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At least 487 records · Page 27Linked to original sources
PubMed2002

Synthesis of isotopically labeled arachidonic acids to probe the reaction mechanism of prostaglandin H synthase.

Prostaglandin H synthase (PGHS) catalyzes the conversion of arachidonic acid to prostaglandin G(2) in the cyclooxygenase reaction. The first step of the mechanism has been proposed to involve abstraction of the pro-S hydrogen atom from C13 to generate a pentadienyl radical spanning C11-C15. We report here the synthesis of six site-specifically deuterated arachidonic acids to investigate the structure of the radical intermediate. The preparation of these compounds was achieved using a divergent scheme that involved one advanced intermediate for all targets. The synthetic design introduced the label late in the routes and allowed the utilization of common synthetic intermediates in the preparation of various targets. Both 13(R)- and 13(S)-deuterium-labeled arachidonic acids were synthesized in high enantiomeric purity as deduced from soybean lipoxygenase assays and mass spectrometric analysis of the resulting enzymatic products. Each synthetic compound was reacted under anaerobic conditions with the wide singlet tyrosyl radical of PGHS-2 to generate a radical intermediate that was analyzed by EPR. Deuterium substitution at positions 11, 13(S), and 15 resulted in the loss of one hyperfine interaction, indicating that the protons at these positions interact with the unpaired electron. Simulation of the spectra was achieved with one set of parameters that are consistent with the assignment of a pentadienyl radical. Use of 16-[(2)H(2)]-arachidonic acid indicated that only one of the protons at C16 gives rise to a strong hyperfine interaction. The findings are discussed in the context of two proposed mechanisms for the cyclooxygenase reaction.

Arachidonic Acids↗
PubMedDate not supplied

Intracameral and lenticular penetration of locally applied stable isotope-labeled vitamin E.

PURPOSE: To confirm the aqueous humor and lens dynamics of 1% deuterium-labeled alpha-tocopherol acetate (D(3)-VEA) solution. METHODS: The concentrations of D(3)-VEA and D(3)-alpha-tocopherol (D(3)-VE), derived from D(3)-VEA, in the aqueous humor and lens were measured after continuous instillation of 1% D(3)-VEA into the cul-de-sac of rat eyes for 1 or 3 weeks. D(3)-VEA and D(3)-VE concentrations were determined by gas chromatography/mass selective detector. RESULTS: In the aqueous humor, the concentrations of D(3)-VEA and D(3)-VE were, respectively, 93.1 and 9.4 ng/mL after 1 week, and, respectively, 498.9 and 21.5 ng/mL after 3 weeks. In the lens, they were, respectively, 15.0 and 9.8 ng/g after 1 week, and 6.1 and 4.8 ng/g after 3 weeks. CONCLUSION: The penetration levels of alpha-tocopherol acetate by eyedrop application were confirmed in the aqueous humor and lens.

Administration, Topical↗
PubMed2006

Quantitative profiling of drug-associated proteomic alterations by combined 2-nitrobenzenesulfenyl chloride (NBS) isotope labeling and 2DE/MS identification.

The identification of drug-responsive biomarkers in complex protein mixtures is an important goal of quantitative proteomics. Here, we describe a novel approach for identifying such drug-induced protein alterations, which combines 2-nitrobenzenesulfenyl chloride (NBS) tryptophan labeling with two-dimensional gel electrophoresis (2DE)/mass spectrometry (MS). Lysates from drug-treated and control samples are labeled with light or heavy NBS moiety and separated on a common 2DE gel, and protein alterations are identified by MS through the differential intensity of paired NBS peptide peaks. Using NBS/2DE/MS, we profiled the proteomic alterations induced by tamoxifen (TAM) in the estrogen receptor (ER) positive MCF-7 breast cancer cell line. Of 88 protein spots that significantly changed upon TAM treatment, 44 spots representing 23 distinct protein species were successfully identified with NBS-paired peptides. Of these 23 TAM-altered proteins, 16 (70%) have not been previously associated with TAM or ER activity. We found the NBS labeling procedure to be both technically and biologically reproducible, and the NBS/2DE/MS alterations exhibited good concordance with conventional 2DE differential protein quantitation, with discrepancies largely due to the comigration of distinct proteins in the regular 2DE gels. To validate the NBS/2DE/MS results, we used immunoblotting to confirm GRP78, CK19, and PA2G4 as bona fide TAM-regulated proteins. Furthermore, we demonstrate that PA2G4 expression can serve as a novel prognostic factor for disease-free survival in two independent breast cancer patient cohorts. To our knowledge, this is the first report describing the proteomic changes in breast cancer cells induced by TAM, the most commonly used selective estrogen receptor modulator (SERM). Our results indicate that NBS/2DE/MS may represent a more reliable approach for cellular protein quantitation than conventional 2DE approaches.

