Sulfated cyclodextrins inhibit the entry of Plasmodium into red blood cells

Crandall, Ian; Szarek, Walter A.; Vlahakis, Jason Z.; Xu, Yiming; Vohra, Rahul; Sui, Jie; Kisilevsky, Robert

doi:10.1016/j.bcp.2006.10.030

Cited by 29 publications

(22 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Several studies have already reported that heparin and other sulfated glycoconjugates inhibit the growth of malarial parasites (7)(8)(9)11). In addition, some sulfated chemical compounds inhibit parasite entry into erythrocytes (6,10). Our results showing the binding inhibition of BAEBL by heparin are not sufficient to explain the almost complete inhibition of the merozoite invasion by heparin because BAEBL is not an essential ligand for the invasion (18).…”

Section: Discussionmentioning

confidence: 61%

Plasmodium falciparum BAEBL Binds to Heparan Sulfate Proteoglycans on the Human Erythrocyte Surface

Kobayashi

Kato

Sugi

et al. 2010

Journal of Biological Chemistry

View full text Add to dashboard Cite

Erythrocyte invasion is critical to the pathogenesis and survival of the malarial parasite, Plasmodium falciparum. This process is partly mediated by proteins that belong to the Duffy binding-like family, which are expressed on the merozoite surface. One of these proteins, BAEBL (also known as EBA-140), is thought to bind to glycophorin C in a sialic acid-dependent manner. In this report, by the binding assay between recombinant BAEBL protein and enzyme-treated erythrocytes, we show that the binding of BAEBL to erythrocytes is mediated primarily by sialic acid and partially through heparan sulfate (HS). Because BAEBL binds to several kinds of HS proteoglycans or purified HS, the BAEBL-HS binding was found to be independent of the HS proteoglycan peptide backbone and the presence of sialic acid moieties. Furthermore, both the sialic acid-and HS-dependent binding were disrupted by the addition of soluble heparin. This inhibition may be the result of binding between BAEBL and heparin. Invasion assays demonstrated that HS-dependent binding was related to the efficiency of merozoite invasion. These results suggest that HS functions as a factor that promotes the binding of BAEBL and merozoite invasion. Moreover, these findings may explain the invasion inhibition mechanisms observed following the addition of heparin and other sulfated glycoconjugates.Malaria caused by Plasmodium falciparum kills approximately 1 million people per year. After entering the human bloodstream, the parasite propagates asexually via repeated cycles of erythrocyte invasion, cell division, and cell rupture. The process by which the parasitic merozoites invade erythrocytes involves the following steps: attachment, apical reorientation, junction formation, and the formation of a protective parasitophorous vacuole (1).The Duffy binding-like (DBL) 2 family is composed of adhesion molecules that are critical for junction formation between the apical end of the merozoite and the erythrocyte surface.Proteins in this family, such as EBA-175 (erythrocyte-binding antigen-175), are homologous to Plasmodium vivax Duffybinding protein. These proteins contain one or more DBL domains, which are composed of conserved cysteine residues and are associated with erythrocyte binding (2). EBA-175 is bound to glycophorin A on the erythrocyte surface in a sialic acid-dependent manner (3). However, erythrocytes that are treated with neuraminidase remain susceptible to the merozoites of some clones (4), indicating the existence of sialic acidindependent invasion pathways. These alternative pathways are thought to be mediated, at least in part, by other members of the DBL family (5).Parasite growth is inhibited by the addition of heparin, some sulfated saccharide anions, and sulfated chemical compounds (6 -11). Although the inhibition mechanisms remain unclear, these reports suggest the possibility that sulfated moieties play a role in merozoite invasion. In addition to invasion, heparan sulfate (HS) is believed to function as a receptor for PfEMP1 (P. falciparum erythr...

show abstract

Section: Discussionmentioning

confidence: 61%

Plasmodium falciparum BAEBL Binds to Heparan Sulfate Proteoglycans on the Human Erythrocyte Surface

