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Biomedical subjects

Min Shi

Publications and source records attributed to Min Shi.

At least 37 records · Page 2Linked to original sources

Estrogens contribute to a sex difference in plasma potassium concentration: a mechanism for regulation of adrenal angiotensin receptors.

BACKGROUND: The adrenal mineralocorticoid aldosterone promotes sodium (Na(+)) reabsorption and potassium (K(+)) loss from the kidney. Female sex steroids such as estrogen and progesterone are known modulators of the renin-angiotensin-aldosterone system. OBJECTIVE: We conducted studies to determine if there is a sex difference in plasma Na(+) concentration ([Na(+)]) and plasma K(+) concentration ([K(+)]), and if interactions between female sex steroids and aldosterone contribute to a sex difference in these electrolytes. METHODS: Plasma [Na(+)] and [K(-)] were determined in weight-matched male and female Sprague-Dawley rats using an ion-selective electrode system. To assess the sensitivity of males and females to aldosterone, the mineralocorticoid was infused chronically by osmotic minipump. The role of female sex steroids in the regulation of plasma electrolyte concentrations was determined in bilaterally ovariectomized (OVX) female rats treated daily with SC injections of progesterone, 17beta-estradiol (E(2)), or selective estrogen receptor (ER) modulators. The role of plasma [K(+)] in the regulation of adrenal angiotensin II type 1 receptor (AT(1)R) expression was determined by manipulating plasma [K(+)] by varying dietary K(-). Adrenal AT(1)R expression was assessed using a radioligand binding assay. RESULTS: Plasma [Na(-)] was not different between male and female rats, but plasma [K(-)] was reduced in females compared with males (P = 0.003). In aldosterone-infused female rats, plasma [Na(+)] was increased and plasma [K(+)] was reduced further than in male rats infused with aldosterone (both, P = 0.001). In OVX female rats, progesterone reduced plasma [Na(+)] (P = 0.04) but had no effect on plasma [K(+)]. In contrast, E(2) increased plasma [Na(+)] (P = 0.01) and reduced plasma [K(+)] (P = 0.001). Dietary K supplementation in E(2)-treated rats returned plasma [K(+)] and adrenal AT(1)R binding to levels observed in control rats. Both an ERa and ERP agonist decreased plasma [K(+)] and decreased adrenal AT(1)R binding (both, P < 0.01). CONCLUSIONS: In these studies, plasma [K(+)] was reduced in female Sprague-Dawley rats compared with males. The effects of aldosterone on plasma electrolytes were enhanced in females compared with males. E(2) treatment reduced plasma [K(+)] and adrenal AT(1)R binding in OVX rats, and the decrease in plasma [K(+)] contributed to the decrease in adrenal AT(1)R binding. Both ERalpha and ERbeta contributed to the estrogen-induced decrease in plasma [K(+)] and adrenal AT(1)R binding.

Adrenal Cortex↗

[In-vitro differentiation of human testicular round spermatids to elongating spermatids].

OBJECTIVE: To investigate the differentiation of human testicular spermatogenic cells during in vitro culture. METHODS: Testicular cells of obstructive azoospermic patients' testis biopsies were dispersed employing mechanic methods. Then, (1) mixed testicular cells were applied to in vitro culture, and changes of the ratio of elongating spermatids and all round cells were analyzed during mixed cell culture; (2) round spermatids were picked up from the mixed cells employing micromanipulator, followed by differentiation of the isolated round spermatids during microdrop culture. RESULTS: The ratio of the elongating spermatids increased significantly (P < 0.05) after 24 hours of mixed cell culture in HTF medium supplemented with FSH and testosterone. During single round spermatid culture, transformation of the round spermatid to elongating spermatid with newly formed flagellum was observed, and the transformation ratio within 48 hours of microdrop culture was 3.54%. The differentiation of human testicular spermatogenic cells cultured in Vero cell conditioned medium was similar to that cultured in HTF medium. CONCLUSION: Human testicular round spermatids can differentiate to elongating spermatids during in vitro culture. Vero cell conditioned medium does not promote the differentiation of human testicular round spermatids to elongating spermatids.

Animals↗

Synthesis of the indene, THF, and pyrrolidine skeletons by Lewis acid mediated cycloaddition of methylenecyclopropanes with aldehydes, N-tosyl aldimines, and acetals.

Methylenecyclopropanes (MCPs 1) react with aldehydes, N-tosyl aldimines, and acetals to give the corresponding indene, THF, and pyrrolidine cycloaddition products in the presence of BF3 x OEt2 under mild reaction conditions. Some special transformations of MCPs 1 with aldehydes have been reported in this paper. A plausible reaction mechanism has been discussed, which is based on a deuterium-labeling experiment and the Prins-type reaction mechanism.

