JEFFERSON CITY, Mo. (AP) — Four former Missouri guards have pleaded not guilty to murder in the death of a Black man in prison, and a fifth has pleaded not guilty to accessory to involuntary manslaughter.

Othel Moore Jr., 38, died on Dec. 8 in the Jefferson City Correctional Center. A criminal complaint filed Friday alleged that the guards pepper-sprayed Moore, placed a mask over his face and left him in a position that caused him to suffocate.

Cole County Associate Circuit Judge Christopher Limbaugh on Monday refused to allow bond for three of the men charged with second-degree murder: Aaron Brown, Jacob Case and Justin Leggins. Gregory Varner, also charged with second-degree murder, is jailed without bond. His arraignment is scheduled for Wednesday. Each were fired in the wake of Moore’s death.

Cole County Prosecuting Attorney Locke Thompson on Monday said Bryanne Bradshaw, who is charged with accessory to involuntary manslaughter, paid bond and has been released from jail. Her next court appearance is scheduled for July 30.

Moore was searched and stripped down to his boxer shorts inside his cell during a prison contraband sweep. He was then handcuffed behind his back and led outside, according to a probable cause statement from deputies. Moore showed no aggression during the process and was complying with orders, investigators wrote.

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While standing handcuffed just outside his cell door, Moore was pepper-sprayed, then put in a spit hood, leg wrap and restraint chair, according to Thompson’s office. Guards told investigators that Moore was not following orders to be quiet and spit at them, although witnesses said Moore was spitting pepper spray out of his mouth.

Thompson said multiple people heard Moore saying he couldn’t breathe and that the events were captured on the prison’s video surveillance system.

Moore was eventually taken to a hospital wing and was pronounced dead. Thompson said the medical examiner ruled Moore’s cause of death was from positional asphyxiation, and his death was listed as a homicide.

Moore, who grew up in St. Louis, was serving a 30-year sentence on range of charges, including second-degree domestic assault and first-degree robbery. His family filed a wrongful-death lawsuit against the defendants and the Missouri Department of Corrections on Friday.

The Corrections Department released a statement saying it cooperated with the Cole County Sheriff’s Department’s investigation and has made policy changes since Moore’s death.

Leggins and Brown on Monday told the judge that they are still trying to hire private lawyers to represent them. No one immediately responded to a Facebook message from The Associated Press to a person associated with Leggins.

It is unclear if Varner and Bradshaw have hired attorneys: Missouri’s online court record system was out statewide on Monday and the jail declined to allow the AP to speak with Varner. A phone message and email to contacts associated with Bradshaw were not immediately answered Monday.

Case said he has a lawyer, but it is unclear who that is because of the court records outage.

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Researcher Rhonda Shafner contributed from New York.