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Ligand recognition by E- and P-selectin : chemoenzymatic synthesis and inhibitory activity of bivalent sialyl Lewis x derivatives and sialyl Lewis x carboxylic acids

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Supporting_Information_Ligand_recognition_by_E_and_P_selectin.pdf
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1998

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Takayama, Shuichi
Gong, Ke Wei
Weitz-Schmidt, Gabriele
Wong, Chi-Huey

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Journal of Organic Chemistry. 1998, 63(15), pp. 5137-5143. ISSN 0022-3263. eISSN 1520-6904. Available under: doi: 10.1021/jo980350s

Zusammenfassung

Described is the preparation of five sLex dimers and five sLex carboxylic acids by coupling chemoenzymatically synthesized amino-substituted sialyl Lewis x (sLex) derivative 4 to homobifunctional cross-linkers 20-24 of varying chain length. 20-24 were obtained by alkylating low-molecular-weight oligoethylene glycols with tert-butyl bromoacetate and subsequent transformation of the di-tert-butyl esters into disuccinimide esters. The products were assayed for inhibition against binding of a sLea-polymer to immobilized E- and P-selectin. In the E-selectin assay all dimers had lower IC50 values than the sLex monomer. The results show that comparable binding enhancements can be obtained with linkers of completely different length and rigidity. In the P-selectin assay four of the five sLex carboxylic acids displayed significantly improved inhibitory potency. The lowest IC50 value was observed for the compound with the shortest spacer between the sLex moiety and the additional carboxylate, being ca. 20-40 times more potent than unmodified sLex. These findings should be of importance for the design of new multivalent forms of sLex as well as sLex mimetics as high-affinity selectin ligands.

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540 Chemie

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ISO 690WITTMANN, Valentin, Shuichi TAKAYAMA, Ke Wei GONG, Gabriele WEITZ-SCHMIDT, Chi-Huey WONG, 1998. Ligand recognition by E- and P-selectin : chemoenzymatic synthesis and inhibitory activity of bivalent sialyl Lewis x derivatives and sialyl Lewis x carboxylic acids. In: Journal of Organic Chemistry. 1998, 63(15), pp. 5137-5143. ISSN 0022-3263. eISSN 1520-6904. Available under: doi: 10.1021/jo980350s
BibTex
@article{Wittmann1998Ligan-9774,
  year={1998},
  doi={10.1021/jo980350s},
  title={Ligand recognition by E- and P-selectin : chemoenzymatic synthesis and inhibitory activity of bivalent sialyl Lewis x derivatives and sialyl Lewis x carboxylic acids},
  number={15},
  volume={63},
  issn={0022-3263},
  journal={Journal of Organic Chemistry},
  pages={5137--5143},
  author={Wittmann, Valentin and Takayama, Shuichi and Gong, Ke Wei and Weitz-Schmidt, Gabriele and Wong, Chi-Huey}
}
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    <dcterms:abstract xml:lang="eng">Described is the preparation of five sLex dimers and five sLex carboxylic acids by coupling chemoenzymatically synthesized amino-substituted sialyl Lewis x (sLex) derivative 4 to homobifunctional cross-linkers 20-24 of varying chain length. 20-24 were obtained by alkylating low-molecular-weight oligoethylene glycols with tert-butyl bromoacetate and subsequent transformation of the di-tert-butyl esters into disuccinimide esters. The products were assayed for inhibition against binding of a sLea-polymer to immobilized E- and P-selectin. In the E-selectin assay all dimers had lower IC50 values than the sLex monomer. The results show that comparable binding enhancements can be obtained with linkers of completely different length and rigidity. In the P-selectin assay four of the five sLex carboxylic acids displayed significantly improved inhibitory potency. The lowest IC50 value was observed for the compound with the shortest spacer between the sLex moiety and the additional carboxylate, being ca. 20-40 times more potent than unmodified sLex. These findings should be of importance for the design of new multivalent forms of sLex as well as sLex mimetics as high-affinity selectin ligands.</dcterms:abstract>
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