Sinister debuted when Chuck was in Shiar space in the 200's of Uncanny vol.1
Skimming vol. 2 Nicieza/Lobdell issues, Sinister appeared in X-cutioner's song but Chuck was unconscious. He tussled with some X-men here and there in the 20's , but I can't recall when he first interacted with Chuck on panel.
Thanks for any help.