One‐Pot Laccase‐Catalysed Synthesis of 5,6‐Dihydroxylated Benzo[b]furans and Catechol Derivatives, and Their Anticancer Activity

Abstract

A commercial laccase, Suberase® from Novozymes, was used to catalyse the synthesis of 5,6-dihydroxylated benzo[b]furans and catechol derivatives. The yields were, in some cases, similar to or better than that obtained by other enzymatic, chemical or electrochemical syntheses. The synthesised derivatives were screened against renal (TK10), melanoma (UACC62), breast (MCF7) and cervical (HeLa) cancer cell lines. GI50, TGI and LC50 are reported for the first time. Anticancer screening showed that the cytostatic effects of the 5,6-dihydroxylated benzo[b]furans were most effective against the melanoma (UACC62) cancer cell line with several compounds exhibiting potent growth inhibitory activities (GI50=0.77-9.76 µM), of which two compounds had better activity than the anticancer agent etoposide (GI50 0.89 µM). One compound exhibited potent activity (GI50=9.73 µM) against the renal (TK10) cancer cell line and two exhibited potent activity (GI50=8.79 and 9.30 µM) against the breast (MCF7) cancer cell line. These results encourage further studies of the 5,6-dihydroxylated benzo[b]furans for their potential application in anticancer therapy.

Investigation of Cobalt(III)‐Tetrachlorocatechol Complexes as Models for Catechol‐Based Anticancer Prodrugs

“…Thus, ortho ‐diphenol (or catechol) derivatives are potential candidates for the cobalt‐prodrug strategy due to a variety of pharmacological properties, including antioxidant, neuroprotective, anti‐inflammatory and antitumor . The ortho ‐diphenol moiety is present in a number of molecules with anticancer activity such as quinalizarine, a strong casein kinase (CK2) inhibitor, and cabozantinib (Cometriq R ), an inhibitor of tyrosine kinase receptors (TKI) that is FDA‐approved to treat advanced renal cell carcinoma and progressive metastatic medullary thyroid cancer, and under trial for renal, prostate, hepatocellular, and lung cancers . Hambley and co‐workers have investigated the complex [Co(CAT)(TPA)]ClO 4 {CAT = 2,3‐naphthyldiol and TPA = tris(2‐pyridylmethyl)amine} .…”

“…[13][14][15][16][17][18] The ortho-diphenol moiety is present in a number of molecules with anticancer activity such as quinalizarine, a strong casein kinase (CK2) inhibitor, and cabozantinib (Cometriq R ), an inhibitor of tyrosine kinase receptors (TKI) that is FDA-approved to treat advanced renal cell carcinoma and progressive metastatic medullary thyroid cancer, and under trial for renal, prostate, hepatocellular, and lung cancers. [19][20][21][22][23][24] Hambley and co-workers have investigated the complex [Co(CAT)(TPA)]ClO 4 {CAT = 2,3-naphthyldiol and TPA = tris(2-pyridylmethyl)amine}. [25] Dissociation of the CAT ligand associated with Co 3+ /Co 2+ by ascorbic acid was not observed.…”

Palladium and Copper Catalyzed Sonogashira cross Coupling an Excellent Methodology for C-C Bond Formation over 17 Years: A Review

“…Oxygen containing heterocycles possess many biological activities, such as anti-inflammatory [75], anticancer [76], antioxidative [77], antiviral [78] and antifungal activity [79]. It was a major challenge for organic chemists to synthesize heterocyclic compounds with a high degree of selectivity, specially the benzo[b]furan from a simple synthon.…”

Spray congealing as innovative technique for enzyme encapsulation

“…As enzyme a laccase from Myceliophthora thermophila , the crude extract Novozym 51003 (N51003), was used. Laccases (EC 1.10.3.2) are versatile enzymes for several applications such as degradation of pollutants, treatment of waste water, selective oxidations and C–C and C–X couplings . Owing to low costs and interesting properties, investigated in prior studies, the enzyme used is highly interesting for immobilization.…”

“…Laccases (EC 1.10.3.2) are versatile enzymes for several applications such as degradation of pollutants, treatment of waste water, selective oxidations and C-C and C-X couplings. [16][17][18][19][20][21]22 Owing to low costs and interesting properties, investigated in prior studies, the enzyme used is highly interesting for immobilization. The microparticles obtained were investigated with regard to activity, particle size, water content and protein release, as well as recyclability.…”