一种双功能二甲基亚砜替代物可提高小分子有机化合物的水溶性。
A bifunctional dimethylsulfoxide substitute enhances the aqueous solubility of small organic molecules.
作者信息
Sprachman Melissa M, Wipf Peter
机构信息
Department of Chemistry, Center for Chemical Methodologies and Library Development, University of Pittsburgh, Pittsburgh, PA 15260, USA.
出版信息
Assay Drug Dev Technol. 2012 Jun;10(3):269-77. doi: 10.1089/adt.2011.0421. Epub 2011 Dec 22.
Abstract
An oxetane-substituted sulfoxide has demonstrated potential as a dimethylsulfoxide substitute for enhancing the dissolution of organic compounds with poor aqueous solubilities. This sulfoxide may find utility in applications of library storage and biological assays. For the model compounds studied, significant solubility enhancements were observed using the sulfoxide as a cosolvent in aqueous media. Brine shrimp, breast cancer (MDA-MB-231), and liver cell line (HepG2) toxicity data for the new additive are also presented, in addition to comparative IC(50) values for a series of PKD1 inhibitors.
摘要
一种氧杂环丁烷取代的亚砜已显示出作为二甲基亚砜替代品的潜力，可用于增强水溶性差的有机化合物的溶解性。这种亚砜可能在文库存储和生物测定应用中有用。对于所研究的模型化合物，在水性介质中使用该亚砜作为助溶剂时，观察到显著的溶解度增强。除了一系列PKD1抑制剂的比较IC(50)值外，还给出了新添加剂的卤虫、乳腺癌（MDA-MB-231）和肝细胞系（HepG2）毒性数据。
相似文献
1
A bifunctional dimethylsulfoxide substitute enhances the aqueous solubility of small organic molecules.一种双功能二甲基亚砜替代物可提高小分子有机化合物的水溶性。
Assay Drug Dev Technol. 2012 Jun;10(3):269-77. doi: 10.1089/adt.2011.0421. Epub 2011 Dec 22.
2
Measuring aqueous solubility in the presence of small cosolvent volume fractions by passive dosing.通过被动给药测量小共溶剂体积分数存在下的水溶解度。
Environ Sci Technol. 2012 Nov 20;46(22):12550-6. doi: 10.1021/es3035363. Epub 2012 Oct 29.
3
Effect of salts and organic additives on the solubility of proteins in aqueous solutions.盐类和有机添加剂对蛋白质在水溶液中溶解度的影响。
Adv Colloid Interface Sci. 2006 Nov 16;123-126:97-103. doi: 10.1016/j.cis.2006.05.018. Epub 2006 Jun 30.
4
Mixed aqueous solutions as dilution media in the determination of residual solvents by static headspace gas chromatography.静态顶空气相色谱法测定残留溶剂时混合水溶液作为稀释剂。
J Sep Sci. 2011 Jun;34(11):1299-308. doi: 10.1002/jssc.201100051. Epub 2011 Apr 27.
5
Synthesis of water-soluble and water-insoluble amphiphilic derivatives of dextran in organic medium.在有机介质中合成水溶性和油溶性两亲性葡聚糖衍生物。
Carbohydr Polym. 2013 Jun 5;95(1):360-5. doi: 10.1016/j.carbpol.2013.03.010. Epub 2013 Mar 13.
6
Peculiarities of direct bioelectrocatalysis by laccase in aqueous-nonaqueous mixtures.漆酶在水-非水混合体系中的直接生物电催化特性
Biosens Bioelectron. 2002 Dec;17(11-12):945-51. doi: 10.1016/s0956-5663(02)00086-6.
7
Graphene oxide liquid crystals as a versatile and tunable alignment medium for the measurement of residual dipolar couplings in organic solvents.氧化石墨烯液晶作为一种通用且可调谐的取向介质，用于测量有机溶剂中的残余偶极耦合。
J Am Chem Soc. 2014 Aug 13;136(32):11280-3. doi: 10.1021/ja506074a. Epub 2014 Aug 5.
8
Organic solvents for pharmaceutical parenterals and embolic liquids: a review of toxicity data.用于注射用药物和栓塞液的有机溶剂：毒性数据综述
PDA J Pharm Sci Technol. 2000 Nov-Dec;54(6):456-69.
9
Technical Capabilities and Limitations of Optical Spectroscopy and Calorimetry Using Water-Miscible Solvents: The Case of Dimethyl Sulfoxide, Acetonitrile, and 1,4-Dioxane.水混溶性溶剂的光学光谱和量热法的技术能力和局限性：以二甲基亚砜、乙腈和 1,4-二氧六环为例。
J Pharm Sci. 2020 Jan;109(1):524-531. doi: 10.1016/j.xphs.2019.10.056. Epub 2019 Nov 1.
10
Prediction of the aqueous solubility: comparison of the general solubility equation and the method using an amended solvation energy relationship.水溶性的预测：通用溶解度方程与使用修正溶剂化能关系方法的比较。
J Pharm Sci. 2002 Feb;91(2):517-33. doi: 10.1002/jps.10022.
引用本文的文献
1
SARS-CoV-2 Spike Protein Induces Oxidative Stress and Senescence in Mouse and Human Lung.SARS-CoV-2 刺突蛋白诱导小鼠和人肺中的氧化应激和衰老。
In Vivo. 2024 Jul-Aug;38(4):1546-1556. doi: 10.21873/invivo.13605.
2
Evaluation of anthoxanthins and their actions on digestive enzyme inhibition when used independently and in combination.对黄酮类化合物及其单独使用和联合使用时对消化酶抑制作用的评估。
Heliyon. 2022 Aug 8;8(8):e10131. doi: 10.1016/j.heliyon.2022.e10131. eCollection 2022 Aug.
