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1.
ABSTRACT

The coat colour in mammals is determined by the relative amounts of eumelanin (black/brown) and phaeomelanin (red/yellow), produced in melanocytes, which are controlled by melanocyte stimulating hormone receptor (MSH-R). Melanocyte stimulating hormone receptor is activated by α-melanocyte-stimulating hormone (α-MSH). Stimulated MSH-R activates adenylyl cyclase (AC), thereby increasing the amount of cyclic AMP in the cell, which activates the enzyme tyrosinase resulting in eumelanin synthesis. In this study the complete coding sequences of five alleles of the MSH-R gene found in Holstein, Red Holstein, Simmental, and Brown Swiss cattle were cloned into a mammalian expression vector and transfected into human embryonic kidney (HEK) 293 cells. The expressed receptors were analyzed for their ability to increase intracellular cAMP in response to stimulation by α-MSH. The recessive red allele (e) found in Red Holstein and Simmental and the dominant black allele (ED) found in Holstein were unresponsive to a wide range of α-MSH concentrations. Two alleles from Brown Swiss (Ed1, Ed2) and one allele found in the Simmental breed (ef) responded to stimulation by α-MSH in a dose-dependent manner. When compared to Ed1 and Ed2, the cells transfected with the ef MSH-R allele, however, reached the corresponding intracellular cAMP concentrations at a 10-fold higher concentration of α-MSH. In conjunction with the mode of inheritance of coat colour, the results indicate that the e MSH-R allele is a non-functional receptor, ED is constitutively activated receptor, and Ed1 and Ed2 are hormonally activated receptors. The delay in ef MSH-R response may explain the similarity between the e and ef phenotypes.  相似文献   

2.

Abstract  

Aiming to apply the multivalency concept to melanoma imaging, we have assessed the in vivo melanocortin type 1 receptor (MC1R)-targeting properties of 99mTc(I)-labeled homobivalent peptide conjugates which contain copies of the α-melanocyte-stimulating hormone (α-MSH) analog [Ac-Nle4, Asp5, d-Phe7, Lys11]α-MSH4–11 separated by linkers of different length (L 2 nine atoms and L 3 14 atoms). The MC1R-binding affinity of L 2 and L 3 is significantly higher than that of the monovalent conjugate L 1 . Metallation of these conjugates yielded the complexes fac-[M(CO)3(k3-L)]+ (M is 99mTc/Re; 1/1a, L is L 1 ; 2/2a, L is L 2 ; 3/3a, L is L 3 ), with IC50 values in the subnanomolar and nanomolar range. The MC1R-mediated internalization of 2 and 3 is higher than that of 1 in B16F1 melanoma cells. Biodistribution studies in melanoma-bearing mice have shown low nonspecific accumulation with a tumor uptake that correlates with IC50 values. However, no correlation between tumor uptake and valency was found. Nevertheless, 2 displayed the highest tumor retention, and the best tumor to nontarget organ ratios.  相似文献   

3.
Since the human body for many reasons can adapt and become resistant to drugs, it is important to develop and validate computer aided drug design (CADD) methods that could help predict binding affinity changes that can result from these resistant enzymes. The free energy perturbation (FEP) methodology is the most accurate means of estimating relative binding affinities between inhibitors and protein variants. In this paper, we describe the role played by hydrophobic residues lining the active site region, particularly 79 Ile and 176 Phe, in the binding of methotrexate to the Escherichia coli (E. coli) thymidylate synthase (TS) enzyme, using the thermodynamic cycle perturbation (TCP) approach. The computed binding free energy differences on the binding of methotrexate to the native and some mutant E. coli TS structures have been compared with experimental results. Computationally, four different ‘mutations’ have been simulated on the TS enzyme with methotrexate (MTX): 79 Ile →  79 Val; 79 Ile → 79 Ala; 79 Ile → 79 Leu; and 176 Phe →  176 Ile. The calculated results indicate that in each of these cases, the native residues ( 79 Ile and 176 Phe) interact more favorably with methotrexate than the mutant residues and these results are corroborated by experimental measurements. Binding preference to wild type residues can be rationalized in terms of their better hydrophobic contacts with the phenyl ring of methotrexate.  相似文献   

