Potent small molecule mouse CD22-inhibitors: Exploring the interaction of the residue at C-2 of sialic acid scaffold

Hajjaj H.M. Abdu-Allah; Kozo Watanabe; Koji Hayashizaki; Chiaki Takaku; Taichi Tamanaka; Hiromu Takematsu; Yasunori Kozutsumi; Takeshi Tsubata; Hideharu Ishida; Makoto Kiso

doi:10.1016/j.bmcl.2009.08.044

Potent small molecule mouse CD22-inhibitors: Exploring the interaction of the residue at C-2 of sialic acid scaffold

Hajjaj H.M. Abdu-Allah, Kozo Watanabe, Koji Hayashizaki, Chiaki Takaku, Taichi Tamanaka, Hiromu Takematsu, Yasunori Kozutsumi, Takeshi Tsubata, Hideharu Ishida, Makoto Kiso

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

Our previous study revealed that compound 1 (9-(4′-hydroxy-4-biphenyl)acetamido-9-deoxy-Neu5Gcα2-6GalOMP) has the most promising affinity for mCD22. Replacing the subterminal galactose residue of 1 with benzyl or biphenylmethyl as aglycone led to 38- and 20-fold higher potency, respectively. This discovery represents a new direction in inhibitor design suitable for pharmaceutical development.

Original language	English
Pages (from-to)	5573-5575
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	19
Issue number	19
DOIs	https://doi.org/10.1016/j.bmcl.2009.08.044
Publication status	Published - 01-10-2009
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2009.08.044

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Abdu-Allah, H. H. M., Watanabe, K., Hayashizaki, K., Takaku, C., Tamanaka, T., Takematsu, H., Kozutsumi, Y., Tsubata, T., Ishida, H., & Kiso, M. (2009). Potent small molecule mouse CD22-inhibitors: Exploring the interaction of the residue at C-2 of sialic acid scaffold. Bioorganic and Medicinal Chemistry Letters, 19(19), 5573-5575. https://doi.org/10.1016/j.bmcl.2009.08.044

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title = "Potent small molecule mouse CD22-inhibitors: Exploring the interaction of the residue at C-2 of sialic acid scaffold",

abstract = "Our previous study revealed that compound 1 (9-(4′-hydroxy-4-biphenyl)acetamido-9-deoxy-Neu5Gcα2-6GalOMP) has the most promising affinity for mCD22. Replacing the subterminal galactose residue of 1 with benzyl or biphenylmethyl as aglycone led to 38- and 20-fold higher potency, respectively. This discovery represents a new direction in inhibitor design suitable for pharmaceutical development.",

keywords = "CD22, ELISA, Hanessian reaction, Inhibitor, Sialoside",

author = "Abdu-Allah, {Hajjaj H.M.} and Kozo Watanabe and Koji Hayashizaki and Chiaki Takaku and Taichi Tamanaka and Hiromu Takematsu and Yasunori Kozutsumi and Takeshi Tsubata and Hideharu Ishida and Makoto Kiso",

note = "Funding Information: H.H.M.A. is grateful to the Egyptian Government for Ph.D. funding scholarship. This work was partly supported by the ministry of Education, Culture, Sports, Science, and Technology (MEXT) of Japan (Grant-in-Aid for Scientific Research to M. Kiso, No. 17101007) and CREST of JST (Japan Science and Technology Corporation). ",

year = "2009",

month = oct,

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doi = "10.1016/j.bmcl.2009.08.044",

language = "English",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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Abdu-Allah, HHM, Watanabe, K, Hayashizaki, K, Takaku, C, Tamanaka, T, Takematsu, H, Kozutsumi, Y, Tsubata, T, Ishida, H & Kiso, M 2009, 'Potent small molecule mouse CD22-inhibitors: Exploring the interaction of the residue at C-2 of sialic acid scaffold', Bioorganic and Medicinal Chemistry Letters, vol. 19, no. 19, pp. 5573-5575. https://doi.org/10.1016/j.bmcl.2009.08.044

TY - JOUR

T1 - Potent small molecule mouse CD22-inhibitors

T2 - Exploring the interaction of the residue at C-2 of sialic acid scaffold

AU - Abdu-Allah, Hajjaj H.M.

AU - Watanabe, Kozo

AU - Hayashizaki, Koji

AU - Takaku, Chiaki

AU - Tamanaka, Taichi

AU - Takematsu, Hiromu

AU - Kozutsumi, Yasunori

AU - Tsubata, Takeshi

AU - Ishida, Hideharu

AU - Kiso, Makoto

N1 - Funding Information: H.H.M.A. is grateful to the Egyptian Government for Ph.D. funding scholarship. This work was partly supported by the ministry of Education, Culture, Sports, Science, and Technology (MEXT) of Japan (Grant-in-Aid for Scientific Research to M. Kiso, No. 17101007) and CREST of JST (Japan Science and Technology Corporation).

PY - 2009/10/1

Y1 - 2009/10/1

N2 - Our previous study revealed that compound 1 (9-(4′-hydroxy-4-biphenyl)acetamido-9-deoxy-Neu5Gcα2-6GalOMP) has the most promising affinity for mCD22. Replacing the subterminal galactose residue of 1 with benzyl or biphenylmethyl as aglycone led to 38- and 20-fold higher potency, respectively. This discovery represents a new direction in inhibitor design suitable for pharmaceutical development.

AB - Our previous study revealed that compound 1 (9-(4′-hydroxy-4-biphenyl)acetamido-9-deoxy-Neu5Gcα2-6GalOMP) has the most promising affinity for mCD22. Replacing the subterminal galactose residue of 1 with benzyl or biphenylmethyl as aglycone led to 38- and 20-fold higher potency, respectively. This discovery represents a new direction in inhibitor design suitable for pharmaceutical development.

KW - CD22

KW - ELISA

KW - Hanessian reaction

KW - Inhibitor

KW - Sialoside

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SN - 0960-894X

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 19

ER -

Potent small molecule mouse CD22-inhibitors: Exploring the interaction of the residue at C-2 of sialic acid scaffold

Abstract

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