Cell Line, Tumor↗
PubMed1987

Structural and electronic properties of the liver fluke hemoglobin heme cavity by nuclear magnetic resonance: hemin isotope labeling.

Reconstitution of liver fluke (Dicrocoelium dendriticum) apo-hemoglobin with hemins selectively deuterated at specific positions has permitted the assignment of several heme resonances in the proton nuclear magnetic resonance spectrum of the Met-aquo and Met-cyano forms of the holoprotein. It was established that in the Met-aquo form the meso protons resonate at positions characteristic of a six-co-ordinated in-plane iron. From this, we deduced that the Met-aquo species retains a bound water molecule at pH values as low as 4.5. The orientation of the proximal histidine imidazole ring with respect to the heme group in the cavity was determined through the identification of the heme methyl signals and the analysis of the hyperfine shift pattern in the Met-cyano hemoglobin proton nuclear magnetic resonance spectrum. Compared to sperm whale myoglobin, the heme appears to be rotated by 180 degrees about the alpha, gamma meso-axis. Protein isomers with the heme group in a reversed orientation were not detected, even shortly after reconstitution. In the Met-cyano form, the resonances most affected by the Bohr transition were shown to arise from the heme propionates.

Animals↗
PubMed2006

Investigation of low-abundant in vitro metabolites of stable isotope-labelled BAL4815 by accurate mass capillary-LC-ESI-qTof-MS and MS/MS.

The metabolic profile of BAL4815, an antifungal azole drug, was determined using in vitro rat hepatocyte incubations and subsequent analysis by capillary LC-qTof-MS and MS/MS including accurate mass determination. For the detection of the metabolites, a mixture of the drug and its deuterium-labelled analogue was used for incubations. Metabolic stability of BAL4815 was high in cultured rat hepatocytes. However, several low-abundant metabolites were detected by the use of capillary LC-qTof-MS and manual investigation of the data. The peak intensity of the most abundant metabolite was close to the limit of detection. Except for an apparent oxidation product, the masses of the other detected metabolites could not be assigned to a single and frequently occurring biotransformation. Accurate mass determination and possible elemental compositions suggested that metabolism occurred through a combination of glutathionylation and defluorination. This was verified using accurate mass MS/MS. The use of accurate mass measurements and the derived suggestions for the elemental compositions were essential to elucidate this atypical metabolic pathway. A mass accuracy better than 8 ppm could be achieved for most assigned MS and MS/MS signals with intensities less than 6 cps in the spectra.

Animals↗
PubMed1986

Isotope labeling studies on the mechanism of N-N bond formation in denitrification.

The mechanism of the denitrification and nitrosation reactions catalyzed by the heme cd-containing nitrite reductase from Pseudomonas stutzeri JM 300 has been studied with whole cell suspensions using H2(18)O, 15NO, and 15NO-2. The extent of H2(18)O exchange with the enzyme-bound nitrosyl intermediate, as determined by the 18O content of product N2O, decreased with increasing nitrite concentration, which is consistent with production of N2O by sequential reaction of two nitrite ions with the enzyme. Reaction of NO with whole cells in H2(18)O gave amounts of 18O in the N2O product consistent with equilibration of nitric oxide with a small pool of free nitrite. Using 15NO and NH2OH, competition between denitrification and nitrosation reactions was demonstrated, as is required if the enzyme-nitrosyl complex is an intermediate in both nitrosation and denitrification reactions. The first evidence for exchange of 18O between H2(18)O and a nitrosation intermediate occurring after the enzyme-nitrosyl complex, presumably an enzyme-bound nitrosamine, has been obtained. The collective results are most consistent with denitrification N2O originating via attack of NO-2 on a coordinated nitrosyl, as proposed earlier (Averill, B. A., and Tiedje, J. M. (1982) FEBS Lett. 138, 8-11).

