Yes / Caffeic acid phenethyl ester (CAPE) is a polyphenolic active compound present in popular apiproduct, ‘propolis’ obtained from beehives. Though it has broad therapeutic capability, the bioavailability of CAPE is limited due to poor solubility. In this study, we report novel cocrystals of CAPE engineered using coformers such as caffeine (CAF), isonicotinamide (INIC), nicotinamide (NIC) with enhanced solubility and bioavailability of CAPE. The cocrystals were prepared by microwave-assisted cocrystallization and characterized using PXRD, DSC and Raman spectroscopy. PXRD and DSC confirm the successful formation and phase purity of CAPE-CAF, CAPE-INIC and CAPE-NIC cocrystals. Raman spectra of CAPE cocrystals complement these results in confirming the formation of novel crystalline phases. CAPE-NIC cocrystal was further subjected to X-ray crystallography to understand its molecular arrangement and hydrogen bonding in the crystal structure. The CAPE-NIC cocrystal structure is found to be stabilized by a rare 1,2-benzenediol-amide heterosynthon. Cocrystallization of CAPE with NIC improved its aqueous solubility and pharmacokinetic profile thereby demonstrating 2.76 folds escalation in bioavailability. / We thank UKIERI: UK-India Education and Research Initiative (TPR26) and EPSRC (EP/J003360/1, EP/L027011/1) for providing financial support during this study.

THESIS ORGANISATION This thesis is organised into nine chapters that include seven international and national publications (six accepted and one submitted for publication). The initial overview chapter outlines the justification and direction for this thesis. With the exception of chapter 8 (accepted for publication on the 1st May 2005); all chapters are exact duplicates of published articles in international and national refereed journals (chapters 2 to 7). The initial chapters (2 and 3) presents research findings using a marine fish species, mullet (Mugil cephalus), to measure trace metal bioavailability in Lake Macquarie, NSW Australia. While subsequent chapters (4 to 8) are presenting research under taken to improve the understanding of arsenic cycling in marine and estuarine environments. The final chapter (chapter 9) is a synopsis of the major findings presented in this thesis. Due to the publication nature of this thesis, an unavoidable degree of replication exists within chapters (publications).