1070270-91-5Relevant articles and documents
Development of 1,8-naphthalimides as clathrin inhibitors
Macgregor, Kylie A.,Robertson, Mark J.,Young, Kelly A.,Von Kleist, Lisa,Stahlschmidt, Wiebke,Whiting, Ainslie,Chau, Ngoc,Robinson, Phillip J.,Haucke, Volker,McCluskey, Adam
, p. 131 - 143 (2014/02/14)
We reported the first small molecule inhibitors of the interaction between the clathrin N-terminal domain (TD) and endocyctic accessory proteins (i.e., clathrin inhibition1). Initial screening of a ～17 000 small molecule ChemBioNet library identified 1. Screening of an existing in-house propriety library identified four substituted 1,8-napthalimides as ～80-120 μM clathrin inhibitors. Focused library development gave 3-sulfo-N-(4-aminobenzyl)- 1,8-naphthalimide, potassium salt (18, IC50 ≈ 18 μM). A second library targeting the 4-aminobenzyl moiety was developed, and four analogues displayed comparable activity (26, 27, 28, 34 with IC50 values of 22, 16, 15, and 15 μM respectively) with a further four (24, 25, 32, 33) more active than 18 with IC50 values of 10, 6.9, 12, and 10 μM, respectively. Docking studies rationalized the structure-activity relationship (SAR) with the biological data. 3-Sulfo-N-benzyl-1,8-naphthalimide, potassium salt (25) with an IC50≈ 6.9 μM, is the most potent clathrin terminal domain-amphiphysin inhibitor reported to date.
Demonstration of bidirectional photoinduced electron transfer (PET) sensing in 4-amino-1,8-naphthalimide based thiourea anion sensors
Veale, Emma B.,Tocci, Gillian M.,Pfeffer, Frederick M.,Kruger, Paul E.,Gunnlaugsson, Thorfinnur
body text, p. 3447 - 3454 (2010/01/06)
The thiourea based 4-amino-1,8-naphthalimide molecules 1-5 were designed as fluorescent anion sensors and their photophysical properties investigated upon recognition of biologically relevant anions such as acetate, dihydrogen phosphate and fluoride in DM
