Sigma-Aldrich

Aldrich-D22606; Cadaverine 0.95; CAS No.: 462-94-2; Synonyms: 1,5-Diaminopentane; 1,5-Pentanediamine; Pentamethylenediamine; Linear Formula: NH2(CH2)5NH2; Empirical Formula: C5H14N2; find related products, papers, technical documents, MSDS & more at Sigma-Aldrich.

Cadaverine 95 462-94-2

Cadaverine

CuI-catalyzed hetarylation of natural di-and polyamines with halopyridines.

Main-Chain Polyimidazolium Polymers by One-Pot Synthesis and Application as Nitrogen-Doped Carbon Precursors.

Lithogenicity of human bile is dependent not only on cholesterol saturation, but also on the presence of nucleating and antinucleating factors. Most of the research in this field is directed toward biliary proteins, particularly glycoproteins. In the present study we have shown that spermine, spermidine, cadaverine and putrescine have a nucleating effect in model bile as well as in native human bile. These findings are based on 183 mixing experiments using biles from 10 patients and model biles. The effect seems to be dose dependent at concentrations up to 10 mmol/l. It is not accompanied by a shift in cholesterol distribution between its vesicular and micellar carriers. It is at present uncertain whether these effects are pharmacologic or physiologic. These findings emphasize, however, the potential importance of non-protein compounds in the cholesterol nucleation process in bile.

Polyamines--potential nucleating factors in bile.

Whereas previous studies have shown correlations between volatile sulphur compounds (VSC) and bad breath levels, it is probable that other compounds found in the oral cavity may contribute to oral malodor. In the present investigation, the possibility that diamines (cadaverine and putrescine) are associated with oral malodor parameters was assessed. Saliva samples from 52 subjects were analyzed for cadaverine and putrescine by HPLC. Oral malodor of whole mouth, tongue, and saliva of the subjects was recorded by an experienced judge on a continuous 10-cm scale; peak and steady-state VSC intraoral levels were measured by the Interscan 1170 sulphide monitor. Log-transformed VSC and diamine levels were compared with odor judge measurements by Pearson analysis and stepwise forward multiple regression. Putrescine scores were not significantly associated with odor judge parameters or with VSC levels (p > 0.1). However, highly significant correlations (p < or = 0.003) were found between cadaverine levels and all three odor judge assessments. In contrast, associations between cadaverine and VSC measurements were non-significant. In an attempt to correlate odor judge results in terms of both VSC and diamines, we carried out stepwise forward multiple regression. Results showed that VSC and cadaverine both factor significantly in explaining each of the odor judge measurements, with multiple r values ranging from 0.545 (p = 0.0002) to 0.604 (p < 0.0001). The results suggest that cadaverine levels are associated with oral malodor, and that this association may be independent of VSC.

Cadaverine as a putative component of oral malodor.

We developed a new simple enzymatic assay method for measuring urinary polyamines (total amount of putrescine, spermidine, and cadaverine), using an acylpolyamine amidohydrolase and a putrescine oxidase. First conjugated polyamines (putrescine, spermidine, and cadaverine) in urine were hydrolyzed by incubation with an acylpolyamine amidohydrolase at 30 degrees for 1 hr. then, free polyamines were separated by cation-exchange chromatography and incubated with a putrescine oxidase at 30 degrees for 30 min. Hydrogen peroxide formed in this reaction was measured spectrophotometrically (at 514 nm). Polyamine levels in urine were determined in 70 normal subjects, 124 patients with cancer, and 52 patients with diseases other than cancer. Elevation above 3 S.D.s of the normal mean was found in 90 (72.6%) of the 124 patients with cancer and in 6 (11.5%) of the 52 patients with diseases other than cancer. Serial studies in 19 patients with cancer indicated that polyamines in urine were reduced after successful surgery. Our new method is simple and rapid and therefore very useful for routine clinical application. Moreover, our data indicate that the determination of polyamine levels is useful as a marker of disease activity in patients with cancer.

A new simple enzymatic assay method for urinary polyamines in humans.

