Suppression of aberrant colonic crypt foci by synthetic sphingomyelins with saturated or unsaturated sphingoid base backbones

References

• Spiegel , S and Merrill , AH Jr . 1996 . “Sphingolipid metabolism and growth regulation” . FASEB J , 10 : 1388 – 1397 .
   PubMed Web of Science ®Google Scholar
• Schmelz , EM , Crall , KJ , Laroque , R , Dillehay , DL and Merrill , AH Jr . 1994 . “Uptake and metabolism of sphingolipids in isolated intestinal loops” . J Nutr , 124 : 702 – 712 .
   PubMed Web of Science ®Google Scholar
• Schmelz , EM , Dillehay , DL , Webb , SK , Reiter , A Adams , J . 1996 . “Sphingomyelin consumption suppresses aberrant colonic crypt foci and increases the proportion of adenomas versus adenocarcinomas in CF1 mice treated with 1,2‐dimethylhydrazine: implications for dietary sphingolipids and colon carcinogenesis” . Cancer Res , 56 : 4936 – 4941 .
   PubMed Web of Science ®Google Scholar
• Dillehay , DL , Webb , SK , Schmelz , EM and Merrill , AH Jr . 1994 . “Dietary sphingomyelin inhibits 1,2‐dimethylhydrazine‐induced colon cancer in CF1 mice” . J Nutr , 124 : 615 – 620 .
   PubMed Web of Science ®Google Scholar
• National Research Council . 1985 . Guide for the Care and Use of Laboratory Animals , Bethesda, MD : Natl Inst Health . [Publ 88–23 (rev)]
   Google Scholar
• Garner , P and Park , JM . 1987 . “The synthesis and configurational stability of differentially protected β‐hydroxy‐α‐amino aldehydes” . J Org Chem , 52 : 2361 – 2364 .
   Web of Science ®Google Scholar
• Garner , P , Park , JM and Malecki , E . 1988 . “A stereodivergent synthesis of d‐erythro‐sphingosine and d‐erythro‐sphinganine from L‐serine” . J Org Chem , 53 : 4395 – 4398 .
   Web of Science ®Google Scholar
• Garner , P and Park , JM . 1991 . “1,1‐Dimethylethyl (S)‐ or (R)‐4‐formyl‐2,2 dimethyl‐3‐oxazolidinecarboxylate: a useful serinal derivative” . Org Synth , 70 : 18 – 28 .
   Google Scholar
• Herold , P . 1988 . “Synthesis of d‐erythro‐ and d‐threo‐sphingosine derivatives from l‐serine” . Helv Chim Acta , 71 : 354 – 362 .
   Web of Science ®Google Scholar
• Yoshida , J , Nakagawa , M , Seki , H and Hino , T . 1992 . “Total synthesis of symbioramide, a novel Ca2+‐ATPase activator, from Symbiodinum sp” . J Chem Soc Perkin Tram , 1 : 343 – 350 .
   Google Scholar
• Nimkar , S , Menaldino , D , Merrill , AH Jr and Liotta , DC . 1988 . “A stereo‐selective synthesis of sphingosine, a protein kinase C inhibitor” . Tetrahedron Lett , 29 : 3037 – 3040 .
   Web of Science ®Google Scholar
• Frantova , AY , Bushnev , AS , Zvonkova , EN and Shvets , VI . 1991 . “H‐Phos‐phonate and phosphoramidite methods for the synthesis of phos‐phosphingolipids” . Bioorgan Khim , 17 : 1562 – 1573 .
   Google Scholar
• 1991 . Chem Abstr , 116 : 1363
   Google Scholar
• Bruzik , KS . 1988 . “Synthesis and spectral properties of chemically and stere‐ochemically homogeneous sphingomyelin and its analogues” . J Chem Soc Perkin Trans , 1 : 423 – 431 .
   Google Scholar
• Ames , BN . 1966 . “Assay of inorganic phosphate, total phosphate and phos‐phatases” . Methods Enzymol , 8 : 115 – 118 .
   Google Scholar
• American Institute of Nutrition . 1977 . “Report of the American Institute of Nutrition Ad Hoc Committee on Standards for Nutrition Studies” . J Nutr , 107 : 1340 – 1348 .
