Sir Philip Green has pledged another £25m to Arcadia’s pension scheme in an eleventh-hour bid to secure regulators’ backing for a restructuring of his Top Shop empire.

Sky News has learnt that the retail tycoon and his advisers have agreed the outline of a deal with pension stakeholders that will involve the total sum being pledged to Arcadia’s‎ retirement fund during the next three years to increase from £360m to £385m.

The new £25m sum, which will be in the form of security over Arcadia property assets, is expected to be confirmed in a statement ahead of a crunch vote of the company’s creditors on Wednesday.

A source close to The Pensions Regulator (TPR) insisted that a deal had not been formally struck but did not dispute the details obtained by Sky News.

‎The additional security falls short of a demand from pension watchdogs – revealed by Sky News on Friday – that Sir Philip agreed to provide an extra £50m to the Arcadia scheme.

Regulators had suggested that they would derail the entire restructuring without that additional sum.

Tuesday evening’s developments effectively place the fate of Arcadia in the hands of its landlords.

Property-owners have told Arcadia that they will not decide how to cast their votes until the meeting to approve a series of Company Voluntary Arrangements (CVAs) gets underway at 12pm in London.

Without landlords’ support in six votes – with the seventh already secured if the pension scheme votes in favour – Arcadia would collapse into administration on Wednesday evening.

Negotiations with the pensions watchdog had already seen Sir Philip’s family agreeing to inject £100m into the Arcadia retirement fund.

The tycoon has also pledged roughly £185m of security in the form of its flagship Top Shop store on London’s Oxford Street and other assets to the pension fund, while the company would also inject £25m in annual contributions during the next three years.

The fact that landlords could yet vote against the CVAs underlines the continued knife-edge on which Sir Philip’s business – and his legacy as a retailer – now hinges.

Wednesday’s votes will determine the future of a retail behemoth employing 18,000 people.

The backing of TPR, the Pension Protection Fund – which is responsible for casting the vote on behalf of Arcadia’s £750m unsecured pension deficit – and Arcadia’s pension trustees has been one of the crucial components needed to win the votes.

Documents sent to creditors have warned that Sir Philip’s empire is “highly likely, either immediately or after a short time period, to enter into insolvent administration or liquidation” if the CVA proposals are defeated.

Trade creditors have already indicated their intention to vote in favour, according to one source close to Arcadia.

If Arcadia does collapse, it would be the most stunning casualty in a sector brutalised by difficult trading conditions in recent years.

While big names such as Debenhams, House of Fraser, Maplin and Toys ‘R’ Us have all entered some form of insolvency or disappeared, the demise of a tycoon widely lauded as ‘the king of the high street’ would be the most notable by far.

Arcadia’s collapse into administration would herald a break-up of the group, with significant interest likely to be registered in buying Top Shop but a lesser appetite for a takeover of brands like Evans and Wallis.

Deloitte is understood to have been placed on standby to act as Arcadia’s administrator, according to creditors who have been briefed on the process.

Sky News quoted an insider on Friday as saying that TPR’s £50m demand was subject to “a negotiation” and could end up with the two sides agreeing on a number “somewhere in the middle”.

When the CVA documents were published two weeks ago, TPR responded by saying it remained “in discussions with the company and the trustees to understand the impact of the CVA proposals on the scheme and to ensure the strongest possible outcome is achieved”.

“We note from the CVA announcement that the shareholder is prepared to put an additional £100m into the scheme over a number of years to bridge a shortfall in deficit recovery contributions.

“However, we do not consider the proposals are sufficient to ensure that members of the scheme are adequately protected.”

Sky News revealed earlier this year that Sir Philip was seeking to halve Arcadia’s £50m annual pension contributions as part of a wider plan to cut the company’s cost base.

Under Arcadia’s proposals, nearly 50 stores will close with the loss of well over 500 jobs.

If approved, the CVAs would result in rents at nearly 200 shops being cut by between 30% and 70%.

In return, landlords would be handed a 20% stake in the company.

Sir Philip – whose wife, Lady Tina, is technically Arcadia’s owner – has also pledged another £50m to the company, which owns the Burton, Dorothy Perkins and Miss Selfridge brands.

That money would be used to support working capital, while another £50m of the tycoon’s fortune has already been used to pay down part of the group’s bank debt.

The tycoon, who paid $1 (76p) to buy back his private equity partner’s 25% stake in Topshop and Topman in April, has been remote from the negotiations about Arcadia’s future.

Ian Grabiner, the company’s chief executive, has been spearheading the talks, while Deloitte and an army of other professional advisers have been working on the CVA proposal.

Under its plans, a number of subsidiaries are being placed into administration, including its US holding company.

A deal between TPR and Sir Philip averts the risk of the regulator being blamed if Arcadia goes bust, which would result in an outcome for nearly 10,000 pension scheme members that is ultimately inferior to the deal proposed by Sir Philip.

In 2017, he agreed to pay up to £363m to compensate BHS pensioners following a furious row over the department store chain’s collapse, little more than a year after he sold it for £1 to the former bankrupt Dominic Chappell.

The efforts to secure Arcadia’s future come after a miserable period for the tycoon, who has been embroiled in a storm over his behaviour towards Arcadia employees and his use of non-disclosure agreements to prevent former workers discussing their severance packages.

On Friday, he was charged in Arizona in relation to his behaviour towards a Pilates instructor, although he has denied any unlawful wrongdoing.

Arcadia and the pensions watchdog declined to comment on Tuesday.

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