Chemical Phenomena↗
PubMed2006

Sugar fragmentation in the maillard reaction cascade: isotope labeling studies on the formation of acetic acid by a hydrolytic beta-dicarbonyl cleavage mechanism.

The formation of acetic acid was elucidated based on volatile reaction products and related nonvolatile key intermediates. The origin and yield of acetic acid were determined under well-controlled conditions (90-120 degrees C, pH 6-8). Experiments with various 13C-labeled glucose isotopomers in the presence of glycine revealed all six carbon atoms being incorporated into acetic acid: C-1/C-2 ( approximately 70%), C-3/C-4 ( approximately 10%), and C-5/C-6 (approximately 20%). Acetic acid is a good marker of the 2,3-enolization pathway since it is almost exclusively formed from 1-deoxy-2,3-diulose intermediates. Depending on the pH, the acetic acid conversion yield reached 85 mol % when using 1-deoxy-2,3-hexodiulose (1) as a precursor. Hydrolytic beta-dicarbonyl cleavage of 1-deoxy-2,4-hexodiuloses was shown to be the major pathway leading to acetic acid from glucose without the intermediacy of any oxidizing agents. The presence of key intermediates was corroborated for the first time, i.e., tetroses and 2-hydroxy-3-oxobutanal, a tautomer of 1-hydroxy-2,3-butanedione, also referred to as 1-deoxy-2,3-tetrodiulose. The hydrolytic beta-dicarbonyl cleavage represents a general pathway to organic acids, which corresponds to an acyloin cleavage or a retro-Claisen type reaction. Although alternative mechanisms must exist, the frequently reported hydrolytic alpha-dicarbonyl cleavage of 1 can be ruled out as a pathway forming carboxylic acids.

Acetic Acid↗
PubMed2005

Combining inducible protein overexpression with NMR-grade triple isotope labeling in the cyanobacterium Anabaena sp. PCC 7120.

The difficulty and expense of preparing protein samples highly enriched in stable isotopes is a bottleneck for structural studies by nuclear magnetic resonance (NMR) spectroscopy. We have developed a new regulatable expression/labeling vector system in the cyanobacterium Anabaena sp. PCC 7120 using the endogenous promoter of the nitrate assimilation nir operon. Standard proteins were overexpressed upon induction with NaNO3, yielding up to 250 mg/L of culture. When the cyanobacteria were grown in the presence of inexpensive 15N-, 13C-labeled mineral salts and 2H2O, the expressed polypeptides were highly (>90%) enriched in stable isotopes. Furthermore, the tight repression of the nir promoter upon induction allowed the production of the toxic oncoprotein E6. In addition, under these conditions, the malE31 protein, while insoluble in Escherichia coli, was found to be soluble in Anabaena. Together, these properties render the described system especially suitable for the production and/or triple labeling of recombinant protein samples. It represents an interesting alternative to conventional protein expression systems used in structural genomics.

Anabaena↗
PubMed1994

Point-mutations affecting the properties of tyrosineD in photosystem II. Characterization by isotopic labeling and spectral simulation.

The reaction center of photosystem II (PSII) contains two redox-active tyrosines, TyrD and TyrZ, which are Tyr160 and Tyr161 of the D2 and D1 proteins, respectively. We have introduced five site-directed mutations in the vicinity of TyrD to analyze the consequences of the mutations on spectral and functional properties of TyrD(ox). Characterization of three mutants, P161A and P161L (Pro161 changed to Ala and Leu, respectively) and Q164L (Gln164 mutated to Leu), is emphasized. Of these three mutants, only P161L is an obligate photoheterotroph; it is capable of oxygen evolution, but is photoinactivated rapidly. The D2 protein of this mutant migrates slower on a SDS-polyacrylamide gel. The EPR spectrum of TyrD(ox) is modified in the three mutants. The EPR spectra of TyrD(ox) in wild type and the mutants were characterized in detail by comparison of EPR spectra of thylakoids from cells grown in the presence and absence of tyrosine that was deuterated in specific positions. The experimentally obtained EPR spectra of wild type, P161A, and Q164L could be simulated satisfactorily using current theoretical models. The angle between one of the hydrogens on the beta-methylene carbon and the 2pz orbital at C1 of the tyrosine ring was found to change slightly but significantly as a function of the mutations (52 degrees in wild type, 50 degrees in P161A, and 48 degrees in Q164L). The overall electronic structure of TyrDox is quite unaffected; only minor redistribution of the unpaired electron spin is observed between the wild type and the mutated systems.(ABSTRACT TRUNCATED AT 250 WORDS)

Cyanobacteria↗
PubMed1977

Semiquantitative determination of Cc and C3 receptors on human lymphocytes by isotope-labelled marker cells.

