Syntheses and PDT activity of new mono- and di-conjugated derivatives of chlorin e6

Syntheses of three new chlorin e6 conjugates for PDT of tumors are reported. One of the new compounds 17 is conjugated with lysine at the 131-position, but the others are mono-conjugated 14 or diconjugated 15 with the non-amino acid species ethanolamine. Cellular experiments with the three new compounds and previously synthesized non-amino acid 152-conjugates (7–10), 131-monoconjugates 14, 16, and a 131,152-diconjugate 12 are reported. In vitro cytotoxicity experiments show that the 131-conjugates are more toxic than the 152-conjugates, and the most toxic derivative (dark- and photo-toxicity) is the 131-ethylenediamine conjugate 11. The most useful PDT photosentitizers appear to be the ethanolamine derivatives, conjugated at the 152- and the 131,152-positions; these show high phototoxicity but relatively low dark toxicity compared with 11, and also the highest dark/photo cytotoxicity ratios.

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5-Alkylamino-N-phenylpyrazine-2-carboxamides: Design, Preparation, and Antimycobacterial Evaluation

Molecules ◽

10.3390/molecules25071561 ◽

2020 ◽

Vol 25 (7) ◽

pp. 1561

Author(s):

Weronika Ambrożkiewicz ◽

Marta Kučerová-Chlupáčová ◽

Ondřej Janďourek ◽

Klára Konečná ◽

Pavla Paterová ◽

...

Keyword(s):

Mycobacterium Tuberculosis ◽

Clinical Importance ◽

Infectious Agent ◽

Antimycobacterial Activity ◽

In Vitro Cytotoxicity ◽

World Health ◽

Health Organization ◽

New Compounds ◽

Derivatives Of

According to the World Health Organization, tuberculosis is still in the top ten causes of death from a single infectious agent, killing more than 1.7 million people worldwide each year. The rising resistance developed by Mycobacterium tuberculosis against currently used antituberculars is an imperative to develop new compounds with potential antimycobacterial activity. As a part of our continuous research on structural derivatives of the first-line antitubercular pyrazinamide, we have designed, prepared, and assessed the in vitro whole cell growth inhibition activity of forty-two novel 5-alkylamino-N-phenylpyrazine-2-carboxamides with various length of the alkylamino chain (propylamino to octylamino) and various simple substituents on the benzene ring. Final compounds were tested against Mycobacterium tuberculosis H37Ra and four other mycobacterial strains (M. aurum, M. smegmatis, M. kansasii, M. avium) in a modified Microplate Alamar Blue Assay. We identified several candidate molecules with micromolar MIC against M. tuberculosis H37Ra and low in vitro cytotoxicity in HepG2 cell line, for example, N-(4-hydroxyphenyl)-5-(pentylamino)pyrazine-2-carboxamide (3c, MIC = 3.91 µg/mL or 13.02 µM, SI > 38) and 5-(heptylamino)-N-(p-tolyl)pyrazine-2-carboxamide (4e, MIC = 0.78 µg/mL or 2.39 µM, SI > 20). In a complementary screening, we evaluated the in vitro activity against bacterial and fungal strains of clinical importance. We observed no antibacterial activity and sporadic antifungal activity against the Candida genus.

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Novel Derivatives of 4-Methyl-1,2,3-Thiadiazole-5-Carboxylic Acid Hydrazide: Synthesis, Lipophilicity, and In Vitro Antimicrobial Activity Screening

Applied Sciences ◽

10.3390/app11031180 ◽

2021 ◽

Vol 11 (3) ◽

pp. 1180

Author(s):

Kinga Paruch ◽

Łukasz Popiołek ◽

Anna Biernasiuk ◽

Anna Berecka-Rycerz ◽

Anna Malm ◽

...

Keyword(s):

Antimicrobial Activity ◽

Carboxylic Acid ◽

Bacterial Infections ◽

Acid Hydrazide ◽

Antimicrobial Effect ◽

In Vitro Antimicrobial Activity ◽

Research Goal ◽

New Compounds ◽

Derivatives Of

Bacterial infections, especially those caused by strains resistant to commonly used antibiotics and chemotherapeutics, are still a current threat to public health. Therefore, the search for new molecules with potential antimicrobial activity is an important research goal. In this article, we present the synthesis and evaluation of the in vitro antimicrobial activity of a series of 15 new derivatives of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid. The potential antimicrobial effect of the new compounds was observed mainly against Gram-positive bacteria. Compound 15, with the 5-nitro-2-furoyl moiety, showed the highest bioactivity: minimum inhibitory concentration (MIC) = 1.95–15.62 µg/mL and minimum bactericidal concentration (MBC)/MIC = 1–4 µg/mL.

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Novel Amino Acid Derivatives of Quinolines as Potential Antibacterial and Fluorophore Agents

Scientia Pharmaceutica ◽

10.3390/scipharm88040057 ◽

2020 ◽

Vol 88 (4) ◽

pp. 57

Author(s):

Oussama Moussaoui ◽

Rajendra Bhadane ◽

Riham Sghyar ◽

El Mestafa El Hadrami ◽

Soukaina El Amrani ◽

...

