110675-86-0Relevant articles and documents
Photoionization of (p-alkylphenyl)triphenylporphyrins in neutral and positively and negatively charged vesicles: Effects of alkyl chain length and addition of chloroalkanes
Sung-Suh, Hyung Mi,Kevan, Larry
, p. 1414 - 1418 (1997)
The photoionization of (p-alkylphenyl)triphenylporphyrins (CnPtPP) in cationic dioctadecyldimethylammonium chloride (DODAC), neutral dipalmitoylphosphatidylcholine (DPPC), and anionic dihexadecyl phosphate (DHP) frozen vesicles has been studied by electron spin resonance (ESR) with visible light irradiation at 77 K with and without addition of chloroalkanes (CCl4, CHCl3, CH2Cl2, or CH3CH2CH2Cl) as electron acceptors. CnPtPP (n = 3, 6, 9, and 12) were synthesized and used to study the effects of alkyl chain length. The photoionization efficiency was found to decrease with increasing alkyl chain length of CnPtPP. The relative photoyield of the porphyrin cation radical (CnPtPP+) measured by ESR decreased in the order DODAC > DPPC > DHP. The addition of CCl4, CHCl3, CH2Cl2, or CH3CH2CH2Cl into C9PtPP/DHP vesicles enhanced the C9PtPP+ radical photoyield. All four chloroalkanes acted as better electron acceptors in competition with water at the vesicle interface. The results are discussed in terms of the alkyl chain length of CnPtPP, the vesicle surface charge, and the effects of chloroalkanes as electron acceptors.
Lipophilic tail modifications of 2-(hydroxymethyl)pyrrolidine scaffold reveal dual sphingosine kinase 1 and 2 inhibitors
Li, Hao,Sibley, Christopher D.,Kharel, Yugesh,Huang, Tao,Brown, Anne M.,Wonilowicz, Laura G.,Bevan, David R.,Lynch, Kevin R.,Santos, Webster L.
, (2021/01/07)
The sphingosine 1-phosphate (S1P) signaling pathway is an attractive target for pharmacological manipulation due to its involvement in cancer progression and immune cell chemotaxis. The synthesis of S1P is catalyzed by the action of sphingosine kinase 1 or 2 (SphK1 or SphK2) on sphingosine and ATP. While potent and selective inhibitors of SphK1 or SphK2 have been reported, development of potent dual SphK1/SphK2 inhibitors are still needed. Towards this end, we report the structure–activity relationship profiling of 2-(hydroxymethyl)pyrrolidine-based inhibitors with 22d being the most potent dual SphK1/SphK2 inhibitor (SphK1 Ki = 0.679 μM, SphK2 Ki = 0.951 μM) reported in this series. 22d inhibited the growth of engineered Saccharomyces cerevisiae and decreased S1P levels in histiocytic lymphoma myeloid cell line (U937 cells), demonstrating inhibition of SphK1 and 2 in vitro. Molecular modeling studies of 22d docked inside the Sph binding pocket of both SphK1 and SphK2 indicate essential hydrogen bond between the 2-(hydroxymethyl)pyrrolidine head to interact with aspartic acid and serine residues near the ATP binding pocket, which provide the basis for dual inhibition. In addition, the dodecyl tail adopts a “J-shape” conformation found in crystal structure of sphingosine bound to SphK1. Collectively, these studies provide insight into the intermolecular interactions in the SphK1 and 2 active sites to achieve maximal dual inhibitory activity.
Fused π-extended discotic triangular porphyrinoids
Arnold, Lena,Puniredd, Sreenivasa Reddy,Von Malotki, Christian,Pisula, Wojciech,Koshino, Nobuyoshi,Higashimura, Hideyuki,Baumgarten, Martin,Wagner, Manfred,Müllen, Klaus
experimental part, p. 564 - 575 (2012/09/21)
A novel fused two-dimensionally π-expanded triangular porphyrinoid has been designed. The synthesis is based on facile hexaazatrinaphthalene chemistry in combination with well-established condensation procedures to simultaneously close three porphyrinic cavities. A series of different functionalized π-expanded triangular derivatives were synthesized and their optical and electrochemical properties, as well as their supramolecular organization investigated. Low lying HOMOLUMO energy gaps between 1.111.32 eV were found for the highly π-conjugated planar triangular hexaazatrinaphthalene derivatives which organize into discotic liquid crystalline columnar stacks. Thereby, derivatives with alkoxy substituents reveal significantly higher order due to their improved flexibility in comparison to their alkyl counterparts.
