Hong Kong police charged two executives from the pro-democracy Apple Daily newspaper on Friday employing a powerful new security law, each day after the company's newsroom was raided over articles it had published.
Police said a 47-year-old and a 59-year-old were charged with "collusion with a far off country or with external elements to endanger national security".
Apple Daily said the 2 charged executives were chief editor Ryan Law and CEO Cheung Kim-hung.
Some 500 officers descended on the paper's newsroom on Thursday, bundling computers and notepads into evidence bags.
Authorities said the operation was sparked by articles that allegedly appealed for sanctions against China.
It was the primary time articles published in Hong Kong have sparked arrests under the new law that cracks down on dissent within the international business and media hub.
Five Apple Daily executives were arrested within the operation.
Police said the remaining three were still in custody and being questioned. the 2 charged executives would seem in court on Saturday morning.
Over 100 people are arrested under the new security law which China imposed on Hong Kong nearly a year ago to kill dissent within the wake of big pro-democracy protests.
More than 60 are charged and therefore the overwhelming majority are denied bail.