Skip to main content
PMC home page
Proceedings of the National Academy of Sciences of the United States of America logoLink to Proceedings of the National Academy of Sciences of the United States of America
. 1988 Jan;85(1):88–92. doi: 10.1073/pnas.85.1.88

Isolation of 1-monomethylphosphoinositol 4,5-bisphosphate [a product of methanolysis of inositol 1,2-(cyclic)-4,5-trisphosphate] from Swiss mouse 3T3 cells.

D L Lips 1, T E Bross 1, P W Majerus 1
PMCID: PMC279487  PMID: 3422429

Abstract

We have noted two previously undescribed inositol polyphosphates in neutral methanol extracts from Swiss mouse 3T3 cells that were grown in [3H]inositol and stimulated with platelet-derived growth factor. They have been identified as 1-monomethylphosphoinositol 4,5-bisphosphate and 1-monomethylphosphoinositol 4-phosphate by comparison to a synthesized standard using HPLC chromatography, paper electrophoresis, and enzymatic dephosphorylation with inositol polyphosphate 5-phosphomonoesterase and intestinal alkaline phosphatase [orthophosphoric-monoester phosphohydrolase (alkaline optimum), EC 3.1.3.1]. We propose that these compounds are formed by methanolysis of inositol 1,2-(cyclic)-4,5-trisphosphate and inositol 1,2-(cyclic)-4-bisphosphate present in the cells. Inositol cyclic phosphates did not react with neutral methanol in the absence of the cells, which are required for the methanolysis reaction. These findings suggest a role for inositol cyclic phosphates as reactive compounds that are added to as yet unidentified cellular acceptors.

