Sigma-Aldrich

Pyrene 98%; CAS Number: 129-00-0; EC Number: 204-927-3; Synonyms: Benzo[def]phenanthrene; find Sigma-Aldrich-185515 MSDS, related peer-reviewed papers, technical documents, similar products & more at Sigma-Aldrich

Pyrene 98 129-00-0

Pyrene

Severe multidrug resistance (MDR) often develops in the process of chemotherapy for most small molecule anticancer drugs, which results in clinical chemotherapy failures. Methods: Here, a nanodrug is constructed through the self-assembly of amphiphilic drug-inhibitor conjugates (ADIC) containing a redox-responsive linkage for reversing the multidrug resistance (MDR) in cancer treatment. Specifically, hydrophilic anticancer irinotecan (Ir) and hydrophobic P-gp protein inhibitor quinine (Qu) are linked by a redox responsive bridge for overcoming MDR of tumors. Results: Ir-ss-Qu is able to self-assemble into nanoparticles (NPs) in water and shows the longer blood retention half-life compared with that of free Ir or Qu, which facilitates drug accumulation in tumor site. After endocytosis of Ir-ss-Qu NPs by drug-resistant tumor cells, the disulfide bond in the linkage between Ir and Qu is cleaved rapidly induced by glutathione (GSH) to release anticancer drug Ir and inhibitor Qu synchronously. The released Qu can markedly reduce the expression of P-gp in drug-resistant tumor cells and inhibits P-gp to pump Ir out of the cells. The increased concentration of intracellular Ir can effectively improve the therapeutic efficacy. Conclusions: Such redox-responsive Ir-ss-Qu NPs, as a drug delivery system, exhibit very high cytotoxicity and the most effective inhibitory to the growth of drug-resistant breast cancer compared with that of free therapeutic agents in vitro and in vivo.

Stimuli-responsive nanodrug self-assembled from amphiphilic drug-inhibitor conjugate for overcoming multidrug resistance in cancer treatment.

A new pyrene-cored π-conjugated molecule has been synthesized through Sonogashira coupling reaction. The single-crystalline microribbon-based FET exhibited the highest mobility of 0.7 cm(2) V(-1) s(-1) (I(on)/I(off) > 10(6)). Single-crystalline microribbons were employed to operate in an organic phototransistor (OPT) under very low light intensity (I = 5.6 μW cm(-2)).

Highly sensitive phototransistor with crystalline microribbons from new π-extended pyrene derivative via solution-phase self-assembly.

Pyrene fluorescence study of chitosan self-association in aqueous solution.

Photoconductivity of liquid crystalline derivatives of pyrene and carbazole.

Pyrene fluorescence lifetime as a probe for oxygen penetration of micelles.

Quenching of pyrene fluorescence by oxygen was used to determine oxygen diffusion coefficients in phospholipid dispersions and erythrocyte plasma membranes. The fluorescence intensity and lifetime of pyrene in both artificial and natural membranes decreases about 80% in the presence of 1 atm O2, while the fluorescence excitation and emission spectra and the absorption spectrum are unaltered. Assuming the oxygen partition coefficient between membrane and aqueous phase to be 4.4, the diffusion coefficients for oxygen at 37 degrees C are 1.51 X 10(-5) cm2/s in dimyristoyl lecithin vesicles, 9.32 X 10(-6) cm2/s in dipalmitoyl lecithin vesicles, and 7.27 X 10(-6) cm2/s in erythrocyte plasma membranes. The heats of activation for oxygen diffusion are low (less than 3 kcal/degree-mol). A dramatic increase in the diffusion constant occurs at the phase transition of dimyristoyl and dipalmitoyl lecithin, which may result from an increase in either the oxygen diffusion coefficient, partition coefficient, or both. The significance of the change in oxygen diffusion below and above the phase transition for biological membranes is discussed.

Oxygen diffusion in biological and artificial membranes determined by the fluorochrome pyrene.

One factor limiting the expansion of nanomedicines has been the high cost of the materials and processes required for their production. We present a continuous, scalable, low cost nanoencapsulation process, Flash Nanoprecipitation (FNP) that enables the production of nanocarriers (NCs) with a narrow size distribution using zein corn proteins. Zein is a low cost, GRAS protein (having the FDA status of "Generally Regarded as Safe") currently used in food applications, which acts as an effective encapsulant for hydrophobic compounds using FNP. The four-stream FNP configuration allows the encapsulation of very hydrophobic compounds in a way that is not possible with previous precipitation processes. We present the encapsulation of several model active compounds with as high as 45 wt % drug loading with respect to zein concentration into ∼100 nm nanocarriers. Three examples are presented: (1) the pro-drug antioxidant, vitamin E-acetate, (2) an anticholera quorum-sensing modulator CAI-1 ((S)-3-hydroxytridecan-4-one; CAI-1 that reduces Vibrio cholerae virulence by modulating cellular communication), and (3) hydrophobic fluorescent dyes with a range of hydrophobicities. The specific interaction between zein and the milk protein, sodium caseinate, provides stabilization of the NCs in PBS, LB medium, and in pH 2 solutions. The stability and size changes in the three media provide information on the mechanism of assembly of the zein/active/casein NC.

