Synthesis of 1d-3-Deoxy-, 1d-2,3-Dideoxy-, and 1d-2,3,6-Trideoxy-myo-inositol 1,4,5-Trisphosphate from Quebrachitol, Their Binding Affinities, and Calcium Release Activity

A. P. Kozikowski; A. P. Kozikowski; V. I. Ognyanov; A. H. Fauq; S. R. Nahorski; R. A. Wilcox

doi:10.1021/ja00064a002

Synthesis of 1d-3-Deoxy-, 1d-2,3-Dideoxy-, and 1d-2,3,6-Trideoxy-myo-inositol 1,4,5-Trisphosphate from Quebrachitol, Their Binding Affinities, and Calcium Release Activity

A. P. Kozikowski, A. P. Kozikowski, V. I. Ognyanov, A. H. Fauq, S. R. Nahorski, R. A. Wilcox

School of Medicine

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

75 Scopus citations

Abstract

Syntheses of three optically pure, deoxygenated myo-inositol 1,4,5-trisphosphate analogues from quebrachitol are reported together with their binding affinities and ⁴⁵Ca²⁺ release activity. The ligand-binding affinities of the analogues were determined using membrane preparations from bovine adrenal cortex. The ⁴⁵Ca²⁺ release activities were compared to that of Ins(1,4,5)P₃, using the calcium mobilizing receptor of saponin permeabilized SH-SY5Y human neuroblastoma cells. 1d-3-deoxy-Ins(1,4,5)P₃ (26) and 1d-2,3-dideoxy-Ins(1,4,5)P₃ (22) exhibited very potent ligand and agonist properties, while 1d-2,3,6-trideoxy-Ins(1,4,5)P₃ (19) was much less potent. These data provide solid evidence of the critical role which HO-6 of Ins(1,4,5)P₃ plays in its binding affinity and its Ca²⁺ mobilizing activity.

Original language	English (US)
Pages (from-to)	4429-4434
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	115
Issue number	11
DOIs	https://doi.org/10.1021/ja00064a002
State	Published - May 1 1993

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja00064a002

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Kozikowski, A. P., Kozikowski, A. P., Ognyanov, V. I., Fauq, A. H., Nahorski, S. R., & Wilcox, R. A. (1993). Synthesis of 1d-3-Deoxy-, 1d-2,3-Dideoxy-, and 1d-2,3,6-Trideoxy-myo-inositol 1,4,5-Trisphosphate from Quebrachitol, Their Binding Affinities, and Calcium Release Activity. Journal of the American Chemical Society, 115(11), 4429-4434. https://doi.org/10.1021/ja00064a002

Synthesis of 1d-3-Deoxy-, 1d-2,3-Dideoxy-, and 1d-2,3,6-Trideoxy-myo-inositol 1,4,5-Trisphosphate from Quebrachitol, Their Binding Affinities, and Calcium Release Activity. / Kozikowski, A. P.; Kozikowski, A. P.; Ognyanov, V. I. et al.
In: Journal of the American Chemical Society, Vol. 115, No. 11, 01.05.1993, p. 4429-4434.

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

Kozikowski, AP, Kozikowski, AP, Ognyanov, VI, Fauq, AH, Nahorski, SR & Wilcox, RA 1993, 'Synthesis of 1d-3-Deoxy-, 1d-2,3-Dideoxy-, and 1d-2,3,6-Trideoxy-myo-inositol 1,4,5-Trisphosphate from Quebrachitol, Their Binding Affinities, and Calcium Release Activity', Journal of the American Chemical Society, vol. 115, no. 11, pp. 4429-4434. https://doi.org/10.1021/ja00064a002

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title = "Synthesis of 1d-3-Deoxy-, 1d-2,3-Dideoxy-, and 1d-2,3,6-Trideoxy-myo-inositol 1,4,5-Trisphosphate from Quebrachitol, Their Binding Affinities, and Calcium Release Activity",

abstract = "Syntheses of three optically pure, deoxygenated myo-inositol 1,4,5-trisphosphate analogues from quebrachitol are reported together with their binding affinities and 45Ca2+ release activity. The ligand-binding affinities of the analogues were determined using membrane preparations from bovine adrenal cortex. The 45Ca2+ release activities were compared to that of Ins(1,4,5)P3, using the calcium mobilizing receptor of saponin permeabilized SH-SY5Y human neuroblastoma cells. 1d-3-deoxy-Ins(1,4,5)P3 (26) and 1d-2,3-dideoxy-Ins(1,4,5)P3 (22) exhibited very potent ligand and agonist properties, while 1d-2,3,6-trideoxy-Ins(1,4,5)P3 (19) was much less potent. These data provide solid evidence of the critical role which HO-6 of Ins(1,4,5)P3 plays in its binding affinity and its Ca2+ mobilizing activity.",

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AU - Kozikowski, A. P.

AU - Ognyanov, V. I.

AU - Fauq, A. H.

AU - Nahorski, S. R.

AU - Wilcox, R. A.

PY - 1993/5/1

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N2 - Syntheses of three optically pure, deoxygenated myo-inositol 1,4,5-trisphosphate analogues from quebrachitol are reported together with their binding affinities and 45Ca2+ release activity. The ligand-binding affinities of the analogues were determined using membrane preparations from bovine adrenal cortex. The 45Ca2+ release activities were compared to that of Ins(1,4,5)P3, using the calcium mobilizing receptor of saponin permeabilized SH-SY5Y human neuroblastoma cells. 1d-3-deoxy-Ins(1,4,5)P3 (26) and 1d-2,3-dideoxy-Ins(1,4,5)P3 (22) exhibited very potent ligand and agonist properties, while 1d-2,3,6-trideoxy-Ins(1,4,5)P3 (19) was much less potent. These data provide solid evidence of the critical role which HO-6 of Ins(1,4,5)P3 plays in its binding affinity and its Ca2+ mobilizing activity.

AB - Syntheses of three optically pure, deoxygenated myo-inositol 1,4,5-trisphosphate analogues from quebrachitol are reported together with their binding affinities and 45Ca2+ release activity. The ligand-binding affinities of the analogues were determined using membrane preparations from bovine adrenal cortex. The 45Ca2+ release activities were compared to that of Ins(1,4,5)P3, using the calcium mobilizing receptor of saponin permeabilized SH-SY5Y human neuroblastoma cells. 1d-3-deoxy-Ins(1,4,5)P3 (26) and 1d-2,3-dideoxy-Ins(1,4,5)P3 (22) exhibited very potent ligand and agonist properties, while 1d-2,3,6-trideoxy-Ins(1,4,5)P3 (19) was much less potent. These data provide solid evidence of the critical role which HO-6 of Ins(1,4,5)P3 plays in its binding affinity and its Ca2+ mobilizing activity.

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Synthesis of 1d-3-Deoxy-, 1d-2,3-Dideoxy-, and 1d-2,3,6-Trideoxy-myo-inositol 1,4,5-Trisphosphate from Quebrachitol, Their Binding Affinities, and Calcium Release Activity

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