The number of Fc and C3 receptors on normal B lymphocytes, isolated from blood, was assessed semiquantitatively by a new method in which the marker cells (pretreated sheep erythrocytes) for Fc and C3 receptors are labelled by 99Tc and 51Cr respectively. The mean number of bound marker cells per rosette was assessed simultaneously by measurements of radioactivity. Control studies showed that a measuring system using 1/4 agglutinating titre of antibody on the marker cells is particularly advantageous: (1) Fc and C3 receptors are not demonstrable on T lymphocytes; thus, B lymphocyte fractions with Fc and/or C3 receptors are well-defined. (2) The binding affinity of the marker cells for normal lymphocytes is so weak that the number of bound marker cells per rosette rarely reaches the maximum which was calculated and measured as about 30 marker cells per rosette; thus, the measuring system is sensitive to changes in the number of receptors. (3) By binding of marker cells to lymphocytes bearing Fc as well as C3 receptors it has been demonstrated that interference phenomena between the two marker cells are not operative. Studies of blood lymphocytes from normal human subjects showed B lymphocytes carrying either Fc and C3 receptors as well as a fraction of B lymphocytes having both Fc and C3 receptors. The latter maker up about 6% of the lymphocyte mass. Comparative assessment of the quantitative distribution of these receptors indicates a developmental sequence, B lymphocyte with Fc receptors evidently developing, via B lymphocytes with Fc as well as C3 receptors, into B lymphocytes having C3 receptors only.

Adult↗
PubMedDate not supplied

Incorporation of isotopically labeled cocaine into human hair: race as a factor.

In order to evaluate race as a possible factor affecting the incorporation of drugs into human hair, 2 mg/kg deuterium-labeled cocaine (cocaine-d5) was administered intranasally to nine male non-Caucasian volunteers under controlled laboratory conditions. Sequential blood samples were collected for up to three days, and scalp hair samples were collected at 24 and 72 h after dosing and at monthly intervals for up to 12 months. The samples were then analyzed by gas chromatography-mass spectrometry for cocaine-d5 and benzoylegonine-d5 (BZE-d5). The amounts of cocaine-d5 found in the hair of these non-Caucasian subjects were compared with the amounts of cocaine-d5 found in the hair of Caucasian subjects who received the same cocaine dose under identical conditions as part of a study we reported previously. The non-Caucasians in the present study had approximately 2.7 times more cocaine-d5 in their hair than the Caucasian subjects in the earlier study. In five of the non-Caucasian subjects, cocaine-d5 could be detected in hair within 24 h after dosing. Curiously, we were unable to detect any cocaine-d5 in one of the non-Caucasian subject's hair at any time after dosing even though cocaine-d5 was in plasma at the expected levels. The results from these studies suggest there may be a racial bias in the incorporation of cocaine into human hair; however, the data are not conclusive because of the relatively small sample size.

Administration, Intranasal↗
PubMed1983

Mathematical analysis of isotope labeling in the citric acid cycle with applications to 13C NMR studies in perfused rat hearts.