Journal Article↗

Palladium-catalyzed cross-coupling reactions of 2-iodo-4-(phenylchalcogenyl)-1-butenes.

[reaction: see text] 2-Iodo-4-(phenylchalcogenyl)-1-butenes 2 or 3, which are derived from the ring-opening reaction of methylenecyclopropanes (MCPs) 1 by iodine, can be applied to some palladium-catalyzed cross-coupling reactions such as the Sonogashira, Heck, Kumada, Suzuki, and Negishi reactions under mild conditions to give the corresponding coupling products in good yields. These reactions proceeded smoothly at room temperature (20 degrees C) in most cases without any phosphine ligand and additive. The phenylchalcogenyl group plays an important role in the reactions and a plausible reaction mechanism has been proposed.

Journal Article↗

Aza-Baylis-Hillman reactions of N-tosylated aldimines with activated allenes and alkynes in the presence of various Lewis base promoters.

[reaction: see text] The attempted aza-Baylis-Hillman reactions of N-tosylated aldimines with ethyl 2,3-butadienoate, ethyl penta-2,3-dienoate, penta-3,4-dien-2-one, methyl propiolate, and but-3-yn-2-one have been systematically investigated in the presence of various nitrogen or phosphine Lewis base promoters. We found that a series of nitrogen-containing heterocyclic compounds, as "abnormal" aza-Baylis-Hillman reaction products, can be formed in the presence of an appropriate Lewis base promoter. The Lewis base and solvent effects in these reactions have been discussed along with the corresponding plausible mechanism.

Journal Article↗

Lewis acid mediated reactions of cyclopropyl aryl ketones with alpha-ketoesters: facile preparation of 5,6-dihydropyran-2-ones.

[reaction: see text] A new general method for the synthesis of 5,6-dihydropyran-2-ones from cyclopropyl aryl ketones (monoactivated cyclopropanes) and alpha-ketoesters in good to excellent yields has been developed. The process involves a cascade of reactions, including a nucleophilic ring-opening reaction of monoactivated cyclopropane by H2O, Lewis acid mediated transesterification, and an aldol type reaction.

Journal Article↗

Lewis acid-catalyzed rearrangement of multi-substituted arylvinylidenecyclopropanes.

An interesting rearrangement of arylvinylidenecyclopropanes having three substituents at the 1- and 2-positions of the corresponding cyclopropane catalyzed by Lewis acids to give 6aH-benzo[c]fluorine derivatives via a double intramolecular Friedel-Crafts reaction or to give an indene derivative via an intramolecular Friedel-Crafts reaction is described.

Boron↗

Ring-expanding reaction of cyclopropyl amides with triphenylphosphine and carbon tetrahalide.

We succeeded in activating cyclopropyl amides (monoactivated cyclopropane) through the corresponding imidoyl halides prepared in situ in the presence of 2 equiv of PPh3 and 1 equiv of CX4, and the ring-expanding products (N-substituted pyrrolidin-2-ones) were obtained in good yields. The reaction mechanism was investigated on the basis of oxygen-18 tracer experiment.

Journal Article↗

Baylis-Hillman reactions of N-tosyl aldimines and aryl aldehydes with 3-methylpenta-3,4-dien-2-one.

The attempted Baylis-Hillman reactions of N-tosyl aldimines and aryl aldehydes with 3-methylpenta-3,4-dien-2-one gave the corresponding Baylis-Hillman adducts 3 and 6 in moderate to good yields in the presence of DMAP in DMSO, respectively. In the case of the aza-Baylis-Hillman reactions of N-tosyl aldimines with 3-methylpenta-3,4-dien-2-one catalyzed by PBu3, the corresponding aza-Baylis-Hillman derivatives 4 and 5 were formed at the same time.

Aldehydes↗

Hindbrain chemical mediators of reflex-induced inhibition of gastric tone produced by esophageal distension and intravenous nicotine.

