Playtech is facing questions over a series of proposed acquisitions in which its founder and major shareholder, Teddy Sagi, has a "beneficial interest".
The online gambling software group, which is no stranger to controversy, has signalled its intention to buy a cluster of assets in areas such as social gaming from Mr Sagi, who owns a 48pc stake in Playtech.
Names and details of the companies have not been disclosed but the group said it is likely to spend €95m (£78m).
Playtech said it is also looking at buying, for £10.5m, an office building in London that is owned by a company in which Mr Sagi is "beneficially interested".
The group is seeking to graduate to the main market from Aim by the summer and has also taken on Mr Sagi as an advisor for €1 a year.
Playtech stressed the moves would be put to an independent shareholder vote but analysts expressed surprise.
Simon Davies of Cannacord Genuity said: "There will be inevitable shareholder sensitivity at a series of transactions with its largest shareholder."
That view was echoed by Simon French of Panmure Gordon. "The market will be disappointed by the related party nature of the transactions," he said.