Madonna has lost her bid to halt the auction of a prison break-up letter from rapper Tupac Shakur, among a number of other personal items.

The pop star filed for an emergency court order last July to stop the sale of letters, photos, a hairbrush, and even a pair of panties that she had once worn.

A Manhattan Supreme Court judge ruled on Monday that Madonna's former friend Darlene Lutz could give the items to auction house Gotta Have It Collectibles.

The break-up letter from Tupac, dated January 1995, reveals the rapper ended their relationship because he feared dating a white woman could jeopardize his career.

Madonna has lost her bid to halt the auction of a prison break-up letter from rapper Tupac Shakur, among a number of other personal items

The break-up letter from Tupac, dated January 1995, reveals the rapper ended their relationship because he feared dating a white woman could jeopardize his career. The former couple are pictured here in New York in March 1994

Shakur began the letter by apologizing to Madonna, writing: 'I haven't been the kind of friend I know I'm capable of being'

Shakur wrote that he had since grown 'both spiritually and mentally' and that he felt compelled to reach out to Madonna just in case something happened to him

Shakur was only 25 when he was killed in a drive-by shooting in Las Vegas in September 1996

Shakur began the letter by apologizing to Madonna, writing: 'I haven't been the kind of friend I know I'm capable of being'.

'For you to be seen with a black man wouldn't in any way jeopardize your career, if anything it would make you seem that much more open and exciting,' he wrote later in the letter.

'I felt due to my "image" I would be letting down half of the people who made me what I thought I was. I never meant to hurt you.'

Shakur also brought up an interview Madonna had given, in which she said she would 'rehabilitate all the rappers and baseball players'.

'Those words cut me deep seeing how I had never known you to be with any rappers beside myself,' Shakur wrote.

'It was at this moment out of hurt and a natural instinct to strike back and defend my heart and ego that I said a lot of things.'

Shakur wrote that he had since grown 'both spiritually and mentally'.

'It no longer matters how I'm perceived,' he said. 'Please understand my previous position as that of a young man with limited experience with an extremely famous sex symbol.'

'I offer my friendship once again, this time much stronger and focused. If you are still interested would like to further discuss this with you, but some of it couldn't wait.'

'I felt compelled to tell you…just in case anything happened to me.'

Shakur was only 25 when he was killed in a drive-by shooting in Las Vegas in September 1996.

Another letter from the early 1990s to John Enos, a former boyfriend, is also part of the auction

Madonna wrote: 'It's so unequivocally frustrating to read that Whitney Houston has the music career I wish I had and Sharon Stone has the film career I'll never have.' Here is page 2 of 2

Madonna's personal items were consigned to auction by Lutz, who the pop star described in court documents as a former friend and art consultant.

She claimed Lutz had 'betrayed my trust in an outrageous effort to obtain my possessions without my knowledge or consent'.

'The fact that I have attained celebrity status as a result of success in my career does not obviate my right to maintain my privacy,' she added.

But a judge ruled that Madonna had forfeited her right to the items after signing a 2004 settlement agreement with Lutz following a nasty dispute.

'(Madonna) knew that throughout her relationship with Lutz, Lutz was in possession of various pieces of (Madonna's) personal property', the judge wrote in his decision, obtained by the New York Daily News.

'Yet before this action began, the plaintiff did not make any demand to return her possessions.'

Madonna has maintained that she did not know Lutz was in possession of the items until news of the auction became public.

The judge also suggested that Madonna should have sued her estranged brother Christopher Ciccone, who gave some of the pop star's items to Lutz.

Sharon Stone wrote an open letter to Madonna on Facebook about the release of the letter written more than 20 years ago

Madonna and Stone have enjoyed a friendship in the years that followed the old letter

Madonna wrote the letter in the early 1990s to her paramour actor John Enos (right)

In another letter up for auction, which was written in the early 1990s, Madonna wrote to former boyfriend John Enos: 'It's so unequivocally frustrating to read that Whitney Houston has the music career I wish I had and Sharon Stone has the film career I'll never have.'

'Not because I want to be these women - because I'd rather die, but they're so horribly mediocre and they're always being held up as paragons of virtue (or) some sort of measuring stick to humiliate me.'

Houston drowned in a Beverly Hills hotel bathtub in 2012.

Stone wrote in a Facebook post last year that she is a friend of Madonna, adding: 'I love and adore you; won't be pitted against you by any invasion of our personal journeys.'