A reinvestigation of the synthesis of arsonolipids (2,3-diacyloxypropylarsonic acids)

Chemistry and Physics of Lipids

Volumn 152, Issue 2, 2008, Pages 113-121

  Tsivgoulis, Gerasimos M ^a   Ioannou, Panayiotis V ^a  

^a UNIVERSITY OF PATRAS   (Greece)

Author keywords

2,3 Diacyloxypropylarsonic acids; Arsonolipids; Glycidol (2,3 epoxypropanol); Trisodium arsenite

Indexed keywords

2,3 DIHYDROXYPROPYLARSONIC ACID; ACID ANHYDRIDE; ALPHA CHLOROHYDRIN; ARSENIC DERIVATIVE; ARSENITE SODIUM; ARSONOLIPID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DIMER; GLYCEROL; GLYCIDOL; HYDROXYL GROUP; LIPID; PHOSPHOTIDIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; PHOSPHOLIPID SYNTHESIS; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS;

ACYLATION; ARSENICALS; ARSENITES; BINDING, COMPETITIVE; CARBOXYLIC ACIDS; CHEMISTRY, PHYSICAL; CHROMATOGRAPHY, THIN LAYER; DIMERIZATION; GLYCEROL; LIPIDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR STRUCTURE; SODIUM COMPOUNDS;

EID: 41549155559     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2008.02.001     Document Type: Article

References (54)

