Synthesis of novel isoluminol probes and their use in rapid bacterial assays

Neelakantan, Sundar; Surjawan, I.; Karacelik, Huseyin; Hicks, C.L.; Crooks, Peter A.

doi:10.1016/j.bmcl.2009.08.004

Cited by 6 publications

(3 citation statements)

References 7 publications

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“…Therefore, amino-acylation was attempted on protected luminol derivatives. Phthalimides have been used as protected phthalhydrazides in the preparation of amino-alkylated isoluminol derivatives [41,42,43]. In this respect, amino-phthalimides 6a , b (Scheme 2) were prepared from the respective nitrophthalic acids 3a , b in a three-step reaction sequence involving consecutive condensation reactions towards anhydrides 4 and then phthalimides 5 , and finally reduction of the nitro group [41,44].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Chemiluminescent Properties of Amino-Acylated luminol Derivatives Bearing Phosphonium Cations

et al. 2019

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The monitoring of reactive oxygen species in living cells provides valuable information on cell function and performance. Lately, the development of chemiluminescence-based reactive oxygen species monitoring has gained increased attention due to the advantages posed by chemiluminescence, including its rapid measurement and high sensitivity. In this respect, specific organelle-targeting trackers with strong chemiluminescence performance are of high importance. We herein report the synthesis and chemiluminescence properties of eight novel phosphonium-functionalized amino-acylated luminol and isoluminol derivatives, designed as mitochondriotropic chemiluminescence reactive oxygen species trackers. Three different phosphonium cationic moieties were employed (phenyl, p-tolyl, and cyclohexyl), as well as two alkanoyl chains (hexanoyl and undecanoyl) as bridges/linkers. Synthesis is accomplished via the acylation of the corresponding phthalimides, as phthalhydrazide precursors, followed by hydrazinolysis. This method was chosen because the direct acylation of (iso)luminol was discouraging. The new derivatives’ chemiluminescence was evaluated and compared with that of the parent molecules. A relatively poor chemiluminescence performance was observed for all derivatives, with the isoluminol-based ones being the poorest. This result is mainly attributed to the low yield of the fluorescence species formation during the chemiluminescence oxidation reaction.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Chemiluminescent Properties of Amino-Acylated luminol Derivatives Bearing Phosphonium Cations

et al. 2019

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“…lactis C2 than for E. coli , S. aureus , or S. typhimurium . Finally, the authors envisaged that these types of probes have more advantages than the conventionally used polymer chain reaction (PCR) and nucleic acid probes assays [ 113 ].…”

Section: Conjugated or Hybrid Moleculesmentioning

confidence: 99%

Conjugation as a Tool in Therapeutics: Role of Amino Acids/Peptides-Bioactive (Including Heterocycles) Hybrid Molecules in Treating Infectious Diseases

et al. 2023

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Peptide-based drugs are gaining significant momentum in the modern drug discovery, which is witnessed by the approval of new drugs by the FDA in recent years. On the other hand, small molecules-based drugs are an integral part of drug development since the past several decades. Peptide-containing drugs are placed between small molecules and the biologics. Both the peptides as well as the small molecules (mainly heterocycles) pose several drawbacks as therapeutics despite their success in curing many diseases. This gap may be bridged by utilising the so called ‘conjugation chemistry’, in which both the partners are linked to one another through a stable chemical bond, and the resulting conjugates are found to possess attracting benefits, thus eliminating the stigma associated with the individual partners. Over the past decades, the field of molecular hybridisation has emerged to afford us new and efficient molecular architectures that have shown high promise in medicinal chemistry. Taking advantage of this and also considering our experience in this field, we present herein a review concerning the molecules obtained by the conjugation of peptides (amino acids) to small molecules (heterocycles as well as bioactive compounds). More than 125 examples of the conjugates citing nearly 100 references published during the period 2000 to 2022 having therapeutic applications in curing infectious diseases have been covered.

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“…Yield: 65%; white solid: mp 55-57°C (CHCl 3 /hexane), lit. mp 49-50°C;27 IR (KBr): 3461 (OH), 1771, 1708 (C@O) cm À1 . Anal.…”

mentioning

confidence: 99%

New N-(phenoxydecyl)phthalimide derivatives displaying potent inhibition activity towards α-glucosidase

Pascale

Carocci

Catalano

et al. 2010

Bioorganic & Medicinal Chemistry

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Synthesis of novel isoluminol probes and their use in rapid bacterial assays

Cited by 6 publications

References 7 publications

Synthesis and Chemiluminescent Properties of Amino-Acylated luminol Derivatives Bearing Phosphonium Cations

Synthesis and Chemiluminescent Properties of Amino-Acylated luminol Derivatives Bearing Phosphonium Cations

Conjugation as a Tool in Therapeutics: Role of Amino Acids/Peptides-Bioactive (Including Heterocycles) Hybrid Molecules in Treating Infectious Diseases

New N-(phenoxydecyl)phthalimide derivatives displaying potent inhibition activity towards α-glucosidase

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