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Naval Chaudhary 70700029 Liposomes:  Improving drug delivery
Phospholipids Polar Head Groups Three carbon glycerol
What is a liposome? ,[object Object],Hydrophilic Hydrophobic
A liposome encapsulates a region on aqueous solution inside a  hydrophobic  membrane; dissolved  hydrophilic   solutes  cannot readily pass through the lipids. Hydrophobic chemicals can be dissolved into the membrane, and in this way liposome can carry both hydrophobic molecules and hydrophilic molecules. To deliver the molecules to sites of action, the lipid bilayer can fuse with other bilayers such as the  cell membrane , thus delivering the liposome contents About the Liposomes :
Liposome Preparation Lipid in organic solvent solution Evaporation Extrusion (or sonication) Liposomes and unencapsulated SRB Lipid film Freeze/thaw cycles Gel filtration Purified liposomes Hydrate with  sulforhodamine B (SRB)  solution
Liposome Preparation
Liposome Preparation
Liposome Preparation
Liposome Preparation http://www.avantilipids.com
Liposome Preparation
Liposome Ingredients 45% DPPC dipalmitoylphosphatidylcholine  45% Cholesterol 5% DPPG dipalmitoylphosphatidylglycerol  5% DPPE dipalmitolyphosphatidylanolamine
 
Uses of Liposomes Chelation therapy for treatment of heavy metal  poisoning Enzyme Replacement Diagnostic imaging of tumors Study of membranes Cosmetics Drug Delivery
Why Use Liposomes in Drug Delivery? ,[object Object],[object Object],[object Object],[object Object],[object Object],Physical:   temperature or pH sensitive liposomes  Drug Targeting
Protection Decrease harmful side effects Pharmokinetics - efficacy and toxicity Changes the absorbance and biodistribution Change where drug accumulates in the body Protects drug Deliver drug in desired form Multidrug resistance Why Use Liposomes in  Drug Delivery?
Release Affect the time in which the drug is released  Prolong time -increase duration of action and  decrease administration Dependent on drug and liposome properties   Liposome composition, pH and osmotic gradient, and  environment Why Use Liposomes in  Drug Delivery?
Modes of Liposome/Cell Interaction  Adsorption  Endocytosis Fusion Lipid transfer
Classes of Liposomes ,[object Object],[object Object],[object Object],Cationic
Liposomes Help Improve Therapeutic index Rapid metabolism Unfavorable pharmokinetics Low solubility Lack of stability Irritation Custom design ,[object Object],[object Object],[object Object],Method of preparation
Current liposomal drug preparations Type of Agents Examples Anticancer Drugs Anti bacterial Antiviral DNA material Enzymes Radionuclide Fungicides Vaccines  *Currently in Clinical Trials or Approved for Clinical Use Malaria merozoite, Malaria sporozoite Hepatitis B antigen, Rabies virus glycoprotein Amphotericin B* In-111*, Tc-99m Hexosaminidase A  Glucocerebrosidase, Peroxidase Duanorubicin, Doxorubicin*, Epirubicin  Methotrexate, Cisplatin*, Cytarabin Triclosan, Clindamycin hydrochloride,  Ampicillin, peperacillin, rifamicin AZT cDNA - CFTR*
CFTR Gene Therapy Deliver cDNA of Cystic Fibrosis Transmembrane Conductance  Regulator (CFTR) to epithelial tissue of respiratory system Fuse to cell membrane and    incorporate cDNA into cell Clinical trials - no significant  change in symptoms Now trying adeno associated  virus Cationic liposome
Doxil ,[object Object],[object Object],[object Object],Treats Kaposi’s sarcoma lesions or cancer tumors ,[object Object],[object Object],[object Object],[object Object],*Just approved by FDA*
Amphotericin B Side effects:  nephrotoxicity, chills, and fevers Systemic fungal  infections in immune compromised patients Fungizone - AmB with deoxycholate AmB - kills ergosterol-containing fungal cells, also    kills cholesterol-containing human cells
No decrease in effectiveness of drug against fungi Liposomal Formulation of AmB Decrease in toxicity Exact Mechanism of liposomes not understood   Cholesterol - only few %moles Phospholipid:AmB ratio Diffusion Lipid transfer AmB Lipid