This method for assay of polyamines (putrescine, spermidine, and spermine) in large numbers of urine samples is based on preliminary analyte isolation by use of a Dowex 50W column, separation by high-voltage paper electrophoresis, reaction with ninhydrin to detect the separated amines, and subsequent direct assay with a dual-wave-length thin-layer chromatography scanner by the zigzag scanning method. By optimizing the conditions for the Dowex 50W column and high-voltage paper electrophoresis, putrescine, cadaverine, spermidine, and spermine were completely separated. The major technical improvements are room-temperature collection of urine with toluene, shorter hydrolysis time, complete separation of putrescine from cadaverine and histamine, and elimination of interference with spermine measurement. Polyamine concentrations as measured by this method agreed with those obtained by use of an amino acid analyzer. Reference intervals by this method were similar to those reported by Russell (Clin. Chem. 23: 22, 1977) with an automated amino acid analyzer. Putrescine, spermidine, and spermine excretion in urine from patients with blood cancers and solid cancers was significantly increased; information on concentrations of putrescine and spermidine were especially useful for following the clinical efficacy of cancer treatments.

Improved analysis for urinary polyamines by use of high-voltage electrophoresis on paper.

Semen is fundamental for sexual reproduction. The non-sperm part of ejaculated semen, or seminal plasma, facilitates the delivery of sperm to the eggs. The seminal plasma of some species with internal fertilization contains anti-aphrodisiac molecules that deter promiscuity in post-copulatory females, conferring fitness benefits to the ejaculating male. By contrast, in some taxa with external fertilization such as fish, exposure to semen promotes spawning behaviors. However, no specific compounds in semen have been identified as aphrodisiac pheromones. We sought to identify a pheromone from the milt (fish semen) of sea lamprey (Petromyzon marinus), a jawless fish that spawns in lek-like aggregations in which each spermiating male defends a nest, and ovulatory females move from nest to nest to mate. We postulated that milt compounds signal to ovulatory females the presence of spawning spermiating males. We determined that spermine, an odorous polyamine initially identified from human semen, is indeed a milt pheromone. At concentrations as low as 10-14 molar, spermine stimulated the lamprey olfactory system and attracted ovulatory females but did not attract males or pre-ovulatory females. We found spermine activated a trace amine-associated receptor (TAAR)-like receptor in the lamprey olfactory epithelium. A novel antagonist to that receptor nullified the attraction of ovulatory females to spermine. Our results elucidate a mechanism whereby a seminal plasma pheromone attracts ready-to-mate females and implicates a possible conservation of the olfactory detection of semen from jawless vertebrates to humans. Milt pheromones may also have management implications for sea lamprey populations.

Spermine in semen of male sea lamprey acts as a sex pheromone.

A capillary gas-chromatographic method with nitrogen-phosphorus detection is used here to simultaneously determine 1,3-diaminopropane, putrescine, cadaverine, spermidine, spermine, isoputreanine , putreanine , and N-(3-aminopropyl)-N'-(2-carboxyethyl)-1,4- diaminobutane in urine. After acid hydrolysis the compounds are isolated by adsorption onto silica gel and converted into their methyl-heptafluorobutyryl derivatives. We give quality-control data and age-dependent values for urinary excretion of these analytes by 76 apparently healthy controls. Circadian rhythmicity in the excretion of spermidine and (especially) isoputreanine was established and is discussed in the light of its implications for monitoring therapy of cancer. Investigation of menstrual-cycle-dependent diurnal variation in one normal woman showed no distinct, consistent fluctuations. We applied the method to monitor (by use of 24-h urine specimens) an uncomplicated, normally progressing pregnancy, a patient with metastatic melanoma being treated with cytostatic drugs, and (in more detail) the treatment of a patient with high-grade non-Hodgkin lymphoma.

Total polyamines and their non-alpha-amino acid metabolites simultaneously determined in urine by capillary gas chromatography, with nitrogen-phosphorus detector; and some clinical applications.

