Synthesis of Phosphatidic Acid Analogues
J ournal of Medicinal Chemistry, 2002, Vol. 45, No. 8 1685
(21) Menger, F. M.; Wood, M. G.; Richardson, S., J r.; Zhou, Q.;
Elrington, A. R.; Sherrod, M. J . Chain-Substituted Lipids in
Monolayer Films. A Study of Molecular Packing. J . Am. Chem.
Soc. 1988, 110, 6797-6803.
(22) Swinnen, J . V.; D’Souza, B.; Conti, M.; Ascoli, M. Attenuation
of cAMP-mediated Responses in MA-10 Leydig Tumor Cells by
Genetic Manipulation of a cAMP-Phosphodiesterase. J . Biol.
Chem. 1991, 266, 14383-14389.
(23) J in, S. L.; Swinnen, J . V.; Conti, M. Characterization of the
Structure of a Low Km, Rolipram-Sensitive cAMP Phosphodi-
esterase. Mapping of the Catalytic Domain. J . Biol. Chem. 1992,
267, 18929-18939.
(24) Thompson, W. J .; Appleman, M. M. Multiple Cyclic Nucleotide
Phophodiesterase Activities from Rat Brain. Biochemistry 1971,
10, 31.
Refer en ces
(1) Conti, M. G.; Nemoz, G.; Sette, C.; Vicini, E. Recent Progress in
Understanding the Hormonal Regulation of Phosphodiesterases.
Endocr. Rev. 1995, 16, 370-389.
(2) Mackenzie, S. J .; Yarwood, S. J .; Peden, A. H.; Bolger, G. B.;
Vernon, R. G.; Houslay, M. D. Stimulation of p70S6 Kinase via
a Growth Hormone-Controlled Phosphatidylinositol 3 Kinase
Pathway Leads to the Activation of a PDE4A Cyclic AMP-
Specific Phosphodiesterase in 3T3-F442A Preadipocytes. Proc.
Natl. Acad. Sci. U.S.A. 1998, 95, 3549-3554.
(3) Naro, F.; Sette, C.; Vicini, E.; De Arcangelis, V.; Grange, M.;
Conti, M.; Lagarde, M.; Molinaro, M.; Adamo, S.; Nemoz, G.
Involvement of Type 4 cAMP-Phosphodiesterase in the Myo-
genic Differentiation of L6 Cells. Mol. Biol. Cell 1999, 10, 4355-
4367.
(4) Oki, N.; Takahashi, S. I.; Hidaka, H.; Conti, M. Short-Term
Feedback Regulation of cAMP in FRTL-5 Thyroid Cells. Role of
PDE4D3 Phosphodiesterase Activation. J . Biol. Chem. 2000, 275,
10831-10837.
(5) Chini, C. C.; Grande, J . P.; Chini, E. N.; Dousa, T. P. Compart-
mentalization of cAMP Signaling in Mesangial Cells by Phos-
phodiesterase Isozymes PDE3 and PDE4. Regulation of Super-
oxidation and Mitogenesis. J . Biol. Chem. 1997, 272, 9854-9859.
(6) J in, S.-L.; Richard, F. J .; Kuo, W. P.; D’Ercole, A. J .; Conti, M.
Impaired Growth and Fertility of cAMP-Specific Phosphodi-
esterase PDE4D-Deficient Mice. Proc. Natl. Acad. Sci. U.S.A.
1999, 96, 11998-12003.
(7) Hansen, G.; J in, S.-L.; Umetsu, D.; Conti, M. Absence of
Muscarinic Cholinergic Airway Responses in Mice Deficient in
the Cyclic Nucleotide Phosphodiesterase PDE4D. Proc. Natl.
Acad. Sci. U.S.A. 2000, 97, 6751-6756.
(8) Torphy, T. J . Phosphodiesterases: The J ourney Towards Thera-
peutics. Trends Pharmacol. Sci. 2000, 21, 157-159.
(9) Ha¨fner, D.; Germann, P.-G. Additive Effects of Phosphodi-
esterase-4 Inhibition on Effects of SP-C Surfactant. Am. J .
