WO2021234731A1 - Compositions à libération prolongée - Google Patents

Compositions à libération prolongée Download PDF

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Publication number
WO2021234731A1
WO2021234731A1 PCT/IN2021/050479 IN2021050479W WO2021234731A1 WO 2021234731 A1 WO2021234731 A1 WO 2021234731A1 IN 2021050479 W IN2021050479 W IN 2021050479W WO 2021234731 A1 WO2021234731 A1 WO 2021234731A1
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WO
WIPO (PCT)
Prior art keywords
composition
plga
drug
peg
additives
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Application number
PCT/IN2021/050479
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English (en)
Inventor
Marina RAJADURAI
Bhavya SUREKHA
Original Assignee
Dr Reddy's Institute Of Life Sciences
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Publication of WO2021234731A1 publication Critical patent/WO2021234731A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7007—Drug-containing films, membranes or sheets
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/24—Heavy metals; Compounds thereof
    • A61K33/26—Iron; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers

Definitions

  • compositions that release an active agent (or active ingredient) over an extended period of time.
  • Sustained drug delivery formulations attract large interest due to advantages they can offer, such as improved patient compliance, reduced 'see- saw' fluctuation, reduced total dose, and improved efficiency in treatment.
  • Another beneficial property of such systems is a possibility to control and manipulate drug release profile in accordance with specific requirements.
  • Long-term sustained release formulations with the capacity of delivering drugs from days to months are very attractive option for conditions required regular administration of the drug, e.g., for management of chronic diseases or malnutrition-related conditions.
  • usually polymeric formulations based on biodegradable and biocompatible polymers are used. Among them, poly(D,L-lactide-co-glycolide) (PLGA) is a very popular choice.
  • formulations based on PLGA suffer from “burst release” of the drug during first few hours, in some cases up to 50% or more of the drug is released, which is not suitable for long-term drug delivery (above 24 h).
  • the present disclosure provides compositions for sustained release of an active agent.
  • the composition comprises an active agent, PLGA and an additive.
  • the present disclosure provides a long-term sustained release composition
  • a long-term sustained release composition comprising an active agent, PLGA, and an additive.
  • Figure 1 illustrates microscope images of Iron (II) sulphate nanoparticles (IS NPs) (A, Stereo Zoom Microscope), and IS NPs containing PLGA-PEG-3 (70:30) film obtained using a) compound microscope (B) and b) stereo zoom microscope (C, D).
  • Figure 2 illustrates IS NPs containing PLGA-PEG-3 (70:30) film on Petri dish.
  • Figure 3 illustrates release profiles of IS (cumulative release) in water from polymeric films of different compositions, insert shows daily release of IS from polymeric composition PLGA-PEG-3.
  • Figure 4 illustrates release profiles of various drugs in water from PLGA-PEG-2 and PLGA-PEG-3 films.
  • the term 'compound(s)' comprises the compounds disclosed in the present invention.
  • phrases "pharmaceutically acceptable” is employed herein to refer to those compounds, materials, compositions and/or dosage forms which are, within the scope of sound medical judgment, suitable for use in contact with the tissues of human beings and/or animals without excessive toxicity, irritation, allergic response or other problem or complication, commensurate with a reasonable benefit/risk ratio.
  • “Pharmaceutically acceptable salt” refers to the salts of the compounds, that is pharmaceutically acceptable and that possesses the desired pharmacological activity of the parent compound.
  • Pharmaceutically acceptable salts of the compounds of this invention include those derived from suitable inorganic and organic acids and bases.
