PolyamineRED (Intracellular Polyamine Detection Reagent)
PolyamineRED <Intracellular Polyamine Detection Reagent >
Cat. No. FNK-FDV-0020
Storage -20°C
Size 0.5 mg
Molecular weight 611 g/mol
Solubility Soluble in DMSO
Fluorophore TAMRA (red fluorescent dye)
Ex/Em 560 nm/585 nm
*Rhodamine filter sets are available
Description
The polyamine species (Figure 1), including putrescine, spermidine and spermine etc. and its acetyl derivatives, are one of the essential classes of metabolites which have linear alkyl structure with two or more amines. Polyamines are found in all living organisms with high concentration, from sub-millimolar to millimolar, in the cells. Polyamines have polycationic properties and show an enormous number of biological functions. For example, polyamines interact with DNA/RNA in the nuclear and regulate gene expression.
Polyamines also interact with negatively charged proteins and control its function. The major source of polyamines is an amino acid ornithine. In the case of mammals, ornithine is converted to putrescine by ornithine decarboxylase (ODC), followed by synthesizing spermidine and spermine. Because ODC is highly expressed in cancer cells, polyamines are considered as one of the cancer markers. Several detection methods of polyamines are developed to date but most of the methods are commonly low-throughput systems using HPLC with polyamine standard compounds. To clear biological functions of polyamines in the cells, the cell-based assay with easy- and high-throughput-procedures is desired. PolyamineRED is the world's first reagent for detecting intracellular polyamines without any pretreatment and cell lysis.
PolyamineRED is a TAMRA (tetramethylrhodamine)-conjugated derivative of glycine propargyl ester which specifically reacting with linear primary alkylamine but not react with secondary amines, bulky amines including amino acids nor monoamines. PolyamineRED has cell-penetrating properties, specifically reacts with polyamines inside the cells and labeled polyamines with red fluorescent dye TAMRA. (Figure 2).
PolyamineRED is a reagent for imaging intracellular polyamines specifically without any pretreatment or cell lysis. This can be used for live cells, therefore it is suitable for detection or semi-quantitative analysis of intracellular polyamines.
This product has been commercialized with the support of Biofunctional Synthetic Chemistry Laboratory, RIKEN.
Background of Polyamines
The polyamine species, such as putrescine, spermidine and spermine etc. and its acetyl derivatives, are some of the essential classes of metabolites which have linear alkyl structure with two or more amines. Polyamines have polycationic properties and show various biological functions. For example, polyamines interact with DNA and RNA in the nuclear and regulate gene expression. Polyamines also interact with negatively charged proteins and control its function. The major source of polyamines is amino acid ornithine. In case of mammals, ornithine is converted to putrescine by ornithine decarboxylase (ODC), followed by synthesizing spermidine and spermine. As ODC is highly expressed in cancer cells, polyamines are considered as cancer markers.
Several detection methods of polyamines have been developed so far, but most of them are low-throughput systems using HPLC with polyamine standard compounds. Therefore, the biological functions of polyamines have been unclear.
PolyamineRED is the world's first reagent for detecting intracellular polyamines without any pre-treatment and cell lysis. This TAMRA (tetramethylrhodamine)-conjugated derivative of glycine propargyl ester specifically reacts with linear primary alkylamine and has cell-penetrating properties, specifically reacts with polyamines inside the cells and labeled polyamines with red fluorescent dye TAMRA.
Figure 2.
Features
- Specifically labels polyamines
- Can be detected by filter set for Rhodamine (Ex./Em. = 560 / 585 nm)
- Cell permeable : compatible with live cell imaging
- No pretreatments required
- Can do semi-quantification of total polyamines amount (*) by intracellular fluorescence intensity.
Chemical Information
- Molecular weight : 611 g/mol
- Solubility : Soluble in DMSO
- Fluorophore : TAMRA (red fluorescent dye)
Fig. 1 Polyamine imaging in cancer or non-cancer cells
Three cancer cell lines (MCF7, MDA-MB-231 and SK-BR-3) and two non-cancer cells (MCF10A and human lymphocyte) were treated with 30 μM of PolyamineRED for 10 min. After incubation, cells were washed three times by PBS, followed by DAPI staining and formalin fixation. Images were obtained at Ex/Em=560 nm/585 nm for TAMRA and at Ex/Em=358 nm/461 nm for DAPI. TAMRA fluorescence was detected in cancer cell lines.
Fig.2 Intracellular distribution of polyamines in MDA-MB-231 cancer cell lines
MDA-MB-231 cells were treated with 30 μM of PolyamineRED for 10 min. After incubation, cells were washed three times by PBS, followed by DAPI-staining and formalin fixation. Images were obtained at Ex/Em=560 nm/585 nm for TAMRA and at Ex/Em=358 nm/461 nm for DAPI. Major TAMRA signal was detected in nucleus. This indicates polyamines in MDA-MB-231 are mainly localized in the nucleus.
Table Selectivity of glycine propargyl ester to polyamines
|
Amine |
Reaction |
|
Spermine |
82% |
|
Spermidine |
78% |
|
Putrescine |
66% |
|
Epinephrine |
<1% |
|
Lysine |
2% |
Data is cited from K. Vong, K. Tsubokura, Y. Nakao, T. Tanei, S. Noguchi, S. Kitazume, N. Taniguchi, K. Tanaka, Chem. Commun., 53, 8403-8406 (2017).
Reconstitution and StorageAfter reconstitution in DMSO, aliquot and store at -20 °C. Avoid repeated freeze-thaw cycles.
Protect from light.
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