Novel 2-substituted quinolin-4-yl-benzenesulfonate derivatives: synthesis, antiproliferative activity, and inhibition of cellular tubulin polymerization

A series of 2‐substituted quinolin‐4‐yl‐benzenesulfonate derivatives were synthesized for the purpose of evaluating antiproliferative activity. Structure–activity relationships of the newly synthesized compounds against human lymphoblastic leukemia and various solid tumor cell growths in culture are discussed. Of these derivatives, 2‐phenyl‐6‐pyrrolidinyl‐4‐quinoline sulfonate analogues 10 f , 10 g , and 10 k , and 4′‐nitrophenyl sulfonate 10 m exhibit superior cytotoxicity over other sulfonates. The antiproliferative activities of these compounds correlate well with their abilities to induce mitotic arrest and apoptosis. Mechanistic studies indicate that they target the vinblastine binding site of tubulin and inhibit cellular tubulin polymerization. Hence, these compounds induce the formation of aberrant mitotic spindles and mitotic arrest, resulting in intensive apoptosis. The tested compounds were shown to be poor substrates for membrane multidrug resistance transporters. The present studies suggest that these newly synthesized compounds are promising tubulin polymerization inhibitors and are worthy of further investigation as antitumor agents.     

酰胺型双子表面活性剂ZK-12的合成与性能研究

以丁二酸、二氯亚砜、对氨基苯磺酸、溴代十二烷等为原料,合成了酰胺型磺酸盐双子表面活性剂ZK-12。采用IR光谱对产物的结构进行了初步鉴定。ZK-12和AEO复配产生了较好的协同效应。该目标产物水溶液的cmc(5.0×10-4 mol/L)是SDBS的1/20,γcmc(22.4 mN/m)比SDBS(41.0 mN/m)低18.6 mN/m。并考察了乙醇对ZK-12表面活性的影响。     

1-Phenylalkane Sulfonates for Studying Interfacial Tensions

Abstract

A series of 1-phenylalkane sulfonates with high purity were synthesized through a simple and effective way. Interfacial tension (IFT) of 1-phenylalkane sulfonates against crude oil from Daqing oil field in China was investigated, interfacial tension minima were observed with changes of surfactant concentrations and time. Alkali concentrations where lowest interfacial tensions were achieved moved to low regions by increasing the chain length of 1-phenylalkane sulfonates, namely, 1-phenyldodecane sulfonate at about 2.2%, 1-phenyltetradecane sulfonate at about 0.6%, 1-phenylhexadecane sulfonate at about 0.3%. No minima were observed when interfacial tensions of pure 1-phenylalkane sulfonates against alkanes were measured. The phenomenon is quite distinct from that of 1-phenylalkane sulfontes against crude oil.     

关于MES性能与应用的疑惑、诀窍和前景

文献报道了MES的许多优点,也提到其性质上可能存在的某些缺点。比如,研究表明纯组分MES的浊点高于其他阴离子表面活性剂,于是怀疑MES的溶解性可能会限制其在冷水中的洗涤。再则,MES的水解稳定性低于其他阴离子表面活性剂,这可能是MES的另一个主要缺点。拟探讨这些问题,并将提出一些证据,以表明MES实际上是一种卓越的表面活性剂,完全可以配方出适用于低温洗涤的洗涤剂产品。介绍了一些采用MES为主要表面活性剂生产洗衣粉和液洗剂的工艺。     

Adsorption of petroleum sulfonate TRS 10-80 on a mineral sand

Adsorption of petroleum sulfonate TRS 10-80 on a mineral sand, characterized by chemical analysis and infrared spectra to be silica, has been studied under conditions relevant to the practical field. The adsorption is significantly affected by the age of the sulfonate solutions. A new mechanism of adsorption involving sulfonate monomers and multimers has been proposed. The adsorption behavior is best characterized by Langmuir and Freundlich models. At higher temperatures, the mineral surface seems to be capable of forming chemical bonds with the sulfonate anions. Micelles are not considered to be the species favored for adsorption. The adsorption, depending upon the concentration of added electrolyte, either reaches a saturation value or decreases abruptly after a fixed surfactant concentration has been reached. The apparent surfactant loss at higher salt concentrations seems to be due to salting-out of the sulfonate rather than its adsorption.     

