The chances for helpful answers are much higher, if you help us reading your post.

Please use markup for formatting.

Furthermore you could make your regex much clearer by using the x-flag, adding comments and outsourcing parts into well named variables, something like this:

$item = '(?:Item|ITEM)[Ss]?';
$punctuation = '(?:\.|\-|\:|\-|\,)';
m/ $item 
   \s? 
   $punctuation 
   ...
/x;
[download]

don't be too surprised if you can answer your question on your own after refactoring the code! ;-)