   PubMed Web of Science ®Google Scholar
• Merrill , AH Jr , Wang , E , Mullins , RE , Jamison , WCL Nimkar , S . 1988 . “Quantitation of free sphingosine in liver by high‐performance liquid chromatography” . Anal Chem , 171 : 373 – 381 .
   Google Scholar
• Bird , RP . 1987 . “Observations and quantification of aberrant crypts in the murine colon treated with a colon carcinogen: preliminary findings” . Cancer Lett , 37 : 147 – 151 .
   PubMed Web of Science ®Google Scholar
• Hannun , YA and Linardic , CM . 1993 . “Sphingolipid breakdown products: antiproliferative and tumor suppressor lipids” . Biochim Biophys Acta , 1154 : 223 – 236 .
   PubMed Web of Science ®Google Scholar
• Zhang , H , Desai , NN , Olivera , A , Seki , T Brooker , G . 1991 . “Sphin‐gosine‐1‐phosphate, a novel lipid, involved in cellular proliferation” . J Cell Biol , 114 : 155 – 167 .
   PubMed Web of Science ®Google Scholar
• Stevens , VL , Nimkar , S , Jameson , WC , Liotta , DC and Merrill , AH Jr . 1990 . “Characteristics of the growth inhibition and cytotoxicity of long‐chain (sphingoid) bases for Chinese hamster ovary cells: evidence for an involvement of protein kinase C” . Biochim Biophys Acta , 1051 : 37 – 45 .
   PubMed Web of Science ®Google Scholar
• Jayadev , S , Liu , B , Bielawska , AE , Lee , JY Nazaire , F . 1995 . “Role for ceramide in cell cycle arrest” . J Biol Chem , 270 : 2047 – 2052 .
   PubMed Web of Science ®Google Scholar
• Merrill , AH Jr , Sereni , AM , Stevens , VL , Hannun , YA Bell , RM . 1986 . “Inhibition of phorbol ester‐dependent differentiation of human promyelocytic leukemic (HL‐60) cells by sphinganine and other long‐chain bases” . J Biol Chem , 261 : 12610 – 12615 .
   PubMed Web of Science ®Google Scholar
• Stevens , VL , Owens , NE , Winton , EF , Kinkade , JM and Merrill , AH Jr . 1990 . “Modulation of retinoic acid‐induced differentiation of human leukemia (HL‐60) cells by serum factors and sphinganine” . Cancer Res , 50 : 222 – 226 .
   PubMed Web of Science ®Google Scholar
• Ohta , H , Sweeney , EA , Masamune , A , Yatomi , Y Hakomori , S‐I . 1995 . “Induction of apoptosis by sphingosine in human leukemic HL‐60 cells: a possible endogenous modulator of apoptotic DNA fragmentation occurring during phorbol ester‐induced differentiation” . Cancer Res , 55 : 691 – 697 .
   PubMed Web of Science ®Google Scholar
• Jarvis , WD , Fornari , FA , Traylor , RS , Martin , HA Kramer , LB . 1996 . “Induction of apoptosis and potentiation of ceramide‐mediated cytotoxicity by sphingoid bases in human myeloid leukemia cells” . J Biol Chem , 271 : 8275 – 8284 .
   PubMed Web of Science ®Google Scholar
• Bielawska , A , Crane , HM , Liotta , DC , Obeid , LM and Hannun , YA . 1993 . “Selectivity of ceramide‐mediated biology. Lack of activity of erythro‐dihydroceramide” . J Biol Chem , 268 : 26226 – 26232 .
   PubMed Web of Science ®Google Scholar
• Tepper , CL , Jayadev , S , Liu , B , Bielawska , A Wolff , RA . 1995 . “Role for ceramide as an endogenous mediator of fas‐induced cytotoxicity” . Proc Natl Acad Sci USA , 92 : 8443 – 8447 .
   PubMed Web of Science ®Google Scholar
• Sawai , H , Okazaki , T , Yamamoto , H , Okano , H Takeda , Y . 1995 . “Requirement of AP‐1 for ceramide‐induced apoptosis in human leukemia HL‐60 cells” . J Biol Chem , 270 : 27326 – 27331 .
   PubMed Web of Science ®Google Scholar
• Brugg , B , Michel , PP , Agid , Y and Ruberg , M . 1996 . “Ceramide induces apoptosis in cultured mesencephalic neurons” . J Neurochem , 66 : 733 – 739 .
