Title: Platelet Activating Factor
CAS Registry Number: 65154-06-5
Synonyms: PAF; 1-
O-alkyl-2-acetyl-
sn-glycero-3-phosphorylcholine; acetyl glyceryl ether phosphorylcholine; AGEPC; PAF-acether; antihypertensive polar renomedullary lipid; APRL
Literature References: Phospholipid mediator of platelet aggregation, inflammation, and anaphylaxis. Produced in response to specific stimuli by a variety of cell types, including neutrophils, basophils, platelets, and endothelial cells. Several molecular species of PAF have been identified which vary in the length of the
O-alkyl side chain.
In vitro identification of a soluble platelet activating factor produced by antigen stimulated leukocytes: P. M. Henson,
J. Exp. Med. 131, 287 (1970). Isoln from rabbit basophils, characterization of PAF response and potential role in immune complex disease: J. Benveniste
et al., ibid. 136, 1356 (1972). Isoln from human leukocytes: J. Benveniste,
Nature 249, 581 (1974). Release of PAF
in vivo during anaphylaxis: R. N. Pinckard
et al., J. Immunol. 123, 1847 (1979). Structural study: J. Benveniste
et al., Nature 269, 170 (1977); and synthetic approaches: J. Benveniste
et al., C.R. Seances Acad. Sci. Ser. D 289, 1037 (1979); C. A. Demopoulos
et al., J. Biol. Chem. 254, 9355 (1979). Identity with APRL and antihypertensive activity: M. L. Blank
et al., Biochem. Biophys. Res. Commun. 90, 1194 (1979). Structures of 1-
O-octadecyl- and 1-
O-hexadecyl-PAF, two of the predominant molecular forms: D. J. Hanahan
et al., ibid. 255, 5514 (1980). Total synthesis of 1-
O-octadecyl-PAF: J. Godfroid
et al., FEBS Lett. 116, 161 (1980). Enantiomeric synthesis of C16- and C18-PAF: M. Ohno
et al., Chem. Pharm. Bull. 33, 572 (1985). Molecular heterogeneity of naturally occurring PAF: R. N. Pinckard
et al., Biochem. Biophys. Res. Commun. 122, 325 (1984); H. W. Mueller
et al., J. Biol. Chem. 259, 14554 (1984). Ulcerogenic effects: A.-C. Rosam
et al., Nature 319, 54 (1986). Effects on human pulmonary and cardiovascular function: F. M. Cuss
et al., Lancet 2, 189 (1986). Review of isoln and analytical methods: D. J. Hanahan, S. T. Weintraub,
Methods Biochem. Anal. 31, 195-219 (1985); of chemical and biochemical characteristics: D. J. Hanahan, R. Kumar,
Prog. Lipid Res. 26, 1-28 (1987). Reviews of biosynthesis, biological activities and PAF antagonists: P. Braquet
et al., Pharmacol. Rev. 39, 97-145 (1987); P. J. Barnes
et al., J. Allergy Clin. Immunol. 81, 919-934 (1988). Books:
Platelet-Activating Factor and Related Lipid Mediators, F. Snyder, Ed. (Plenum Press, New York, 1987) 471 pp;
Prog. Biochem. Pharmacol. 22 entitled "Biologically Active Ether Lipids" by P. Braquet
et al., Eds. (Karger, Basel, 1988).
Derivative Type: 1-
O-Hexadecyl PAF
Synonyms: (
R)-7-(Acetyloxy)-4-hydroxy-
N,N,N-trimethyl-3,5,9-trioxa-4-phosphapentacosan-1-aminium hydroxide inner salt 4-oxide; C16-PAF
Molecular Formula: C26H54NO7P
Molecular Weight: 523.68
Percent Composition: C 59.63%, H 10.39%, N 2.67%, O 21.39%, P 5.91%
Properties: White, amorphous solid, mp 247° (dec). [a]D21 -3.66° (c = 0.71 in chloroform).
Melting point: mp 247° (dec)
Optical Rotation: [a]D21 -3.66° (c = 0.71 in chloroform)
Derivative Type: 1-
O-Octadecyl-PAF
Synonyms: (
R)-7-(Acetyloxy)-4-hydroxy-
N,N,N-trimethyl-3,5,9-trioxa-4-phosphaheptacosan-1-aminium hydroxide inner salt 4-oxide; C18-PAF
Molecular Formula: C28H58NO7P
Molecular Weight: 551.74
Percent Composition: C 60.95%, H 10.60%, N 2.54%, O 20.30%, P 5.61%
Properties: mp 212-215° (dec). [a]D20 -4.00° (c = 0.71 in chloroform).
Melting point: mp 212-215° (dec)
Optical Rotation: [a]D20 -4.00° (c = 0.71 in chloroform)