  • Such salts include: salts derived from inorganic bases such as Li, Na, K, Ca, Mg, Fe, Cu, Zn, Al, Mn; salts of organic bases such as N,N'-diacetylethylenediamine, 2-dimethylaminoethanol, isopropylamine, morpholine, piperazine, piperidine, procaine, diethylamine, triethylamine, trimethylamine, tripropylamine, tromethamine, choline hydroxide, dicyclohexylamine, metformin, benzylamine, phenylethylamine, dialkylamine, trialkylamine, thiamine, aminopyrimidine, aminopyridine, purine, pyrimidine, spermidine, and the like; chiral bases like alkylphenylamine, glycinol, phenyl glycinol and the like, salts of natural amino acids such as glycine, alanine, valine, leu
  • Salts may include acid addition salts where appropriate which are sulphates, nitrates, phosphates, perchlorates, borates, hydrohalides, acetates, tartrates, maleates, citrates, succinates, methanesulfonates, benzoates, salicylates, hydroxynaphthoates, benzenesulfonates, ascorbates, and the likes thereof.
  • “Pharmaceutically acceptable solvates” may be hydrates or comprising other solvents of crystallization such as alcohols.
  • stereoisomer or “stereoisomers” refers to any enantiomers, diastereomers or geometrical isomers of the compounds as described herein, wherever they are chiral or when they bear one or more double bond. When the compounds are chiral, they can exist in racemic or in optically active form. It should be understood that the invention encompasses all stereochemical isomeric forms, including diastereomeric, enantiomeric and epimeric forms, as well as -isomers and /-isomers and mixtures thereof.
  • Individual stereoisomers of compounds can be prepared synthetically from commercially available starting materials which contain chiral centers or by preparation of mixtures of enantiomeric products followed by separation such as conversion to a mixture of diastereomers followed by separation or recrystallization, chromatographic techniques, direct separation of enantiomers on chiral chromatographic columns, or any other appropriate method known in the art.
  • Starting compounds of particular stereochemistry are either commercially available or can be made and resolved by techniques known in the art.
  • the compounds of the present invention may exist as geometric isomers.
  • the present invention includes all cis, trans, syn, anti,
  • E Electronic Data
  • Z data isomers
  • treat means treating the disease, disorder, or condition, or ameliorating, alleviating, reducing, or suppressing symptoms of the disease, or slowing or stopping the progress of the disease.
  • transdermal refers generally to application, administration, or delivery of a drug by means of direct contact with skin or mucosa. Such application, administration or delivery is also known as dermal, percutaneous, transmucosal and buccal. As used herein, “dermal” includes skin and mucosa, which includes buccal, nasal, oral, rectal, and vaginal mucosa. The term “transdermal delivery” refers to drug delivery across the skin, usually accomplished without breaking the skin.
  • transdermal drug delivery system refers to a system (e.g., a device) comprising a composition that releases drug upon application to the skin (or any other surface noted above).
  • a transdermal drug delivery system may comprise a drug-containing composition, and, optionally, a backing layer and/or a release liner layer. Many such systems are known in the art and commercially available, such as transdermal drug delivery patches.
  • compositions disclosed herein can be administered to a mammal, such as a human, but can also be other mammals, for example, an animal in need of veterinary treatment, for example, domestic animals (for example, dogs, cats, and the like), zoo and wild animals, farm animals (for example, cows, sheep, pigs, horses, and the like) and laboratory animals (for example, rats, mice, guinea pigs, and the like).
  • the subject may be in need of treatment by delivery of a therapeutic agent, for example, transcutaneous delivery of a vaccine or transdermal delivery of a drug.
  • the present disclosure provides a composition for sustained release of an active agent.
  • the composition comprises an active agent, PLGA and an additive.
  • active agent refers to any substance, a compound, a molecule, a drug, composition of matter or any combination thereof that provides some pharmacologic effect or beneficial effect.
  • the active agent includes, but are not limited to, vitamins, nutrients, drugs, foods, food supplements, and other beneficial agents.
  • the active agent may present in the form of a free base, salt, hydrate or complex.
  • the active agent may present in the form of a free base.
  • the active agent may present in the form of a salt.