3
Combined injury: irradiation with skin or bone wounds in rodent models.复合伤：在啮齿类动物模型中出现皮肤或骨创伤的照射。
J Radiol Prot. 2021 Nov 15;41(4). doi: 10.1088/1361-6498/ac125b.
4
Oxetanyl Sulfoxide MMS-350 Ameliorates Pulmonary Fibrosis , , and .氧杂环丁烷亚砜MMS - 350改善肺纤维化，以及。 （你提供的原文最后部分不完整，翻译可能会因原文信息缺失而不太准确）
ACS Med Chem Lett. 2020 Sep 10;11(11):2312-2317. doi: 10.1021/acsmedchemlett.0c00433. eCollection 2020 Nov 12.
5
Continuous One Year Oral Administration of the Radiation Mitigator, MMS350, after Total-Body Irradiation, Restores Bone Marrow Stromal Cell Proliferative Capacity and Reduces Senescence in Fanconi Anemia (Fanca) Mice.连续一年口服辐射缓解剂 MMS350 后全身照射，可恢复骨髓基质细胞的增殖能力，并减少范可尼贫血（Fanca）小鼠的衰老。
Radiat Res. 2019 Feb;191(2):139-153. doi: 10.1667/RR15199.1. Epub 2018 Nov 30.
6
A Mitochondrial-Targeted Nitroxide Is a Potent Inhibitor of Ferroptosis.一种线粒体靶向的氮氧化物是铁死亡的有效抑制剂。
ACS Cent Sci. 2016 Sep 28;2(9):653-659. doi: 10.1021/acscentsci.6b00199. Epub 2016 Sep 7.
7
An uncharged oxetanyl sulfoxide as a covalent modifier for improving aqueous solubility.一种作为共价修饰剂用于提高水溶性的不带电荷的氧杂环丁烷亚砜
ACS Med Chem Lett. 2014 Jun 27;5(8):900-4. doi: 10.1021/ml5001504. eCollection 2014 Aug 14.
8
9
Amelioration of radiation-induced pulmonary fibrosis by a water-soluble bifunctional sulfoxide radiation mitigator (MMS350).水溶性双功能亚砜辐射防护剂（MMS350）对放射性肺纤维化的改善作用。
Radiat Res. 2013 Nov;180(5):474-90. doi: 10.1667/RR3233.1. Epub 2013 Oct 14.
10
Evaluation of potential ionizing irradiation protectors and mitigators using clonogenic survival of human umbilical cord blood hematopoietic progenitor cells.采用人脐带血造血祖细胞集落生成法评价潜在的致电离辐射防护剂和缓解剂。
Exp Hematol. 2013 Nov;41(11):957-66. doi: 10.1016/j.exphem.2013.08.001. Epub 2013 Aug 7.
本文引用的文献
1
Design, Synthesis, and Biological Evaluation of PKD Inhibitors.PKD 抑制剂的设计、合成与生物评价。
Pharmaceutics. 2011;3(2):186-228. doi: 10.3390/pharmaceutics3020186.
2
Synthesis and Structure-Activity Relationships of Benzothienothiazepinone Inhibitors of Protein Kinase D.蛋白激酶D的苯并噻吩并噻氮杂卓酮抑制剂的合成与构效关系
ACS Med Chem Lett. 2011 Feb 14;2(2):154-159. doi: 10.1021/ml100230n.
3
Alkylating potential of oxetanes.氧杂环丁烷的烷化潜力。
Chem Res Toxicol. 2010 Jul 19;23(7):1275-81. doi: 10.1021/tx100153w.
4
Oxetanes in drug discovery: structural and synthetic insights.药物发现中的氧杂环丁烷：结构和合成见解。
J Med Chem. 2010 Apr 22;53(8):3227-46. doi: 10.1021/jm9018788.
5
Synthesis of novel dendrimers having aspartate grafts and their ability to enhance the aqueous solubility of model drugs.合成具有天冬氨酸接枝的新型树枝状大分子及其提高模型药物水溶性的能力。
Eur J Med Chem. 2010 Jun;45(6):2705-11. doi: 10.1016/j.ejmech.2010.01.069. Epub 2010 Feb 2.
6
Overcoming problems of compound storage in DMSO: solvent and process alternatives.克服二甲基亚砜中化合物储存的问题：溶剂及工艺替代方案
J Biomol Screen. 2009 Jul;14(6):708-15. doi: 10.1177/1087057109335670. Epub 2009 Jun 16.
7
Advances in improving the quality and flexibility of compound management.提高化合物管理质量和灵活性方面的进展。
J Biomol Screen. 2009 Jun;14(5):444-51. doi: 10.1177/1087057109335262. Epub 2009 May 29.
8
Nonracemizable isocyanoacetates for multicomponent reactions.用于多组分反应的不可外消旋化的异氰基乙酸酯。
J Org Chem. 2009 Jan 16;74(2):884-7. doi: 10.1021/jo802420c.
9
Potent and selective disruption of protein kinase D functionality by a benzoxoloazepinolone.一种苯并恶唑并氮杂环丁烷酮对蛋白激酶D功能的强效且选择性破坏作用
J Biol Chem. 2008 Nov 28;283(48):33516-26. doi: 10.1074/jbc.M805358200. Epub 2008 Sep 30.
10
Solubility improvement of drugs using N-methyl pyrrolidone.使用N-甲基吡咯烷酮提高药物溶解度
AAPS PharmSciTech. 2008;9(2):366-76. doi: 10.1208/s12249-008-9050-z. Epub 2008 Feb 20.
Zotero 插件