Nanocarriers from GRAS Zein Proteins to Encapsulate Hydrophobic Actives.

Intramolecular pyrene excimer fluorescence: a probe of proximity and protein conformational change.

Although distance dependence of Förster resonance energy transfer (FRET) is well-studied and FRET has been extensively applied as "molecular ruler", only limited examples of orientation-dependent FRET have been reported. To create a robust FRET system that precisely reflects the orientation between donor and acceptor, donor and acceptor fluorophores were introduced into a DNA via a D-threoninol scaffold. Strong stacking interactions among intercalated dyes and natural base-pairs suppress free movement of the dyes, clamping them in the duplex in a fixed orientation. Pyrene and perylene were used as donor and acceptor, respectively, and both the distance and orientation between these dyes were systematically controlled by varying the number of intervening AT pairs from 1 to 21 (corresponding to two turns of helix). FRET efficiency determined from static fluorescence measurement did not decrease linearly with the number (n) of inserted AT pairs but dropped significantly every 5 base pairs (i.e., n = 8, 13, and 18), corresponding to a half-turn of the B-type helix. This clearly demonstrates that FRET efficiency reflects the orientation between pyrene and perylene. We also measured time-resolved fluorescence spectroscopy with a streak camera and successfully observed the time-course of the energy transfer directly. As expected, the FRET efficiencies determined from the lifetime of pyrene emission were in good agreement with static measurements. Theoretical calculation of FRET efficiency assuming that the DNA duplex is a rigid cylinder with B-type geometry coincided with the experimental results. We believe that our method of using d-threoninol will contribute to further development of FRET-based measurement techniques.

Development of a robust model system of FRET using base surrogates tethering fluorophores for strict control of their position and orientation within DNA duplex.

The biodegradation of polycyclic aromatic hydrocarbons (PAHs) by marine-derived fungi was reported in this work. Marine-derived fungi (Trichoderma harzianum CBMAI 1677, Cladosporium sp. CBMAI 1237, Aspergillus sydowii CBMAI 935, Penicillium citrinum CBMAI 1186 and Mucor racemosus CBMAI 847) biodegraded anthracene (14days, 130rpm, 50mgmL-1 initial concentration in malt 2% medium). Cladosporium sp. CBMAI 1237 was the most efficient strain and biodegraded more anthracene in the presence (42% biodegradation) than in the absence (26%) of artificial seawater, suggesting that the biodegradation of PAHs may be faster in seawater than in non-saline environment. After 21days, Cladosporium sp. CBMAI 1237 biodegraded anthracene (71% biodegradation), anthrone (100%), anthraquinone (32%), acenaphthene (78%), fluorene (70%), phenanthrene (47%), fluoranthene (52%), pyrene (62%) and nitropyrene (64%). Previous undocumented metabolites were identified and, anthraquinone was a common product of different PAHs biodegradation. The marine-derived fungus Cladosporium sp. CBMAI 1237 showed potential for bioremediation of PAHs.

Biodegradation of anthracene and several PAHs by the marine-derived fungus Cladosporium sp. CBMAI 1237.

We present theoretical absolute charge exchange cross sections for multiply charged cations interacting with the Polycyclic Aromatic Hydrocarbon (PAH) molecules pyrene C(14)H(10), coronene C(24)H(12), or circumcoronene C(54)H(18). These planar, nearly circular, PAHs are modelled as conducting, infinitely thin, and perfectly circular discs, which are randomly oriented with respect to straight line ion trajectories. We present the analytical solution for the potential energy surface experienced by an electron in the field of such a charged disc and a point-charge at an arbitrary position. The location and height of the corresponding potential energy barrier from this simple model are in close agreement with those from much more computationally demanding Density Functional Theory (DFT) calculations in a number of test cases. The model results compare favourably with available experimental data on single- and multiple electron transfer reactions and we demonstrate that it is important to include the orientation dependent polarizabilities of the molecules (model discs) in particular for the larger PAHs. PAH ionization energy sequences from DFT are tabulated and used as model inputs. Absolute cross sections for the ionization of PAH molecules, and PAH ionization energies such as the ones presented here may be useful when considering the roles of PAHs and their ions in, e.g., interstellar chemistry, stellar atmospheres, and in related photoabsorption and photoemission spectroscopies.

