Hydrogen-bonded chains in three<i>cis</i>-dichloridoplatinum(II) complexes bearing piperidine and amine ligands

Thanh, Chi Nguyen Thi; Bich, Ngan Nguyen; Meervelt, Luc Van

doi:10.1107/s2053229614003386

Cited by 7 publications

(6 citation statements)

References 13 publications

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“…Since ropivacaine contains a dimethylbenzene group ( Figure 1B ) and Q11 contains three phenylalanine residues, it is possible that π-π stacking force can be formed between their phenyl rings and links the two molecules together. 35 , 36 The existence of π-π stacking force can be proved by the auto-fluorescent spectrum for RH/Q11 mixture shown in Figure 1F . RH or Q11 alone exhibited a weak fluorescence peak around 530 nm, while the RH/Q11 mixture exhibited an enhanced fluorescence peak around 482 nm, which could be attributed to the orderly interaction of π-π stacking.…”

Section: Resultsmentioning

confidence: 89%

Interaction Between Ropivacaine and a Self-Assembling Peptide: A Nanoformulation for Long-Acting Analgesia

Peng¹,

Liu²,

Zhang³

et al. 2022

IJN

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Introduction Ropivacaine as a conventional local anesthetic has been used more and more frequently in the treatment of postoperative pain, but its analgesic effect can only last for several hours. In order to fulfill the clinic requirement for long-term analgesia, a long-acting ropivacaine nanocrystal formulation was fabricated through the interaction between ropivacaine and a self-assembling peptide. Methods Transmission electron microscopy, dynamic light scattering, circular dichroism and fluorescence spectrometry were used to examine the structural changes caused by the interaction between ropivacaine and the peptide. Scanning electron microscopy, dynamic light scattering, Fourier transform infrared spectrometry, X-ray diffraction and optical microscopy were used to characterize the ropivacaine-peptide nanocrystal. In vitro drug release and pharmacokinetics study were conducted to evaluate the slow-release profile of the nanocrystal formulation. A rodent cutaneous trunci muscle reflex model was used to evaluate the nociceptive blockade effects, and histological analysis was used to evaluate the local toxicity. A rodent plantar incisional pain model was used to evaluate the analgesic effect. Results Soluble ropivacaine monomers interacted with the Q11 peptide through π-π stacking and remolded its self-assembling structure, leading to the formation of drug/peptide nanoparticles which could be mineralized to form drug/peptide nanocrystals by adjusting the pH. Under physiological condition, the nanocrystals could release free ropivacaine slowly. As evaluated in rodent models, the anesthetic and analgesic effects of this formulation were significantly extended without causing toxicity. Conclusion Based on the interaction between ropivacaine and Q11, a controllable biomineralization process could be induced to obtain homogeneous nanocrystals, which could be used as an injectable long-acting analgesic formulation. This crystallization strategy utilizing the peptide-drug interaction also provided a promising pathway to fabricate long-acting formulations for many other small molecular drugs.

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Section: Resultsmentioning

confidence: 89%

Interaction Between Ropivacaine and a Self-Assembling Peptide: A Nanoformulation for Long-Acting Analgesia

Peng¹,

Liu²,

Zhang³

et al. 2022

IJN

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“…In comparison with the earlier reported complex [PtCl 2 (pip)(quinoline)] (Nguyen Thi Thanh et al, 2014), the quinoline ligand is replaced by an N,Obidentate quinaldate ligand. It is interesting to note that in the [PtCl 2 (pip)(quinoline)] complex, the quinoline and piperidine ligands are arranged in cis positions (Nguyen Thi Thanh et al, 2014). In the title compound, the quinoline ring of the quinaldate ligand occupies a trans position with respect to the piperidine ring.…”

Section: Chemical Contextmentioning

confidence: 78%

“…The title compound belongs to a series of platinum(II) complexes bearing piperidine (pip) as a ligand, which exhibit notable antitumour activity (Da et al, 2001;Rounaq Ali Khan et al, 2000;Solin et al, 1982). In comparison with the earlier reported complex [PtCl 2 (pip)(quinoline)] (Nguyen Thi Thanh et al, 2014), the quinoline ligand is replaced by an N,Obidentate quinaldate ligand. It is interesting to note that in the [PtCl 2 (pip)(quinoline)] complex, the quinoline and piperidine ligands are arranged in cis positions (Nguyen Thi Thanh et al, 2014).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of chlorido(piperidine-κN)(quinoline-2-carboxylato-κ²N,O)platinum(II)