Rat hearts have been perfused in vitro with 5 mM glucose and either 5 mM acetate or 1 mM pyruvate to achieve steady state conditions, followed by replacement of the acetate with 90% enriched [2-13C]acetate or pyruvate with 90% enriched [3-13C]pyruvate. The hearts were frozen different times after addition of 13C-substrate and neutralized perchloric acid extracts from three pooled hearts per time point were used to obtain high resolution proton-decoupled 13C NMR spectra at 90.55 MHz. The 13C fractional enrichment of individual carbons of different metabolites was calculated from the area of the resolved resonances after correction for nuclear Overhauser enhancement and saturation effects. A mathematical flux model of the citric acid cycle and ancillary transamination reactions was constructed with the FACSIMILE program, and used to solve unknown flux parameters with constant pool sizes by nonlinear least squares analysis of the approximately 200 simultaneous differential equations required to describe the reactions. With [2-13C] acetate as substrate, resonances and line splittings due to 13C-13C spin coupling of the C-2, C-3, and C-4 carbons of glutamate were well resolved. The half-times to reach maximum 13C enrichment were 2.6 min for glutamate C-4 and 8 min for glutamate C-2 and C-3. From these data, a well determined citric acid cycle flux of 8.3 mumol/g dry weight X min was calculated for an observed oxygen consumption of 31 mumol/g dry weight X min. With [3-13C]pyruvate as substrate, resonances of aspartate C-2 and C-3 and of alanine C-3 were well resolved in addition to those of glutamate C-2, C-3, and C-4. Nonlinear least squares fitting of these data to the model gave nonrandomly distributed residuals for the 13C fractional enrichments of glutamate C-4, suggesting an incomplete model, but a well determined cycle flux of 11.9 mumol/g dry weight X min for an oxygen uptake of 35 mumol/g dry weight X min. Our studies demonstrate the practicality of 13C NMR, used in conjunction with mathematical modeling, for the measurement of metabolic flux parameters in living systems.

Animals↗
PubMed2006

Combined chemical and enzymatic stable isotope labeling for quantitative profiling of detergent-insoluble membrane proteins isolated using Triton X-100 and Brij-96.

Effective quantitative profiling of detergent-insoluble membrane proteins using high-throughput mass spectrometry (MS)-based proteomics would allow a better understanding of physiological and pathological processes that take place at the cell surface. To increase the coverage of proteins present in detergent-resistant membrane microdomains (DRMMs), a combination of 16O/18O and isotope coded affinity tags (ICAT) labeling was used in a comparative analysis of detergent-insoluble membrane proteins isolated from rat basophilic leukemia cells (RBL-2H3), with either Triton X-100 or Brij-96. The analysis resulted in the quantification of 738 unique proteins from Triton X-100 and Brij-96 isolated DRMMs, significantly exceeding the number of proteins quantified from either single labeling technique. Twenty-five noncysteine-containing proteins were quantified, as well as 32 cysteine-containing proteins that would have been missed if either 16O/18O or ICAT labeling had been used exclusively, which illustrate better proteome coverage and enhanced ability to quantitate. The comparative analysis revealed that proteins were more readily extracted using Triton X-100 than Brij-96; however, Triton X-100 also extracted larger quantities of non-DRMMs-associated proteins. This result confirms previous, targeted studies suggesting that DRMMs isolated using Triton X-100 and Brij-96 differ in their protein content.

Amino Acid Sequence↗
PubMedDate not supplied

Incorporation of isotopically labeled cocaine and metabolites into human hair: 1. dose-response relationships.

Deuterium-labeled cocaine (cocaine-d5) was administered intravenously and/or intranasally in doses of 0.6-4.2 mg/kg to 25 human volunteers under laboratory clinical conditions. Sequential blood samples were collected for up to 3 days, and hair samples were collected for up to 10 months. Samples were analyzed by gas chromatography-mass spectrometry (GC-MS) for cocaine-d5 and its major metabolite, benzoylecgonine-d5 (BZE-d5). The parent drug, cocaine-d5, was the predominant analyte in hair, whereas BZE-d5 was the major analyte in blood, especially at later time periods. The amount of cocaine-d5 incorporated into hair ranged from 0.1 to 5 ng/mg hair, whereas the amount of BZE-d5 was approximately one-sixth of that concentration. The threshold dose for detection was estimated to be 25-35 mg of drug administered intravenously. A single dose could be detected for 2-6 months. Subjects receiving the same dose differed (from two to 12 times as much depending upon how it was measured) in the amount of cocaine-d5 incorporated into their hair. Non-Caucasians, in particular, incorporated more cocaine-d5 in hair than did Caucasians. Also, segmental analysis of the samples revealed considerable intersubject variability in the time drug first appeared in hair and the rate at which the drug moved along the hair shaft with time. These interindividual differences could not be explained by differences in plasma pharmacokinetics. Considered together, these results suggest that cocaine incorporation into hair may occur by way of multiple mechanisms--by way of sweat and sebum, for example--and at various times during the hair growth cycle. Thus, hair analysis using GC-MS appears to be a very sensitive method for detecting cocaine ingestion. However, within the range of doses used in the present study, hair does not provide a particularly accurate record of either the amount, time, or duration of drug use.

