The antibacterial resistance burden is currently one of the most serious and unmanageable problems worldwide, and unless immediate action is taken globally, soon minor surgeries can no longer be conducted, and cuts and wounds will once again kill. As endeavoured herein, all is not lost, and with many incentives to develop the next generation of effective antibacterial agents, in particular, drug conjugates with lower susceptibility to bacterial resistance, this field of research has had a renewed interest from both academia and industry. With that borne in mind, herein this work presents the design and synthesis of a set of novel NInCs of therapeutic potential featuring cleavable linkers. The initial hydrazone linker was not compatible with the carboxyl ester hydrolysis of the aforementioned NInCs; however, it may be feasible for such novel antibacterial drug conjugates to be developed into a set of ester prodrugs. In this discussion of NInC esters, painstaking efforts were made to hydrolyse various esters of this type e.g. ethyl and methyl NInCs, but as yet this transformation proved, in practice, impractical. In most cases, if the reaction conditions were sufficiently suitable for the hydrolysis to take place, the hydrazone linker was also cleaved, with the exception of only one example for which difficulties in purification led to no or infinitesimal quantities of the desired product, and cases in which the reaction conditions were just too mild to hydrolyse anything, the intact NInC esters were recovered. Thus it is not necessarily safe to conclude that tinkering with kinetics can beat unfavourable thermodynamics. Some kinetic alterations manifest in thermodynamic allegiance better than do others, but the overall success of a transformation is demonstrated by the way in which thermodynamic soundness is evident. Moreover, attempts at finding a suitable PG for the carboxyl moiety in the NInCs were futile; however, naked zwitterionic NInCs were accomplished via stabilisation of the cleavable linker, and C-7 modifications of the indole core.