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Research ArticleArticle

2-Aminoethoxydiphenyl Borate as a Prototype Drug for a Group of Structurally Related Calcium Channel Blockers in Human Platelets

Yuliya Dobrydneva, Christopher J. Abelt, Beth Dovel, Celina M. Thadigiri, Roy L. Williams and Peter F. Blackmore
Molecular Pharmacology January 2006, 69 (1) 247-256; DOI: https://doi.org/10.1124/mol.105.015701
Yuliya Dobrydneva
Department of Physiological Sciences, Eastern Virginia Medical School, Norfolk, Virginia (Y.D., P.F.B.); Department of Chemistry and Biochemistry, Old Dominion University, Norfolk, Virginia (B.D., C.M.T., R.L.W.); and Department of Chemistry, The College of William and Mary, Williamsburg, Virginia (C.J.A.)
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Christopher J. Abelt
Department of Physiological Sciences, Eastern Virginia Medical School, Norfolk, Virginia (Y.D., P.F.B.); Department of Chemistry and Biochemistry, Old Dominion University, Norfolk, Virginia (B.D., C.M.T., R.L.W.); and Department of Chemistry, The College of William and Mary, Williamsburg, Virginia (C.J.A.)
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Beth Dovel
Department of Physiological Sciences, Eastern Virginia Medical School, Norfolk, Virginia (Y.D., P.F.B.); Department of Chemistry and Biochemistry, Old Dominion University, Norfolk, Virginia (B.D., C.M.T., R.L.W.); and Department of Chemistry, The College of William and Mary, Williamsburg, Virginia (C.J.A.)
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Celina M. Thadigiri
Department of Physiological Sciences, Eastern Virginia Medical School, Norfolk, Virginia (Y.D., P.F.B.); Department of Chemistry and Biochemistry, Old Dominion University, Norfolk, Virginia (B.D., C.M.T., R.L.W.); and Department of Chemistry, The College of William and Mary, Williamsburg, Virginia (C.J.A.)
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Roy L. Williams
Department of Physiological Sciences, Eastern Virginia Medical School, Norfolk, Virginia (Y.D., P.F.B.); Department of Chemistry and Biochemistry, Old Dominion University, Norfolk, Virginia (B.D., C.M.T., R.L.W.); and Department of Chemistry, The College of William and Mary, Williamsburg, Virginia (C.J.A.)
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Peter F. Blackmore
Department of Physiological Sciences, Eastern Virginia Medical School, Norfolk, Virginia (Y.D., P.F.B.); Department of Chemistry and Biochemistry, Old Dominion University, Norfolk, Virginia (B.D., C.M.T., R.L.W.); and Department of Chemistry, The College of William and Mary, Williamsburg, Virginia (C.J.A.)
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Abstract

We have synthesized a series of 2-aminoethoxydiphenyl borate (2-APB, 2,2-diphenyl-1,3,2-oxazaborolidine) analogs and tested their ability to inhibit thrombin-induced Ca2+ influx in human platelets. The analogs were either synthesized by adding various substituents to the oxazaborolidine ring (methyl, dimethyl, tert-butyl, phenyl, methyl phenyl, and pyridyl) or increasing the size of the oxazaborolidine ring to seven- and nine-membered rings. NMR analysis of the boron-containing analogs suggests that each of them exist as a ring structure through the formation of an N→B coordinate bond (except for the hexyl analog). The possibility that these boron-containing compounds formed dimers was also considered. All compounds dose-dependently inhibited thrombin-induced Ca2+ influx in human platelets, with the 2,2-diphenyl-1,3,2-oxazaborolidine-5-one derivative having the weakest activity at 100 μM, whereas the (S)-4-benzyl and (R)-4-benzyl derivatives of 2-APB were approximately 10 times more potent than the parent 2-APB. Two nonboron analogs (3-methyl and 3-tert-butyl 2,2-diphenyl-1,3-oxazolidine) were synthesized; they had approximately the same activity as 2-APB, and this implies that the presence of boron was not necessary for inhibitory activity. All of the compounds tested were also able to inhibit thrombin-induced calcium release. We concluded that extensive modifications of the oxazaborolidine ring in 2-APB can be made, and Ca2+-blocking activity was maintained.

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Molecular Pharmacology: 69 (1)
Molecular Pharmacology
Vol. 69, Issue 1
1 Jan 2006
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Research ArticleArticle

2-Aminoethoxydiphenyl Borate as a Prototype Drug for a Group of Structurally Related Calcium Channel Blockers in Human Platelets

Yuliya Dobrydneva, Christopher J. Abelt, Beth Dovel, Celina M. Thadigiri, Roy L. Williams and Peter F. Blackmore
Molecular Pharmacology January 1, 2006, 69 (1) 247-256; DOI: https://doi.org/10.1124/mol.105.015701

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Research ArticleArticle

2-Aminoethoxydiphenyl Borate as a Prototype Drug for a Group of Structurally Related Calcium Channel Blockers in Human Platelets

Yuliya Dobrydneva, Christopher J. Abelt, Beth Dovel, Celina M. Thadigiri, Roy L. Williams and Peter F. Blackmore
Molecular Pharmacology January 1, 2006, 69 (1) 247-256; DOI: https://doi.org/10.1124/mol.105.015701
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