Prostaglandin phospholipid conjugates with unusual biophysical and cytotoxic properties.
The synthesis of two secretory phospholipase A(2) IIA sensitive 15-deoxy-Delta(12,14)-prostaglandin J(2) phospholipid conjugates is described and their biophysical and biological properties are reported. The conjugates spontaneously form particles in the liposome size region upon dispersion in an aqueous buffer and both phospholipids are hydrolyzed by phospholipase A(2), but with different conversion rates and extent of hydrolysis. The cytotoxicity was evaluated in HT-29 and Colo205 cells and the conjugates induced cell death in the presence of phospholipase A(2) and surprisingly also in the absence of the enzyme.
Pedersen
Palle J
PJ
Department of Chemistry, Technical University of Denmark, Kemitorvet, Lyngby, Denmark.
Adolph
Sidsel K
SK
Andresen
Thomas L
TL
Madsen
Mogens W
MW
Madsen
Robert
R
Clausen
Mads H
MH
D017209:Apoptosis; D045744:Cell Line, Tumor; D054501:Group II Phospholipases A2 / Q000378:metabolism; D006801:Humans; D006868:Hydrolysis; D010743:Phospholipids / Q000737:chemistry*; D015230:Prostaglandin D2 / Q000031:analogs & derivatives* / Q000737:chemistry; D011453:Prostaglandins / Q000737:chemistry*
C097240:15-deoxy-delta(12,14)-prostaglandin J2; D010743:Phospholipids; D011453:Prostaglandins; D054501:Group II Phospholipases A2; D015230:Prostaglandin D2