Name Trade name Company Indication Liposomal amphotericin B Abelcet Enzon Fungal infections Liposomal amphotericin B Ambisome Gilead Sciences Fungal and protozoal infections Liposomal cytarabine Depocyt Pacira  (formerly SkyePharma) Malignant lymphomatous meningitis Liposomal daunorubicin DaunoXome Gilead Sciences HIV-related Kaposi’s sarcoma Liposomal doxorubicin Myocet Zeneus Combination therapy with cyclophosphamide in metastatic breast cancer Liposomal IRIV vaccine Epaxal Berna Biotech Hepatitis A Liposomal IRIV vaccine Inflexal V Berna Biotech Influenza Liposomal morphine DepoDur SkyePharma , Endo Postsurgical analgesia Liposomal verteporfin Visudyne QLT,  Novartis Age-related macular degeneration, pathologic myopia, ocular histoplasmosis Liposome-PEG doxorubicin Doxil / Caelyx Ortho Biotech ,  Schering-Plough HIV-related Kaposi’s sarcoma, metastatic breast cancer, metastatic ovarian cancer Micellular estradiol Estrasorb Novavax Menopausal therapy
Problems with Liposomal Preparations of Drugs $$$$   ,[object Object],[object Object],[object Object],Lack long term stability (short shelf life) Freeze dry and pH adjustment Low “Pay Load” - poor encapsulation Physical and chemical instability  Polar drugs and drugs without opposite charge Modifications
Possibility of new side effects Doxil  “hand and foot syndrome” Problems continued Efficacy CFTR
Studies with insulin show that liposomes may  be an effective way to package proteins  and peptides for use Clinical Trials for several liposomal formulations More studies on the manipulation of liposomes Future
References Journals Allen, Theresa M.  "Liposomal Drug Formulations: Rationale for Development and What We Can Expect for the Future."  Drugs 56:  747-756, 1998. Allen, Theresa M.  "Long-circulating (sterically stabilized) liposomes for targeted drug delivery ."  TiPs  15:  214-219,  1994. Allen, Theresa M.  "Opportunities in Drug Delivery."  Drugs 54 Suppl. 4:  8-14, 1997 Janknegt, Robert.  "Liposomal and Lipid Formulations of Amphotericin B."  Clinical Pharmacokinetics.   23(4):  279-291, 1992.  Kim, Anna et al.  "Pharmacodynamics of insulin in polyethylene glycol-coated liposomes."  International Journal of Pharmaceutics.  180:  75-81, 1999. Quilitz, Rod. "Oncology Pharmacotherapy:  The Use of Lipid Formulations of Amphotericin B in Cancer  Patients."  Cancer Control. 5:439-449, 1998.  Ranade, Vasant V.  "Drug Delivery Systems:  Site-Specific Drug Delivery Using Liposomes as Carriers."  Pharmacology.   29:  685-694, 1989.  Storm, Gert and Daan J.A. Crommelin.  "Liposomes:quo vadi?"  PSTT  1:  19-31, 1998.  Taylor, KMG and JM Newton.  "Liposomes as a vecicle for drug delivery."  British Journal of Hospital  Medicine.  51:  55-59, 1994
Websites James, John S.  "Doxil Approved for KS." www.immunet. org.imminet/atn.nsf/page/a-235-03. Wasan, Ellen.  "Targeted Gene Transfer."  Member.tripod.com/~rrishna/lipos1.html "Introduction to Controlled Drug Delivery Systems."  www5.bae.ncsu.edu/bae/reearch/blak… k/otherprojects/drugDeliver_97/ http://www. Mssm.edu/medicine/thrombosis/phosphol.html "Doxorubicin."  http://tirgan.com/adria.htm "Clinical Pharmacology Online."  http://www.cponline.gsm.com/scripts/fullmono/showmono.  "Drugstore.com"  http://www.drugstore.com/pharmacy/prices/Amphotec. "Sequus' Doxil Becomes First Liposome Product Approved In U.S."  www.slip.net/~mcdavis/ database/doxor_1 "Liposomes."  www.collabo.com/liposom0.htm Paustin, Timothy.  “Cellular Membranes.”www.bact.wisc.edu/microtextbook/bacterialstructure/Membranegen.html www.cbc.umn.edu/~mwd/cell_www/chapter2/membrane.html#PHOSPHOLIPIDS Books Jones, Macolm N. and Chapman, David.  Micelles, Monolayers and Biomembranes .  Wiley-Liss.  New York (1995). Garrett, R. and Grisham C.  Biochemistry , 2 nd  ed.  Saunders Colleges Publishing.  New York (1999).  264.

