périgaud, C, Pellet, A and Vial, H (2012) Choline analogues in malaria chemotherapy. Current Pharmaceutical Design 18, 3454–3466.Google ScholarPubMed
Sarkar, S, Siddiqui, AA, Saha, SJ, De, R, Mazumder, S, Banerjee, C, Iqbal, MS, Nag, S, Adhikari, S and Bandyopadhyay, U (2016) Antimalarial activity of small-molecule benzothiazole hydrazones. Antimicrobial Agents and Chemotherapy 60, 4217.CrossRefGoogle ScholarPubMed
Varona, S, Martín, Á and Cocero, MJ (2011) Liposomal incorporation of lavandin essential oil by a thin-film hydration method and by particles from gas-saturated solutions. Industrial & Engineering Chemistry Research 50, 2088–2097.CrossRefGoogle Scholar
Waako, PJ, Gumede, B, Smith, P and Folb, PI (2005) The in vitro and in vivo antimalarial activity of Cardiospermum halicacabum L. and Momordica foetida Schumch. Et Thonn. Journal of Ethnopharmacology 99, 137–143.CrossRefGoogle ScholarPubMed
Wein, S, Maynadier, M, Bordat, Y, Perez, J, Maheshwari, S, Bette-Bobillo, P, Tran Van Ba, C, Penarete-Vargas, D, Fraisse, L, Cerdan, R and Vial, H (2012) Transport and pharmacodynamics of albitiazolium, an antimalarial drug candidate. British Journal of Pharmacology 166, 2263–2276.CrossRefGoogle ScholarPubMed
Yang, ZS, Wang, JX, Zhou, Y, Zuo, JP and Li, Y (2006) Synthesis and immunosuppressive activity of new artemisinin derivatives. Part 2: 2-[12(beta or alpha)-dihydroartemisinoxymethyl(or 1′-ethyl)] phenoxyl propionic acids and esters. Journal of Medicinal Chemistry 14, 8043–8049.Google Scholar
Zhang, H (2017) Thin-film hydration followed by extrusion method for liposome preparation. Methods in Molecular Biology 1522, 17–22.CrossRefGoogle ScholarPubMed
Supplementary material: File

Duan et al. supplementary material

Duan et al. supplementary material

Download Duan et al. supplementary material(File)
File 462.1 KB