镧系金属磺酸盐催化剂在CL-20合成中的应用

针对N_2O_5/HNO_3硝化四乙酰基六氮杂异伍兹烷(TAIW)合成六硝基六氮杂异伍兹烷(CL-20)反应时间长、收率低的缺点,以甲磺酸、苯磺酸、对甲苯磺酸、2-萘磺酸及三氟甲磺酸的镧系金属盐为催化剂,通过N_2O_5/HNO_3硝化TAIW合成CL-20;研究了镧系金属磺酸盐种类和用量、反应时间、循环利用次数对CL-20收率和纯度的影响。结果表明,金属钐的磺酸盐具有较好的催化性能,其中对甲苯磺酸钐(Sm(Tos)3)催化性能最优;当反应温度为65~75℃,反应时间为4h,投料比m(Sm(Tos)3)∶m(TAIW)∶m(N_2O_5)∶V(HNO_3)=0.3g∶3g∶4g∶15mL时,CL-20收率为95.2%,纯度为98.6%;重复使用5次后,催化性能无明显降低。     

Self‐Aggregation and Emulsifying Properties of Methyl Ester Sulfonate Surfactants

Methyl ester sulfonate (MES) anionic surfactants made from natural resources are of particular interest as sustainable surfactants. They offer good physicochemical properties for applications as detergents and emulsifiers. The liquid crystal structures of MES surfactants synthesized in a previous work were determined by polarizing optical microscopy (POM) and small‐angle X‐ray scattering (SAXS). The emulsifying activity for each surfactant was also measured, and the stability of emulsions was estimated and compared to that induced by sodium dodecyl sulfate (SDS). The POM micrographs showed the presence of birefringent textures. Several factors, including temperature and hydration, influenced the stability of the phases and their structure. SAXS confirmed the structure of the phases formed by dry and hydrated ф‐MES surfactants at 25 °C, giving the position of peaks corresponding to the ratio 1:2:3 and revealing the phase transitions of lamellar to double lamellar or the reverse. Also, the Bragg distance (d) decreased with an increase in chain length from 13 to 17 carbon atoms and an increase in the area per molecule of surfactant. The geometric packing parameters were also determined, and suggest that surfactants are tilted. The stability of surfactant emulsions is around 60%, which is comparable to that of SDS. The micrographs show that the emulsions formed are O/W, and an increase in chain length gives rise to a decrease in the size of the emulsion droplets. These results are confirmed by the values of hydrophilic‐lipophilic balance (HLB) which reveals the hydrophilic nature of these surfactants.     

Fatty acid ecological tracers highlight the role of diet in perfluoroalkyl acid contaminant exposure in eggs of an omnivorous bird

Herring gulls (Larus argentatus) are generalist feeders; contaminant levels in their eggs reflect chemical exposure and uptake due to foraging in both aquatic and terrestrial environments. Hence, contaminant levels in their eggs provide insights into sources and relative importance of aquatic versus terrestrial pathways of chemical transfer. Here, perfluoroalkyl acids (PFAAs) known to be bioaccumulative were measured in individual herring gull eggs from one site on Lake Superior, Ontario, Canada. Thirteen perfluorinated carboxylates (PFCA, C₄-C₁₈) and four perfluorinated sulfonates (PFSA, C₄-C₁₀) were measured. Total PFCA and total PFSA concentrations varied 4- and 5-fold, respectively, among eggs. To understand these differences, stable carbon and nitrogen isotopes and fatty acid dietary tracers were measured in the same eggs. Stable isotopes were not useful in explaining inter-egg differences in PFAA concentrations. However, a variety of omega 3 (n-3) and omega 6 (n-6) fatty acid measures were correlated with C₉-C₁₃ PFCAs as well as the PFSAs: perfluoro-1-hexanesulfonic acid (PFHxS) and perfluoro-1-octanesulfonic acid (PFOS). In general, n-3 fatty acids were positively correlated with egg PFAA concentrations while only the n-6 fatty acids exhibited negative relationships with egg PFAA levels. Proportions of n-3 and n-6 fatty acids in eggs would be expected to increase and decrease, respectively, with increased aquatic food in the gull diet. Results indicate that increased use of aquatic food led to heightened PFAA exposure in these generalist consumers sampled in a relatively remote area. They also highlight the utility of employing a variety of dietary markers for understanding contaminant exposure and accumulation.     

两种不同链长烷基苯的磺化工艺比较

讨论了三氧化硫膜式磺化工艺生产长链(C20~24)烷基苯磺酸盐的可行性,并根据长链烷基苯的物理『生质,从反应原理、工艺条件、产能及设备选型等方面对比了十二烷基苯和长链烷基苯磺酸盐的生产工艺。     

脂肪醇聚氧乙烯醚磺酸钠的泡沫性能研究

磺酸盐类阴离子表面活性剂在采油工业中应用广泛,其泡沫性能(起泡性和泡沫稳定性)对采收率影响很大。文章用改进的Ross-Miles法对十四醇聚氧乙烯(3)醚磺酸钠(AE3SO 3-Na)在不同条件下的泡沫性能进行了研究。结果表明,十四醇聚氧乙烯(3)醚磺酸钠水溶液的泡沫性能随体系浓度变化而变化,在1500mgL/时泡沫性能较佳,起泡能力随着温度的升高而增强,60℃达到最高,泡沫体系有一定的抗钙能力,可反复起泡消泡。因此,十四醇聚氧乙烯(3)醚磺酸钠可作为循环泡沫流体的主剂应用于采油工业。