Ions interacting with planar aromatic molecules: modeling electron transfer reactions.

Pyrene is one of the most frequently used lipid-linked fluorophores. Its most characteristic features are a long excited state lifetime and (local) concentration-dependent formation of excimers. Pyrene is also hydrophobic and thus does not significantly distort the conformation of the labeled lipid molecule. These characteristics make pyrene lipids well-suited for studies on a variety of biophysical phenomena like lateral diffusion, inter- or transbilayer movement of lipids and lateral organization of membranes. Pyrene lipids have also been widely employed to determine protein binding to membranes, lipid conformation and the activity of lipolytic enzymes. In cell biology, pyrene lipids are promising tools for studies on lipid trafficking and metabolism, as well as for microscopic mapping of membrane properties. The main disadvantage of pyrene lipids is the relatively large size of the fluorophore. Another disadvantage is that they require UV-excitation, which is not feasible with all microscopes.

Pyrene-labeled lipids as tools in membrane biophysics and cell biology.

The nutrient requirements and metabolic pathways used by the developing embryo transition from predominantly pyruvate during early cleavage stages to glucose at the blastocyst; however, the complexities involved in the regulation of metabolism at different developmental stages are not clear. The aims of this study were to examine the role of the malate-aspartate shuttle (MAS) in nutrient metabolism pathways in the developing mouse blastocyst and the consequences of impaired metabolism on embryo viability and fetal and placental growth. Eight-cell-stage mouse embryos were cultured in the presence of the MAS inhibitor amino-oxyacetate, with or without pyruvate as an energy substrate in the media. When the MAS was inhibited, the rate of glycolysis and lactate production was significantly elevated and glucose uptake reduced, relative to control cultured embryos in the presence of pyruvate. Despite these changes in embryo metabolism, this did not influence development to the blastocyst stage, but it did reduce the number of inner cell mass and trophectoderm cells. When these embryos were transferred to psuedopregnant females, inhibition of the MAS significantly reduced the proportion of embryos that implanted and developed into fetuses on Day 18 of pregnancy. Finally, fetal growth was reduced while placental weight was maintained, leading to a decreased fetal:placental weight ratio relative to control embryos. These results suggest that impaired metabolism of glucose in the blastocyst via the MAS alters the ability of the embryos to implant and form a pregnancy and leads to reduced fetal weight, likely via altered placental development and function.

Disruption of mitochondrial malate-aspartate shuttle activity in mouse blastocysts impairs viability and fetal growth.

Pyrene-functionalized oligonucleotides (PFOs) are increasingly explored as tools in fundamental research, diagnostics and nanotechnology. Their popularity is linked to the ability of pyrenes to function as polarity-sensitive and quenchable fluorophores, excimer-generating units, aromatic stacking moieties and nucleic acid duplex intercalators. These characteristics have enabled development of PFOs for detection of complementary DNA/RNA targets, discrimination of single nucleotide polymorphisms (SNPs), and generation of π-arrays on nucleic acid scaffolds. This critical review will highlight the physical properties and applications of PFOs that are likely to provide high degree of positional control of the chromophore in nucleic acid complexes. Particular emphasis will be placed on pyrene-functionalized Locked Nucleic Acids (LNAs) since these materials display interesting properties such as fluorescence quantum yields approaching unity and recognition of mixed-sequence double stranded DNA (144 references).

Pyrene-functionalized oligonucleotides and locked nucleic acids (LNAs): tools for fundamental research, diagnostics, and nanotechnology.

A drug delivery system based on gold nanoparticles (Au NPs) stabilized by an thiol-functionalized amphiphilic diblock copolymer was developed. The copolymer, poly(ethylene glycol)-b-poly(n-butyl acrylate) (MPEG-b-PBA), was synthesized by Reversible Addition-Fragmentation Transfer (RAFT) polymerization and the thiocarbonylthio group at the end of the hydrophobic block PBA was further reduced to thiol group. Pyrene, used as a model molecule for the hydrophobic drugs, was loaded in the hydrophobic interior of the shell around Au NPs by physical entrapment. The analysis performed by UV-Vis spectrophotometer show that the obtained Au NPs-pyrene nanocomposites have good stability in the aqueous solution and high drug loading capacity in comparison with Au NPs decorated with small molecular ligands. In addition, both their loading capacity and release behavior were found closely related to the chain length of hydrophobic block. In conclusion, we report here a versatile and simple procedure to fabricate Au NP-polymer hybrids that is applicable to various amphiphilic copolymers synthesized by RAFT polymerization and useful to produce efficient Au NP based drug carriers.

Gold nanoparticles decorated by amphiphilic block copolymer as efficient system for drug delivery.