1. Adams S.R., Sparkes M.J., and Dixon H.B.F. The arsonomethyl analogue of adenosine 5′-phosphate. Biochem. J. 221 (1984) 829-836
2. Albers H., Künzel W., and Schuler W. Zur Kenntnis der acylierten Arsenwasserstoff- und Phosphorwasserstoff-Derivate und der isoarsile. Chem. Ber. 85 (1952) 239-249
3. 13C NMR spectra of rac-2,3-bis(palmitoyloxy)propyl(2-trimethylarsonioethyl) phosphonate, an arsenic-containing phosphonolipid. Magn. Reson. Chem. 28 (1990) 856-861
4. Antimisiaris S.G., Ioannou P.V., and Loiseau P.M. In vitro antileishmanial and trypanocidal activities of arsonoliposomes and preliminary in vivo distribution in BALB/c mice. J. Pharm. Pharmacol. 55 (2003) 647-652
5. Antimisiaris S.G., Klepetsanis P., Zachariou V., Gianopoulou E., and Ioannou P.V. In vivo distribution of arsenic after i.p. injection of arsonoliposomes in balb-c mice. Int. J. Pharm. 289 (2005) 151-158
6. Baer C.D., Edwards J.O., Rieger P.H., and Silva C.M. Reaction kinetics of several alkyl arsenite hydrolyses. Inorg. Chem. 22 (1983) 1402-1404
7. Baer E., and Basu H. Synthesis of α-phosphotidic acids. Can. J. Biochem. 48 (1970) 1010-1013
8. Barber H.J. Some derivatives of arylthioarsinous acids. J. Chem. Soc. (1929) 1020-1024
9. Brill T.B., and Campbell N.C. Arsenites and antimonites. II. Vibrational, nuclear quadrupole resonance, and mass spectral properties of arsenic(III) and antimony(III) esters and thioesters. Inorg. Chem. 12 (1973) 1884-1888
10. Cassel S., Debaig C., Benvegnu T., Chaimbault P., Lafosse M., Plusquellec D., and Rollin P. Original synthesis of linear, branched and cyclic oligoglycerol standards. Eur. J. Org. Chem. (2001) 875-896
11. Chelintsev G.V., and Kuskov B.K. Diadic tautomerism. Zh. Obshch. Khim. 16 (1946) 1481-1484 (Chem. Abs. 41 5441a (1947))
12. Dixon H.B.F. The biochemical action of arsonic acids especially as phosphate analogues. Adv. Inorg. Chem. 44 (1997) 191-227
13. Dworak A., Walach W., and Trzebicka B. Cationic polymerization of glycidol. Polymer structure and polymerization mechanism. Macromol. Chem. Phys. 196 (1995) 1963-1970
14. Eibl H., McIntyre J.O., Fleer E.A.M., and Fleischer S. Synthesis of labeled phospholipids in high yield. Methods Enzym. 98 (1983) 623-632
15. Étiene A. Arsénicaux et antimoniés furyliques-α. II. Arsénicaux primaries, secondaires et tertiaires dérivés du furan non substituté. Bull. Soc. Chim. France (1947) 47-50
16. Faturos D.G., Gortzi O., Klepetsanis P., Antimisiaris S.G., Stuart M.C.A., Brisson A., and Ioannou P.V. Preparation and properties of arsonolipid-containing liposomes. Chem. Phys. Lipids 109 (2001) 75-89
17. Fatouros D.G., Klepetsanis P., Ioannou P.V., and Antimisiaris S.G. The effect of pH on the electrophoretic behaviour of a new class of liposomes: arsonoliposomes. Int. J. Pharm. 288 (2005) 151-156
18. Fatouros D.G., Piperoudi S., Gortzi O., Ioannou P.V., Frederik P., and Antimisiaris S.G. Physical stability of sonicated arsonoliposomes: effect of calcium ions. J. Pharm. Sci. 94 (2005) 46-55
19. Fatouros D.G., Ioannou P.V., and Antimisiaris S.G. Arsonoliposomes: novel nanosized arsenic-containing vesicles for drug delivery. J. Nanosci. Nanotechnol. 6 (2006) 2618-2637
20. Gattow G., and Schwank H. Untersuchungen über Acetate von Elementen der V. Hauptgruppe des Periodensystems. Z. Anorg. Allg. Chem. 382 (1971) 49-60
21. Gortzi O., Klepetsanis P., Antimisiaris S.G., and Ioannou P.V. Capability of arsonolipids to transport divalent cations: a Pressman cell study. Chem. Phys. Lipids 112 (2001) 21-29
22. Gortzi O., Papadimitriou E., Kontoyannis C.G., Antimisiaris S.G., and Ioannou P.V. Arsonoliposomes, a novel class of arsenic-containing liposomes: effect of palmitoyl-arsonolipid-containing liposomes on the viability of cancer and normal cells in culture. Pharm. Res. 19 (2002) 79-86
23. Gortzi O., Antimisiaris S.G., Klepetsanis P., Papadimitriou E., and Ioannou P.V. Arsonoliposomes: effect of arsonolipid acyl chain length and vesicle composition on their toxicity towards cancer and normal cells in culture. Eur. J. Pharm. Sci. 18 (2003) 175-183
24. Gupta C.M., Radhakrishnan R., and Khorana H.G. Glycerophospholipid synthesis: improved general method and new analogs containing photoactivable groups. Proc. Natl. Acad. Sci. U.S.A. 74 (1977) 4315-4319
25. 3As: evidence for binding and activation of triplet dioxygen by arsenic(III). Phosphorus, Sulfur, and Silicon 181 (2006) 363-376
26. Ioannou P.V. On the direct reduction of arsonic acids to arsenoso compounds: mechanisms and preparations. Appl. Organometal. Chem. 14 (2000) 261-272