4.
Summary Syntheses are described of new endomorphin 1 and 2 peptoid–peptide hybrids in which Tyr1 and either one or both Phe3 and Phe4 have been replaced by N-substituted-glycine. The preparation is also described of two glycosylated Hyp2-endomorphin 2 analogues in which either 2,3,4,6-tetra-O-acetyl glucose or glucose are β-O-glycosidically linked to the hydroxyproline residue. The Hyp2-endomorphin sequences have also been elongate by adding a C-terminal β-alanine residue and several linear dimers have been prepared by coupling either the native peptides or the modified analogues. The cyclo endomorphin 2 has also been synthesized. Preliminary pharmacological experiments on isolated organ preparations showed that the agonist activities of both endomorphin 1 and 2 are not significantly affected by the Pro/Hyp substitution. Phe4/Nphe substitution in the endomorphin 1 reduced the potency on guinea pig ileum (GPI) by about 100 times and abolished the agonist activity on mouse vas deferens (MVD) preparation. The decrease of the agonist activity induced by modification of one phenylalanine residue only, either Phe3 or Phe4, is lower on endomorphin 2. Either modification of both Phe3 and Phe4 or glycosylation of the Hyp2-endomorphin 2 cancelled any agonist activity on both preparations. The linear peptide dimers [endomorphin 1]2, [endomorphin 2]2, [Hyp2-endomorphin 1]2, [Hyp2-endomorphin 2]2, [Hyp2-endomorphin 1-Hyp2-endomorphin 2]2 or [Hyp2-endomorphin 2-Hyp2-endomorphin 1]2, are 7–19 times less potent than endomorphin 1 on GPI and significantly less active than endomorphins 1 and 2 on MVD. The other afforded modifications significantly affected or abolished the agonist activity of the resulting endomorphin analogues on both GPI and MVD preparations.The α-amino acid residues are of the L-configuration. Standard abbreviations for amino acid derivatives and peptides are according to the suggestions of the IUPAC-IUB Commission on Biochemical Nomenclature (1984) Eur. J. Biochem., 138, 9–37. Abbreviations listed in the guide published in (2003) J. Peptide Sci., 9, 1–8 are used without explanation.  相似文献   

5.
Abstract

Azo linked salicyldehyde and a new 2-hydroxy acetophenone based ligands (HL1 and HL2) with their copper(II) complexes [Cu(L1)2] (1) and [Cu(L2)2] (2) were synthesized and characterized by spectroscopic methods such as 1H, 13C NMR, UV–Vis spectroscopy and elemental analyses. Calculation based on Density Functional Theory (DFT), have been performed to obtain optimized structures. Binding studies of these copper (II) complexes with calf thymus DNA (ct-DNA) and torula yeast RNA (t-RNA) were analyzed by absorption spectra, emission spectra and Viscosity studies and Molecular Docking techniques. The absorption spectral study indicated that the copper(II) complexes of 1 and 2 had intrinsic binding constants with DNA or RNA in the range of 7.6?±?0.2?×?103?M?1 or 6.5?±?0.3?×?103M?1 and 5.7?±?0.4?×?104 M?1 or 1.8?±?0.5?×?103 M?1 respectively. The synthesized compounds and nucleic acids were simulated by molecular docking to explore more details mode of interaction of the complexes and their orientations in the active site of the receptor.  相似文献   

6.