Cadaver dogs are trained on a variety of materials, including artificial or pseudo scents. The chemical components of commercially available pseudo scents are not known, so their accuracy as a decomposition odour mimic and their effectiveness as a canine training aid have not been evaluated. Two pseudo scents that are commercially available and used for training cadaver dogs were analysed using comprehensive two-dimensional gas chromatography-time of flight mass spectrometry (GC×GC-TOFMS). The two formulations were determined to be simplistic in their composition, compared to real cadaveric volatile organic compound (VOC) mixtures, with only a few major components. The enhanced GC×GC-TOFMS peak capacity was nevertheless useful to discriminate less intense peaks from large overloaded peaks. The availability of both dimension retention times combined with the peak finding and deconvolution algorithm, enabled the chemical characterization of the two formulations. Additionally, high resolution (HR) TOFMS was used to extract molecular formulae and confirm identities of analytes. The seven compounds identified by this work have not been reported previously as volatile products of decomposition, indicating that these pseudo scents are not to be considered as an accurate representation of cadaveric decomposition odour. Further research on the olfaction of scent detection canines and the chemical composition of their target odourants needs to be conducted to develop improved canine training aids.

Analysis of synthetic canine training aids by comprehensive two-dimensional gas chromatography-time of flight mass spectrometry.

The performance of three different types of ion mobility spectrometer (IMS) devices: GDA2 with a radioactive ion source (Airsense, Germany), UV-IMS with a photo-ionization source (G.A.S. Germany) and VG-Test with a corona discharge source (3QBD, Israel) was studied. The gas-phase ion chemistry in the IMS devices affected the species formed and their measured reduced mobility values. The sensitivity and limit of detection for trimethylamine (TMA), putrescine and cadaverine were compared by continuous monitoring of a stream of air with a given concentration of the analyte and by measurement of headspace vapors of TMA in a sealed vial. Preprocessing of the mobility spectra and the effectiveness of multivariate curve resolution techniques (MCR-LASSO) improved the accuracy of the measurements by correcting baseline effects and adjusting for variations in drift time as well as enhancing the signal to noise ratio and deconvolution of the complex data matrix to their pure components. The limit of detection for measurement of the biogenic amines by the three IMS devices was between 0.1 and 1.2ppm (for TMA with the VG-Test and GDA, respectively) and between 0.2 and 0.7ppm for putrescine and cadaverine with all three devices. Considering the uncertainty in the LOD determination there is almost no statistically significant difference between the three devices although they differ in their operating temperature, ionization method, drift tube design and dopant chemistry. This finding may have general implications on the achievable performance of classic IMS devices.

Comparison of the performance of three ion mobility spectrometers for measurement of biogenic amines.

A capillary gas-chromatographic method with nitrogen-phosphorus detection is used to determine simultaneously urinary 1,3-diaminopropane, monoacetyl-1,3-diaminopropane, putrescine, monoacetylputrescine, cadaverine, monoacetylcadaverine, spermidine, N1-acetylspermidine, N beta-acetylspermidine, spermine, N1-acetylspermine, isoputreanine, N-(3-aminopropyl)pyrrolidin-2-one, and putreanine. The compounds are isolated by adsorption onto silica and converted into their methyl-heptafluorobutyryl derivatives. We give quality-control data and age-dependent "normal" values for urinary excretion of these analytes from 51 apparently healthy control subjects. Normal values for 31 adults are compared with those reported in the literature. Monoacetyl-1,3-diaminopropane and N1-acetylspermine are identified by mass fragmentography. We applied the method to monitor chemotherapeutic treatment of a patient with advanced non-Hodgkin's lymphoma; we identified by mass spectrometry N1,N12-diacetylspermine in this patient's urine.

Simultaneous gas-chromatographic determination of free and acetyl-conjugated polyamines in urine.

It is known that some modified, especially methylated, nucleosides originating from RNA degradation are excreted in abnormal levels in the urine of patients with malignant tumours and they have been proposed as tumour markers. Their measurement could provide a non-invasive diagnostic method, be helpful in the identification of different cancers and in the monitoring of therapeutic effects. In this study, we developed and optimized an analytical procedure to isolate and quantify normal and modified ribonucleosides. The extraction of urinary nucleosides was performed by affinity chromatography on a phenylboronic acid column prior to separation. The reversed-phase high-performance liquid chromatography method allowed a complete separation of sixteen urinary ribonucleosides. The recoveries for the different nucleosides ranged from 83 to 100%, except for xanthosine (66%) and pseudouridine (74%). In normal 24 h urine, the mean levels of thirteen nucleosides (in nmol of nucleoside/mumol of creatinine) were found to be as follows: dihydrouridine (6.37), pseudouridine (25.52), cytidine (0.07), uridine (0.21), 1-methyladenosine (2.19), inosine (0.30), guanosine (0.06), xanthosine (0.59), 3-methyluridine (0.11), 1-methylinosine (1.13). 1-methylguanosine (0.74), adenosine (0.21) and 5'-deoxy-5'-methylthioadenosine (0.12). The first results concerning two kinds of tumours, i.e. breast and floor of mouth tumours, showed some abnormal levels of ribonucleosides. Further experiments are now in progress to measure the modified nucleosides in urine of patients with different forms of cancer.