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Liposomes

  • 1. Naval Chaudhary 70700029 Liposomes: Improving drug delivery
  • 2. Phospholipids Polar Head Groups Three carbon glycerol
  • 3.
  • 4. A liposome encapsulates a region on aqueous solution inside a hydrophobic membrane; dissolved hydrophilic solutes cannot readily pass through the lipids. Hydrophobic chemicals can be dissolved into the membrane, and in this way liposome can carry both hydrophobic molecules and hydrophilic molecules. To deliver the molecules to sites of action, the lipid bilayer can fuse with other bilayers such as the cell membrane , thus delivering the liposome contents About the Liposomes :
  • 5. Liposome Preparation Lipid in organic solvent solution Evaporation Extrusion (or sonication) Liposomes and unencapsulated SRB Lipid film Freeze/thaw cycles Gel filtration Purified liposomes Hydrate with sulforhodamine B (SRB) solution
  • 11. Liposome Ingredients 45% DPPC dipalmitoylphosphatidylcholine 45% Cholesterol 5% DPPG dipalmitoylphosphatidylglycerol 5% DPPE dipalmitolyphosphatidylanolamine
  • 12.  
  • 13. Uses of Liposomes Chelation therapy for treatment of heavy metal poisoning Enzyme Replacement Diagnostic imaging of tumors Study of membranes Cosmetics Drug Delivery
  • 14.
  • 15. Protection Decrease harmful side effects Pharmokinetics - efficacy and toxicity Changes the absorbance and biodistribution Change where drug accumulates in the body Protects drug Deliver drug in desired form Multidrug resistance Why Use Liposomes in Drug Delivery?
  • 16. Release Affect the time in which the drug is released Prolong time -increase duration of action and decrease administration Dependent on drug and liposome properties Liposome composition, pH and osmotic gradient, and environment Why Use Liposomes in Drug Delivery?
  • 17. Modes of Liposome/Cell Interaction Adsorption Endocytosis Fusion Lipid transfer
  • 18.
  • 19.
  • 20. Current liposomal drug preparations Type of Agents Examples Anticancer Drugs Anti bacterial Antiviral DNA material Enzymes Radionuclide Fungicides Vaccines *Currently in Clinical Trials or Approved for Clinical Use Malaria merozoite, Malaria sporozoite Hepatitis B antigen, Rabies virus glycoprotein Amphotericin B* In-111*, Tc-99m Hexosaminidase A Glucocerebrosidase, Peroxidase Duanorubicin, Doxorubicin*, Epirubicin Methotrexate, Cisplatin*, Cytarabin Triclosan, Clindamycin hydrochloride, Ampicillin, peperacillin, rifamicin AZT cDNA - CFTR*
  • 21. CFTR Gene Therapy Deliver cDNA of Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) to epithelial tissue of respiratory system Fuse to cell membrane and incorporate cDNA into cell Clinical trials - no significant change in symptoms Now trying adeno associated virus Cationic liposome
  • 22.