The sorptive behavior of bacteria—iron oxide composites was investigated in batch metal sorption assays using ferrihydrite in isolation (0.13 and 0.14 g/L ferrihydrite in cadmium and lead systems, respectively) as well as in combination with Bacillus subtilis (0.25 g/L adsorbent mixture) and Escherichia coli (0.27 g/L adsorbent mixture). A pH range from 3.0 to 6.5 was studied using total metal concentrations of 1.0 × 10 ? 4.0 and 3.2 × 10 ? 5 M with adsorbent mixtures proportioned on a 1:1 mass/volume basis. The log of the apparent surface complex formation constants (log K S M ) and sorption capacity (S max ) values were determined by fitting the experimental data to one-site Langmuir sorption isotherms. The one-site model effectively described the sorption data (r 2 > 0.9), where Cd 2 + exhibited somewhat lower sorption affinities (log K S M = ?3 for ferrihydrite, ?1.7 for B. subtilis–ferrihydrite, and ?1.1 for E. coli–ferrihydrite) than Pb 2 + (log K S M = ?0.9 for ferrihydrite, ? 0.2 forB. subtilis–ferrihydrite, and –0.1 for E. coli–ferrihydrite). The corresponding S max values for Cd 2 + and Pb 2 + on ferrihydrite were 0.78 mmole/g and 1.34 mmole/g, respectively. For the B. subtilis–ferrihydrite composites, Cd 2 + and Pb 2 + S max values were lower at 0.29 mmole/g and 0.5 mmole/g, respectively. Similar values were determined for the E. coli–ferrihydrite composites (0.15 mmole/g and 0.68 mmole/g for Cd 2 + and Pb 2 + , respectively). The sorption of Cd 2 + and Pb 2 + by each of the sorbent systems exhibited a strong dependence on pH with sorption edges in the range of pH 4.0 to 7.3. The observed S max of the composites were lower than values predicted upon available site additivity (Cd 2 + B. subtilis ?ferrihydrite : 0.29 mmole/g (observed) < 0.57 mmole/g (calculated); Cd 2 + E. coli ?ferrihydrite : 0.15 mmole/g (observed) < 0.44 mmole/ g (calculated); Pb 2 + B. subtilis ?ferrihydrite : 0.5 mmole/g (observed) < 0.805 mmole/g (calculated); Pb 2 + E. coli –ferrihydrite : 0.68 mmole/g (observed) < 0.775 mmole/g (calculated)), implying that a masking of reactive surface sites by attachment had occurred between the bacteria and ferrihydrite. Electrophoretic mobility analysis indicated that the ferrihydrite surface properties dominate the net surface charge for each composite system with lesser contributions from the bacteria.  相似文献   

7.

Seasonal variations in precipitation changed the community composition and microbial activity in a hypersaline, tropical microbial mat, in Cabo Rojo, PR. Using a combination of dissection, light, and transmission electron microscopy, terminal restriction fragment length polymorphism (T-RFLP), in situ microelectrode studies, and 35 S isotope incubations, we documented the major differences between wet and dry seasons. During the wet season (precipitation 177 mm), cyanobacterial (green layer) and anoxyphototrophic (pink layer) communities, as well as the black FeS layer were well-developed, and T-RFLP patterns indicated a diverse community. The rate of oxygenic photosynthesis was 49 μ M min ? 1 . Aerobic respiration was 29 μ M min ? 1 , and sulfate reduction was 264 nmol cm ? 3 h ? 1 . During the dry season (precipitation 51 mm), cyanobacteria and anoxyphototrophs were less diverse and abundant, and T-RFLP patterns were less complex. The O 2 production rate was reduced to 9 μ M min ? 1 , as was O 2 consumption (7 μ M min ? 1 ) and sulfate reduction (26 nmol cm ? 3 h ? 1 ). Aragonite, calcite, halite, and quartz were the predominant minerals. Seasonal differences were found in the green and pink layers for both halite and quartz. Gypsum was not observed, likely due to a sample handling artifact. The fluctuations in community composition and metabolic activity, principally reflected in fluctuations in binding and trapping potential of the uppermost mat community, might be responsible for the observed differences in mineralogy.  相似文献   

8.

The synthesis and properties of oligonucleotides (ONs) containing 9-(2,3,4-trihydroxybutyl)adenine, A C2 and A C3, are described. The ON containing A C2 involves the 3′ → 4′ and 3′ → 5′ phosphodiester linkages in the strand, whereas that containing A C3 possesses the 3′ → 4′ and 2′ → 5′ phosphodiester linkages. It was found that incorporation of the analogs, A C2 or A C3, into ONs significantly reduces the thermal and thermodynamic stabilities of the ON/DNA duplexes, but does not largely decrease the thermal and thermodynamic stabilities of the ON/RNA duplexes as compared with the case of the ON/DNA duplexes. It was revealed that the base recognition ability of A C2 is greater than that of A C3 in the ON/RNA duplexes.  相似文献   