Quantitation of urinary nucleosides by high-performance liquid chromatography.

Patients with Marfan syndrome (MFS) are at high risk of life-threatening aortic dissections. The condition is caused by mutations in the gene encoding fibrillin-1, an essential component in the formation of elastic fibers. While experimental findings in animal models of the disease have shown the involvement of transforming growth factor-β (TGF-β)- and angiotensin II-dependent pathways, alterations in the vascular extracellular matrix (ECM) may also play a role in the onset and progression of the aortic disease. Lysyl oxidases (LOX) are extracellular enzymes, which initiates the formation of covalent cross-linking of collagens and elastin, thereby contributing to the maturation of the ECM. Here we have explored the role of LOX in the formation of aortic aneurysms in MFS. We show that aortic tissue from MFS patients and MFS mouse model (Fbn1(C1039G/+)) displayed enhanced expression of the members of the LOX family, LOX and LOX-like 1 (LOXL1), and this is associated with the formation of mature collagen fibers. Administration of a LOX inhibitor for 8weeks blocked collagen accumulation and aggravated elastic fiber impairment, and these effects correlated with the induction of a strong and rapidly progressing aortic dilatation, and with premature death in the more severe MFS mouse model, Fbn1(mgR/mgR), without any significant effect on wild type animals. This detrimental effect occurred preferentially in the ascending portion of the aorta, with little or no involvement of the aortic root, and was associated to an overactivation of both canonical and non-canonical TGF-β signaling pathways. The blockade of angiotensin II type I receptor with losartan restored TGF-β signaling activation, normalized elastic fiber impairment and prevented the aortic dilatation induced by LOX inhibition in Fbn1(C1039G/+) mice. Our data indicate that LOX enzymes and LOX-mediated collagen accumulation play a critical protective role in aneurysm formation in MFS.

Elevated expression levels of lysyl oxidases protect against aortic aneurysm progression in Marfan syndrome.

ATP13A2 (PARK9) is a late endolysosomal transporter that is genetically implicated in a spectrum of neurodegenerative disorders, including Kufor-Rakeb syndrome-a parkinsonism with dementia1-and early-onset Parkinson's disease2. ATP13A2 offers protection against genetic and environmental risk factors of Parkinson's disease, whereas loss of ATP13A2 compromises lysosomes3. However, the transport function of ATP13A2 in lysosomes remains unclear. Here we establish ATP13A2 as a lysosomal polyamine exporter that shows the highest affinity for spermine among the polyamines examined. Polyamines stimulate the activity of purified ATP13A2, whereas ATP13A2 mutants that are implicated in disease are functionally impaired to a degree that correlates with the disease phenotype. ATP13A2 promotes the cellular uptake of polyamines by endocytosis and transports them into the cytosol, highlighting a role for endolysosomes in the uptake of polyamines into cells. At high concentrations polyamines induce cell toxicity, which is exacerbated by ATP13A2 loss due to lysosomal dysfunction, lysosomal rupture and cathepsin B activation. This phenotype is recapitulated in neurons and nematodes with impaired expression of ATP13A2 or its orthologues. We present defective lysosomal polyamine export as a mechanism for lysosome-dependent cell death that may be implicated in neurodegeneration, and shed light on the molecular identity of the mammalian polyamine transport system.

ATP13A2 deficiency disrupts lysosomal polyamine export.