Kobayashi

Kato

Sugi

et al. 2010

Journal of Biological Chemistry

View full text Add to dashboard Cite

show abstract

“…As antimalarials (Crandall, et al, 2007) 6,6'-telluroxy-bis(6-deoxy-β -cyclodextrin) and related compounds MALDI Demonstration that telloroxides exhibit hydrolysis capacity (Dong, et al, 2007) Thiol-modified β-CD TOF Construction of gold nanoparticles for fingerprint detection (Becue, et al, 2007) Cyclodextrin plus γ-valerolactone TOF Ring-opening polymerization of cyclic esters by cyclodextrins ) Polymers Amphiphilic block copolymers TOF Self-association of bis-(α,β-Dglucopyranosyl)-polyisobutylene (Orosz, et al, 2007) Biotin α-end-functionalized glycopolymers TOF (CHCA) RAFT copolymerization of acrylamide derivs. of Gal with N-acryloylmorpholine in the presence of a biotin CTA (Gody, et al, 2008) Branched supramolecular polymers from CDs TOF From 3-cinnamamide-α-CD and 3-Ncinnamamidehexane-carbonyl-N ε -cinnamamide-lysinamide-α-CD (Miyawaki, et al, 2008a) Cellulose acetate modified with caprolactone R-TOF Various reaction conditions.…”

Section: Maldi Osw Saponinsmentioning

confidence: 99%

“…Six matrices were used but although these were said to give different results, presumably because of sulfate loss, details were not reported. Consequently, elemental analysis was employed to determine the average degree of sulfation (Crandall et al, 2007).…”

Section: Carbohydrate Synthesismentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

View full text Add to dashboard Cite

This review is the fifth update of the original review, published in 1999, on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2008. The first section of the review covers fundamental studies, fragmentation of carbohydrate ions, use of derivatives and new software developments for analysis of carbohydrate spectra. Among newer areas of method development are glycan arrays, MALDI imaging and the use of ion mobility spectrometry. The second section of the review discusses applications of MALDI MS to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, biopharmaceuticals, glycated proteins, glycolipids, glycosides and various other natural products. There is a short section on the use of MALDI mass spectrometry for the study of enzymes involved in glycan processing and a section on the use of MALDI MS to monitor products of the chemical synthesis of carbohydrates with emphasis on carbohydrate-protein complexes and glycodendrimers. Corresponding analyses by electrospray ionization now appear to outnumber those performed by MALDI and the amount of literature makes a comprehensive review on this technique impractical. However, most of the work relating to sample preparation and glycan synthesis is equally relevant to electrospray and, consequently, those proposing analyses by electrospray should also find material in this review of interest.

show abstract

“…Further 504 studies are needed to assess whether the structural features required for merozoite invasion 505 inhibition are also important in sequestration and rosette inhibition. However, the pursuit of 506 sulfate HLMs as base compounds for novel drug development is supported by several reports 507 of the inhibitory capacity of similar compounds to both disrupt parasite invasion as well as 508 sequestration in in vivo models (11,14,25,73,79,80). 509…”

Section: Activity 430mentioning

confidence: 99%

Identification of Heparin Modifications and Polysaccharide Inhibitors of Plasmodium falciparum Merozoite Invasion That Have Potential for Novel Drug Development

Boyle

Skidmore

Dickerman

et al. 2017

Antimicrob Agents Chemother

View full text Add to dashboard Cite

26Despite recent successful control efforts, malaria remains a leading global health 27 burden. Alarmingly, resistance to current antimalarials is increasing, and the development of 28 new drug families is needed to maintain malaria control. Current antimalarials target the 29 intra-erythrocytic developmental stage of the Plasmodium falciparum life cycle. However, 30 the invasive extracellular parasite form, the merozoite, is also an attractive target for drug 31

show abstract

Sulfated cyclodextrins inhibit the entry of Plasmodium into red blood cells

Cited by 29 publications

References 28 publications

Plasmodium falciparum BAEBL Binds to Heparan Sulfate Proteoglycans on the Human Erythrocyte Surface

Plasmodium falciparum BAEBL Binds to Heparan Sulfate Proteoglycans on the Human Erythrocyte Surface

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Identification of Heparin Modifications and Polysaccharide Inhibitors of Plasmodium falciparum Merozoite Invasion That Have Potential for Novel Drug Development

Contact Info

Product

Resources

About