9.
Abstract

2′-5′ and 3′-5′ linked 2-aminoadenylyl-2-aminoadenosines [(2′-5′)n2Apn2A (1) and (3′-5′)n2Apn2A (2)] were synthesized by condensation of 5′-O-monomethoxytrityl-N 2 N 6-dibenzoyl-2-aminoadenosine and N 2,N 6,2′,3′-O-tetrabenzoyl-2-aminoadenosine 5′-phosphate using dicyclohexylcarbodiimide (DCC). The conformational properties of these dimers 1 and 2 were examined by UV, NMR and CD spectroscopy. The results reveal that the 2′-5′-isomer 1 takes a stacked conformation, which contains a larger base-base overlap and is more stable against thermal perturbation with respect to the 3′-5′-isomer 2. Interactions of 1 and 2 with polyuridylic acid (Poly (U)) were also examined by Tm, mixing curves, UV and CD spectra. Both the dinucleoside isomers 1 and 2 formed a complex of 1 : 2 stoichiometry with poly(U), which was much more stable than that of the corresponding ApA isomer  相似文献   

10.
Abstract

The 5-alkoxymethyl-2,2,7,8-tetramethyl-6-chromanols (II) are excellent antioxidants against autoxidising safflower oil (ASO), although not as good as 2,2,5,7,8-pentamethyl-6-chromanol (I), the model compound of -tocopherol. The aim of this work was to determine whether the rate of reaction of (II) with the radicals diphenylpicrylhydrazyl (DPP·) and galvinoxyl (ArO·) was directly proportional to their antioxidant activity against ASO. Compounds (II) reacted faster with DPP·. than with ArO·. but, in each case, slower than compound (I). The rates of reaction of I and II with both radicals followed the order I > II (R = H) > II (R = CH3) > II (R = other alkyls) and were directly proportional to their antioxidant activity against ASO.  相似文献   

11.
Abstract

The synthesis of phosphoramidites (2 and 3) derived from hypoxanthine and isoguanine N7-21-deoxyribonucleosides is described. Solid-phase synthesis furnishes oligonucleotides containing N7-glycosylated purines. New base pairs between purine N7- and N9-nucleosides are proposed.  相似文献   

12.

The extreme environments of South Africa mines were investigated to determine microbial community structure and biomass in the deep subsurface. These community parameters were determined using phospholipid fatty acid (PLFA) technique. Air, water and rock samples were collected from several levels and shafts in eight different mines. Biomass estimates ranged over nine orders of magnitude. Biofilm samples exhibited the highest biomass with quantities ranging from 10 3 to 10 7 pmol PLFA g ?1 . Rock samples had biomass ranging from 10 3 to 10 6 pmol PLFA g ?1 . Mine service waters and rock fracture waters had biomass estimates ranging from 10 0 to 10 6 pmol PLFA L ?1 . Air samples biomass values ranged from 10 ?2 to 10 0 pmol PLFA L ?1 . The biomass estimates were similar to those estimates for other deep subsurface sites. Redundancy analysis of the PLFA profiles distinguished between the sample types, where signature lipid biomarkers for aerobic and anaerobic prokaryotes, sulfate-and metal-reducing bacteria were associated with biofilms. Rock samples were enriched in 18:1 ω 9 c , 18:2 ω 6, br17:1s and br18:1s, which are indicative of microeukaryotes and metal- reducing bacteria. Air samples were enriched with 22:0, 17:1, 18:1, and a polyunsaturated fatty acid. Service waters had monounsaturated fatty acids. Fracture waters contained i17:0 and 10Me18:0 which indicated gram-positive and other anaerobic bacteria. When the fracture and service water sample PLFA responses to changes in environmental parameters of temperature, pH, and anion concentrations were analyzed, service waters correlated with higher nitrate and sulfate concentrations and the PLFAs 18:1 ω 7 c and 16:1 ω 7 c . Dreifontein shaft 5 samples correlated with chloride concentrations and terminally branched saturated fatty acids and branched monounsaturated fatty acids. Kloof, Tau Tona, and Merriespruit fracture waters aligned with temperature and pH vectors and 18:0, 20:0 and 22:6 ω 3. The redundancy analysis provided a robust method to understand the PLFA responses to changes in environmental parameters.  相似文献   

