DLP use case

Hello,

How can we achieve below use case in DLP Endpoint (Discover & Prevent). I requires this to be tested in enviroment..

use case 1:

If file is encrypted via Symantec encryption is it’s header is encrypted. Concern is that we create a custom script to read multiple value of file, If it’s match then DLP will block that file.

If header is encrypted how DLP will read file header.

use case 2:

To block outlook mail which contains keywords like “ financial “ ,” credit card”, etc.

Outlook mail client ver 2007.

Use case 3:

To block file uploads in cloud apps such as box & Dropbox.

Thanks in advance.