  • vitamins include, but are not limited to, vitamin A, vitamin Bl, vitamin B2, vitamin B3, vitamin B5, vitamin B6, vitamin B7, vitamin B9, vitamin B12, vitamin C, vitamin D, vitamin E, and vitamin K.
  • nutrients include, but are not limited to, minerals and electrolytes in its elemental form or in form of salt or complex, such as iron, manganese, copper, zinc, iodine, fluoride, selenium, folate, magnesium, phosphorus, molybdenum, sodium, and potassium.
  • drugs examples include, but are not limited to, drugs for management of chronic, incurable or other diseases required prolonged treatment, such as allergies (e.g. antihistamines, corticosteroids), alzheimer's disease (e.g., tacrine, rivastigmine, galantamine, donepezil, memantine, etc.), arthritis and chronic pains (acetaminophen, ibuprofen, naproxen sodium, celecoxib, amitriptyline, nortriptyline, opioids, etc.), Parkinson's disease (levodopa, COMT inhibitors, Dopamine agonists, MAO-B inhibitors, etc.), depression, anxiety or panic disorder (Imipramine), hypercholesterolemia (Fenofibrate), psychiatric conditions (Haloperidol), inflammation (Nimesulide) or rare disease, such as Duchenne muscular dystrophy (MDM, Corticosteroids, Ataluren,
  • allergies e.g. antihist
  • the drug can be any pharmaceutically acceptable salt form of a basic, acidic, or zwitterionic drug that meets these criteria.
  • the drug may be in any pharmaceutically acceptable form.
  • pharmaceutically acceptable form means any pharmaceutically acceptable derivative or variation, including salt forms, stereoisomers, stereoisomer mixtures, enantiomers, solvates, hydrates, prodmgs. polymorphs, isomorphs, and pseudomorphs.
  • salt forms for basic drugs include, but are not limited to, acetate, citrate, chloride, bromide, iodide, mesylate, sulfate, tartrate phosphate, maleate, and lactate.
  • salt forms for acidic drugs include the sodium, potassium, calcium, lithium, aluminium, zinc, magnesium, choline, meglumine, benzathine, procaine, diethanolamine, and the like.
  • iron sulphate nanoparticles IS NPs are used as drug.
  • the drug may be in the form of drug particles having small or reduced particle size, nanoparticles of drug, or amorphous form of the drug. In some instances, the drug may be in the form of nanoparticles.
  • nanoparticle refers to particles having a particle size of nanometers. In certain embodiments, the nanoparticle may have a particle size of about 1-1000 nm. In some instances, the nanoparticle may have a particle size of about 1-500 nm, about 1-250 nm, about 1-100 nm, or about 1-50 nm.
  • the nanoparticles of the drug can be prepared using any method known in the art.
  • the preparation of nanoparticles of the hydrophilic drug comprises of dissolution of the drug (5 mg) in an aqueous phase consisting of a solvent (0.3 ml of distilled water) and a co-solvent (0.6 ml of methanol).
  • Polymer 25 mg of PLGA
  • an organic phase consisting of a non-solvent (4 ml of chloroform) and the organic phase is added drop wise to aqueous phase under stirring.
  • the above mixture is added drop wise to 10 ml of distilled water containing 0.5% w/v of Pluronic F-68.
  • Organic solvent is removed by stirring overnight.
  • Nanoparticles are recovered by centrifugation for 30 min at 25,000 rpm, washed two times with distilled water to remove unentrapped drug and lyophilized for 24 h to yield freeze-dried nanoparticles.
  • the preparation of nanoparticles of the hydrophobic drug comprises of the polymer of choice, e. g. poly (Methacyclic acid-co-methyl-methyacrylate) polymer (100 mg) mixed with 10 mg of the drug and dissolved in 10 ml of organic solvent (e. g. dimethyl sulphoxide).
  • the prepared organic phase is transferred into 500 ml beaker containing 100 mg of poloxamer 188 in 20 ml of distilled water under mechanical stirring for lh.