Administration, Intranasal↗
PubMed1985

1H-15N heteronuclear NMR studies of Escherichia coli thioredoxin in samples isotopically labeled by residue type.

Ten samples of Escherichia coli thioredoxin were individually isotopically enriched by residue type via growth of an appropriate auxotrophic strain on media supplemented with one 2H, 15N-enriched amino acid. 1H observe-heteronuclear decoupling experiments were conducted on these samples making use of the 95-Hz 1H-15N amide J1 coupling. Subtraction of near-resonance from off-resonance 15N decoupled spectra generated difference patterns corresponding only to protons directly bonded to 15N nuclei. For the ten different enriched residue types observed to date, every labeled position (60) has been observed as a resolved resonance. The spectral dispersion in both the 1H and the 15N dimensions was roughly 1500 Hz (at 500-MHz field strength) with rather little apparent dependence on residue type. With the exception of the glycine-enriched sample, the range of the J1 coupling constants was not much greater than the precision of the measurements (1.5-2.0 Hz). However, for the glycine residues the J1 amide coupling values varied over a range of 10 Hz.

Bacterial Proteins↗
PubMed1994

Incorporation of stable isotope-labeled arachidonic acid into cellular phospholipid molecular species and analysis by fast atom bombardment tandem mass spectrometry.

The source of arachidonic acid metabolized to eicosanoids by 5-lipoxygenase was studied in a cultured neoplastic mast cell using a stable isotope tracer and tandem mass spectrometry strategy. Selected reaction monitoring and fast atom bombardment were used to analyze eight major arachidonate molecular species of glycerophosphocholine, nine major molecular species of glycerophosphoethanolamine, three major species of glycerophosphocholine, nine major molecular species of glycerophosphoethanolamine, three major species of glycerophosphoinositol, and three major glycerophosphoserine molecular species. Incubation of the mast cells with (2H8)arachidonic acid led to a time-dependent isotopic incorporation in each of these molecular species. Following stimulation with calcium ionophore A23187, the isotope incorporation of leukotriene B4 (LTB4) was found to be higher than that of the major arachidonate-containing glycerophospholipid molecular species. The isotope incorporation of LTB4 was similar to that found for free arachidonic acid present in the unstimulated cell. In order to prevent direct labeling of the intracellular, free arachidonic acid pool, (2H4)linoleic acid was added to the culture medium as a biochemical precursor of labeled arachidonic acid. There was a time-dependent increase of the specific incorporation of labeled arachidonic acid into each of the phospholipid molecular species of each lipid class after incubation with (2H4)linoleic acid. Importantly, (2H4)linoleic acid incubation also resulted in deuterium-labeled arachidonic acid in the free arachidonic acid, intracellular pool. The arachidonic acid isotopic incorporation in this pool very closely correlated with the isotopic incorporation of LTB4 (correlation coefficient 0.97) synthesized after A23187 stimulation, while the isotopic incorporation of the extracellularly released, not esterified arachidonic acid, after stimulation, did not.(ABSTRACT TRUNCATED AT 400 WORDS)

Animals↗
PubMed2005

A simple, artificial-membrane feeding method for the radio-isotope labelling of Aedes aegypti polypeptides in vivo.

An artificial feeding unit has been designed and constructed to feed laboratory-bred Aedes aegypti with a radio-isotope (35S), so that the mosquitoes' polypeptides can be labelled in vivo. In the unit, a piece of Parafilm M barrier film is stretched over the bottom, outer surface of a polystyrene Petri dish, to create a small gap in which the mixture of blood and radio-isotope is placed. Warm water is placed in the dish, to keep the blood at about 37 degrees C. When such units were placed on net-covered rearing cages, almost all (80%-90%) of the female mosquitoes in the cages took bloodmeals from them. When checked by polyacrylamide-gel electrophoresis and autoradiography 1 h after feeding had begun, the blood-fed mosquitoes were found to have radio-labelled polypeptides. The unit is simple, easy to handle, disposable and can be used to offer small blood samples (>or=50 microl) to Ae. aegypti and, presumably, other mosquito species.

Aedes↗