  • 23. Amphotericin B Side effects: nephrotoxicity, chills, and fevers Systemic fungal infections in immune compromised patients Fungizone - AmB with deoxycholate AmB - kills ergosterol-containing fungal cells, also kills cholesterol-containing human cells
  • 24. No decrease in effectiveness of drug against fungi Liposomal Formulation of AmB Decrease in toxicity Exact Mechanism of liposomes not understood Cholesterol - only few %moles Phospholipid:AmB ratio Diffusion Lipid transfer AmB Lipid
  • 25. Name Trade name Company Indication Liposomal amphotericin B Abelcet Enzon Fungal infections Liposomal amphotericin B Ambisome Gilead Sciences Fungal and protozoal infections Liposomal cytarabine Depocyt Pacira (formerly SkyePharma) Malignant lymphomatous meningitis Liposomal daunorubicin DaunoXome Gilead Sciences HIV-related Kaposi’s sarcoma Liposomal doxorubicin Myocet Zeneus Combination therapy with cyclophosphamide in metastatic breast cancer Liposomal IRIV vaccine Epaxal Berna Biotech Hepatitis A Liposomal IRIV vaccine Inflexal V Berna Biotech Influenza Liposomal morphine DepoDur SkyePharma , Endo Postsurgical analgesia Liposomal verteporfin Visudyne QLT, Novartis Age-related macular degeneration, pathologic myopia, ocular histoplasmosis Liposome-PEG doxorubicin Doxil / Caelyx Ortho Biotech , Schering-Plough HIV-related Kaposi’s sarcoma, metastatic breast cancer, metastatic ovarian cancer Micellular estradiol Estrasorb Novavax Menopausal therapy
  • 26.
  • 27. Possibility of new side effects Doxil “hand and foot syndrome” Problems continued Efficacy CFTR
  • 28. Studies with insulin show that liposomes may be an effective way to package proteins and peptides for use Clinical Trials for several liposomal formulations More studies on the manipulation of liposomes Future
  • 29. References Journals Allen, Theresa M. "Liposomal Drug Formulations: Rationale for Development and What We Can Expect for the Future." Drugs 56: 747-756, 1998. Allen, Theresa M. "Long-circulating (sterically stabilized) liposomes for targeted drug delivery ." TiPs 15: 214-219, 1994. Allen, Theresa M. "Opportunities in Drug Delivery." Drugs 54 Suppl. 4: 8-14, 1997 Janknegt, Robert. "Liposomal and Lipid Formulations of Amphotericin B." Clinical Pharmacokinetics. 23(4): 279-291, 1992. Kim, Anna et al. "Pharmacodynamics of insulin in polyethylene glycol-coated liposomes." International Journal of Pharmaceutics. 180: 75-81, 1999. Quilitz, Rod. "Oncology Pharmacotherapy: The Use of Lipid Formulations of Amphotericin B in Cancer Patients." Cancer Control. 5:439-449, 1998. Ranade, Vasant V. "Drug Delivery Systems: Site-Specific Drug Delivery Using Liposomes as Carriers." Pharmacology. 29: 685-694, 1989. Storm, Gert and Daan J.A. Crommelin. "Liposomes:quo vadi?" PSTT 1: 19-31, 1998. Taylor, KMG and JM Newton. "Liposomes as a vecicle for drug delivery." British Journal of Hospital Medicine. 51: 55-59, 1994
  • 30. Websites James, John S. "Doxil Approved for KS." www.immunet. org.imminet/atn.nsf/page/a-235-03. Wasan, Ellen. "Targeted Gene Transfer." Member.tripod.com/~rrishna/lipos1.html "Introduction to Controlled Drug Delivery Systems." www5.bae.ncsu.edu/bae/reearch/blak… k/otherprojects/drugDeliver_97/ http://www. Mssm.edu/medicine/thrombosis/phosphol.html "Doxorubicin." http://tirgan.com/adria.htm "Clinical Pharmacology Online." http://www.cponline.gsm.com/scripts/fullmono/showmono. "Drugstore.com" http://www.drugstore.com/pharmacy/prices/Amphotec. "Sequus' Doxil Becomes First Liposome Product Approved In U.S." www.slip.net/~mcdavis/ database/doxor_1 "Liposomes." www.collabo.com/liposom0.htm Paustin, Timothy. “Cellular Membranes.”www.bact.wisc.edu/microtextbook/bacterialstructure/Membranegen.html www.cbc.umn.edu/~mwd/cell_www/chapter2/membrane.html#PHOSPHOLIPIDS Books Jones, Macolm N. and Chapman, David. Micelles, Monolayers and Biomembranes . Wiley-Liss. New York (1995). Garrett, R. and Grisham C. Biochemistry , 2 nd ed. Saunders Colleges Publishing. New York (1999). 264.