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Original Article

PEGylation of αα-Hb using succinimidyl propionic acid PEG 5K: Conjugation chemistry and PEG shell structure dictate respectively the oxygen affinity and resuscitation fluid like properties of PEG αα-Hbs

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Pages 270-281 | Received 14 Oct 2013, Accepted 16 Jan 2014, Published online: 06 Mar 2014

References

  • Acharya SA, Friedman JM, Manjula BN, Intaglietta M, Tsai AG, Winslow RM, et al. 2005. Enhanced molecular volume of conservatively PEGylated Hb: (SP-PEG5K)6-HbA is non-hypertensive. Artif Cells Blood Substit Immobil Biotechnol. 33:239–255.
  • Acharya SA, Acharya VN, Kanika ND, Tsai AG, Intaglietta M, Manjula BN. 2007a. Non-hypertensive tetraPEGylated canine haemoglobin: correlation between PEGylation, O2 affinity and tissue oxygenation. Biochem J. 405:503–511.
  • Acharya SA, Intaglietta M, Tsai AG. 2007b. Modulation of the polyethylene glycol-hemoglobin structure to increase the efficiency of plasma expansion and O2 carrying capacity. Transfus Altern Transfus Med. 9:254–264.
  • Ampulski RS, Ayers VE, Morell SA. 1969. Determination of the reactive sulfhydryl groups in heme proteins with 4, 4′-dipyridinedisulfide. Anal Biochem. 32:163–169.
  • Ananda K, Manjula BN, Meng F, Acharya VN, Intaglietta M, Acharya SA. 2012. Packing density of the PEG-shell in PEG-albumins: PEGylation induced viscosity and COP are inverse correlate of packing density. Artif Cells Blood Substit Immobil Biotechnol. 40:14–27.
  • Ananthakrishnan R, Li Q, O’Shea KM, Quadri N, Wang L, Abuchowski A, Schmidt AM, Ramasamy R. 2013. Carbon monoxide form of PEGylated hemoglobin protects myocardium against ischemia/reperfusion injury in diabetic and normal mice. Artif Cells Nanomed Biotechnol. 41:428–36 [Epub ahead of print].
  • Busch MR, Ho CE. 1990. Effects of anions on the molecular basis of the Bohr effect of hemoglobin. Biophys Chem. 37:313–322.
  • Cabrales P, Tsai AG, Ananda K, Acharya SA, Intaglietta M. 2008. Volume resuscitation from hemorrhagic shock with albumin and hexaPEGylated human serum albumin. Resuscitation. 79:139–146.
  • Chatterjee R, Welty EV, Walder RY, Pruitt SL, Rogers PH, Arnone A, Walder JA. 1986. Isolation and characterization of a new hemoglobin derivative cross-linked between the α chains (lysine 99α1→lysine 99α2). J Biol Chem. 261:9929–9937.
  • Cole, RH, Vandegriff KD. 2011. MP4, a vasodilatory PEGylated hemoglobin. Adv Exp Med Biol. 701:85–90.
  • Cole R, Vandegriff K, Szeri A, Savas O, Winslow R. 2008. Targeted O2 delivery by blood substitutes: in vitro arteriolar simulations of first- and second-generation products. Microvasc Res. 76:169–179.
  • Fronticelli C, Bucci E, Orth C. 1984. Solvent regulation of oxygen affinity in hemoglobin. J Biol Chem. 259:10841–10844.
  • Hu T, Prabhakaran M, Acharya SA, Manjula BN. 2005. Influence of the chemistry of conjugation of poly(ethylene glycol) to Hb on the oxygen-binding and solution properties of the PEG-Hb conjugate. Biochem J. 392:555–564.
  • Hu T, Manjula B, Brenowitz M, Acharya SA. 2007. Influence of intramolecular cross-links on the molecular, structural and functional properties of PEGylated haemoglobin. Biochem J. 402:143–151.
  • Hu T, Li D, Manjula, BN, Acharya SA. 2008. Autoxidation of the site-specifically PEGylated hemoglobins: role of the PEG chains and the sites of PEGylation in the autoxidation. Biochemistry. 47:10981–10990.
  • Hu T, Li D, Manjula BN, Brenowitz M, Prabhakaran M, Acharya SA. 2009. PEGylation of Val-1(alpha) destabilizes the tetrameric structure of hemoglobin. Biochemistry. 48:608–616.
  • Intaglietta M, Cabrales P, Tsai AG. 2006. Microvascular perspective of oxygen-carrying and -noncarrying blood substitutes. Ann Rev Biomed Eng. 8:289–321.
  • Khan I, Dantsker D, Samuni U, Friedman AJ, Bonaventura C, Manjula B, Acharya SA, Friedman JM. 2001. Beta 93 modified hemoglobin: kinetic and conformational consequences. Biochemistry. 40:7581–7592.
  • Li D, Manjula BN, Acharya AS. 2006. Extension arm facilitated PEGylation of hemoglobin: correlation of the properties with the extent of PEGylation. Protein J. 25:263–274.
  • Li D, Hu T, Manjula BN, Acharya SA. 2008. Non-conservative surface decoration of hemoglobin: influence of neutralization of positive charges at PEGylation sites on molecular and functional properties of PEGylated hemoglobin. Biochim Biophys Acta. 1784:1395–1401.
  • Li D, Hu T, Manjula BN, Acharya SA. 2009. Extension arm facilitated pegylation of alphaalpha-hemoglobin with modifications targeted exclusively to amino groups: functional and structural advantages of free Cys-93(beta) in the PEG-Hb adduct. Bioconjug Chem. 20:2062–2070.
