Pentamidine
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| Category | Others |
| Catalog number | BBF-03788 |
| CAS | 100-33-4 |
| Molecular Weight | 340.42 |
| Molecular Formula | C19H24N4O2 |
| Purity | >98% |
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Description
Pentamidine is an antiprotozoal and antifungal agent.
Specification
| Synonyms | MP-601205; MP 601205; MP601205; 4,4'-(Pentane-1,5-diylbis(oxy))dibenzimidamide |
| Storage | Store at -20°C |
| IUPAC Name | 4-[5-(4-carbamimidoylphenoxy)pentoxy]benzenecarboximidamide |
| Canonical SMILES | C1=CC(=CC=C1C(=N)N)OCCCCCOC2=CC=C(C=C2)C(=N)N |
| InChI | InChI=1S/C19H24N4O2/c20-18(21)14-4-8-16(9-5-14)24-12-2-1-3-13-25-17-10-6-15(7-11-17)19(22)23/h4-11H,1-3,12-13H2,(H3,20,21)(H3,22,23) |
| InChI Key | XDRYMKDFEDOLFX-UHFFFAOYSA-N |
Properties
| Appearance | Orange Solid |
| Application | Antifungal Agents |
| Antibiotic Activity Spectrum | Fungi; Parasites |
| Boiling Point | 539.4°C at 760 mmHg |
| Melting Point | 186°C (dec.) |
| Density | 1.2 g/cm3 |
| Solubility | Soluble in DMSO |
| LogP | 4 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | The mode of action of pentamidine is not fully understood. It is thought that the drug interferes with nuclear metabolism producing inhibition of the synthesis of DNA, RNA, phospholipids, and proteins. |
Reference Reading
1. DNA minor-groove recognition by small molecules
Stephen Neidle. Nat. Prod. Rep., 2001, 18, 291–309
A major impetus for studies on aromatic bis-amidinium compounds has been the finding that 1,5-bis(4-amidinophenoxy)pentane 22 (“pentamidine”) has clinical activity in the treatment of Pneumocystis carinii pneumonia, the commonest opportunistic life-threatening infection in AIDS patients. Pentamidine is one of the drugs of choice in treating this pathogen, although its effectiveness is limited and it causes a number of side-effects such as leucopenia and hypoglycaemia. Pentamidine and a number of closely-related analogues have been shown to bind to duplex DNA, with a preference for A/T sequences. Footprinting studies have shown that the binding site size for both pentamidine and its short-chain analogue propamidine is approximately four base pairs, with neither drug tolerating a G:C base pair within the site. These conclusions are in agreement with X-ray crystallographic studies of propamidine and pentamidine complexes with the sequence d(CGCGAATTCGCG).
2. Bis-phenanthroline copper(II) phthalate complexes are potent in vitro antitumour agents with ‘self-activating’ metallo-nuclease and DNA binding properties
Andrew Kellett,* Mark O’Connor, MalachyMcCann, Michael Devereux*. Dalton Trans., 2011, 40, 1024–1027
In an effort to elucidate the binding mode of complexes 4–6, fluorescence quenching (Qvalues) of duplex adenine–thymine (A–T) and guanine–cytosine (G–C) polymers were conducted. Under conditions of limited Et bound to an excess of DNA, exogenous intercalating agents (e.g. actinomycin D) demonstrate high affinities toward G–C base pairs, while minor groove binding species (e.g. pentamidine) prefer A–T base paired regions. Complexes 4–6 display greater affinities toward poly[d(A–T)] 2 than pentamidine but low Q values are also evident within poly[d(G–C)]2, possibly indicating flexible or multimodal binding.
3. Light-controlled DNA binding of bisbenzamidines
Mateo I. Sanchez, Olalla Vazquez, M. Eugenio Vazquez* and Jose L. Mascarenas*. Chem. Commun., 2011, 47, 11107–11109
This work arouse in the context of our recent studies on the development of fluorogenic aza-bisbenzamidines DNA binders. Bisbenzamidines like pentamidine (1b) are attractive drugs from the clinical point of view, as they display antiparasitic and antifungal activities. Indeed pentamidine is indicated for treatment of Pneumocystis carinii, Leishmaniasis or early-phase African sleeping sickness, among other diseases. It is believed that the biological activity results from its binding to short stretches of A/T-rich DNA sequences, binding which requires the presence of the amidinium groups because they establish hydrogen bonds with the edges of the bases and make electrostatic contacts with the bottom of the minor groove.
4. Glycosaminoglycans are potential pharmacological targets for classic DNA minor groove binder drugs berenil and pentamidine
Ferenc Zsila. Phys. Chem. Chem. Phys., 2015, 17,24560—24565
Increasing the sodium concentration in the sample to the physiological level cancels the ICD signals of PNT but a small UV hypochromism still can be observed (ESI,† Fig. S7). The physiological sodium concentration used here (140 mM) is characteristic to the extracellular space. However, intracellular organelles such as lysosomes are featured with lower cationic contents, ~60 mM Na+ and ~20 mM K+, that is very close to the ionic strength used in the present study (80–100 mM Na+, see Table 1). Importantly, the catabolism of GAGs is intimately related to lysosomes and pentamidine was shown to be selectively accumulated in these subcellular compartments. Accordingly, by non-covalent association with GAGs, pentamidine (and presumably berenil) may perturb a lysosome function.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C19H24N4O2
Molecular Weight (Monoisotopic Mass): 340.1899 Da
Molecular Weight (Avergae Mass): 340.4195 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C19H24N4O2
Molecular Weight (Monoisotopic Mass): 340.1899 Da
Molecular Weight (Avergae Mass): 340.4195 Da
LC-MS/MS Spectrum - LC-ESI-QTOF , positive
Experimental Conditions
Instrument Type: LC-ESI-QTOF
Ionization Mode: positive
Ionization Mode: positive
Predicted LC-MS/MS Spectrum - 10V, Negative
Experimental Conditions
Ionization Mode: Negative
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C19H24N4O2
Molecular Weight (Monoisotopic Mass): 340.1899 Da
Molecular Weight (Avergae Mass): 340.4195 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C19H24N4O2
Molecular Weight (Monoisotopic Mass): 340.1899 Da
Molecular Weight (Avergae Mass): 340.4195 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
