WO2011015628A1 - Novel antipathogenic peptides - Google Patents

Novel antipathogenic peptides Download PDF

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Publication number
WO2011015628A1
WO2011015628A1 PCT/EP2010/061424 EP2010061424W WO2011015628A1 WO 2011015628 A1 WO2011015628 A1 WO 2011015628A1 EP 2010061424 W EP2010061424 W EP 2010061424W WO 2011015628 A1 WO2011015628 A1 WO 2011015628A1
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WO
WIPO (PCT)
Prior art keywords
amino acid
atoms
compound
side chain
acid residue
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2010/061424
Other languages
English (en)
French (fr)
Inventor
Andrea Giuliani
Giovanna Pirri
Lorena Pizzuto
Santo Landolfo
Giorgio Gribaudo
David Lembo
Davide Gibellini
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SPIDERBIOTECH Srl
Original Assignee
SPIDERBIOTECH Srl
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by SPIDERBIOTECH Srl filed Critical SPIDERBIOTECH Srl
Priority to JP2012523341A priority Critical patent/JP2013501030A/ja
Priority to EP10739940.4A priority patent/EP2462155B1/en
Priority to AU2010280682A priority patent/AU2010280682A1/en
Priority to CA2768748A priority patent/CA2768748A1/en
Priority to US13/387,154 priority patent/US8877738B2/en
Priority to CN2010800283316A priority patent/CN102574893A/zh
Publication of WO2011015628A1 publication Critical patent/WO2011015628A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/08—Linear peptides containing only normal peptide links having 12 to 20 amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses
    • A61P31/22—Antivirals for DNA viruses for herpes viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/001—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof by chemical synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Definitions

  • dendrimers A particular subclass of dendrimers is represented by peptide dendrimers or wedge-like branched macromolecules consisting of a peptidyl branching core and/or covalently attached surface functional units (Niederhafner et al., 2005).
  • a subject-matter of the present invention is a peptidic compound having a length of up to 35 amino acid residues comprising an amino acid sequence represented by the general formula (I): wherein R is an amino acid residue with an arginine side chain or an ⁇ /-alkyl substituted guanidine side chain, particularly L-arginine,
  • R, K, Q, V, I, A, L and S are as defined above, in particular wherein R is an amino acid residue with an arginine side chain or an N-alkyl substituted guanidine side chain, particularly L-arginine,
  • L is an amino acid residue with a leucine side chain, particularly L-leucine.
  • ni and n 2 in each case independently are a whole number of at least 2, preferably 2, 3 or 4, more preferably 2,
  • FIG. 7B shows an electron micrograph of the same PsV stock. PsV routinely exhibited an average diameter of 50-60 nm, which is similar to that of an authentic HPV capsid, and appeared as individual, well-defined particles with minimal aggregation.
  • SB105_Ai 0 treatment significantly decreased both HIV-1 RNA load and HIV-1 p24 content whereas SB104 did not induce signi- ficant inhibition of HIV-1 replication activity (Figure 8 and 9).
  • concentration of SB1O5_Aio causing 50% inhibition of HIV-1 m b replication (IC 50 ) was 2.5 ⁇ g/ml. Since the antiretroviral activity may be related to possible cell toxicity of the tested compounds, we analyzed the cell viability by Trypan blue exclusion technique demonstrating that SB105-Ai 0 did not significantly affect cell survival (Figure 10). Altogether these results demonstrated that HIV-1 m b replication was significantly impaired by SB105_Ai 0 under these experimental conditions and then this molecule might be considered as a new antiretroviral drug.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Virology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biotechnology (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
PCT/EP2010/061424 2009-08-05 2010-08-05 Novel antipathogenic peptides Ceased WO2011015628A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP2012523341A JP2013501030A (ja) 2009-08-05 2010-08-05 新規抗病原性ペプチド
EP10739940.4A EP2462155B1 (en) 2009-08-05 2010-08-05 Novel antipathogenic peptides
AU2010280682A AU2010280682A1 (en) 2009-08-05 2010-08-05 Novel antipathogenic peptides
CA2768748A CA2768748A1 (en) 2009-08-05 2010-08-05 Novel antipathogenic peptides
US13/387,154 US8877738B2 (en) 2009-08-05 2010-08-05 Antipathogenic peptides
CN2010800283316A CN102574893A (zh) 2009-08-05 2010-08-05 新的抗致病肽

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI2009A001425A IT1395137B1 (it) 2009-08-05 2009-08-05 Nuovi peptidi antipatogeni
ITMI2009A001425 2009-08-05

Publications (1)