Respir. Crit. Care Med. 2000, 161, 1495-1500.
(10) Nemoz, G.; Sette, C.; Conti, M. Selective activation of rolipram-
sensitive cAMP-specific phosphodiesterase isoforms by phos-
phatidic acid. Mol. Pharmacol. 1997, 51, 242-249.
(11) English, D. Phosphatidic Acid: A Lipid Messenger Involved in
Intracellular and Extracellular Signalling. Cell. Signalling 1996,
8, 341-347.
(12) Flores, I.; Casaceca, T.; Martinez-A, C.; Kanoh, H.; Merida, I.
Phosphatidic Acid Generation through Interleukin 2 (IL-2)-
Induced Alpha-diacylglycerol Kinase Activation Is an Essential
Step in IL-2-Mediated Lymphocyte Proliferation. J . Biol. Chem.
1996, 271, 10334-10340.
(13) Grange, M.; Sette, C.; Cuomo, M.; Conti, M.; Lagarde, M.;
Prigent, A. F.; Nemoz, G. The cAMP-Specific Phosphodiesterase
PDE4D3 Is Regulated by Phosphatidic Acid Binding. J . Biol.
Chem. 2000, 275, 33379-33387.
(14) Zakaroff-Girard, A.; El Bawab, S.; Nemoz, G.; Lagarde, M.;
Prigent, A. F. Relationships between Phosphatidic Acid and
Cyclic Nucleotide Phosphodiesterases in Activated Human Blood
Mononuclear Cells. J . Leukocyte Biol. 1999, 65, 381-390.
(15) Tomic, S.; Greiser, U.; Lammers, R.; Kharitonenkov, A.; Imya-
nitov, E.; Ulrich, A.; Bohmer, F. D. Association of SH2 Domain
Protein Tyrosine Phosphatases with the Epidermal Growth
Factor Receptor in Human Tumor Cells. Phosphatidic Acid
Activates Receptor Dephosphorylation by PTP1C. J . Biol. Chem.
1995, 270, 21277-21284.
(16) Ghosh, S.; Strum, J . C.; Sciorra, V. A.; Daniel, L.; Bell, R. M.
Raf-1 Kinase Possesses Distinct Binding Domains for Phos-
phatidylserine and Phosphatidic Acid. J . Biol. Chem. 1996, 271,
8472-8480.
(25) Sette, C.; Conti, M. Phosphorylation and activation of a cAMP-
specific phosphodiesterase by the cAMP-dependent protein
kinase. J . Biol. Chem. 1996, 271, 16526-16534.
(26) (a) Alcaraz, M. L.; Peng, L.; Klotz, P.; Goeldner, M. Synthesis
and Properties of Photoactivable Phospholipid Derivatives De-
signed To Probe the Membrane-Associate Domain of Proteins.
J . Org. Chem. 1996, 61, 192-201. (b) Bisson, R.; Montecucco,
C. Photolabelling of membrane proteins with photoactive phos-
pholipids. Biochem. J . 1981, 193, 757-763. (c) Pradhan, D.;
Williamson, P.; Schlegel, R. A. Bilayer/cytoskeleton interactions
in lipid-symmetric erythrocytes assessed by a photoactivable
phospholipid analogue. Biochemistry 1991, 31, 7754-7758. (d)
Borle, F.; Sanger, M.; Sigrist, H. Planar bilayer membranes from
photoactivable phospholipids. Biochim. Biophys. Acta 1991,
1066, 144-150. (e) Van der Bend, R. L.; Brunner, J .; J alink, K.;
van Corven, E. J .; Moolenaar, W. H.; van Blitterswijk, W. J .
Identification of a putative membrane receptor for the bioactive
phospholipid lysophosphatidic acid. EMBO J . 1992, 11, 2495-
2501. (f) Desneves, J .; Berman, A.; Dynan, K.; La Greca, N.;
Foley, M.; Tilley, L. Human erythrocyte band 7.2b is preferen-
tially labeled by a photoreactive phospholipid. Biochem. Biophys.
