Catzi is said to be the oldest. Other sources report her as the youngest, with Bertie as the next youngest, then Avery, then Prizma as the oldest. It is clearly said in the anime that Prizma is older than Avery. If it is to be believed that Catzi is the oldest and not the youngest, then the order would be, from oldest to youngest: Catzi, Prizma, Avery, and Bertie.
Eventually, the Negamoon Sisters and Rubeus faced off against the Sailor Scouts. Catzi fought Sailor Mars, Bertie fought Sailor Mercury, Avery fought Sailor Venus, and Prizma fought Sailor Jupiter. They were forced to retreat when Sailor Moon gained the upper hand on Rubeus.
Eventually, they all turned good and were healed by Sailor Moon with Moon Crystal Healing Activation: First Catzi, then Bertie, then Avery and Prizma. They opened a cosmetic shop following this.
Their final appearance was in Episode 39. They found Sapphire after he was attacked by Wiseman. Later, when Sapphire leaves to warn Diamond of Wiseman's true intentions, concerned, Catzi calls Serena to let her know, and when Sapphire dies, Prizma senses it and sobs while clutching Sapphire's blazer jacket he left behind.
In Sailor Moon Crystal, due to it following the original manga more accurately, when each of the sisters are sent to capture their Sailor Guardian counterpart, each of them are killed off by Sailor Moon and the Moon Scepter, but not without Catzi, Bertie, and Prizma succeeding in capturing Sailors Mars, Mercury, and Jupiter for Rubeus to take back to Nemesis before being slain, while Avery is unable to capture Sailor Venus before being overpowered by Tuxedo Mask's new attack and then slain by Sailor Moon, forcing Rini to confess of her being from the 30th century and asking Sailor Moon, Sailor Venus, and Tuxedo Mask to help her save her future from the Black Moon Clan/Negamoon Family.