Publication Number Publication Date
WO2011015628A1 true WO2011015628A1 (en) 2011-02-10

Family

ID=42046263

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2010/061424 Ceased WO2011015628A1 (en) 2009-08-05 2010-08-05 Novel antipathogenic peptides

Country Status (8)

Country Link
US (1) US8877738B2 (https=)
EP (1) EP2462155B1 (https=)
JP (1) JP2013501030A (https=)
CN (1) CN102574893A (https=)
AU (1) AU2010280682A1 (https=)
CA (1) CA2768748A1 (https=)
IT (1) IT1395137B1 (https=)
WO (1) WO2011015628A1 (https=)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2803354A1 (de) * 2013-05-14 2014-11-19 NajöPharm GmbH i.G. Kombination aus Polyacrylsäure und 2-Amino-2-methylpropanol zur Verwendung in der Behandlung von Herpesinfektionen
CN120349386A (zh) * 2025-04-29 2025-07-22 中国农业科学院兰州兽医研究所(中国动物卫生与流行病学中心兰州分中心) 人工合成多肽p2及其在抗疱疹病毒感染中的应用

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10702572B2 (en) * 2015-07-28 2020-07-07 Carnegie Mellon University Methods and compounds to suppress viral genome release and packaging
RU2655763C2 (ru) * 2016-10-24 2018-05-29 Общество С Ограниченной Ответственностью "Айвикс" Фармацевтическая композиция и способ лечения женских сексуальных дисфункций
US11174288B2 (en) 2016-12-06 2021-11-16 Northeastern University Heparin-binding cationic peptide self-assembling peptide amphiphiles useful against drug-resistant bacteria

Citations (7)

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WO2000024782A2 (en) * 1998-10-23 2000-05-04 Amgen Inc. Modified peptides, comprising an fc domain, as therapeutic agents
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US7001983B1 (en) * 1997-02-20 2006-02-21 Yeda Research And Development Co., Ltd. Antipathogenic synthetic peptides and compositions comprising them
EP1572079A4 (en) * 2002-03-29 2006-09-06 Centocor Inc MAMMAL-CDR MIMETIC BODIES, COMPOSITIONS, PROCESSES AND APPLICATION PURPOSES
RU2006110561A (ru) * 2003-09-30 2007-10-10 Янссен Фармацевтика Н.В. (Be) Соединения бензоимидазола
CA2660668C (en) * 2006-08-21 2016-06-28 The University Of British Columbia Small cationic antimicrobial peptides

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000024782A2 (en) * 1998-10-23 2000-05-04 Amgen Inc. Modified peptides, comprising an fc domain, as therapeutic agents
US20040214272A1 (en) * 1999-05-06 2004-10-28 La Rosa Thomas J Nucleic acid molecules and other molecules associated with plants
WO2002079299A1 (en) 2001-03-30 2002-10-10 Starpharma Limited Agent for the prevention and treatment of sexually transmitted diseases-i
WO2005081687A2 (en) * 2003-09-30 2005-09-09 Centocor, Inc. Human hinge core mimetibodies, compositions, methods and uses
WO2006010057A2 (en) * 2004-07-08 2006-01-26 Amgen Inc. Therapeutic peptides
WO2006018431A2 (en) 2004-08-18 2006-02-23 Ipf Pharmaceuticals Gmbh Peptides for the treatment of herpes virus infections
WO2009024445A1 (en) * 2007-08-22 2009-02-26 Ribovax Biotechnologies Sa Antibodies against human cytomegalovirus (hcmv)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2803354A1 (de) * 2013-05-14 2014-11-19 NajöPharm GmbH i.G. Kombination aus Polyacrylsäure und 2-Amino-2-methylpropanol zur Verwendung in der Behandlung von Herpesinfektionen
WO2014184223A1 (de) 2013-05-14 2014-11-20 Najöpharm Gmbh Mittel und verfahren zur behandlung von herpes
CN120349386A (zh) * 2025-04-29 2025-07-22 中国农业科学院兰州兽医研究所(中国动物卫生与流行病学中心兰州分中心) 人工合成多肽p2及其在抗疱疹病毒感染中的应用

Also Published As

Publication number Publication date
ITMI20091425A1 (it) 2011-02-06
EP2462155B1 (en) 2015-05-27
US20120121623A1 (en) 2012-05-17
CN102574893A (zh) 2012-07-11
AU2010280682A1 (en) 2012-01-19
US8877738B2 (en) 2014-11-04
CA2768748A1 (en) 2011-02-10
JP2013501030A (ja) 2013-01-10
IT1395137B1 (it) 2012-09-05
EP2462155A1 (en) 2012-06-13

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