I don't see why not. Big Mom cannot break free from seastone cuffs and the same should apply to Kaido, Blackbeard and Whitebeard. Shanks is not weakened by seastone, as far as we know, and will still be able to use haki so he might break free.
Shiki was an usual case. He was cuffed only by his ankles and somebody was foolish enough to give him access to a blade, probably a Jailer Beast that tried to torture him.
This was the first public escape 22 years ago. Security measures has been upgraded since then. Even more so after Luffy and Blackbeard broke in and out. Doflamingo today has cuffs around his arms, his legs, even chains around his torso. How will they escape, by cutting off both arms and legs? You become a useless torso. Besides, I'm sure nobody but Magellan himself is allowed to walk in there and torture Doflamingo with a sharp quality blade.