Keyword(s):

Amino Acid ◽

Methyl Esters ◽

Amino Acid Derivatives ◽

Bacterial Strains ◽

Fluorescent Properties ◽

Topoisomerase Iv ◽

Microdilution Method ◽

Hydrolysis Of ◽

Derivatives Of

A new series of amino acid derivatives of quinolines was synthesized through the hydrolysis of amino acid methyl esters of quinoline carboxamides with alkali hydroxide. The compounds were purified on silica gel by column chromatography and further characterized by TLC, NMR and ESI-TOF mass spectrometry. All compounds were screened for in vitro antimicrobial activity against different bacterial strains using the microdilution method. Most of the synthesized amino acid-quinolines show more potent or equipotent inhibitory action against the tested bacteria than their correspond esters. In addition, many of them exhibit fluorescent properties and could possibly be utilized as fluorophores. Molecular docking and simulation studies of the compounds at putative bacterial target enzymes suggest that the antimicrobial potency of these synthesized analogues could be due to enzyme inhibition via their favorable binding at the fluoroquinolone binding site at the GyrA subunit of DNA gyrase and/or the ParC subunit of topoisomerase-IV.

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New Compounds: Amino Acid Derivatives of Nicotinic Acid

Journal of Pharmaceutical Sciences ◽

10.1002/jps.2600610338 ◽

1972 ◽

Vol 61 (3) ◽

pp. 477-478 ◽

Cited By ~ 3

Author(s):

M.T. Wu ◽

R.E. Lyle

Keyword(s):

Amino Acid ◽

Nicotinic Acid ◽

Amino Acid Derivatives ◽

New Compounds ◽

Derivatives Of

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Preparation and in vitro cytotoxicity of oxaliplatin derivatives with chiral amino acid as the carrier group

Journal of Coordination Chemistry ◽

10.1080/00958972.2014.945922 ◽

2014 ◽

Vol 67 (13) ◽

pp. 2195-2203 ◽

Cited By ~ 6

Author(s):

Chuanzhu Gao ◽

Tianshuai Wang ◽

Ji Chen ◽

Yan Zhang ◽

Bo Yang ◽

...

Keyword(s):

Amino Acid ◽

In Vitro Cytotoxicity

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In vitro studies on the inhibition of colon cancer by amino acid derivatives of bromothiazole

Bioorganic & Medicinal Chemistry Letters ◽

10.1016/j.bmcl.2017.05.073 ◽

2017 ◽

Vol 27 (15) ◽

pp. 3507-3510 ◽

Cited By ~ 5

Author(s):

Nuno Vale ◽

Ana Correia-Branco ◽

Bárbara Patrício ◽

Diana Duarte ◽

Fátima Martel

Keyword(s):

Colon Cancer ◽

Amino Acid ◽

In Vitro Studies ◽

Amino Acid Derivatives ◽

Derivatives Of

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In vitro cytotoxicity of L-amino acid oxidase from the venom of Crotalus mitchellii pyrrhus

Toxicon ◽

10.1016/j.toxicon.2017.09.012 ◽

2017 ◽

Vol 139 ◽

pp. 20-30 ◽

Cited By ~ 7

Author(s):

Kok Keong Tan ◽

Siok Ghee Ler ◽

Jayantha Gunaratne ◽

Boon Huat Bay ◽

Gopalakrishnakone Ponnampalam

Keyword(s):

Amino Acid ◽

In Vitro Cytotoxicity ◽

Acid Oxidase ◽

Amino Acid Oxidase ◽

Crotalus Mitchellii

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P-113d, an Antimicrobial Peptide Active againstPseudomonas aeruginosa, Retains Activity in the Presence of Sputum from Cystic Fibrosis Patients

Antimicrobial Agents and Chemotherapy ◽

10.1128/aac.45.12.3437-3444.2001 ◽

2001 ◽

Vol 45 (12) ◽

pp. 3437-3444 ◽

Cited By ~ 61

Author(s):

Umadevi S. Sajjan ◽

Linh T. Tran ◽

Nuria Sole ◽

Christopher Rovaldi ◽

Alan Akiyama ◽

...

Keyword(s):

Cystic Fibrosis ◽

Amino Acid ◽

Mirror Image ◽

Suppressive Therapy ◽

Significant Activity ◽

Amino Acid Residues ◽

Parent Molecule ◽

Histatin 5 ◽

Derivatives Of

ABSTRACT Antimicrobial peptides are a source of novel agents that could be useful for treatment of the chronic lung infections that afflict cystic fibrosis (CF) patients. Efficacy depends on antimicrobial activity against the major pathogens of CF patients, Pseudomonas aeruginosa, Staphylococcus aureus, and Haemophilus influenzae, in the environment of the CF patient's airway. We describe the in vitro efficacies of derivatives of histatins, which are histidine-rich peptides produced by the salivary glands of humans and higher primates. P-113, a peptide containing 12 of the 24 amino acid residues of the parent molecule, histatin 5, retained full antibacterial activity and had a good spectrum of activity in vitro against the prominent pathogens of CF patients. However, P-113 was not active in the presence of purulent sputum from CF patients. In contrast, P-113d, the mirror-image peptide with the amino acid residues in the d configuration, was stable in sputum, was as active as P-113 against pathogens of CF patients in the absence of sputum and retained significant activity in the presence of sputum from CF patients. Recombinant human DNase, which effectively liquefies sputum, enhanced the activity of P-113d in undiluted sputum against both exogenous (added) bacteria and endogenous bacteria. Because of its properties, P-113d shows potential as an inhalant in chronic suppressive therapy for CF patients.

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