  • Manjula BN, Acharya AS. 2003. Purification and molecular analysis of hemoglobin by high-performance liquid chromatography. Methods Mol Med: Hemoglobin Disord. 82:31–47.
  • Manjula BN, Tsai A, Upadhya R, Perumalsamy K, Smith PK, Malavalli A, et al. 2003. Site-specific PEGylation of hemoglobin at Cys-93(beta): correlation between the colligative properties of the PEGylated protein and the length of the conjugated PEG chain. Bioconjug Chem. 14:464–472.
  • Manjula BN, Tsai AG, Intaglietta M, Tsai CH, Ho C, Smith PK, et al. 2005. Conjugation of multiple copies of polyethylene glycol to hemoglobin facilitated through thiolation: influence on hemoglobin structure and function. Protein J. 24:133–146.
  • Meng F, Manjula BN, Tsai AG, Cabrales P, Intaglietta M, Smith PK, Prabhakaran M, Acharya SA. 2009. Hexa-thiocarbamoyl phenyl PEG5K Hb: vasoactivity and structure: influence of rigidity of the conjugation linkage on the PEGylation induced plasma expander-like solution properties of PEG-Hb adducts. Protein J. 28:199–212.
  • Nacharaju P, Friedman JM, Prabhakaran M, Acharya SA, Manjula BN. 2007. Combining the influence of two low O2 affinity-inducing chemical modifications of the central cavity of hemoglobin. Biochemistry. 46:4554–4564.
  • Nho K, Glower D, Bredehoeft S, Shankar H, Shorr R, Abuchowski A. 1992. PEG-bovine hemoglobin: safety in a canine dehydrated hypovolemic-hemorrhagic shock model. Biomater Artif Cell Immobil Biotechnol. 20:511–524.
  • Shorr RG, Kwong S, Gilbert C, Benesch RE. 1999Changes in the functional properties of bovine hemoglobin induced by covalent modification with polyethylene glycol. Artif Cells Blood Substit Immobil Biotechnol. 27:185–202.
  • Song D, Olano M, Wilson DF, Pastuszko A, Tammela O, Nho K, Shorr RG. 1995. Comparison of the efficacy of blood and polyethylene glycol-hemoglobin in recovery of newborn piglets from hemorrhagic hypotension: effect on blood pressure, cortical oxygen, and extracellular dopamine in the brain. Transfusion. 35:552–558.
  • Sriram K, Tsai AG, Cabrales P, Meng F, Acharya SA, Tartakovsky DM, Intaglietta M. 2012. PEG-albumin supraplasma expansion is due to increased vessel wall shear stress induced by blood viscosity shear thinning. Am J Physiol Heart Circ Physiol. 302:H2489–2497.
  • Tsai AG, Vandegriff KD, Intaglietta M, Winslow RM. 2003. Targeted O2 delivery by low-P50 hemoglobin: a new basis for O2 therapeutics. Am J Physiol Heart Circ Physiol. 285:H1411–1419.
  • Tsai AG, Johnson PC, Intaglietta M. 2007. Is the distribution of tissue pO(2) homogeneous?Antioxid Redox Signal. 9:979–984.
  • Tsai AG, Cabrales P, Intaglietta M. 2010. The physics of oxygen delivery: facts and controversies. Antioxid Redox Signal. 12:683–691.
  • Vandegriff KD, Winslow RM. 2009. Hemospan: design principles for a new class of oxygen therapeutic. Artif Organs. 33:133–138.
  • Vandegriff KD, McCarthy M, Rohlfs RJ, Winslow RM. 1997. Colloid osmotic properties of modified hemoglobins: chemically cross-linked versus polyethylene glycol surface-conjugated. Biophys Chem. 69:23–30.
  • Vandegriff KD, Malavalli A, Wooldridge J, Lohman J, Winslow RM. 2003. MP4, a new nonvasoactive PEG-Hb conjugate. Transfusion. 43:509–516.
  • Vandegriff KD, Malavalli A, Minn C, Jiang E, Lohman J, Young MA, Samaja M, Winslow RM. 2006. Oxidation and haem loss kinetics of poly(ethylene glycol)-conjugated haemoglobin (MP4): dissociation between in vitro and in vivo oxidation rates. Biochem J. 399:463–471.
  • Vandegriff KD, Malavalli A, Mkrtchyan GM, Spann SN, Baker DA, Winslow RM. 2008. Sites of modification of hemospan, a poly (ethylene glycol)-modified human hemoglobin for use as an oxygen therapeutic. Bioconjug Chem. 19:2163–2170.
  • Winslow RM. 2000. Alpha-alpha-crosslinked hemoglobin: was failure predicted by preclinical testing?Vox Sang. 79:1–20.
  • Winslow RM. 2005. Targeted O2 delivery by low-p50 hemoglobin: a new basis for hemoglobin-based oxygen carriers. Artif Cell Blood Substit Immobil Biotechnol. 33:1–12.
  • Winslow RM. 2008. Cell-free oxygen carriers: scientific foundations, clinical development, and new directions. Biochim Biophys Acta. 1784:1382–1386.
  • Young MA, Riddez L, Kjellström BT, Bursell J, Winslow F, Lohman J, Winslow RM. 2005. MalPEG-hemoglobin (MP4) improves hemodynamics, acid-base status, and survival after uncontrolled hemorrhage in anesthetized swine. Crit Care Med. 33:1794–1804.

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