13.
The synthesis of ruthenium(II) and osmium(II) arene complexes with the closely related indolo[3,2-c]quinolines N-(11H-indolo[3,2-c]quinolin-6-yl)-ethane-1,2-diamine (L 1 ) and N′-(11H-indolo[3,2-c]quinolin-6-yl)-N,N-dimethylethane-1,2-diamine (L 2 ) and indolo[3,2-d]benzazepines N-(7,12-dihydroindolo-[3,2-d][1]benzazepin-6-yl)-ethane-1,2-diamine (L 3 ) and N′-(7,12-dihydroindolo-[3,2-d][1]benzazepin-6-yl)-N,N-dimethylethane-1,2-diamine (L 4 ) of the general formulas [(η6-p-cymene)MII(L 1 )Cl]Cl, where M is Ru (4) and Os (6), [(η6-p-cymene)MII(L 2 )Cl]Cl, where M is Ru (5) and Os (7), [(η6-p-cymene)MII(L 3 )Cl]Cl, where M is Ru (8) and Os (10), and [(η6-p-cymene)MII(L 4 )Cl]Cl, where M is Ru (9) and Os (11), is reported. The compounds have been comprehensively characterized by elemental analysis, electrospray ionization mass spectrometry, spectroscopy (IR, UV–vis, and NMR), and X-ray crystallography (L 1 ·HCl, 4·H2O, 5, and 9·2.5H2O). Structure–activity relationships with regard to cytotoxicity and cell cycle effects in human cancer cells as well as cyclin-dependent kinase (cdk) inhibition and DNA intercalation in cell-free settings have been established. The metal-free indolo[3,2-c]quinolines inhibit cancer cell growth in vitro, with IC50 values in the high nanomolar range, whereas those of the related indolo[3,2-d]benzazepines are in the low micromolar range. In cell-free experiments, these classes of compounds inhibit the activity of cdk2/cyclin E, but the much higher cytotoxicity and stronger cell cycle effects of indoloquinolines L 1 and 7 are not paralleled by a substantially higher kinase inhibition compared with indolobenzazepines L 4 and 11, arguing for additional targets and molecular effects, such as intercalation into DNA.  相似文献   

14.
Phosphoramido acid esters (CH3)2NP(O)X(p-OC6H4-CH3) (containing P-Cl (1), P-O (2), P-F (3), P-CN (5), and P-N (4,6) bonds, X for 2, 4 and 6 is OCH3, (C2H5)2N and morpholin) have been synthesized to investigate the structure-activity study of AChE enzyme inhibition, through the parameters logP, δ31P and IC50. After their characterization by 31P, 31P{1H}, 13C, 1H NMR, IR and mass spectroscopy, the parameters logP and δ31P (31P chemical shift in NMR) were used to evaluated the lipophilicity and electronical properties. The ability of compounds to inhibit human AChE was predicted by PASS software (version 1.193), and experimentally evaluated by a modified Ellman's assay.  相似文献   

15.
Analogs of (E)-5-(2-bromovinyl)-2 ′-deoxycytidine (BrVdCyd) (1) by substitution at N4 were synthesized to impart resistance against deamination. The anti-HSV-1 activity and solution conformation of these analogs were determined. N4-Acetyl-BrVdCyd (2) was a potent inhibitor of HSV-1 replication whereas N4-propanoyl-BrVdCyd (3) had good activity and N4-Butanoyl-BrVdCyd (4) had only low activity against HSV-1 replication. N4-Methyl-BrVdCyd (5) was devoid of activity against HSV-1.  相似文献   

16.
A sugar-aza-crown ether (SAC)-based fluorescent sensor 4 was prepared. It contains a pyrene as the fluorophore and its fluoroionophoric properties toward transition metal ions were investigated. Chemosensor 4 exhibits highly selective recognition toward Cu2+ and Hg2+ ions among a series of tested metal ions in methanol solution. The association constants for 4*Cu2+ and 4*Hg2+ in methanol solution were calculated to be 7.4 × 101 M−1 and 4.4 × 103 M−1, respectively. Chemosensor 4 formed complexes with the Cu2+ or Hg2+ ion at a 1:1 ligand-to-metal ratio with a detection limit of 1.3 × 10−4 M Cu2+ and 1.26 × 10−5 M Hg2+, respectively.  相似文献   

