Independent News & Media has raised €65 million from the sale of APN convertible notes.
It is understood the money will be used to help fund its bid for the newspaper division of Scottish Media Group (SMG).
Independent is believed to be one of two remaining bidders for the Scottish titles, which include Glasgow's Herald and Sunday Herald newspapers.
Independent, which owns 44 per cent of APN, sold the bonds at 3.60 Australian dollars (€2.02) each yesterday.
The price represents a discount of 9.1 per cent to their face value and an 8.9 per cent discount to the price quoted on the Australian Stock Exchange yesterday, brokers said.
The sale does not affect Independent's stake in the Australian company, which accounts for around 50 per cent of both its revenue and profits.
Independent News & Media will remain APN's largest shareholder and has said it does not intend to sell any of its APN shares.
The convertible notes, which were acquired to facilitate APN's acquisition of New Zealand-based Wilson & Horton last year, were sold to assist in the ongoing expansion of Independent's worldwide operations, particularly in Britain and Ireland, the company said.
APN's chief executive, Mr Brendan Hopkins, who is also an executive director of Independent, said yesterday the money would help fund the bid for the Scottish Media Group unit.
Along with private investment firm Providence Equity Partners, Independent has lodged a bid for the Scottish titles believed to be in the region of £200 million (€312 million).