use strict;
my $str = ';s:27:"2018/08/hello-there-003.jpg";s:5:"sizes";a:23:{s:9:"thumbnail";a:4:{s:4:"file";s:27:"hello-there-003-150x150.jpg";s:5:"width";i:150;s:6:"height";i:150;s:9:"mime-type";s:10:"image/jpeg";}s:6:"medium";a:4:{s:4:"file";s:27:"hello-there-003-300x200.jpg"
';
my $regex = qr/"\K[\w-]+(\.jpg)(?=")/p;
my $subst = 'replacement$1';
my $result = $str =~ s/$regex/$subst/rg;
print "The result of the substitution is' $result\n";
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for Perl, please visit: http://perldoc.perl.org/perlre.html