Brazil’s Federal Police carried out several temporary arrest warrants and search-and-seizure orders on Friday, including to two individuals who were sanctioned by the U.S., in an operation that happened earlier than initially planned.

About $2 billion in their assets were frozen by the courts.

Stella Stefanie Nunes Henrique de Oliveira was arrested on Friday, while Victor Henrique de Oliveira Shimada remains at large, Federal Police chief Andrei Rodrigues said in a news conference in Brasilia on Friday. Both were sanctioned July 1 by Treasury’s Office of Foreign Assets Control on allegations they helped launder proceeds for Latin America’s largest criminal organization, known as Primeiro Comando da Capital, or PCC.

The operation, code-named Operation Exchange, was being planned by Brazilian authorities ahead of the U.S. Treasury decision, Rodrigues said, and had to be brought forward from its initial schedule, he added.

“Actually, if there hadn’t been this designation, maybe the outcome would be different, and we could have located this person,” Rodrigues said. “There was a damage to our investigation.”

Shimada’s lawyer said the defense team was aware of the investigation but declined to comment because it had not yet had access to the court decisions supporting the measures. Oliveira’s legal representative couldn’t immediately be reached.

In total, 50 federal officers were executing 11 temporary arrest warrants and 13 search-and-seizure warrants in several cities across Sao Paulo state. Brazilian courts also ordered the freezing of assets, funds and crypto holdings belonging to the suspects, totaling about 10.4 billion reais ($2 billion), according to a Federal Police statement. Rodrigues didn’t detail the composition of the amount, and just added that it was identified through financial transactions composing the probe.

The suspects operated a sophisticated financial network to move illicit proceeds through cryptocurrency transfers, cash transportation, high-value bank transactions, transfers between individuals and companies, the Brazilian police said in a statement Friday. The suspects may face charges including criminal conspiracy, money laundering and illegal transfers of funds abroad, as well as additional offenses that may emerge during the investigation, the statement added.

According to the U.S., Shimada served as a key intermediary between Florida-based PCC operatives and international drug traffickers. It was first time Brazilian individuals were sanctioned since U.S. Secretary of State Marco Rubio announced in May that PCC, alongside Comando Vermelho, or CV, were being named as foreign terrorist organization.

Shimada and his network laundered more than $30 million in criminal proceeds within the U.S. before sending funds back to the PCC in Brazil through cryptocurrency transactions, according to U.S. authorities. Treasury officials also said he had been under house arrest in Brazil after one of his companies, Victory Trading, was accused of laundering money stolen from a Brazilian soccer club through an advertising fraud scheme.

(Gabriel Diniz Tavares contributed to this report.)

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