The European Union on Monday imposed sanctions on two organizations and 32 Iranians, including the culture and education ministers, intelligence officials and lawmakers, accused of links to Iran’s security crackdown on protesters.

The protests began after the Sept. 16 death of 22-year-old Mahsa Amini following her arrest by the Islamic Republic’s morality police and have grown into one of the most serious challenges to Iran’s theocracy since the 1979 Islamic Revolution.

At least 529 people have been killed in demonstrations, according to Human Rights Activists in Iran. Over 19,700 others have been detained by authorities amid a violent crackdown trying to suppress the dissent. Some people linked to the protests have been executed.

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The EU said it had imposed asset freezes and travel bans on the 32 officials and frozen the assets of the two organizations due to their involvement “in serious human rights violations in Iran.”

The 27-nation bloc had already imposed four rounds of sanctions on Iranian officials and organizations — including other ministers, military officers and Iran’s morality police — for alleged rights abuses.