Thanh¹,

Bich²,

Meervelt³

2014

Acta Cryst E

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“…Piperidines are known to have CNS depressant action at low dosage levels and stimulant activity with increased doses. They have been used as antitumor (Nguyen Thi Thanh et al, 2014), antimicrobial (Perumal et al, 2014), antifungal, hypoglycaemic, hypolipidemic, anti-acetyl cholinesterase (Singh et al, 2009), anti-coagulant (Mochizuki et al, 2008), antihistamines, anaesthetics, tranquilizers, analgesic, ganglionic blocking and as hypotensive agents (Pandey & Chawla, 2012). The properties of piperidine derivatives depends on the nature of the side groups and their orienta- tions.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structures of two 2,9-dithia-13-azadispiro[4.1.4⁷.3⁵]tetradecan-6-ones

et al. 2015

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In the title compounds 4,11-dihydroxy-13-methyl-1,8-di-p-tolyl-2,9-dithia-13-azadispiro [4.1.4 7 . 3 5 ]tetradecan-6-one, C 26 H 31 NO 3 S 2 , (I), and 13-benzyl-4,11-dihydroxy-1,8-bis(4-methylphenyl)-2,9-dithia-13-azadispiro [4.1.4 7 .3 5 ]tetradecan-6-one, C 32 H 35 NO 3 S 2 , (II), the piperidine rings adopt distorted chair conformations. The thiophene rings in (I) have envelope conformations, with the spiro C atoms as the flaps. In (II), one thiophene ring (D) has an envelope conformation, with the hydroxy-substituted C atom as the flap, while the other thiophene ring (E) has a twisted conformation on the C-C bond involving the spiro C atom and the toluyl-substituted C atom. In (I), the mean plane of the piperidine ring makes dihedral angles of 75.16 (9) and 73.33 (8) with the mean planes of the thiophene rings (D and E), respectively. In (II), the corresponding dihedral angles are 70. 95 (11) and 77.43 (12) . In both compounds, there is an intramolecular O-HÁ Á ÁO hydrogen bond forming an S(6) ring motif. In the crystal of (I), molecules are linked via O-HÁ Á ÁN and C-HÁ Á ÁO hydrogen bonds, forming chains along [010]. There are also -interactions present involving inversion-related benzene rings, linking the chains to form slabs parallel to (100). In the crystal of (II), molecules are linked via O-HÁ Á ÁO hydrogen bonds, forming inversion dimers with an R 4 4 (8) ring motif. The dimers are linked by C-HÁ Á Á interactions, forming slabs parallel to (001). Chemical contextPiperidine derivatives have had an important impact in the medical field due to their wide variety of pharmacological activities, and they form an essential part of the molecular structure of important drugs (Hema et al., 2005a,b). Piperidine derivatives are used clinically to prevent post-operative vomiting, to speed up gastric emptying before anaesthesia or to facilitate radiological evaluation, and to correct a variety of disturbances of gastro-intestinal functions (Hema et al., 2005a,b). The piperidine structural motif is present in natural alkaloids (Raghuvarman et al., 2014). Notably it is found in the fire ant toxin solenopsin and is an inhibitor of phosphatidylinositol-3-kinase signalling and angiogenesis (Rajalakshmi et al., 2012). Piperidines are known to have CNS depressant action at low dosage levels and stimulant activity with increased doses. They have been used as antitumor (Nguyen Thi Thanh et al., 2014) ]tetradecan-6-one derivatives, each incorporating a piperidine ring, and report herein on their crystal structures. Structural commentaryThe molecular structure of compounds, (I) and (II), are shown in Figs. 1 and 2, respectively. A view of the structural overlay of the two compounds is shown in Fig. 3. The essential differences appear to be related to the orientations of the toluyl substituents, viz. rings B an C.In both molecules there is an intramolecular O-HÁ Á ÁO hydrogen bond present forming an S(6) ring motif. The molecular structure of compound (I), showing the atom labelling. Displacement ellipsoids ar...

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Hydrogen-bonded chains in threecis-dichloridoplatinum(II) complexes bearing piperidine and amine ligands

Cited by 7 publications

References 13 publications

Interaction Between Ropivacaine and a Self-Assembling Peptide: A Nanoformulation for Long-Acting Analgesia

Interaction Between Ropivacaine and a Self-Assembling Peptide: A Nanoformulation for Long-Acting Analgesia

Crystal structure of chlorido(piperidine-κN)(quinoline-2-carboxylato-κ²N,O)platinum(II)

Crystal structures of two 2,9-dithia-13-azadispiro[4.1.4⁷.3⁵]tetradecan-6-ones

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Hydrogen-bonded chains in threecis-dichloridoplatinum(II) complexes bearing piperidine and amine ligands

Cited by 7 publications

References 13 publications

Interaction Between Ropivacaine and a Self-Assembling Peptide: A Nanoformulation for Long-Acting Analgesia

Interaction Between Ropivacaine and a Self-Assembling Peptide: A Nanoformulation for Long-Acting Analgesia

Crystal structure of chlorido(piperidine-κN)(quinoline-2-carboxylato-κ2N,O)platinum(II)

Crystal structures of two 2,9-dithia-13-azadispiro[4.1.47.35]tetradecan-6-ones

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Crystal structure of chlorido(piperidine-κN)(quinoline-2-carboxylato-κ²N,O)platinum(II)

Crystal structures of two 2,9-dithia-13-azadispiro[4.1.4⁷.3⁵]tetradecan-6-ones