Carbonic anhydrases (CAs, EC 4.2.1.1) are inhibited by sulfonamides, phenols, and coumarins. Polyamines such as spermine, spermidine, and many synthetic congeners are described to constitute a novel class of CA inhibitors (CAIs), interacting with the different CA isozymes with efficiency from the low nanomolar to millimolar range. The main structure-activity relationship for these CAIs have been delineated: the length of the molecule, number of amine moieties, and their functionalization are the main parameters controlling activity. The X-ray crystal structure of the CA II-spermine adduct allowed understanding of the inhibition mechanism. Spermine anchors to the nonprotein zinc ligand through a network of hydrogen bonds. Its distal amine moiety makes hydrogen bonds with residues Thr200 and Pro201, which further stabilize the adduct. Spermine binds differently compared to sulfonamides, phenols, or coumarins, rendering possible to develop CAIs with a diverse inhibition mechanism, profile, and selectivity for various isoforms.

Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule.

The maintenance and control of pluripotency is of great interest in stem cell biology. The dual specificity T-box/basic-helix-loop-helix-zipper transcription factor Mga is expressed in the pluripotent cells of the inner cell mass (ICM) and epiblast of the peri-implantation mouse embryo, but its function has not been investigated previously. Here, we use a loss-of-function allele and RNA knockdown to demonstrate that Mga depletion leads to the death of proliferating pluripotent ICM cells in vivo and in vitro, and the death of embryonic stem cells (ESCs) in vitro. Additionally, quiescent pluripotent cells lacking Mga are lost during embryonic diapause. Expression of Odc1, the rate-limiting enzyme in the conversion of ornithine into putrescine in the synthesis of polyamines, is reduced in Mga mutant cells, and the survival of mutant ICM cells as well as ESCs is rescued in culture by the addition of exogenous putrescine. These results suggest a mechanism whereby Mga influences pluripotent cell survival through regulation of the polyamine pool in pluripotent cells of the embryo, whether they are in a proliferative or quiescent state.

Mga is essential for the survival of pluripotent cells during peri-implantation development.

Myeloperoxidase (MPO), which is secreted during activation of neutrophils, may serve as one mechanistic link among persistent inflammation, oxidative stress, and cardiovascular disease. This study related MPO activity to inflammatory and oxidative stress biomarkers, comorbidity, and ongoing medication in prevalent hemodialysis (HD) patients. In a cross-sectional evaluation of 115 prevalent (vintage 25 mo) HD patients (62 men; 63 +/- 1 yr), data on comorbidity (Davies score), diabetes, medication (statins and antihypertensive drugs), nutritional status (subjective global assessment), blood lipids (cholesterol, HDL cholesterol, and triglycerides), inflammatory biomarkers (serum albumin, C-reactive protein, TNF-alpha, and IL-6), oxidative stress biomarkers (pentosidine, 8-hydroxydeoxyguanosine, and MPO activity) were recorded. Patients with MPO activity greater than the median had significantly (P < 0.05) lower serum albumin levels (33.2 +/- 0.7 versus 35.0 +/- 0.5 g/L), higher 8-hydroxydeoxyguanosine levels (1.26 +/- 0.08 versus 1.05 +/- 0.06 ng/ml), and a lower prevalence of statin treatment (18 versus 36%). Therefore, the median MPO activity was significantly (P < 0.05) lower (17.7 versus 26.6 deltaOD630/min per mg protein) in the subgroup of 31 HD patients with ongoing statin treatment. In a multiple regression model, correction for the impact of age, gender, vintage, serum cholesterol, serum albumin, comorbidity, diabetes, and statin use, only diabetes (P < 0.01) and statin use (P < 0.01) were significantly associated to MPO activity. Fourteen patients who had diabetes and were receiving statin treatment had markedly (P = 0.001) lower median (19.9 versus 41.2 deltaOD630/min per mg protein) MPO activity compared with 18 who had diabetes and were not taking statins. This cross-sectional study suggests that both diabetes and statin treatment affect MPO activity in prevalent HD patients.

Statin treatment and diabetes affect myeloperoxidase activity in maintenance hemodialysis patients.