The purpose of this study was to activate a vagovagal reflex by using esophageal distension and nicotine and test whether hindbrain nitric oxide and norepinephrine are involved in this reflex function. We used double-labeling immunocytochemical methods to determine whether esophageal distension (and nicotine) activates c-Fos expression in nitrergic and noradrenergic neurons in the nucleus tractus solitarii (NTS). We also studied c-Fos expression in the dorsal motor nucleus of the vagus (DMV) neurons projecting to the periphery. Esophageal distension caused 19.7 +/- 2.3% of the noradrenergic NTS neurons located 0.60 mm rostral to the calamus scriptorius (CS) to be activated but had little effect on c-Fos in DMV neurons. Intravenous administration of nicotine caused 19.7 +/- 4.2% of the noradrenergic NTS neurons 0.90 mm rostral to CS to be activated and, as reported previously, had no effect on c-Fos expression in DMV neurons. To determine whether norepinephrine and nitric oxide were central mediators of esophageal distension-induced decrease in intragastric pressure (balloon recording), N(G)-nitro-L-arginine methyl ester microinjected into the NTS (n = 5), but not into the DMV, blocked the vagovagal reflex. Conversely, alpha2-adrenergic blockers microinjected into the DMV (n = 7), but not into the NTS, blocked the vagovagal reflex. These data, in combination with our earlier pharmacological microinjection data with nicotine, indicate that both esophageal distension and nicotine produce nitric oxide in the NTS, which then activates noradrenergic neurons that terminate on and inhibit DMV neurons.

Animals↗

Palladium-catalyzed isomerization of methylenecyclopropanes in acetic acid.

[reaction: see text] Pd(PPh3)4-catalyzed isomerization of MCPs 1 in acetic acid proceeds smoothly at 80 degrees C in toluene to give the corresponding 1-substituted or 1,1-disubstituted dienes 2 in good to excellent yields under mild conditions. The plausible mechanism has been disclosed on the basis of a deuterium-labeling experiment.

Journal Article↗

Enynylation of 2-iodo-4-(phenylchalcogenyl)-1-butenes via intramolecular chelation: approach to the synthesis of conjugated dienynes or trienynes.

[reaction: see text] 2-Iodo-4-(phenylchalcogenyl)-1-butenes 3 and 4, which are derived from methylenecyclopropanes 1, can be enynylated with alkynes catalyzed by Pd(OAc)(2) to give conjugated dienynes 5 and 6 in the absence of any phosphine ligand and copper salt, and trienyne 9a can be obtained by oxidation of compound 5a. A plausible reaction mechanism has been proposed.

Journal Article↗

Facile synthesis of multisubstituted buta-1,3-dienes via Suzuki-Miyaura and Kumada cross-coupling strategy of 2,4-diiodo-buta-1-enes with arylboronic acids and Grignard reagents.

One-pot Suzuki-Miyaura-type and Kumada-type cross-coupling reactions of 2,4-diiodo-buta-1-enes with arylboronic acids and alkyl/aryl magnesium bromides were carried out in the presence of accessibly simple catalysts under mild conditions. As a result, some 1,1,2-trisubstituted buta-1,3-dienes were obtained including the Tamoxifen-type, which have potential adjuvant therapy in women who have suffered from breast cancer and cyclooxygenase-2-type (COX-2-type) inhibitors, some of which have been proved to elicit efficient anti-inflammatory analgesic activities and less adverse gastrointestinal side effects and to be very useful in the prophylactic treatment of a wide variety of cancers and neurodegenerative disorders.

Alkenes↗

Chiral phosphine lewis bases catalyzed asymmetric aza-Baylis-Hillman reaction of N-sulfonated imines with activated olefins.

In the aza-Baylis-Hillman reaction of N-sulfonated imines (N-arylmethylidene-4-methylbenzenesulfonamides and others) with methyl vinyl ketone, ethyl vinyl ketone, and acrolein, we found that, in the presence of a catalytic amount of chiral phosphine Lewis base such as (R)-2'-diphenylphosphanyl-[1,1']binaphthalenyl-2-ol LB1 (10 mol %) and molecular sieve 4A, the corresponding aza-Baylis-Hillman adducts could be obtained in good yields with good to high ee (70-95% ee) at low temperature (approximately -30 to -20 degrees C) or at room temperature in THF, respectively. In CH2Cl2 upon heating at 40 degrees C, the aza-Baylis-Hillman reaction of N-sulfonated imines with phenyl acrylate or naphthyl acrylate gave the adducts in good to high yields (60-97%) with moderate ee (52-77%). The mechanistic insight has been investigated by 31P and 1H NMR spectroscopic measurements. The key enolate intermediate, which has been stabilized by intramolecular hydrogen bonding, has been observed by 31P and 1H NMR spectroscopy. An effective bifunctional Lewis base and Bronsted acid phosphine Lewis base system has been disclosed in this catalytic, asymmetric aza-Baylis-Hillman reaction.

Journal Article↗