A crown worn by the rapper Notorious B.I.G. in what is said to have been his last photoshoot has sold for nearly £500,000.

He was pictured wearing the crown, which he signed, in 1997 – three days before he was killed in Los Angeles, according to the auction house that sold it.

The Notorious B.I.G., also known as Biggie Smalls, wore the crown in his famous King Of New York photoshoot with Rap Pages Magazine.

(Sotheby’s/PA)

It sold for 594,750 US dollars (about £458,000) in a sale in New York on Wednesday.

The Sotheby’s auction also featured love letters written by another late rapper, Tupac Shakur, while he was a teenager.

A total of 22 letters written when he was 16 to Kathy Loy, who he went to school with, sold for 75,600 US dollars (£59,000).

Sotheby’s said the documents, which span 42 pages, chronicle their two-month romance and include a letter of regret sent around a year later.

(Sotheby’s/PA)

Cassandra Hatton, vice president and senior specialist in Sotheby’s books and manuscripts department, said: “We are thrilled with the results from tonight’s historic hip hop auction in New York, the birthplace of hip hop.

“Throughout the sale, we saw strong bidding from across age brackets and countries, with significant interest from leading cultural institutions in the US.”

A 12in Beat Bop single by Rammellzee and K-Rob, featuring original artwork by Jean-Michel Basquiat, from 1983 sold for 126,000 US dollars (£97,000).

A portion of Sotheby’s profits from the sale were donated to Queens Public Library Foundation’s hip hop programmes in New York and Building Beats, a community organisation teaching young people through DJ and music courses.