  • Drug-polymeric nanoparticles are recovered by centrifugation for 30 min at 25,000 rpm, washed two times with distilled water to remove unentrapped drug and lyophilized for 24 h to yield freeze-dried nanoparticles.
  • the active agent may present in an amount from about 10% to about 50% or from about 20% to about 50% by weight of the composition. In some instances, the active agent may present in an amount from about 20% to about 40% by weight of the composition such as about 21%, about 22%, about 23%, about 24%, about 25%, about 26%, about 27%, about 28%, about 29%, about 30%, about 31%, about 32%, about 33%, about 34%, about 35%, about 36%, about 37%, about 38%, or about 39% by weight of the composition. In other instances, the active agent may present in an amount from about 10% to about 30% or from about 10% to about 20% by weight of the composition.
  • the PLGA used in the composition may present in an amount from about 20% to about 80% by weight of the composition. In certain embodiments, the PLGA may present in an amount from about 20% to about 60% or from about 20% to about 40% or from about 20% to about 30% by weight of the composition. In certain embodiments, the molecular weight of the PLGA is from 05 kDa to 200 kDa. In some instances, the molecular weight of the PLGA is 60 kDa.
  • PLGA is a copolymer of poly lactic acid (PLA) and poly glycolic acid (PGA).
  • the PLA and PGA may present in any ratio.
  • polymer ratio of lactic acid and glycolic acid in the PLGA is from about 30:70 to 70:30.
  • the polymer ratio of lactic acid and glycolic acid in the PLGA is 50:50.
  • the content of glycolc acid unit is higher than the lactic acid unit.
  • the free carboxylic acids of the PLGA may present in the form of esters.
  • the composition as described herein further comprises one or more additives.
  • the additives may be added to increase mechanical strength or stability towards humidity (in the fabrication of microneedles), and to control drug release from the polymeric composition.
  • the additive may present in an amount from about 2% to about 45% or from about 5% to about 30% or from about 5% to about 20% by weight of the composition.
  • the additive is selected from a group comprising polyethylene glycol (PEG), polyvinyl alcohol (PVA), poly (2-hydroxypropyl methacrylamide) (PHPMA), polysiloxanes, polycaprolactone (PCL) hyaluronic acid, chitosan (CS), carboxymethylcellulose sodium, hydroxymethyl cellulose, polyethylene oxide, polyvinyl- 107, molidones and natural gums.
  • PEG polyethylene glycol
  • PVA polyvinyl alcohol
  • PPMA poly (2-hydroxypropyl methacrylamide)
  • PCL polycaprolactone
  • CS chitosan
  • carboxymethylcellulose sodium hydroxymethyl cellulose
  • polyethylene oxide polyethylene oxide
  • polyvinyl- 107 polyvinyl- 107
  • molidones molidones and natural gums.
  • the additive is PEG or PVA.
  • the PEG of different molecular weight may be used in the present disclosure.
  • the PEG is selected from a group comprising PEG 2000, PEG 6000, PEG 10000 and PEG 20000.
  • the PEG is PEG 2000.
  • the PLGA and one or more additives may be present at any ratio. In certain embodiments, the ratio of PLGA to one or more additives is from about 1:100 to about 100:1.
  • the ratio of PLGA to additive is from about 1:50 to about 50:1 or from about 1:20 to about 20:1 or from about 1:10 to about 10:1 or from about 1:5 to about 5:1 or from about 1:4 to about 4:1 or from about 1:3 to about 3:1 or from about 1:2.5 to about 2.5:1 or from about 1:2 to about 2:1.
  • the ratio of PLGA to additive is from about 1:2.5 to about 2.5:1.
  • the ratio of PLGA to one or more additives is about 1:1 or about 70:30.
  • the present disclosure provides a composition comprising: an active agent in an amount from about 10% to about 50% by weight of the composition;
  • PLGA in an amount from about 20% to about 80% by weight of the composition; and one or more additives, wherein the additive is present in an amount from about 2% to about 45% by weight of the composition.
