Cationic diamineplatinum (II) complexes of nalidixic acid

Lee, Sung Sil; Jung, Ok‐Sang; Lee, Chong Ock; Choi, Sang Un; Jun, Mira; Sohn, Youn Soo

doi:10.1016/0020-1693(95)04734-4

Cited by 26 publications

(7 citation statements)

References 14 publications

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“…6 ppm for the carboxylate C24, similar to that of the carboxylate C26 in the Bamet-R1 complex. All these data are in agreement with the monodentate union of cholylglycinate and ursodeoxycholate to the metal in both Bamet-R1 and Bamet-UD2 complexes (27)(28)(29).…”

Section: Resultssupporting

confidence: 88%

Structural Characterization, Kinetic Studies, and in Vitro Biological Activity of Newcis-Diamminebis-cholylglycinate(O,O‘) Pt(II) andcis-Diamminebis-ursodeoxycholate(O,O‘) Pt(II) Complexes

et al. 2000

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The complexes cis-diamminebis-cholylglycinate (O,O') [Pt(II) C(52)H(90)N(4)O(12)Pt, for convenience referred to as Bamet-R1] and cis-diamminebis-ursodeoxycholate (O,O') Pt(II) (C(48)H(84)N(2)O(8)Pt, Bamet-UD2) were prepared. The structural integrity of the compounds was confirmed by elemental analysis, FT-IR, NMR, FAB-MS, and UV spectroscopies. The kinetic study of both compounds was accomplished by combining the conductivity measurement and those of the analysis of the electronic spectra in aqueous solution for NaCl concentrations of 4 mM (similar to cytoplasmatic concentration), 150 mM (similar to plasmatic concentration), and 500 mM. In water, the compound Bamet-R1 showed a half-life, t(1/2), of 3.0 h. This compound forms the chelate species through loss of a ligand, and the other one acts as a bidentate ligand. Ring opening in the presence of chloride ion was produced with a k(Cl)()-of 0.25 M(-)(1) h(-)(1). The half-life of Bamet-UD2 in aqueous solution was 3.2 h. However, since this species is not able to chelate and has a lower degree of solubility in the presence of chloride ion, its kinetic behavior was very different from that of the other compound. We consider this to be of great interest with regards to its cytostatic activity. All kinetic measurements were performed under pseudo-first-order conditions, and a pseudo-first-order behavior was found. The antitumoral effect of Bamet-UD2 on several cell lines derived from rat hepatoma, human hepatoma, mouse leukemia, and human colon carcinoma was found to be, in general, similar to that of cisplatin, but higher than that observed for Bamet-R1.

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Section: Resultssupporting

confidence: 88%

Structural Characterization, Kinetic Studies, and in Vitro Biological Activity of Newcis-Diamminebis-cholylglycinate(O,O‘) Pt(II) andcis-Diamminebis-ursodeoxycholate(O,O‘) Pt(II) Complexes

et al. 2000

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“…Regarding metal complexes, some work has already been disclosed involving the coordination of nalidixic acid to Cu, Ru, Cd, Zn, and Pt. − None of these coordination compounds form frameworks, and, with exception of a Zn complex, they all involve a second organic ligand (Table ). The coordination of nalidixic acid to the metal sites is always achieved via the carbonyl and carboxylic moieties.…”

Section: Introductionmentioning

confidence: 99%

Mechanochemical Assembly of Nalidixic Acid Bioinspired Metal–Organic Compounds and Complexes toward Improved Solubility

André

Galego

Martins

2018

Crystal Growth & Design

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Nalidixic acid is an antibiotic from the quinolones family whose bioavailability is limited due to its low solubility. The development of complexes and bioinspired metal−organic frameworks has been explored as a way to achieve controlled drug delivery and release, and we demonstrate that they can also be used to tune drugs' physicochemical properties, such as solubility. Herein we disclose a series of complexes and frameworks of nalidixic acid and Zn. One of these frameworks duplicates the solubility of nalidixic acid, and it is stable on the shelf and to 77% room humidity. The incorporation of a second ligand into the frameworks is also presented, showing the possibility to develop extended networks with further potential applications.

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“…Several metal-based nalidixic acid complexes have been synthesized in the past few years as binary or ternary complexes with one or more O- (water, methanol) or N-bearing donor ligands or coligands (pyridine, 2,2′-bipyridine, 1 R ,2 R -diaminocyclo-hexane, etc.). This activity was prompted by the synergetic effect of a metal ion to quinolone drugs with an improved pharmacological activity, including potential as anticancer agents. − ,− Very recently, André et al reported a coordination network with Zn 2+ showing a higher water solubility . Herein, we report two new BioMOFs with divalent magnesium and manganese ions.…”

Section: Introductionmentioning

confidence: 91%

“…We disclose here one example in which nalidixic acid MOFs present benefits. Nalidixic acid (NALD) is a first generation drug of the quinolone family with a broad spectrum of biological activity, such as antimicrobial, anti-inflammatory, and antitumor. − It is bacteriostatic at low concentrations and bactericidal at higher doses. However, nalidixic acid has a low oral bioavailability due to its poor solubility and slow dissolution rate .…”

Section: Introductionmentioning

confidence: 99%

Mg- and Mn-MOFs Boost the Antibiotic Activity of Nalidixic Acid

André

Silva

Fernandes

et al. 2019

ACS Appl. Bio Mater.

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The development of metal–organic frameworks (MOFs) enclosing active pharmaceutical ingredients is of considerable interest, as their use in controlled drug release and delivery is very promising. Although nalidixic acid is an antibiotic with a broad spectrum of biological applications, effective mainly against Gram-negative infections, its oral bioavailability is low due to a poor solubility and slow dissolution. Herein, we report new metal–organic frameworks (BioMOFs) comprising nalidixic acid and divalent magnesium and manganese ions. These compounds showed an adequate cytotoxicity and improved antimicrobial activity, especially against Gram-negative bacteria. These BioMOFS are among the first examples containing active pharmaceutical ingredients as linkers. Importantly, it is shown that a remarkable increase of the antimicrobial activity of certain antibiotics may be achieved by delivering them in the form of BioMOFs.

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Cationic diamineplatinum (II) complexes of nalidixic acid

Cited by 26 publications

References 14 publications

Structural Characterization, Kinetic Studies, and in Vitro Biological Activity of Newcis-Diamminebis-cholylglycinate(O,O‘) Pt(II) andcis-Diamminebis-ursodeoxycholate(O,O‘) Pt(II) Complexes

Structural Characterization, Kinetic Studies, and in Vitro Biological Activity of Newcis-Diamminebis-cholylglycinate(O,O‘) Pt(II) andcis-Diamminebis-ursodeoxycholate(O,O‘) Pt(II) Complexes

Mechanochemical Assembly of Nalidixic Acid Bioinspired Metal–Organic Compounds and Complexes toward Improved Solubility

Mg- and Mn-MOFs Boost the Antibiotic Activity of Nalidixic Acid

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