   PubMed Web of Science ®Google Scholar
• Karasavvas , N , Erukulla , RK , Bittman , R , Lockshin , R and Zakeri , Z . 1996 . “Stereospecific induction of apoptosis in U937 cells by N‐octanoyl‐sphingosine stereoisomers and N‐octyl‐sphingosine” . Eur J Biochem , 236 : 729 – 737 .
   PubMedGoogle Scholar
• Endo , K , Igarashi , Y , Nisar , M , Zhou , QH and Hakomori , S‐I . 1991 . “Cell membrane signaling as target in cancer therapy: inhibitory effect of N,N‐dimethyI and N,N,N‐trimethl sphingosine derivatives on in vitro and in vivo growth of human tumor cells in nude mice” . Cancer Res , 51 : 1613 – 1618 .
   PubMed Web of Science ®Google Scholar
• Sweeney , EA , Sakakura , C , Shirahama , T , Masamune , A Ohta , H . 1996 . “Sphingosine and its methylated derivative N,N‐dimethylsphingo‐sine (MS) induce apoptosis in a variety of human cancer cell lines” . Int J Cancer , 66 : 358 – 366 .
   PubMed Web of Science ®Google Scholar
• Sakakura , C , Sweeney , EA , Shirahama , T , Hakomori , S‐I and Igarashi , Y . 1996 . “Suppression of Bcl‐2 gene expression by sphingosine in the apoptosis of human leukemic HL‐60 cells during phorbol ester‐induced terminal differentiation” . FEBS Lett , 379 : 177 – 180 .
   PubMed Web of Science ®Google Scholar
• Chen , M , Quintans , J , Fuks , Z , Thompson , C Kufe , DW . 1995 . “Suppression of Bcl‐2 messenger RNA production may mediate apoptosis after ionizing radiation, tumor necrosis factor a, and ceramide” . Cancer Res , 55 : 991 – 994 .
   PubMed Web of Science ®Google Scholar
• Reynes , JG , Robayna , IG , Delgado , PS , Gonzales , IH Aguiar , JQ . 1996 . “C‐jun is a downstream target for ceramide‐activated protein phos‐phatase in A431 cells” . J Biol Chem , 271 : 21375 – 21380 .
   PubMed Web of Science ®Google Scholar
• Kim , MY , Linardic , C , Obeid , LM and Hannun , YA . 1991 . “Identification of sphingomyelin turnover as an effector mechanism for the action of tumor necrosis factor α‐ and γ‐interferon” . J Biol Chem , 266 : 484 – 489 .
   PubMed Web of Science ®Google Scholar
• Marcu , KB , Bossone , SA and Patel , AJ . 1992 . “Myc function and regulation” . Annu Rev Biochem , 61 : 809 – 860 .
   PubMed Web of Science ®Google Scholar
• Dudeja , PK , Dahiya , R and Brasitus , TA . 1986 . “The role of sphingomyelin synthase and sphingomyelinase in 1,2‐dimethylhydrazine‐induced lipid alterations of rat colonic plasma membranes” . Biochim Biophys Acta , 863 : 309 – 312 .
   PubMed Web of Science ®Google Scholar
• Wright , SC , Zheng , H and Zhong , J . 1996 . “Tumor cell resistance to apoptosis due to a defect in the activation of sphingomyelinase and the 24 kDa apoptotic protease” . FASEB J , 10 : 325 – 332 .
   PubMed Web of Science ®Google Scholar
• Zeisel , SH , Char , D and Shear , NF . 1986 . “Choline, phosphatidylcholine and sphingomyelin in human and bovine milk and infant formulas” . J Nutr , 116 : 50 – 58 .
   PubMed Web of Science ®Google Scholar
• Blank , ML , Cress , EA , Smith , ZL and Snyder , NF . 1992 . “Meats and fish consumed in the American diet contain substantial amounts of ether‐linked phospholipids” . J Nutr , 122 : 1656 – 1661 .
   PubMed Web of Science ®Google Scholar
• Ohnishi , M and Fujino , Y . 1982 . “Sphingolipids in immature and mature soybeans” . Lipids , 17 : 803 – 810 .
   Web of Science ®Google Scholar