17.
The title family of mixed-ligand oxidovanadium(V) hydrazone complexes are [VVO(HL1)(hq)] (1) and [VVO(HL2)(hq)] (2), where (HL1)2? and (HL2)2? are the dinegative form of 2-hydroxybenzoylhydrazone of acetylacetone (H3L1) and benzoylacetone (H3L2), respectively, and hq? is the mononegative form of 8-hydroxyquinoline (Hhq). Complexes were used to determine their binding constant with CT DNA using various spectroscopic techniques namely, electronic absorption, fluorescence and circular dichroism spectroscopy. The binding constant values suggest the intercalative mode of binding with the CT DNA and follow the order: 2 > 1. The bulky size as well as electron withdrawing property of the phenyl group (which is present in the β-diketone part of the hydrazone moiety in complex 2 in place of a CH3 group in complex 1) is responsible for the higher activity of 2 than 1. Complexes were screened for cytotoxic activity on cervical cancer cells and were found to be potentially active (IC50 value for 1 and 2 is 33 and 29 μM, respectively), even better than the widely used cis-platin (IC50 = 63.5 μM) and carboplatin (IC50 = > 200 μM) which is evident from the respective IC50 value. Nuclear staining experiment suggests that these complexes kill the SiHa cancer cells through apoptotic mode. The molecular docking study also suggested the intercalative mode of binding of these complexes with CT DNA and HPV 18 DNA.  相似文献   

18.
A series of dihydro-pyrimidine-5-carbonitrile derivatives (3–16) were synthesized and evaluated for their anticonvulsant activity against MES and scPTZ models. Motor impairment screening was carried out by rotarod test method and CNS depressant effect was determined by Porsolt’s force swim pool method. Compounds 4 and 9 having p-substituted bromo and m-substituted nitro groups, respectively, were found to be most active showing activity both in MES and scPTZ screen at lower doses of 30 mgkg?1 at 0.5?h and 100 mgkg?1 at 4?h. In the rotarod motor impairment screen, compound 4 did not show any motor impairment even at the maximum dose of 300 mgkg?1; however, compound 9 showed motor impairment at 300 mgkg?1 dose after 4.0?h. The compounds were also tested for their CNS depression effect. The compounds 4 and 9 showed 41.38 and 43.44% increase in immobility time with respect to control. The pharmacophore hypothesis also fits best for compounds 4 and 9.  相似文献   

19.
Two novel structurally related phosphoramidate compounds, 1 and 2, with likely β-diketone system were synthesized and characterized by 1H, 13C, 31P NMR, IR spectroscopy and elemental analysis. Compound 2 exhibited a 31P NMR signal which was significantly shielded (8 ppm) relative to compound 1. Determination of human erythrocyte acetylcholinesterase (hAChE) inhibitory activity was carried out according to Ellman's modified kinetic method and the IC50 values of compounds 1 and 2 were 1.567 and 2.986 mM, respectively. The ki values of 1 and 2 were 1.39 to 2.65 min? 1 respectively. A comparison of the bimolecular rate constant (ki) and IC50 values for the irreversible inhibitors 1 and 2 revealed that the oxono analogue has greater affinity for hAChE than the thiono compound. Furthermore effects of two conventional oximes paralidoxime (A) and obidoxime (B) on reactivation of the inhibited hAChE were studied but low reactivity was shown by both the oximes.  相似文献   

20.
Bishomotriborirane anions with a B-H-B bridge, 7, have been synthesized by a) protonation and b) methylation of bishomodianions, 3, as well as by c) hydride addition to 1,2,4-triboracyclopentanes, 15. Compounds 7 were characterized by 1H, 13C and 11B NMR spectroscopy and X-ray diffraction analyses. The suggested mechanism for the formation of 7 is supported by MP4SDTQ/6-311++G**//MP2(fc)/6-31+G* computations on [C2B3H8]- model compounds. Classical 1,2-dibora-4-borata-cyclopentane intermediates 16 undergo an intramolecular hydrogen shift to the B-B unit in their envelope conformation to give intermediates 17, which easily isomerize to 7. Relative energies for the parent compounds, 16u, 17u, 7u and the transition structures, TS-16/17u and TS-7/17u are predicted to be 30.7, 14.5, 0.0, 32.6 and 23.5 kcal mol-1, respectively. The terms classical and non-classical homobridges are suggested for methylene and hydrogen bridges in 7 and in related compounds on the grounds of common building principles. The strength of homoaromaticity in 7u was estimated to be at least 23.5 kcal mol-1, neglecting the much higher strain in 7u compared to TS-7/17u without a 3c2e bond.Electronic Supplementary Material available.  相似文献   

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