  • compositions described herein are provided for sustained release of an active agent.
  • the compositions provided herein provide sustained release of an active agent for at least 1 day, 2 days, 3 days, 4 days, 5 days, 6 days, 7 days, 8 days, 9 days, 10 days, 11 days, 12 days, 13 days, 14 days or longer.
  • the compositions provided herein provide sustained release of an active agent for at least 12 days.
  • the compositions provided herein provide sustained release of an active agent for at least 14 days.
  • the present disclosure also provides a drug delivery system comprising a composition as described herein.
  • the drug delivery system may be useful for sustained release of the drug.
  • the sustained release of the drug may be up to 14 days or more. In some instances, the sustained release of the drug is up to 14 days.
  • Such drug delivery system may be in the form of depot, transdermal patches, or microneedles.
  • compositions described herein may be administered alone or in combination with one or more pharmaceutically or nutraceutically acceptable carriers, diluents or excipients.
  • “Pharmaceutically or nutraceutically acceptable carriers, diluents or excipients” include any adjuvant, preservative, stabilizer, emulsifier wetting agent, carrier, sweetening agent, suspending agent, isotonic agent, flavor enhancer, excipient, glidant, dye/colorant, dispersing agent, diluent, surfactant, or solvent, which has been approved by the United States Food and Drug Administration (USFDA) as being acceptable for use in humans or animals.
  • USFDA United States Food and Drug Administration
  • Suitable pharmaceutically or nutraceutically acceptable carriers, diluents, or excipients are selected based on the intended form of administration, and consistent with conventional pharmaceutical or nutraceutical practices.
  • Suitable pharmaceutical carriers, diluents, excipients or vehicles are known in the art, e.g., as described in Remington's Pharmaceutical Sciences (1990) 18th ed.
  • compositions described herein may be administered by known routes of administration, such as, oral, parenteral, intravenous, intra-arterial, topical, intramuscular, intracranial, intraorbital, cutaneous, subcutaneous, ophthalmic, intraventricular, intravitreal, intraspinal, intracapsular, intraperitoneal, intranasal, intracisternal, central nervous system (CNS) administration, and aerosol.
  • routes of administration such as, oral, parenteral, intravenous, intra-arterial, topical, intramuscular, intracranial, intraorbital, cutaneous, subcutaneous, ophthalmic, intraventricular, intravitreal, intraspinal, intracapsular, intraperitoneal, intranasal, intracisternal, central nervous system (CNS) administration, and aerosol.
  • the dosage administered will vary depending upon various factors such as the activity of the specific active agent employed; the metabolic stability and length of action of the active agent; the age, sex, body weight, and health of the host or patient; the mode and time of administration; the rate of excretion; and the severity of the particular disorder or condition, etc.
  • compositions as described herein may be useful for sustained release of one or more active agents.
  • the present disclosure also includes the use of the compositions described herein in the manufacture of a medicament.
  • compositions as described herein may minimize or eliminate initial burst release of the drug. In some instances, the compositions as described herein may deliver equal amount of the drug daily thereby reducing toxicity of the drug and improving efficiency in the treatment of a subject.
  • the present disclosure further includes a method of treating a disease or condition, comprising administering the composition as described herein to a subject suffering from the disease or condition.
  • the disease or condition is selected from a group comprising depression, anxiety, panic disorder, hypercholesterolemia, psychiatric conditions, inflammation, chronic, incurable diseases, such as allergies, alzheimer's disease, arthritis and chronic pain, and Parkinson's disease.
  • a dissolving polymeric composition with improved long-term sustained drug release up to 14 days is developed and tested using iron sulphate nanoparticles (IS NPs) as an example drug.
  • IS NPs iron sulphate nanoparticles
  • FIG. 1A displays microscope images of IS NPs obtained using Stereo Zoom Microscope.