Trimethylamine (TMA) is a short-chain tertiary aliphatic amine that is derived from the diet either directly from the consumption of foods high in TMA or by the intake of food high in precursors to TMA, such as trimethylamine-N-oxide (TMNO), choline and L-carnitine. The clinical significance of TMA may be related to its potential to contribute to neurological toxicity and 'uraemic breath' in patients with end-stage renal disease (ESRD). Concentrations of TMA and TMNO in plasma from 10 healthy adults (not on haemodialysis) and 10 adults with ESRD undergoing haemodialysis (pre- and post-dialysis) were determined by gas chromatography-mass spectrometry. The concentrations of TMA and TMNO in pre-dialysis plasma (1.39+/-0.483 and 99.9+/-31.9 microM, respectively) were significantly (P<0.05) higher than the corresponding levels in healthy subjects (0.418+/-0.124 and 37.8+/-20.4 microM, respectively). However, there were no significant differences between post-dialysis and healthy subject plasma concentrations. In the ESRD patients, there was a significant (P<0.05) reduction in plasma TMA (from 1.39+/-0.483 to 0.484+/-0.164 microM) and TMNO (from 99.9+/-31.9 to 41.3+/-18.8 microM) during a single haemodialysis session. TMA and TMNO accumulate between haemodialysis sessions in ESRD patients, but are efficiently removed during a single haemodialysis session.

Accumulation of trimethylamine and trimethylamine-N-oxide in end-stage renal disease patients undergoing haemodialysis.

The purpose of this study was to examine the effect of nocturnal hemodialysis (NHD) on serum amino acid (AA) profile. In a cross-over trial, we studied the AA profile in 11 patients who were switched from conventional hemodialysis to NHD. Plasma levels of AA were measured at monthly intervals for a period of 1 year. Concentrations of AA isoleucine, threonine, phenylalanine, valine, glycine, glutamine and taurine increased on switch to NHD. Total AA (2,907.2 +/- 542.2 vs. 3,870.2 +/- 715.2 micromol/l, p = 0.03), essential AA (EAA, 842.2 +/- 259.4 vs. 1,125. 8 +/- 235.3 micromol/l, p = 0.03), nonessential AA (NEAA, 2,307.2 +/- 399.1 vs. 2,879.5 +/- 581.2 micromol/l, p = 0.03), and branched chain AA (315.5 +/- 90.8 vs. 386.0 +/- 114.3 micromol/l, p = 0.05) concentrations were significantly higher on NHD. However, abnormalities in the ratios of EAA/NEAA, valine/glycine and tyrosine/phenylalanine persisted during NHD. NHD alleviated some abnormalities in the aminogram of uremia, but other metabolic derangements lingered.

Plasma amino acid profile on nocturnal hemodialysis.

Multiple, complex molecular events characterize cancer development and progression. Deciphering the molecular networks that distinguish organ-confined disease from metastatic disease may lead to the identification of critical biomarkers for cancer invasion and disease aggressiveness. Although gene and protein expression have been extensively profiled in human tumours, little is known about the global metabolomic alterations that characterize neoplastic progression. Using a combination of high-throughput liquid-and-gas-chromatography-based mass spectrometry, we profiled more than 1,126 metabolites across 262 clinical samples related to prostate cancer (42 tissues and 110 each of urine and plasma). These unbiased metabolomic profiles were able to distinguish benign prostate, clinically localized prostate cancer and metastatic disease. Sarcosine, an N-methyl derivative of the amino acid glycine, was identified as a differential metabolite that was highly increased during prostate cancer progression to metastasis and can be detected non-invasively in urine. Sarcosine levels were also increased in invasive prostate cancer cell lines relative to benign prostate epithelial cells. Knockdown of glycine-N-methyl transferase, the enzyme that generates sarcosine from glycine, attenuated prostate cancer invasion. Addition of exogenous sarcosine or knockdown of the enzyme that leads to sarcosine degradation, sarcosine dehydrogenase, induced an invasive phenotype in benign prostate epithelial cells. Androgen receptor and the ERG gene fusion product coordinately regulate components of the sarcosine pathway. Here, by profiling the metabolomic alterations of prostate cancer progression, we reveal sarcosine as a potentially important metabolic intermediary of cancer cell invasion and aggressivity.

Cadaverine

95%

Properties

Quality Level

assay

form

refractive index

bp

mp

density

SMILES string

InChI

InChI key

Related Categories

Description

Application

Packaging

Safety Information

Pictograms

Signal Word

Hazard Statements

Precautionary Statements

Hazard Classifications

Storage Class Code

WGK

Flash Point(F)

Flash Point(C)

Personal Protective Equipment

Documentation

Certificate of Analysis

Certificate of Origin

More Documents

Quotes and Ordering

Peer Reviewed Papers

Technical Service