27. Ioannou P.V. Synthesis of arsinolipids. II. A non-isosteric analogue of fully acylated cardiolipin. Chem. Phys. Lipids 117 (2002) 7-18
28. Ioannou P.V. On C-As bond formation: preparation of aliphatic arsonic acids. Phosphorus, Sulfur, and Silicon 117 (2002) 1-14
29. Kamai G., and Chadaeva N.A. Action of halides and anhydride of acetic acid on glycol esters of phenylarsonous acid. Dokl. Akad. Nauk SSSR 109 (1956) 309-311 (Chem. Abs. 51 1876i (1957))
30. Kamai G., and Chadaeva N.A. Alkyl esters of ethylthioarsinous [ethylthioarsonous] acid. Proc. Acad. Sci. USSR 115 (1957) 717-719
31. Kordalis N.L., and Ioannou P.V. Syntheses of arsinolipids: non-isosteric analogues of phospholipids. Appl. Organometal. Chem. 14 (2000) 273-280
32. Lacoste A.-M., Dumora C., Ali B.R.S., Neuzil E., and Dixon H.B.F. Utilization of 2-aminoethylarsonic acid in Pseudomonas aeruginosa. J. Gen. Microbiol. 138 (1992) 1283-1287
33. Lapidot Y., Barzilay I., and Hajdu J. The synthesis of diacyl-dl- (and -l-) α-glycerol phosphate. Chem. Phys. Lipids 3 (1969) 125-134
34. Mangroo D., and Gerber G.E. Phospholipid synthesis: effects of solvents and catalysts on acylation. Chem. Phys. Lipids 48 (1988) 99-108
35. Meyer G. Ueber einige anomale Reaktionen. Ber. Dtsch. Chem. Ges. 16 (1883) 1439-1443
36. Pietsch R. Untersuchungen zur Umsetzung von Alkylbromiden mit Trinatrium arsenite. Monatsch. Chem. 96 (1965) 138-146
37. Rider T.H., and Hill A.J. Studies on glycidol. I. Preparation from glycerol monochlorohydrin. J. Am. Chem. Soc. 52 (1930) 1521-1530
38. 2. Biochemistry 35 (1996) 9375-9384
39. Serdarevich B. Glyceride isomerizations in lipid chemistry. J. Am. Oil Chem. Soc. 44 (1967) 381-393
40. Serves S.V., Tsivgoulis G.M., Sotiropoulos D.N., and Ioannou P.V. Synthesis of (R)- and (S)-1,2-diacyloxypropyl-3-arsonic acids: optically active arsonolipids. Phosphorus, Sulfur, and Silicon 71 (1992) 99-105
41. Serves S.V., Sotiropoulos D.N., Ioannou P.V., and Jain M.K. One pot synthesis of arsonolipids via thiorsenite precursors. Phosphorus, Sulfur, and Silicon 81 (1993) 181-190
42. Serves S.V., Sortiropoulos D.N., Ioannou P.V., and Dixon H.B.F. On the mechanism of the Meyer reaction with epoxides and 2-haloalcohols as substrates. Phosphorus, Sulfur, and Silicon 90 (1994) 103-109
43. Serves S.V., Sotiropoulos D.N., Ioannou P.V., Mutenda E.K., Sparkes M.J., and Dixon H.B.F. rac-3,4-Dihydroxybutylarsonic acid: a key entermediate for isosteric arsonolipids. Phosphorus, Sulfur, and Silicon 101 (1995) 75-87
44. Serves S.V., Charalambidis Y.C., Sotiropoulos D.N., and Ioannou P.V. Reaction of arsenic(III) oxide, arsenous and arsenic acids with thiols. Phosphorus, Sulfur, and Silicon 105 (1995) 109-116
45. Steinkopf W., Schubart I., and Schmidt S. Zur Kenntnis organischer Arsenverbindungen. XII.: Die Einwirkung von Säurechoriden auf Diphenylarsin. Chem. Ber. 61 (1928) 678-682
46. Sunder A., Hanselmann R., Frey H., and Mülhaupt R. Controlled synthesis of hyperbranched polyglycerols by ring-opening multibranching polymerization. Macromolecules 32 (1999) 4240-4246
47. Supuran C.T., Serves S.V., and Ioannou P.V. Carbonic anhydrase inhibitors. Part 33. Isozyme II inhibition with 2,3-dihydroxypropylarsonic acid and arsonolipids. J. Inorg. Biochem. 62 (1996) 207-212
48. Swell L., and Treadwell C.R. Cholesterol esterase. VI. Relative specificity and activity of pancreatic cholesterol esterase. J. Biol. Chem. 212 (1955) 141-150
49. Terzis A., and Ioannou P.V. Preparation of pseudo-arsonolipids: 2-acyloxypropane-1,3-bis(arsonic acids). The crystal structure of 2-hydroxypropane-1,3-bis(arsonic acid). Chem. Phys. Lipids 117 (2002) 53-61
50. Tokar R., Kubisa P., Penczek S., and Dworak A. Cationic polymerization of glycidol. Coexistence of the activated monomer and active chain end mechanism. Macromolecules 27 (1994) 320-322
51. Tsivgoulis G.M., Sotiropoulos D.N., and Ioannou P.V. 1,2-Dihydroxypropyl-3-arsonic acid: a key intermediate for arsonolipids. Phosphorus, Sulfur, and Silicon 57 (1991) 189-193
52. Tsivgoulis G.M., Sotiropoulos D.N., and Ioannou P.V. rac-1,2-Diacyloxypropyl-3-arsonic acids: arsonolipid analogues of phosphonolipids. Phosphorus, Sulfur, and Silicon 63 (1991) 329-334
53. Tsivgoulis G.M., Lala M.A., and Ioannou P.V. Preparation of dl-2,3,4-trihydroxybutylarsonic acid and dl-2,3-dihydroxybutane-1,4-bis(arsonic acid): starting compounds for novel arsonolipids. Chem. Phys. Lipids 148 (2007) 97-104
54. 2 towards non-activated and activated carboxylic acid anhydrides, Phosphorus, Sulfur, and Silicon, submitted for publication.