94885-04-8

C6 NBD sphingomyelin is a biologically active derivative of sphingomyelin (Item Nos. 22674 | 24345) that is tagged with a fluorescent C6 nitrobenzoxadiazole (C6 NBD; ) group. C6 NBD sphingomyelin has been used to study the metabolism and transport of sphingomyelins. It is degraded in the plasma membrane to C6 NBD ceramide by neutral sphingomyelinase, an enzyme with three-fold higher activity in undifferentiated HT29 cells than in differentiated cells. Unlike endogenous long-chain sphingomyelin and C6 sphingomyelin, C6 NBD sphingomyelin can be transported to the cell surface even in the presence of the vesicular transport inhibitor brefeldin A , but this transport can be blocked by multidrug resistance protein inhibitors in CHO cells. This product is a mixture of the D-erythro and L-threo isomers of sphingomyelin. [Matreya, LLC. Catalog No. 1912]

A probe that fluorescently labels membranous fatty acid phospholipids and has shown to excite the NBD group at 460 nm and emit at 534 nm.

[1] J W KOK. Fluorescent, short-chain C6-NBD-sphingomyelin, but not C6-NBD-glucosylceramide, is subject to extensive degradation in the plasma membrane: implications for signal transduction related to cell differentiation.[J]. Biochemical Journal, 1995, 309 ( Pt 3): 905-912. DOI: 10.1042/bj3090905
[2] A VAN HELVOORT. Transport of sphingomyelin to the cell surface is inhibited by brefeldin A and in mitosis, where C6-NBD-sphingomyelin is translocated across the plasma membrane by a multidrug transporter activity.[J]. Journal of cell science, 1997, 110 ( Pt 1): 75-83. DOI: 10.1242/jcs.110.1.75