Res. Commun. 1996, 224, 108-114. (g) Tall, E.; Dorman, G.;
Garcia, P.; Runnels, L.; Shah, S.; Chen, J .; Profit, A.; Gu, Q. M.;
Chaudhary, A.; Prestwich, G. D.; Rebecchi, M. J . Phosphoino-
sotide binding specificity among phospholipase C isozymes as
determined by photo-cross-linking to novel substrate and product
analogs. Biochemistry 1997, 36, 7239-7248. (h) Zegers, M. M.;
Kok, J . W.; Hoekstra, D. Use of photoactivable analogues to
monitor lipid transport in mammalian cells. Biochem. J . 1997,
328, 489-498.
(27) El Bawab, S.; Macovschi, O.; Sette, C.; Conti, M.; Lagarde, M.;
Ne´moz, G.; Prigent, A. F. Selective Stimulation of a cAMP-
Specific Phosphodiesterase (PDE4A5) Isoform by Phosphatidic
Acid Molecular Species Endogenously Formed in Rat Thy-
mocytes. Eur. J . Biochem. 1997, 247, 1151-1157.
(28) Leyva, E.; Munoz, D.; Platz, M. S. Photochemistry of fluorinated
aryl azides in toluene solution and in frozen polycrystals. J . Org.
Chem. 1989, 54, 5938-5945.
(29) Pinney, K. G.; Katzenellenbogen, J . A. Synthesis of tetrafluoro-
substituted aryl azides and its protio analogues as photolabeling
affinity reagents for the estrogen receptor. J . Org. Chem. 1991,
56, 3125-3133.
(30) Croset, M.; Brossard, N.; Polette, A.; Lagarde, M. Characteriza-
tion of Plasma Unsaturated Lysophosphatidylcholines in Human
and Rat. Biochem. J . 2000, 345, 61-67.
(31) Ho¨fle, G.; Steglich, W.; Vorbru¨ggen, H. 4-Dialkylaminopyridines
as higly active acylation catalysts. Angew. Chem. 1978, 17, 569-
583.
(32) Gupta, C. M.; Radhakrishnan, R.; Khorana, H. G. Glycerophos-
pholipid Synthesis: Improved General Methods and New Ana-
logs Containing Photoactivable Groups. Proc. Natl. Acad. Sci.
U.S.A. 1977, 74, 4315-4319.
(33) Ali, C.; Bittman, L. Mixed-Chain Phosphatidylcholine Analogues
Modified in the Choline Moiety: Preparation of Isomerically
Pure Phospholipids with Bulky Head Groups and One Acyl
Chain Twice as Long as the Other. Chem. Phys. Lipids 1989,
50, 11-21.
(34) Giembycz, M. A. Phosphodiesterase 4 Inhibitors and the Treat-
ment of Asthma: Where Are We Now and Where Do We Go
From Here? Drugs 2000, 59, 193-212.
(17) Limatola, C.; Schaap, D.; Moolenaar, W. H.; Van Blitterswijk,
W. J . Phosphatidic Acid Activation of Protein Kinase C-zeta
Overexpressed in COS Cells: Comparison with Other Protein
Kinase C Isotypes and Other Acidic Lipids. Biochem. J . 1994,
15, 1001-1008.
(18) Pawelczyk, T.; Matecki, A. Phospholipase C-delta3 Binds with
High Specificity to Phosphatidylinositol 4,5-Bisphosphate and
Phosphatidic Acid in Bilayer Membranes. Eur. J . Biochem. 1999,
262, 291-298.
(19) Grange, M.; Picq, M.; Prigent, A. F.; Lagarde, M.; Nemoz, G.
Regulation of PDE-4cAMP Phosphodiesterases by Phosphatidic
Acid. Cell. Biochem. Biophys. 1998, 29, 1-17.
(20) Keana, J . F. W.; Cai, S. X. New Reagents for Photoaffinity
Labeling Synthesis and Photolysis of Functionalized Perfluo-
rophenyl Azides. J . Org. Chem. 1990, 55, 3640-3647.
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