Two machines. Both with .NET 3.5 and the VS 2008 VC++ SP1 redistributables
A single exe which uses two signed DLLs, one in C++/CLI and one in C#
The exe load
In my case, I had the same issue with Visual Studio 2015 and I already had signed the assembly.
I fixed it by this way: Right click on the project which causes the issue -> "Properties" -> "Build" -> Change the value of the "Platform target" field.
I had to change it from Any CPU to x86 but I guess that in function of the project and the library which is failing, you should change its value to x64.