  • PLGA polymer ratio of lactic acid and glycolic acid is 50:50, molecular weight is 60 kDa, 45.9 mg
  • additives 5-20%) were dissolved in ACN to form 10% w/v polymer solution.
  • Table 1 Composition of IS NPs-containing PLGA films
  • EXAMPLE 3 PREPARATION OF PLGA-PEG FILM CONTAINING IS NPs
  • PLGA polymer ratio of lactic acid and glycolic acid is 50:50, molecular weight is 60 kDa
  • PEG PEG 2000, PEG 6000, PEG 10000 or PEG 20000
  • a specific amount of IS NPs was added to the solution and sonicated for 20-30 min to ensure equal dispersion of NPs in PLGA.
  • the resulting final mixture was drop casted on a clean surface of the Petri dish and allowed dry.
  • PLGA polymer ratio of lactic acid and glycolic acid is 50:50, molecular weight is 60 kDa
  • PEG PEG 2000 or PEG 10000
  • drug for example, Imipramine, Fenofibrate, Haloperidol or Nimesulide was used in this example
  • the resulting final mixture was drop casted on a clean surface of the Petri dish and allowed dry.
  • Table 2 Composition of IS NPs-containing PLGA-PEG films
  • EXAMPLE 5 IS RELEASE FROM PLGA AND PLGA-PEG FILMS
  • the release of IS from PLGA films was measured in nano-pure water with or without iron detection kit.
  • the IS NPs loaded polymeric films were immersed in tightly closed falcon tubes filled with 3.5 mL of water.
  • the samples were stirred continuously at 180 rpm maintained at 37 °C, at last day the sample was sonicated for 1 h in ultrasonic bath to ensure complete release of whole loaded amount of IS.
  • the samples were measured by a UV spectrophotometer at 260 nm.
  • EXAMPLE 6 DRUG RELEASE FROM PLGA-PEG FILMS The release of drug from PLGA-PEG films was measured in nano-pure water using UV absorption method.
  • the drug loaded polymeric films were immersed in tightly closed falcon tubes filled with 3.5 mL of water.
  • the samples were stirred continuously at 180 rpm maintained at 37 °C, at last day the sample was sonicated for 1 h in ultrasonic bath to ensure complete release of whole loaded amount of drug.
  • the samples were measured by a UV spectrophotometer. At last day, the absorbance was defined as 100% of drug release. Every experiment was repeated at least thrice, and an average value was calculated using calibration curve obtained using known amounts of drug.
  • Table 4 Drug release profile from PLGA-PEG-2 and PLGA-PEG-3 films at various time points

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
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  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
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  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Proteomics, Peptides & Aminoacids (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention concerne des compositions pour la libération prolongée d'un agent actif. Les compositions comprennent un agent actif, du poly (lactide-co-glycolide) PLGA et un ou plusieurs additifs.
PCT/IN2021/050479 2020-05-18 2021-05-18 Compositions à libération prolongée WO2021234731A1 (fr)

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IN202041020828 2020-05-18
IN202041020828 2020-05-18

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WO2021234731A1 true WO2021234731A1 (fr) 2021-11-25

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ529968A (en) * 2001-06-29 2005-08-26 Takeda Pharmaceutical Sustained-release composition comprising lactic acid-glycolic acid copolymer and process for producing the same

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ529968A (en) * 2001-06-29 2005-08-26 Takeda Pharmaceutical Sustained-release composition comprising lactic acid-glycolic acid copolymer and process for producing the same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHARLOTTE L HUANG, TERRY WJ STEELE, EFFENDI WIDJAJA, FREDDY YC BOEY, SUBBU S VENKATRAMAN & JOACHIM SC LOO: "The influence of additives in modulating drug delivery and degradation of PLGA thin films", NPG ASIA MATERIALS, vol. 5, no. 7, e54, 1 July 2013 (2013-07-01), pages 1 - 11, XP055874198, ISSN: 1884-4049, DOI: 10.1038/am.2013.26 *

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