A solvent switchable rotaxane equipped with a pyrene stopper and with two ferrocenyl units on the macrocycle is reported, in which three different states, two nondegenerate and one degenerate, can be obtained in different solvents at room temperature. This is accompanied by high contrast changes in fluorescence intensity of the pyrene stopper by the presence of the ferrocenyl moieties on the macrocycle, which quench the emission of pyrene more efficiently with proximity.

A three-level luminescent response in a pyrene/ferrocene rotaxane.

Fluorophores that are conjugated with N-methylpyrrole-N-methylimidazole (Py-Im) polyamides postulates versatile applications in biological and physicochemical studies. Here, we show the design and synthesis of new types of pyrene-conjugated hairpin Py-Im polyamides (1-5). We evaluated the steady state fluorescence of the synthesized conjugates (1-5) in the presence and absence of oligodeoxynucleotides 5'-CGTATGGACTCGG-3' (ODN 1) and 5'-CCGAGTCCATACG-3' (ODN 2) and observed a distinct increase in emission at 386nm with conjugates 4 and 5. Notably, conjugate 5 that contains a β-alanine linker had a stronger binding affinity (K(D)=1.73×10(-8)M) than that of conjugate 4 (K(D)=1.74×10(-6)M). Our data suggests that Py-Im polyamides containing pyrene fluorophore with a β-alanine linker at the γ-turn NH(2) position can be developed as the competent fluorescent DNA-binding probes.

Design of a new fluorescent probe: pyrrole/imidazole hairpin polyamides with pyrene conjugation at their γ-turn.

Methoxy poly(ethylene oxide)-block-poly-(α-carboxylate-ε-caprolactone) (PEO-b-PCCL) was used to develop pH-responsive polymeric micelles for the delivery of cisplatin (CDDP). Micelles were prepared through complexation of CDDP with the pendant carboxyl groups on the poly(ε-caprolactone) core, perhaps through coordinate bonding. The obtained micelles were characterized using dynamic light scattering (DLS) measurement for size and stability. The in vitro release of CDDP at different pHs (7.4, 6.0 and 5.0) was evaluated. The in vitro cell uptake as well as cytotoxicity of developed micelles against two breast cancer cell lines, i.e. MDA-MB-435 and MDA-MB-231, were also assessed and compared to free CDDP as control. DLS results showed PEO-b-PCCL to form stable micelles with an average diameter of <50 nm upon complexation with CDDP. Developed polymeric micelles were capable of slowly releasing CDDP in physiological pH. However, CDDP release from polymeric micelles was triggered upon exposure to electrolytes and/or acidic pHs mimicking that of extracellular tumor microenvironment or intracellular organelles. Consistent with the slow release of CDDP from its polymeric micellar formulation, polymeric micellar CDDP exhibited lower cytotoxicity and CDDP intracellular uptake compared to free drug. The results indicate a great potential for the developed formulation in platinum therapy of breast cancer.

Polymeric micelles for pH-responsive delivery of cisplatin.

We previously reported a classical quantitative structure-activity relationship (QSAR) equation for permeability coefficients (P(app-pampa)) by parallel artificial membrane permeation assay (PAMPA) of structurally diverse compounds with simple physicochemical parameters, hydrophobicity at a particular pH (logP(oct) and |pK(a)-pH|), hydrogen-accepting ability (SA(HA)), and hydrogen-donating ability (SA(HD)); however, desipramine, imipramine, and testosterone, which have high logP(oct) values, were excluded from the derived QSAR equation because their measured P(app-pampa) values were lower than calculated. In this study, for further investigation of PAMPA permeability of hydrophobic compounds, we experimentally measured the P(app-pampa) of more compounds with high hydrophobicity, including several pesticides, and compared the measured P(app-pampa) values with those calculated from the QSAR equation. As a result, compounds having a calculated logP(app-pampa)>-4.5 showed lower measured logP(app-pampa) than calculated because of the barrier of the unstirred water layer and the membrane retention of hydrophobic compounds. The bilinear QSAR model explained the PAMPA permeability of the whole dataset of compounds, whether hydrophilic or hydrophobic, with the same parameters as the equation in the previous study. In addition, PAMPA permeability coefficients correlated well with Caco-2 cell permeability coefficients. Since Caco-2 cell permeability is effective for the evaluation of human oral absorption of compounds, the proposed bilinear model for PAMPA permeability could be useful for not only effective screening for several drug candidates but also the risk assessment of chemicals and agrochemicals absorbed by humans.

Pyrene

98%

Properties

Quality Level

assay

mp

SMILES string

InChI

InChI key

Gene Information

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

Support

Orders

Company

Social Media

MilliporeSigma