Full text

PDF
88

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Auchus R. J., Kaiser S. L., Majerus P. W. Synthesis of inositol 1,2-(cyclic)-4,5-trisphosphate. Proc Natl Acad Sci U S A. 1987 Mar;84(5):1206–1209. doi: 10.1073/pnas.84.5.1206. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Berridge M. J., Irvine R. F. Inositol trisphosphate, a novel second messenger in cellular signal transduction. Nature. 1984 Nov 22;312(5992):315–321. doi: 10.1038/312315a0. [DOI] [PubMed] [Google Scholar]
  3. Binder H., Weber P. C., Siess W. Separation of inositol phosphates and glycerophosphoinositol phosphates by high-performance liquid chromatography. Anal Biochem. 1985 Jul;148(1):220–227. doi: 10.1016/0003-2697(85)90649-9. [DOI] [PubMed] [Google Scholar]
  4. Cohen P., Broekman M. J., Verkley A., Lisman J. W., Derksen A. Quantification of human platelet inositides and the influence of ionic environment on their incorporation of orthophosphate-32P. J Clin Invest. 1971 Apr;50(4):762–772. doi: 10.1172/JCI106547. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Connolly T. M., Bansal V. S., Bross T. E., Irvine R. F., Majerus P. W. The metabolism of tris- and tetraphosphates of inositol by 5-phosphomonoesterase and 3-kinase enzymes. J Biol Chem. 1987 Feb 15;262(5):2146–2149. [PubMed] [Google Scholar]
  6. Connolly T. M., Bross T. E., Majerus P. W. Isolation of a phosphomonoesterase from human platelets that specifically hydrolyzes the 5-phosphate of inositol 1,4,5-trisphosphate. J Biol Chem. 1985 Jul 5;260(13):7868–7874. [PubMed] [Google Scholar]
  7. Dawson R. M., Freinkel N., Jungalwala F. B., Clarke N. The enzymic formation of myoinositol 1:2-cyclic phosphate from phosphatidylinositol. Biochem J. 1971 May;122(4):605–607. doi: 10.1042/bj1220605. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Dixon J. F., Hokin L. E. The formation of inositol 1,2-cyclic phosphate on agonist stimulation of phosphoinositide breakdown in mouse pancreatic minilobules. Evidence for direct phosphodiesteratic cleavage of phosphatidylinositol. J Biol Chem. 1985 Dec 25;260(30):16068–16071. [PubMed] [Google Scholar]
  9. Downes C. P., Mussat M. C., Michell R. H. The inositol trisphosphate phosphomonoesterase of the human erythrocyte membrane. Biochem J. 1982 Apr 1;203(1):169–177. doi: 10.1042/bj2030169. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. GRADO C., BALLOU C. E. Myo-inositol phosphates obtained by alkaline hydrolysis of beef brain phosphoinositide. J Biol Chem. 1961 Jan;236:54–60. [PubMed] [Google Scholar]
  11. Graham R. A., Meyer R. A., Szwergold B. S., Brown T. R. Observation of myo-inositol 1,2-(cyclic) phosphate in a Morris hepatoma by 31P NMR. J Biol Chem. 1987 Jan 5;262(1):35–37. [PubMed] [Google Scholar]
  12. Hawkins P. T., Berrie C. P., Morris A. J., Downes C. P. Inositol 1,2-cyclic 4,5-trisphosphate is not a product of muscarinic receptor-stimulated phosphatidylinositol 4,5-bisphosphate hydrolysis in rat parotid glands. Biochem J. 1987 Apr 1;243(1):211–218. doi: 10.1042/bj2430211. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Hofmann S. L., Majerus P. W. Identification and properties of two distinct phosphatidylinositol-specific phospholipase C enzymes from sheep seminal vesicular glands. J Biol Chem. 1982 Jun 10;257(11):6461–6469. [PubMed] [Google Scholar]
  14. Hokin L. E. Receptors and phosphoinositide-generated second messengers. Annu Rev Biochem. 1985;54:205–235. doi: 10.1146/annurev.bi.54.070185.001225. [DOI] [PubMed] [Google Scholar]
  15. Ishii H., Connolly T. M., Bross T. E., Majerus P. W. Inositol cyclic triphosphate [inositol 1,2-(cyclic)-4,5-triphosphate] is formed upon thrombin stimulation of human platelets. Proc Natl Acad Sci U S A. 1986 Sep;83(17):6397–6401. doi: 10.1073/pnas.83.17.6397. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. Koch M. A., Diringer H. Isolation of cyclic inositol-1,2-phosphate from mammalian cells and a probable function of phosphatidylinositol turnover. Biochem Biophys Res Commun. 1974 May 20;58(2):361–367. doi: 10.1016/0006-291x(74)90373-8. [DOI] [PubMed] [Google Scholar]
  17. Majerus P. W., Connolly T. M., Deckmyn H., Ross T. S., Bross T. E., Ishii H., Bansal V. S., Wilson D. B. The metabolism of phosphoinositide-derived messenger molecules. Science. 1986 Dec 19;234(4783):1519–1526. doi: 10.1126/science.3024320. [DOI] [PubMed] [Google Scholar]
  18. Nishizuka Y. Studies and perspectives of protein kinase C. Science. 1986 Jul 18;233(4761):305–312. doi: 10.1126/science.3014651. [DOI] [PubMed] [Google Scholar]
  19. Ross T. S., Majerus P. W. Isolation of D-myo-inositol 1:2-cyclic phosphate 2-inositolphosphohydrolase from human placenta. J Biol Chem. 1986 Aug 25;261(24):11119–11123. [PubMed] [Google Scholar]
  20. SPIRO R. G., SPIRO M. J. THE CARBOHYDRATE COMPOSITION OF THE THYROGLOBULINS FROM SEVERAL SPECIES. J Biol Chem. 1965 Mar;240:997–1001. [PubMed] [Google Scholar]
  21. Seiffert U. B., Agranoff B. W. Isolation and separation of inositol phosphates from hydrolysates of rat tissues. Biochim Biophys Acta. 1965 Jun 1;98(3):574–581. doi: 10.1016/0005-2760(65)90154-2. [DOI] [PubMed] [Google Scholar]
  22. Sekar M. C., Dixon J. F., Hokin L. E. The formation of inositol 1,2-cyclic 4,5-trisphosphate and inositol 1,2-cyclic 4-bisphosphate on stimulation of mouse pancreatic minilobules with carbamylcholine. J Biol Chem. 1987 Jan 5;262(1):340–344. [PubMed] [Google Scholar]
  23. Shayman J. A., Auchus R. J., Morrison A. R. Bradykinin-induced changes in myo-inositol 1,2-(cyclic)phosphate in rabbit papillary collecting tubule cells. Biochim Biophys Acta. 1986 Sep 19;888(2):171–175. doi: 10.1016/0167-4889(86)90018-2. [DOI] [PubMed] [Google Scholar]
  24. TREVELYAN W. E., PROCTER D. P., HARRISON J. S. Detection of sugars on paper chromatograms. Nature. 1950 Sep 9;166(4219):444–445. doi: 10.1038/166444b0. [DOI] [PubMed] [Google Scholar]
  25. Wilson D. B., Bross T. E., Hofmann S. L., Majerus P. W. Hydrolysis of polyphosphoinositides by purified sheep seminal vesicle phospholipase C enzymes. J Biol Chem. 1984 Oct 10;259(19):11718–11724. [PubMed] [Google Scholar]
  26. Wilson D. B., Bross T. E., Sherman W. R., Berger R. A., Majerus P. W. Inositol cyclic phosphates are produced by cleavage of phosphatidylphosphoinositols (polyphosphoinositides) with purified sheep seminal vesicle phospholipase C enzymes. Proc Natl Acad Sci U S A. 1985 Jun;82(12):4013–4017. doi: 10.1073/pnas.82.12.4013. [DOI] [PMC free article] [PubMed] [Google Scholar]
  27. Wilson D. B., Connolly T. M., Bross T. E., Majerus P. W., Sherman W. R., Tyler A. N., Rubin L. J., Brown J. E. Isolation and characterization of the inositol cyclic phosphate products of polyphosphoinositide cleavage by phospholipase C. Physiological effects in permeabilized platelets and Limulus photoreceptor cells. J Biol Chem. 1985 Nov 5;260(25):13496–13501. [PubMed] [Google Scholar]

Articles from Proceedings of the National Academy of Sciences of the United States of America are provided here courtesy of National Academy of Sciences

RESOURCES