WOBURN, Mass. (AP) — Four people have pleaded guilty to their roles in an armed heist at a Woburn jewelry store that left a police officer suffering from multiple gunshot wounds.

Antonio Matos, Hector Baez-Cruz, and Erianiss Murillo, all of Boston, as well as Allegra Martinez, of Providence, R.I., pleaded guilty Monday in Middlesex Superior Court to a slew of charges in connection with the September 2011 robbery at Musto Jewelers. The robbery left 16-year police veteran Robert DeNapoli with multiple injuries that ultimately ended his police career.

The 27-year-old Matos, who shot DeNapoli, received the stiffest sentence, 25 to 30 years in prison.

Baez-Cruz was sentenced to 20 to 25 years, while Murillo and Martinez received seven to eight years.

The defendants were also ordered to pay restitution to DeNapoli and another officer.