Johor Sultanate
During the rule of Sultan Mansur Shah (1459–1466), the Riau archipelago became the part of the Malacca Sultanate. The Malacca Sultanate then included Kedah, Trengganu, Pahang, Johore, Jambi, Kampar, Bengkalis, Karimun Islands and Bintan. The fall of Malacca Empire started in 1511 when Malacca fell to the Portuguese. Sultan Mahmud Shah fled to Pahang and then to Johor and Bintan in 1521. There, he held out against Portuguese attacks, he even laid siege on Malacca in 1524, before a Portuguese counterattack forced him to flee to Sumatra where he died in 1528. Sultan Alauddin succeeded his father and made a new capital in the south. His realm was the Johor Sultanate, the successor of Malacca. The archipelago became the part of "war triangle" between the Portuguese, the Johor Sultanate and the Achehnese of northern Sumatra.